Co-reporter:Dong-Peng Li;Zhao-Yang Wang;Hao Su;Jun-Ying Miao
Chemical Communications 2017 vol. 53(Issue 3) pp:577-580
Publication Date(Web):2017/01/03
DOI:10.1039/C6CC06459K
Probe L-HF1, which featured large (pseudo) Stokes shifts and high FRET efficiency, was designed on a new ESIPT enhanced FRET platform for the detection of HSO3−/SO32−. L-HF1 could detect endogenous bisulfite in HepG2 cells but not in L-02 cells, implying the different bisulfite levels in normal and cancer cells of liver.
Co-reporter:Shi-Li Shen;Xuan Zhao;Xiao-Fan Zhang;Xuan-Li Liu;Hao Wang;Yi-Ying Dai;Jun-Ying Miao
Journal of Materials Chemistry B 2017 vol. 5(Issue 2) pp:289-295
Publication Date(Web):2017/01/04
DOI:10.1039/C6TB01992G
A novel ratiometric probe (RCP) for −OCl was developed based on the fluorescence resonance energy transfer (FRET) platform. The probe was constructed by integrating the coumarin moiety (FRET donor) with the rhodamine moiety (FRET acceptor). Upon treatment with −OCl, the coumarin emission at 483 nm decreased and the rhodamine emission at 570 nm increased, enabling the probe to provide accurate detection of −OCl (in the concentration range of 0–50 μM). The probe exhibited brilliant selectivity and sensitivity, rapid response and low cytotoxicity. More importantly, the introduction of the quaternized pyridine moiety can not only manage to increase the solubility, but also achieve mitochondria-targeting. The probe was applied successfully to imaging endogenous −OCl in mitochondria, highlighting its potential applications in bioanalysis.
Co-reporter:Li-Jie Zhang, Zhao-Yang Wang, Jin-Ting Liu, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2017 Volume 253(Volume 253) pp:
Publication Date(Web):1 December 2017
DOI:10.1016/j.snb.2017.06.072
•A new ICT/FRET platform was designed for ratiometric fluorescent probes.•The probe has excellent selectivity and anti-interference for sulfite.•The probe can detect endogenous sulfite in HepG2 and L-02 cells.•The probe can preferably target mitochondria.A new ICT/FRET platform composed of coumarin-hemicyanine dyad was rationally designed for ratiometric fluorescent probes. The platform could concert the spectral overlap and the emission shifts by changing ICT donor. The mitochondria-targeting probe was developed to sense endogenous sulfite in living cells with high selectivity, sensitivity and fast response.Download high-res image (99KB)Download full-size image
Co-reporter:Qiong Yuan, Zhi-Min Zhao, Yan-Ru Zhang, Le Su, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2017 Volume 247(Volume 247) pp:
Publication Date(Web):1 August 2017
DOI:10.1016/j.snb.2017.03.049
•A ratiometric fluorescent probe for HOCl was developed based on the coumarin –rhodamine FRET platform.•The probe exhibited high selectivity and excellent sensitivity toward HOCl.•The probe was applied to image exogenous and endogenous HOCl in the living cells.•The probe could target lysosomes.A ratiometric fluorescent probe (DICX) based on Förster resonance energy transfer (FRET) system for hypochlorous acid (HOCl) was developed, in which coumarin moiety was connected to rhodamine by monothio-bishydrazide linker. DICX could fast respond to HOCl under acidic condition and showed high selectivity and sensitivity toward HOCl over other reactive oxygen species, reactive nitrogen species, and ions. The FRET energy transfer efficiency is very high (93.75%). Moreover, DICX could target lysosome and could be suitable for sensing exogenous and endogenous HOCl in living cells.Download high-res image (79KB)Download full-size image
Co-reporter:Wen-Li Wu, Han-Lin Ma, Miao-Fei Huang, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2017 Volume 241() pp:239-244
Publication Date(Web):31 March 2017
DOI:10.1016/j.snb.2016.10.028
•A ratiometric mitochondria-targeted fluorescent probe DSPT for bisulfate was developed based on FRET mechanism.•DSPT has competitive limit of detection (69 nM).•DSPT was applied to detect exogenous and endogenous bisulfite in living Hela and HepG2 cells.•DSPT was also successful applied to discriminate liver cancer cells from normal liver cells.A new FRET-based ratiometric fluorescent probe (DSPT) for the detection of bisulfite was developed by the dansyl-piperazine-benzothiazolium conjugate platform, in which CC conjugated with benzothiazolium was recognition unit and benzothiazolium moiety was mitochondria-targeted unit. The CC double bond group would undergo Michael addition reaction with bisulfite, triggering significant fluorescence ratio increasing which was linear to the concentrations of bisulfite. The probe can be used in real sample including dry white wine and tap water. Besides, the test strips for bisulfite were prepared. Moreover, cell imaging results indicate that this probe is cell-membrane permeable and mitochondria-targetable, and can be applied to monitor both exogenous and endogenous bisulfite in ratiometric fluorescence imaging.A ratiometric mitochondria-targeted fluorescent probe DSPT for bisulfite was developed based on FRET mechanism.
Co-reporter:Xiao Feng, Tao Zhang, Jin-Ting Liu, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2016 vol. 52(Issue 15) pp:3131-3134
Publication Date(Web):19 Jan 2016
DOI:10.1039/C5CC09267A
We have developed a new ratiometric fluorescent probe composed of a coumarin–merocyanine dyad based on the FRET mechanism. The probe showed clear dual-emission signal changes in blue and red spectral windows upon addition of H2S in a dose dependent manner under a single wavelength excitation. The probe targeted mitochondria with high selectivity and sensitivity toward H2S.
Co-reporter:Dong-Peng Li, Zhao-Yang Wang, Xiang-Jian Cao, Jie Cui, Xin Wang, Hao-Zhong Cui, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2016 vol. 52(Issue 13) pp:2760-2763
Publication Date(Web):05 Jan 2016
DOI:10.1039/C5CC09092J
A new mitochondria-targeted fluorescent probe HCy-D, constructed by dansyl and hemicyanine fluorophores, for SO2 derivatives (HSO3−/SO32−) was presented. This probe was designed based on a new FRET platform. HCy-D showed a ratiometric, sensitive and rapid response to HSO3−/SO32−. Importantly, HCy-D was successfully used for fluorescence imaging of endogenous bisulfite in HepG2 cells, which may benefit cancer diagnosis by discriminating liver cancer cells from normal liver cells.
Co-reporter:Xi Dai, Zhi-Fang Du, Li-Hong Wang, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2016 Volume 922() pp:64-70
Publication Date(Web):30 May 2016
DOI:10.1016/j.aca.2016.04.003
•This probe can discriminate glutathione from sulfhydryl compound by PET process.•This probe can be used to determine glutathione in aqueous solution within 1 min.•This probe has been successfully applied in living cell image.We have designed and synthesized a simple but effective fluorescent probe for sensing glutathione (GSH) by PET process based on coumarin and quinone, which worked as fluorophore and reaction site, respectively. The probe could discriminate GSH from cysteine and homocysteine within 1 min in PBS-buffered solution. The sensing mechanism was confirmed by density functional theory (DFT), viscosity test, fluorescence spectrum analysis and HRMS, respectively. The probe has a low limit of detection (0.1 μM) and finally been used in cell imaging successfully.
Co-reporter:Ying Liu, Zhi-Min Zhao, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2016 Volume 921() pp:77-83
Publication Date(Web):19 May 2016
DOI:10.1016/j.aca.2016.03.045
•A probe based on BODIPY and rhodamine was developed for sensing HOCl.•The probe could sense HOCl in a ratiometric manner based on the FRET platform in PBS buffer solution.•The probe can detect HOCl in 15 s accompanied with a fluorescence colour change.•This probe was successfully used to monitor HOCl in living RAW 264.7 cells.We have developed a ratiometric fluorescent probe BRT based on boron dipyrromethene (BODIPY) and rhodamine-thiohydrazide Förster resonance energy transfer (FRET) platform for sensing hypochlorous acid (HOCl) with high selectivity and sensitivity. The probe can detect HOCl in 15 s with the detection limit of 38 nM. Upon mixing with HOCl the fluorescence colour of probe BRT changed from green to orange. Moreover, probe BRT was applied to successfully monitor HOCl in living RAW 264.7 cells.
Co-reporter:Yan-Ru Zhang, Zhi-Min Zhao, Le Su, Jun-Ying Miao and Bao-Xiang Zhao
RSC Advances 2016 vol. 6(Issue 21) pp:17059-17063
Publication Date(Web):04 Feb 2016
DOI:10.1039/C5RA26027B
Studies showed that the intravascular pH of neutrophils fell to 4.5–5.0 with stimulation for a few minutes. Under this condition, myeloperoxidase was activated to catalyze H2O2 and Cl− to form hypochlorous acid (HOCl). Therefore, it is of significance to develop fluorescence probes for sensing HOCl in acid conditions. In this work, we reported a ratiometric probe CRSH based on a fluorescence resonance energy transfer (FRET) platform for detecting HOCl under acid conditions. Probe CRSH exhibited excellent sensitivity, high selectivity and a rapid response toward HOCl and is suitable for imaging endogenous HOCl in living cells.
Co-reporter:Guang-Jie Song, Su-Yun Bai, Xi Dai, Xiao-Qun Cao and Bao-Xiang Zhao
RSC Advances 2016 vol. 6(Issue 47) pp:41317-41322
Publication Date(Web):20 Apr 2016
DOI:10.1039/C5RA25947A
A new pH-activatable ratiometric fluorescent probe (RhMP) has been developed, in which an imidazo[1,5-a]pyridine fluorophore as a fluorescence resonance energy transfer (FRET) donor linked to a rhodamine B fluorophore as a FRET acceptor. The simultaneous fluorescence intensity enhancement of imidazo[1,5-a]pyridine and rhodamine B moieties along with the decrease of pH value should result from the integration of ICT and FRET processes. It's the first time a ratiometric fluorescent probe based on FRET system using imidazo[1,5-a]pyridine derivative as a fluorophore donor has been reported. At pKa = 4.96, the fluorescence intensity ratio (I476.5/I577.5) of the probe displayed excellent pH-dependent performance and responded linearly to minor pH changes in the range of 4.0–5.8. The probe exhibited excellent selectivity among different metal cations and brilliant reversibility. In addition, RhMP has low cytotoxicity and has been successfully applied in HeLa cells. The fluorescence microscopic images demonstrated this probe could image weak acid pH changes of the lysosome in live cells.
Co-reporter:Li-Jie Zhang, Zhao-Yang Wang, Xiang-Jian Cao, Jin-Ting Liu, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 236() pp:741-748
Publication Date(Web):29 November 2016
DOI:10.1016/j.snb.2016.06.055
•A novel ratiometric fluorescent probe toward sulfite was developed.•The probe has excellent selectivity and fast respond time within 30 s.•The probe was successfully applied in living cells.•The testing mechanism was verified by theoretical calculation.We have developed a ratiometric fluorescent probe based on ICT mechanism for imaging intracellular sulfite (SO32−) in HeLa cells. The probe could selectively stain cells with scarce cytotoxicity and excellent photostability. The probe displayed a high selectivity for sulfite over other anions and active small biological molecules including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) at room temperature. The reaction could complete within 30 s and detection limit was as low as 76 nM, which is superior to some reported probes. The detecting mechanism was proved by MS, 1H NMR and theoretical calculation. The probe can also detect endogenous sulfite in HepG2 cells.A fast-response fluorescent probe for SO32− has been developed. Upon addition of sulfite, the apparently fluorescence variation is confirmed in a ratiometric manner and ICT mechanism in DMSO:PBS = 1:1 (pH = 5). The mechanism has been proved by HRMS and theoretical calculation.
Co-reporter:Jie Cui, Tao Zhang, Yi-Qing Sun, Dong-Peng Li, Jin-Ting Liu, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 232() pp:705-711
Publication Date(Web):September 2016
DOI:10.1016/j.snb.2016.04.025
•This probe was very sensitive with a detection limit of 90 nM.•This probe showed good stability and low cytotoxicity.•This probe was applied to sense H2S in living Hela cells.Constructed by coumarin fluorophore and dinitrophenyl ether moiety, a new probe CTN was synthesized for hydrogen sulfide (H2S) detection. The probe featured with high sensitivity and good selectivity. Compound CTO produced by the reaction of CTN with H2S possesses very high quantum yield. Up to 200-fold fluorescence enhancement toward H2S was observed and the detection limit was calculated to be as low as 90 nM. Moreover, CTN is membrane-permeable and suitable for visualization of H2S in living cells.
Co-reporter:Wen-Li Wu, Zhi-Min Zhao, Xi Dai, Le Su, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 232() pp:390-395
Publication Date(Web):September 2016
DOI:10.1016/j.snb.2016.03.155
•A colorimetric and fluorescent probe based on new fluorophore was developed.•The probe could respond to hypochlorite in as fast as 30 s.•The probe has a detection limit as low as 0.43 nM.•This probe successfully used to living cell imaging.We have designed and synthesized a fluorescent probe for hypochlorite based on the oxidation of hydrazone to carboxyl group. The probe was constructed from 2-hydrazinylpyridine and 3-butyl-1-chloroimidazo[1,5-a]pyridine-7-carbaldehyde which possesses good optical properties as a novel fluorophore. The detection limit was measured to be as low as 0.43 nM. Moreover, the probe can realize fast-detection for hypochlorite in as short as 30 s. The probe was also successfully applied to image living cells.A fast-response colorimetric fluorescent probe for hypochlorite has been developed with a detection limit as low as 0.43 nM.
Co-reporter:Yan-Ru Zhang, Zhi-Min Zhao, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 229() pp:408-413
Publication Date(Web):28 June 2016
DOI:10.1016/j.snb.2016.01.146
•A ratiometric fluorescence sensor (CARSH) was designed on novel FRET platform for HOCl.•Probe CARSH showed high selectivity and excellent sensitivity toward HOCl.•Probe CARSH was suitable for imaging endogenous HOCl in the living cells.A ratiometric fluorescence probe (CARSH) was designed on a novel FRET platform for HOCl. The novel platform enlarged spectral overlap between the donor emission band and the acceptor absorption band comparing to the traditional coumarin–rhodamine FRET platform, and the energy transfer reached up to 81.1%. The probe showed high selectivity, excellent sensitivity, fast response, good membrane permeability and stability.
Co-reporter:Dong-Peng Li, Jin-Feng Zhang, Jie Cui, Xiao-Feng Ma, Jin-Ting Liu, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 234() pp:231-238
Publication Date(Web):29 October 2016
DOI:10.1016/j.snb.2016.04.164
•The probe could detect H2S in a ratiometric manner.•The probe exhibited good selectivity and high sensitivity.•The probe could differentiate biological thiols from H2S.•Living cell imaging of H2S was successfully conducted.A new fluorescent probe based on the cleavage of disulfide bond and subsequent intramolecular cyclization process was designed for the detection of H2S. The selectivity was guaranteed by use of the unique nucleophilicity of H2S. The impacts of biological thiols were neglectable and biological thiols could lead to a fluorescence emission band different from H2S with longer response time. The probe was also applied to detect H2S in living cells successfully.
Co-reporter:Xi Dai, Zhao-Yang Wang, Zhi-Fang Du, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 232() pp:369-374
Publication Date(Web):September 2016
DOI:10.1016/j.snb.2016.03.159
•A colorimetric and ratiometric near-infrared fluorescent probe was developed.•The probe-loaded TLC plates were made to detect vapor of hydrazine.•This probe was successfully used to living cell imaging and fetal bovine serum.A simple but effective near-infrared ratiometric fluorescent probe for hydrazine has been developed by a hybrid fluorophore of coumarin and benzopyrylium. The recognition mechanism involving spirocyclic ring-opening and −closing toward hydrazine is first reported. The probe showed high selectivity and sensitivity toward hydrazine with lower detection limit (1.5 ppb) under single wavelength excitation. Upon addition of trace amounts of hydrazine, the probe showed a remarkable ratiometric change in the absorption (Δλ = 167 nm) and emission (Δλ = 201 nm) spectra and a color change from green to yellow. Furthermore, the probe-loaded TLC plates were made to detect vapor of hydrazine by naked eyes. Moreover, this ratiometric probe was successfully used for the imaging of hydrazine in fetal bovine serum and living cells.
Co-reporter:Xi Dai, Tao Zhang, Jun-Ying Miao, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2016 Volume 223() pp:274-279
Publication Date(Web):February 2016
DOI:10.1016/j.snb.2015.09.106
•A ratiometric fluorescent probe based on DNBS group was first developed.•The probe could detect thiols in PBS buffer solution with two-photon excited.•This probe successfully used to living cell imaging and calf serum.A ratiometric fluorescent probe containing a comarin-pyrazoline fluorophore and a 2,4-dinitrobenzenesulfonyl (DNBS) group for thiols has been developed. The probe can fast recognize thiols under both one-photon and two-photon excitations in PBS solution with low detection limits (one-photon 10−8 M and two-photon 10−7 M). The sensing mechanism was confirmed by using ESI-MS and fluorescent spectra. Moreover, the probe was successfully used for the fluorescent imaging of living cells and calf serum.Graphical abstract
Co-reporter:Guang-Jie Song;Su-Yun Bai;Jing Luo;Xiao-Qun Cao
Journal of Fluorescence 2016 Volume 26( Issue 6) pp:2079-2086
Publication Date(Web):2016 November
DOI:10.1007/s10895-016-1902-4
A new ratiometric fluorescent probe based on Förster resonance energy transfer (FRET) for sensing lysosomal pH has been developed. The probe (RMPM) was composed of imidazo[1,5-α]pyridine quaternary ammonium salt fluorophore as the FRET donor and the rhodamine moiety as the FRET acceptor. It’s the first time to report that imidazo[1,5-α]pyridine quaternary ammonium salt acts as the FRET donor. The ratio of fluorescence intensity of the probe at two wavelengths (I424/I581) changed significantly and responded linearly toward minor pH changes in the range of 5.4–6.6. It should be noted that it’s rare to report that a ratiometric pH probe could detect so weak acidic pH with pKa = 6.31. In addition, probe RMPM exhibited excellent water-solubility, fast-response, all-right selectivity and brilliant reversibility. Moreover, RMPM has been successfully applied to sensing lysosomal pH in HeLa cells and has low cytotoxicity.
Co-reporter:Xiao-Fan Zhang, Tao Zhang, Shi-Li Shen, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2015 vol. 3(Issue 16) pp:3260-3266
Publication Date(Web):04 Mar 2015
DOI:10.1039/C4TB02082K
In this study, a novel ratiometric pH probe RNL based on fluorescence resonance energy transfer (FRET) was well developed. It was fabricated by integrating the naphthalimide moiety as an FRET donor with the rhodamine moiety as an FRET acceptor. Meanwhile, 4-(2-aminoethyl)morpholine, which was a lysosome-locating group, was introduced. The sensing mechanism was the integration of PET and FRET processes and the comprehensive effect led to the simultaneous intensity enhancement of naphthalimide and rhodamine along with the pH value decrease. With a pKa of 4.82, the fluorescence intensity ratio (I529/I580) of the probe changed significantly within the pH range from 4.50 to 5.50. The probe showed excellent selectivity among various metal cations, amino acids and ATP. Moreover, RNL has been successfully applied in HeLa cells, and the results demonstrated that it could be used to detect lysosomal pH changes. The probe could also selectively stain lysosome in HeLa cells. Besides, the probe exhibited low cytotoxicity and satisfactory photostability in living HeLa cells.
Co-reporter:Shi-Li Shen, Xin-Peng Chen, Xiao-Fan Zhang, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2015 vol. 3(Issue 5) pp:919-925
Publication Date(Web):21 Nov 2014
DOI:10.1039/C4TB01763C
A novel rhodamine B-based fluorescent probe (RML) for lysosomal pH was developed by integrating a 4-(2-aminoethyl)morpholine moiety, which is a lysosome-targetable group, into a rhodamine B fluorophore, which is associated with rhodamine B dyes possessing spirocyclic (non-fluorescent) and ring-opening (fluorescent) forms with response to pH. The probe responded to acidic pH at low concentration in a short amount of time. In addition, RML showed good membrane permeability and brilliant selectivity among various amino acids and metal cations. RML exhibited an 80-fold increase in fluorescence intensity at 583 nm throughout the pH range of 7.40–4.00 with a pKa of 5.16, which indicates that RML is valuable for studying intracellular acidic organelles. Moreover, RML has been successfully applied in HeLa cells, and the results demonstrated that RML could selectively stain lysosomes in living HeLa cells. Note that RML could be used to detect the pH increase in lysosomes induced by bafilomycin A1 within HeLa cells.
Co-reporter:Xi Dai, Tao Zhang, Zhi-Fang Du, Xiang-Jian Cao, Ming-Yu Chen, Sheng-Wen Hu, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2015 Volume 888() pp:138-145
Publication Date(Web):12 August 2015
DOI:10.1016/j.aca.2015.07.026
•A colorimetric and ratiometric fluorescent probe was developed.•The probe could detect bisulfite in PBS buffer solution and real samples.•Bisulfite test paper was made to naked-eye detect bisulfite.•This probe successfully used to living cell imaging in ratiometric manner.We have developed the first two-photon colorimetric and ratiometric fluorescent probe, BICO, for the detection of bisulfite (HSO3−) in aqueous solution. The probe contains coumarin and benzimidazole moieties and can detect HSO3− based on the Michael addition reaction with a limit of detection 5.3 × 10−8 M in phosphate-buffered saline solution. The probe was used to detect bisulfite in tap water, sugar and dry white wine. Moreover, test strips were made and used easily. We successfully applied the probe to image living cells, using one-photon fluorescence imaging. BICO overcomes the limitations in sensitivity of previously reported probes and the solvation effect of bisulfite, which demonstrates its excellent value in practical application.
Co-reporter:Jie Cui, Dong-Peng Li, Shi-Li Shen, Jin-Ting Liu and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 5) pp:3875-3880
Publication Date(Web):05 Dec 2014
DOI:10.1039/C4RA12649A
A new simple-structure fluorescent probe RL based on the special affinity of Pd2+ to double bond ligands has been designed and synthesized. RL shows high selectivity and sensitivity for Pd2+ with a detection limit of 21.3 nM (2.3 ppb) in the presence of other competing metal ions in aqueous media. Furthermore, RL has potential applications in Pd2+ analysis in natural water and in a reactor involving a Pd2+catalytic reaction.
Co-reporter:Shi-Li Shen, Xiao-Fan Zhang, Su-Yun Bai, Jun-Ying Miao and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 18) pp:13341-13346
Publication Date(Web):20 Jan 2015
DOI:10.1039/C4RA16398B
In this study, a novel ratiometric pH probe RC1 was successfully developed. RC1 was constructed by integrating a coumarin fluorophore as a fluorescence resonance energy transfer (FRET) donor into a rhodamine B fluorophore as a FRET acceptor, which is associated with rhodamine B dyes possessing spirocyclic (non-fluorescent) and ring-opening (fluorescent) forms with response to pH. At weak basic pH, the photo-induced electron transfer (PET) process of the N atom of aromatic imino in the rhodamine moiety partly quenches the coumarin emission. At acidic pH, the PET process is gradually inhibited upon acidification, enhancing the fluorescence intensity of coumarin remarkably; at the same time, the spirolactam form of rhodamine changes to a ring-opening form followed by the FRET process between coumarin and rhodamine. Hence, the emission intensities of coumarin and the rhodamine moiety simultaneously increase along with the pH decrease. The sensing mechanism is an integration of the PET and FRET processes. Based on the ratios of fluorescence intensity at 583 nm and 470 nm (I583/I470), RC1 with a pKa of 3.21 could be used in the ratiometric detection of pH in the range 2.20–4.20 with high selectivity. Furthermore, it can be applied to visualize extreme acidity in bacteria. The results demonstrate that RC1 can serve as an ideal probe for extremely acidic pH levels with excellent biological significance.
Co-reporter:Ying Liu, Sheng-Qing Wang and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 42) pp:32962-32966
Publication Date(Web):02 Apr 2015
DOI:10.1039/C5RA04933D
We have designed and synthesized a new fluorescent probe, 2-(3-(2-((tert-butyldiphenylsilyl)oxy)phenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzo[d]thiazole (probe 1), to detect fluoride ion with high selectivity and sensitivity in aqueous media. Upon mixing with NaF, desilylation reaction of probe 1 can be induced to the fluorescence quenching with the detection limit of F− 0.74 μM. Moreover, the probe can be used to detect fluoride ion on real life samples.
Co-reporter:Xiao-Fan Zhang, Tao Zhang, Shi-Li Shen, Jun-Ying Miao and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 61) pp:49115-49121
Publication Date(Web):28 May 2015
DOI:10.1039/C5RA06246B
In this study, we developed a coumarin–rhodamine based fluorescence resonance energy transfer (FRET) system RC1 as a ratiometric pH probe. The probe with a pKa of 4.98 was constructed by integrating a coumarin moiety as an FRET donor with a rhodamine moiety as an FRET accepter. Upon addition of H+, the coumarin emission at 477 nm decreased and the rhodamine emission at 582 nm increased simultaneously. The fluorescence intensity ratio (I477/I582) displayed excellent pH-dependent performance and responded linearly to minor pH changes in the range of 4.20–6.00. The probe exhibited brilliant selectivity among different amino acids, metal cations and the ATP. Moreover, it has been successfully applied in fluorescence imaging in HeLa cells and the results indicated that the probe could selectively stain lysosomes with low cytotoxicity and excellent photostability. We also applied RC1 to monitor intracellular pH variations induced by dexamethasone. Therefore, RC1 could act as a practical tool for the detection of pH in weakly acidic conditions and provide essential information in medicinal analysis and real biological systems.
Co-reporter:Zheng Tang, Xiao-Ling Ding, Ying Liu, Zhi-Min Zhao and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 121) pp:99664-99668
Publication Date(Web):16 Nov 2015
DOI:10.1039/C5RA20188H
We have developed a novel fluorescent probe (RBT) based on rhodamine B and benzothiazole hydrazine units for the detection of hypochlorite in living cells and real water samples with excellent selectivity and sensitivity. In the presence of hypochlorite in a mixture solution of MeCN–PBS (v/v = 3:7, pH = 7.4) at room temperature, the fluorescence intensity of RBT increased by 350 fold with the color change from colorless to red. The detection limit of the probe for hypochlorite is 1.06 × 10−9 M. Moreover, RBT was successfully used to image endogenous hypochlorite in living cells and detect hypochlorite in real water samples.
Co-reporter:Xuan Zhang, Guang-Jie Song, Xiang-Jian Cao, Jin-Ting Liu, Ming-Yu Chen, Xiao-Qun Cao and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 109) pp:89827-89832
Publication Date(Web):15 Oct 2015
DOI:10.1039/C5RA14174E
A new imidazo[1,5-a]pyridine-based pH fluorescent probe has been synthesized and characterized. It is the first time that imidazo[1,5-a]pyridine is used as a fluorescent probe. This probe responds to acidic pH with fast response (within 3 min), high selectivity and sensitivity. It has good reversibility and nearly no interference from common metal ions. The probe is suitable for acidic conditions and can quantitatively detect pH value based on the equilibrium equation, pH = pKa − log[(Ia − Ix)/(Ix − Ib)], with a good linear relationship. Moreover, we verified that the protonation of the 2-nitrogen in the imidazole decreases the electron density on the fused ring by 1H NMR analysis and DFT calculation. We proposed that intramolecular charge transfer and solvation of the probe in aqueous solutions might be the mechanism of the fluorescence enhancement under strongly acidic conditions.
Co-reporter:Yan-Ru Zhang, Qing-Rong Wang, Peng Su, Fei Zhao, Jun Huang and Bao-Xiang Zhao
RSC Advances 2015 vol. 5(Issue 27) pp:20634-20638
Publication Date(Web):06 Feb 2015
DOI:10.1039/C4RA16267F
We have synthesized rhodol hydrazide (RDH) as a simple fluorescent probe for detecting Hg2+. The probe can be applied in nontoxic solvents (EtOH and H2O). The probe has high selectivity and sensitivity to Hg2+ at pH 6–8. In addition, the probe has a superior capacity to resist interference from other ions. Both fluorescence intensity and absorbance have a linear relationship with the concentration of Hg2+, which ensured the precise detection of Hg2+. Furthermore, we have studied the intracellular Hg2+ imaging behavior of the probe on mammalian cells, which indicated that the probe can be applied to monitor Hg2+ within biological samples, especially in mammalian cells.
Co-reporter:Ning Meng;Lei Han;XiaoHong Pan;Le Su;Zheng Jiang
Cell Biology and Toxicology 2015 Volume 31( Issue 1) pp:15-27
Publication Date(Web):2015 February
DOI:10.1007/s10565-014-9291-4
Nano-Mg(OH)2 is efficiently used in pollutant adsorption and removal due to its high adsorption capability, low-cost, and recyclability. A recent research from our group showed that Mg(OH)2 nanoflakes are not evidently internalized by cancer cells and are not cytotoxic. But the biocompatibility and potential toxicity of nano-Mg(OH)2 in a normal biological system are largely unclear. Nanoparticles could affect the function of endothelial cells, and endothelial dysfunction represents an early sign of lesion within the vasculature. Here, we applied the human umbilical vein vascular endothelial cells (HUVECs) as an in vitro model of the endothelium to study the cytotoxicity of nano-Mg(OH)2. Our results showed that nano-Mg(OH)2 at 200 μg/ml impaired proliferation and induced dysfunction of HUVECs, but did not result in cell necrosis and apoptosis. Transmission electron microscopy images and immunofluorescence results showed that the nano-Mg(OH)2 could enter HUVECs through caveolin-1-mediated endocytosis. Nano-Mg(OH)2 at high concentrations decreased the level of caveolin-1 and increased the activity of endothelial nitric oxide synthase (eNOS), thus leading to the production of excess nitric oxide (NO). In this work, we provide the cell damage concentrations of nano-Mg(OH)2 nanoparticles, and we propose a mechanism of injury induced by nano-Mg(OH)2 in HUVECs.
Co-reporter:Shuai Zhou, Ze-Quan Zhou, Xuan-Xuan Zhao, Yu-Hao Xiao, Gang Xi, Jin-Ting Liu, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 148() pp: 348-354
Publication Date(Web):
DOI:10.1016/j.saa.2015.03.126
Co-reporter:Xuan-Xuan Zhao, Di Ge, Xi Dai, Wen-Li Wu, Jun-Ying Miao, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 151() pp:218-224
Publication Date(Web):5 December 2015
DOI:10.1016/j.saa.2015.06.111
•A novel pH probe based on quaternary ammonium salt soluble in water was developed.•The charge-induced effect can avoid the “alkalizing effect” and improve the sensitivity.•The probe responds linearly to pH 4.6–5.8 and is reversible between pH 4.2–7.2.•The probe with excellent anti-interference capability was well used for monitoring the pH fluctuations in lysosome.A novel fluorescence probe Rhodamine–Ethanediamine–Iodomethane (REI) was successfully prepared to serve as an efficient sensing platform for H+ with fully reversibility mainly between the pH 4.2 and 7.2 in simple buffer solution. The introduction of quaternary ammonium salt with positive charge can not only manage to increase the solubility and sensitivity of probe REI, but also avoid the “alkalizing effect” due to charge-induced effect compared to the reference probe Rhodamine–Ethanediamine (RE). In particular, probe REI was well used for monitoring the weak acid pH fluctuations in lysosome of the live HeLa cells due to its excellent biological properties, including low cytotoxicity, high selectivity, good sensitivity and membrane permeability.
Co-reporter:Rong-Rong Zhang, Jin-Feng Zhang, Sheng-Qing Wang, Yan-Long Cheng, Jun-Ying Miao, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 137() pp:450-455
Publication Date(Web):25 February 2015
DOI:10.1016/j.saa.2014.08.108
•This probe can detect thiols in DMSO:HEPES = 1:1 solution at pH 7.4.•The structure of the probe was characterized by IR, NMR and HRMS spectroscopy analysis.•This probe can be used for living cell imaging.A new compound, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-acrylamide (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting thiol from other amino acids. On being mixed with thiol in buffered DMSO:HEPES = 1:1 solution at pH 7.4, the probe exhibited the blue emission at 474 nm. This probe is very sensitive and displayed a linear fluorescence off–on response to thiol. The fluorescence emission of the probe is pH independent in the physiological pH range. Living cell imaging of HeLa cells confirmed its cell permeability and its ability to selectively detect thiol in cells. The structure of the probe was characterized by IR, NMR and HRMS spectroscopy analysis.A highly sensitive and selective fluorescent probe for recognizing and detecting thiol from other amino acids was developed.Figure optionsDownload full-size imageDownload as PowerPoint slide
Co-reporter:Rui-Zhe Zhang, Xiao Feng, Ying Liu, Sheng-Qing Wang, Jin-Ting Liu, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 139() pp:165-170
Publication Date(Web):15 March 2015
DOI:10.1016/j.saa.2014.11.106
•A series of novel boron azo chelate complexes were synthesized.•A new rearrangement mechanism was proposed.•The structure was characterized by single crystal X-ray analysis.We synthesized novel boron chelate complexes by the reaction of pyrazoline derivatives and boron trifluoride diethyl etherate followed by a new rearrangement. The structures of the compounds were characterized by IR, NMR and HRMS, especially, a typical compound 3c was confirmed by X-ray single crystal analysis. We proposed a mechanism of the rearrangement. Moreover, the absorption and fluorescence spectroscopy of these compounds were measured.A series of boron chelate complexes were synthesized and a mechanism of the rearrangement was proposed.
Co-reporter:Yu Xu, Xi Dai, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 138() pp:164-168
Publication Date(Web):5 March 2015
DOI:10.1016/j.saa.2014.11.013
•A novel colorimetric and turn-on fluorescent probe for CN− has been developed.•The probe has a low detection limit of 0.50 μM.•The probe has been successfully applied in cyanide detection in tap water.A novel coumarin–indole based chemodosimeter with a simple structure was designed and prepared via a condensation reaction in high yield. The probe exhibited very high selectivity towards cyanide on both fluorescence and UV–vis spectra, which allowed it to quantitatively detect and imaging cyanide ions in organic–aqueous solution by either fluorescence enhancement or colorimetric changes. Confirmed by 1H NMR and HRMS spectra, the detection mechanism was proved to be related with the Michael addition reaction induced by cyanide ions, which blocked the intramolecular charge transfer (ICT) of the probe. Moreover, the probe was able to be utilized efficiently in a wide pH range (7.5–10) with negligible interference from other anions and a low detection limit of 0.51 μM. Application in 5 kinds of natural water source and accurate detection of cyanide in tap water solvent system also indicated the high practical significance of the probe.Graphical abstract
Co-reporter:Xiao-Xin Zheng, Sheng-Qing Wang, Hao-Yan Wang, Rong-Rong Zhang, Jin-Ting Liu, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015 Volume 138() pp:247-251
Publication Date(Web):5 March 2015
DOI:10.1016/j.saa.2014.11.045
•Design and synthesize a novel pyrazoline-based fluorescent probe for the detection of hydrazine.•The probe is of high selectivity and has low detection limit.•The probe can work over a pH range of 5.0–8.0.•The probe has long emission wavelength (520 nm) and a large stokes shift (∼140 nm).A novel pyrazoline-based fluorescent probe, 2-[4-(3,5-diphenyl-4,5-dihydro-pyrazol-1-yl)-benzylidene]-malononitrile, with a simple structure and low detection limit (6.16 × 10−6 M) for the detection of hydrazine is designed and synthesized. The probe responds selectively to hydrazine over other molecules with marked fluorescence enhancement. The probe can detect hydrazine effectively at pH 5.0–9.0 with a special emission wavelength at 520 nm. Moreover, the probe can be used to detect hydrazine from variety of natural source water.Hydrazine is a very toxic material widely used in industry. A novel pyrazoline-based fluorescent probe with a simple structure and low detection limit for the detection of hydrazine is designed and synthesized. The probe can respond selectively to hydrazine over other molecules with marked fluorescence enhancement.
Co-reporter:Xuan-Xuan Zhao, Jin-Feng Zhang, Wei Liu, Shuai Zhou, Ze-Quan Zhou, Yu-Hao Xiao, Gang Xi, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2014 vol. 2(Issue 42) pp:7344-7350
Publication Date(Web):08 Sep 2014
DOI:10.1039/C4TB01192A
We developed a new dansyl phthalimide-based fluorescent chemosensor for hydrazine detection. Upon a Gabriel type-based hydrazinolysis of dansyl phthalimide (DPI) in the presence of hydrazine in a mixture of HEPES buffer (pH 7.0, 20 mM) and DMSO (1/9, v/v) at room temperature, the chemosensor produces fluorescent dansyl-NH2 with the maximum emission wavelength changed from 475 nm to 512 nm along with a color change from yellow to colorless, allowing colorimetric detection of hydrazine by the naked eye. DPI can selectively detect hydrazine over other environmentally abundant ions. Moreover, DPI coated with silica gel TLC plates could act as a visual and fluorimetric probe for hydrazine vapor at a partial pressure of 5.5 × 10−3 mm Hg over other potentially interfering volatile analytes, including hydrogen peroxide, ethylenediamine, urea, ammonium hydroxide and methylamine. DPI can also be used for the detection of hydrazine in water samples and HeLa cells without appreciable interference from other biologically abundant analytes. The limit of detection is 6.01 ppb (1.88 × 10−7 M), which is well below the accepted limit (10 ppb) for hydrazine set by the U.S. Environmental Protection Agency (EPA).
Co-reporter:Yan-Ru Zhang, Xin-Peng Chen, Jing-Shao, Jia-Yi Zhang, Qiong Yuan, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2014 vol. 50(Issue 91) pp:14241-14244
Publication Date(Web):25 Sep 2014
DOI:10.1039/C4CC05976J
We developed a ratiometric fluorescent probe for sensing HOCl based on coumarin and rhodamine acid that is directly used as a detection moiety. The probe shows high selectivity and sensitivity toward HOCl under best working conditions of myeloperoxidase by which HOCl can be generated from hydrogen peroxide and chloride.
Co-reporter:Meng-Meng Li, Fang-Wu Wang, Xiao-Yun Wang, Ting-Ting Zhang, Yu Xu, Yu Xiao, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2014 Volume 826() pp:77-83
Publication Date(Web):15 May 2014
DOI:10.1016/j.aca.2014.04.001
•A new pyrazoline-based turn-on fluorescence probe toward Zn2+ was synthesized.•Upon addition of Zn2+, the fluorescence intensity was enhanced up to 80-fold.•The fast response to Zn2+ makes the probe suitable to monitor Zn2+ in living cell.We designed and synthesized a new pyrazoline-based turn-on fluorescence probe for Zn2+ by the reaction of chalcone and thiosemicarbazide. The structure of the probe was characterized by IR, NMR and HRMS spectroscopy. The probe (L) exhibits high selectivity and sensitivity for detecting Zn2+ in buffered EtOH/HEPES solution (EtOH/HEPES = 1/1, pH 7.2) with 80-fold fluorescence enhancement, which is superior to previous reports. Job’s plot analysis revealed 1:1 stoichiometry between probe L and Zn2+ ions. The association constant estimated by the Benesi–Hildebrand method and the detection limit were 3.92 × 103 M−1 and 5.2 × 10−7 M, respectively. A proposed binding mode was confirmed by 1H NMR titration experiments and density functional theory (DFT) calculations. The probe is cell-permeable and stable at the physiological pH range in biological systems. Because of its fast response to Zn2+, the probe can monitor Zn2+ in living cells. Moreover, the selective binding of L and Zn2+ was reversible with the addition of EDTA in buffered EtOH/HEPES solution and Zn2+ could be imaged in SH-SY5Y neuron cells.
Co-reporter:Yu Xu, Zheng Jiang, Yu Xiao, Ting-Ting Zhang, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2014 Volume 807() pp:126-134
Publication Date(Web):7 January 2014
DOI:10.1016/j.aca.2013.11.042
•A new fluorescence probe for Hg2+ was designed, synthesized and characterized.•The probe can monitor Hg2+ in mammalian cells and living organisms.•The probe has a low detection limit with a clear detection process.Using the Hg2+-induced desulfurization reaction of thiosemicarbazide derivative, we designed and synthesized a novel “turn on” coumarin-based fluorescent probe L with a simple structure for detecting mercury ion (II). Spectroscopy revealed that the probe responds selectively to mercury ions over other metal ions with marked fluorescence enhancement. Detection of Hg2+ was effective at pH 7.0–9.5, with high selectivity and significant effect in HeLa cells, human umbilical vein endothelial cells and Escherichia coli, but no cytotoxicity. This probe could be an ideal and practical Hg2+ probe with important biological significance.A new coumarin-based fluorescent chemodosimeter can monitor mercury poisoning and has high selectivity, sensitivity and applicability for imaging mercury ions in mammalian cells and bacteria.
Co-reporter:Fang-Wu Wang, Sheng-Qing Wang, Bao-Xiang Zhao and Jun-Ying Miao
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 19) pp:3062-3070
Publication Date(Web):26 Feb 2014
DOI:10.1039/C3OB42429D
A series of 2′-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 2–7 possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.
Co-reporter:Xue-Wen Zhou, Han-Lin Ma, Xuan Zhang, Shi-Yao Jing, Jun-Ying Miao, Bao-Xiang Zhao
European Journal of Medicinal Chemistry 2014 Volume 79() pp:95-101
Publication Date(Web):22 May 2014
DOI:10.1016/j.ejmech.2014.03.087
•Synthesis of novel 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives.•Preliminary biological activity of the compounds was evaluated.•The compounds suppress the growth of A549 lung cancer cells by autophagy and cell cycle arrest.A series of novel 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives was synthesized. The structures of compounds were characterized by 1H NMR, IR, and MS. Moreover, representative crystal structure was determined by X-ray diffraction analysis. The preliminary biological evaluation of all these compounds showed that compounds 3a–3d would suppress the growth of A549 lung cells effectively by inducing autophagy and cell cycle arrest.A series of novel 6-cinnamoyl-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives was synthesized. Some compounds suppress the growth of A549 lung cancer cells by inducing autophagy and cell cycle arrest.
Co-reporter:Jin-Feng Zhang, Meng Li, Jun-Ying Miao, Bao-Xiang Zhao
European Journal of Medicinal Chemistry 2014 Volume 83() pp:516-525
Publication Date(Web):18 August 2014
DOI:10.1016/j.ejmech.2014.06.065
•New pyrazolyl hydroxamic acid derivatives (4a–4l) were synthesized.•Compounds 4a–4l inhibited the growth of A549 cancer cells.•Compounds 4b, 4f and 4h induced cell cycle arrest at G1 phase.•Compounds 4b, 4f and 4h are effective autophagy inducers.We synthesized a series of novel pyrazolyl hydroxamic acid derivatives (4a–4l) and investigated their biological activities against human lung cancer cell line A549 in vitro to determine their mechanism of action. The results showed that the majority of derivatives had inhibitory effects on the growth of A549 cancer cells in dose and time-dependent manners, in which the compounds 4b, 4f, 4h and 4j (10 μM) exerted more effective anti-proliferation activity. However, it should be noted that 4j may result in necrosis at 10 μM. Furthermore, the three compounds 4b, 4f and 4h induced cell cycle arrest at G1 phase and triggered autophagy, but could not obviously induce apoptosis and necrosis under the stimulatory condition. Therefore, the pyrazolyl hydroxamic acid derivatives 4b, 4f and 4h can be used to investigate the regulatory mechanism of autophagy and offer new approaches to the prevention of lung cancer.
Co-reporter:Meng Li, Bao-Xiang Zhao
European Journal of Medicinal Chemistry 2014 Volume 85() pp:311-340
Publication Date(Web):6 October 2014
DOI:10.1016/j.ejmech.2014.07.102
•We summarize nearly all reported condensed pyrazoles from 2010 to mid-2013.•The bioactivities of each kind of compound are briefly introduced.•The synthetic methods of each kind of compounds are figured out and compared.Condensed pyrazole derivatives are important heterocyclic compounds due to their excellent biological activities and have been widely applied in pharmaceutical and agromedical fields. In recent years, numerous condensed pyrazole derivatives have been synthesized and advanced to clinic studies with various biological activities. In this review, we summarized the reported synthesis methods of condensed pyrazole derivatives from 2010 until now. All compounds are divided into three parts according to the rings connected to pyrazole-ring, i.e. [5, 5], [5,F 6], and [5, 7]-condensed pyrazole derivatives. The biological activities and applications in pharmaceutical fields are briefly introduced to offer an orientation for the design and synthesis of condensed pyrazole derivatives with good biological activities.This review briefly introduces the bioactivities and summarizes the synthetic methodology of condensed pyrazole derivatives.
Co-reporter:Xi Dai, Tao Zhang, Yun Li, Tao Yan, Peng-Chong Wang, Jun-Ying Miao and Bao-Xiang Zhao
RSC Advances 2014 vol. 4(Issue 97) pp:54650-54654
Publication Date(Web):16 Oct 2014
DOI:10.1039/C4RA09712B
We designed and synthesized a two-photon fluorescent probe, 2-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)naphthalen-1-yl acrylate (PPN) with improved properties based on the naphthalene–pyrazoline fluorophore. The probe exhibits high sensitivity to glutathione (GSH) in PBS–CTAB buffer solution with a low detection limit of 1.5 × 10−8 M and a response time less than 10 min. According to the HRMS and fluorescence spectra analysis, the detection mechanism was confirmed to be a Michael addition reaction induced by the sulfhydryl of GSH. In addition, probe PPN has very good selectivity and is able to discriminate GSH from cysteine (Cys), homocysteine (Hcy) and other sulfhydryl compounds with bright two-photon-excited fluorescence. Moreover, we have successfully applied PPN to calf serum samples and living cell imaging with good effect.
Co-reporter:Xuan-Xuan Zhao, Xin-Peng Chen, Shi-Li Shen, Dong-Peng Li, Shuai Zhou, Ze-Quan Zhou, Yu-Hao Xiao, Gang Xi, Jun-Ying Miao and Bao-Xiang Zhao
RSC Advances 2014 vol. 4(Issue 92) pp:50318-50324
Publication Date(Web):01 Oct 2014
DOI:10.1039/C4RA07555B
We developed a rhodamine–rhodanine-based pH probe with pKa = 4.85 in buffer solution. The fluorescence intensity exhibited strong pH-dependent performance and responded linearly to minor pH fluctuations within the range of 4.2–5.2. In addition, the fluorescence microscopic images suggested this probe had excellent cell membrane permeability and could image weak acid pH changes of lysosomes in live cells without auto-fluorescence and interference from the complex intracellular environment. The results demonstrated that the probe had great potential in monitoring H+ in vitro and in living cells.
Co-reporter:Ting-Ting Zhang, Xin-Peng Chen, Jin-Ting Liu, Liang-Zhong Zhang, Jia-Ming Chu, Le Su and Bao-Xiang Zhao
RSC Advances 2014 vol. 4(Issue 33) pp:16973-16978
Publication Date(Web):28 Mar 2014
DOI:10.1039/C4RA00584H
A new pyrazoline-based fluorescent probe was designed and synthesized. The probe can induce a 60-fold fluorescence enhancement after 5 equiv. of Zn2+ was added, which is superior to a previous report (13-fold), and exhibits high sensitivity and selectivity for response to Zn2+ in aqueous solution. The detection limit and association constant were calculated as 1.23 × 10−7 M and 3.89 × 103 M−1 by a fluorescence titration experiment. The 1:1 binding stoichiometry of L–Zn2+ complex was analysed by Job's plot. The probe showed good reversibility upon addition of EDTA or TPEN. Furthermore, the probe L showed good membrane permeability and can be applied to monitor Zn2+ ions in living HeLa cells.
Co-reporter:Hong-Shui Lv, Shu-Ya Huang, Yu Xu, Xi Dai, Jun-Ying Miao, Bao-Xiang Zhao
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 2) pp:535-538
Publication Date(Web):15 January 2014
DOI:10.1016/j.bmcl.2013.12.025
A new rhodamine B-based pH fluorescent probe has been synthesized and characterized. The probe responds to acidic pH with short response time, high selectivity and sensitivity, and exhibits a more than 20-fold increase in fluorescence intensity within the pH range of 7.5–4.1 with the pKa value of 5.72, which is valuable to study acidic organelles in living cells. Also, it has been successfully applied to HeLa cells, for its low cytotoxicity, brilliant photostability, good membrane permeability and no ‘alkalizing effect’ on lysosomes. The results demonstrate that this probe is a lysosome-specific probe, which can selectively stain lysosomes and monitor lysosomal pH changes in living cells.
Co-reporter:Xi Dai, Qing-Hua Wu, Peng-Chong Wang, Jie Tian, Yu Xu, Sheng-Qing Wang, Jun-Ying Miao, Bao-Xiang Zhao
Biosensors and Bioelectronics 2014 Volume 59() pp:35-39
Publication Date(Web):15 September 2014
DOI:10.1016/j.bios.2014.03.018
•A simple and effective coumarin-based fluorescent probe for cysteine was synthesized.•The probe can detect cysteine with high selectivity and sensitivity in aqueous solution.•The probe was successfully used for detecting Cys in calf serum and living imaging.Acrylic acid 3-acetyl-2-oxo-2 H-chromen-7-yl ester (ACA) was rationally designed and synthesized as a simple and effective fluorescent probe for sensing cysteine with high selectivity and naked-eye detection. The probe can detect cysteine by fluorescence spectrometry with a detection limit of 0.657 μM and can be used with calf serum and in live cell imaging. The conjugate addition/cyclization sequence mechanism of the reaction between ACA and cysteine was confirmed by ESI-MS and fluorescence spectra.
Co-reporter:Sheng-Qing Wang, Qing-Hua Wu, Hao-Yan Wang, Xiao-Xin Zheng, Shi-Li Shen, Yan-Ru Zhang, Jun-Ying Miao, Bao-Xiang Zhao
Biosensors and Bioelectronics 2014 Volume 55() pp:386-390
Publication Date(Web):15 May 2014
DOI:10.1016/j.bios.2013.12.047
•A pyrazoline-based selective and sensitive fluorescent probe was synthesized.•The probe was highly selective for glutathione.•The detection limit for glutathione was 8.2×10−8 M.•The probe can detect glutathione in cells.A novel compound, 2-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl acrylate (probe L), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among cysteine, homocysteine and other amino acids. The structures of related compounds were characterized using IR, NMR and HRMS spectroscopy analysis. The probe is a non-fluorescent compound. On being mixed with glutathione in buffered EtOH:PBS=3:7 solution at pH 7.4, the probe exhibited the blue emission of the pyrazoline at 474 nm and a 83-fold enhancement in fluorescence intensity. This probe is very sensitive and displayed a linear fluorescence off–on response to glutathione with fluorometric detection limit of 8.2×10−8 M. The emission of the probe is pH independent in the physiological pH range. Live-cell imaging of HeLa cells confirmed the cell permeability of the probe and its ability to selectively discriminate GSH from Cys and Hcy in cells. The toxicity of the probe was low in cultured HeLa cells.
Co-reporter:Yu Xu, Zheng Jiang, Yu Xiao, Fu-Zhen Bi, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2014 820() pp: 146-151
Publication Date(Web):
DOI:10.1016/j.aca.2014.02.029
Co-reporter:Sheng-Qing Wang;Shu-Yan Liu;Hao-Yan Wang;Xiao-Xin Zheng
Journal of Fluorescence 2014 Volume 24( Issue 3) pp:657-663
Publication Date(Web):2014 May
DOI:10.1007/s10895-013-1339-y
This paper presents the preparation of a pyrazoline compound and the properties of its UV–Vis absorption and fluorescence emission. Moreover, this compound can be used to determine Hg2+ ion with selectivity and sensitivity in the EtOH:H2O = 9:1 (v/v) solution. This sensor forms a 1:1 complex with Hg2+ and shows a fluorescent enhancement with good tolerance of other metal ions. This sensor is very sensitive with fluorometric detection limit of 3.85 × 10−10 M. In addition, the fluorescent probe has practical application in cells imaging.
Co-reporter:H Li, S Huang, S Wang, J Zhao, L Su, B Zhao, Y Zhang, S Zhang and J Miao
Cell Death & Disease 2013 4(9) pp:e806
Publication Date(Web):2013-09-01
DOI:10.1038/cddis.2013.317
Phosphatidylcholine-specific phospholipase C (PC-PLC) is a key factor in apoptosis and autophagy of vascular endothelial cells (VECs), and involved in atherosclerosis in apolipoprotein E−/− (apoE−/−) mice. But the endogenous regulators of PC-PLC are not known. We recently found a small chemical molecule (6-amino-2, 3-dihydro-3-hydroxymethyl-1, 4-benzoxazine, ABO) that could inhibit oxidized low-density lipoprotein (oxLDL)-induced apoptosis and promote autophagy in VECs, and further identified ABO as an inhibitor of annexin A7 (ANXA7) GTPase. Based on these findings, we hypothesize that ANXA7 is an endogenous regulator of PC-PLC, and targeting ANXA7 by ABO may inhibit atherosclerosis in apoE−/− mice. In this study, we tested our hypothesis. The results showed that ABO suppressed oxLDL-induced increase of PC-PLC level and activity and promoted the co-localization of ANXA7 and PC-PLC in VECs. The experiments of ANXA7 knockdown and overexpression demonstrated that the action of ABO was ANXA7-dependent in cultured VECs. To investigate the relation of ANXA7 with PC-PLC in atherosclerosis, apoE−/− mice fed with a western diet were treated with 50 or 100 mg/kg/day ABO. The results showed that ABO decreased PC-PLC levels in the mouse aortic endothelium and PC-PLC activity in serum, and enhanced the protein levels of ANXA7 in the mouse aortic endothelium. Furthermore, both dosages of ABO significantly enhanced autophagy and reduced apoptosis in the mouse aortic endothelium. As a result, ABO significantly reduced atherosclerotic plaque area and effectively preserved a stable plaques phenotype, including reduced lipid deposition and pro-inflammatory macrophages, increased anti-inflammatory macrophages, collagen content and smooth muscle cells, and less cell death in the plaques. In conclusion, ANXA7 was an endogenous regulator of PC-PLC, and targeting ANXA7 by ABO inhibited atherosclerosis in apoE−/− mice.
Co-reporter:Wei-Yong Liu, Shi-Li Shen, Hai-Ying Li, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta 2013 Volume 791() pp:65-71
Publication Date(Web):12 August 2013
DOI:10.1016/j.aca.2013.07.022
•A new fluorescence probe for detection of Hg2+ ions was developed.•The probe can monitor Hg2+ ions in aqueous media and in blood in ppb level.•The probe facilitates naked-eye detection of Hg2+ ions.The heavy metal mercury (Hg) is a threat to the health of people and wildlife in many environments. Among various chemical forms, Hg2+ salts are usually more toxic than their counterparts because of their greater solubility in water; thus, they are more readily absorbed from the gastrointestinal tract into circulation. Therefore, new chemical receptors for detecting Hg2+ ions in circulation are needed. In this study, we developed a rhodamine-based turn-on fluorescence probe to monitor Hg2+ in aqueous solution and in blood of mice with toxicosis. The chemodosimeter responds to Hg2+ ions stoichiometrically, rapidly, and irreversibly at room temperature as a result of a chemical reaction that produces strongly fluorescent oxadiazole. The new fluorescent probe shows good fluorescence response, with high sensitivity and selectivity, toward Hg2+ ions in aqueous solution and in blood from mice with toxicosis and facilitates the naked-eye detection of Hg2+ ions.A rhodamine-based turn-on fluorescence probe can monitor the blood Hg2+ ions in toxicosis mice with high sensitivity and selectivity, and facilitates naked-eye detection of Hg2+ ions.
Co-reporter:Hong-Shui Lv, Shu-Ya Huang, Bao-Xiang Zhao, Jun-Ying Miao
Analytica Chimica Acta 2013 Volume 788() pp:177-182
Publication Date(Web):25 July 2013
DOI:10.1016/j.aca.2013.06.038
•A new rhodamine B-based fluorescent pH probe was synthesized.•This probe has a pKa of 4.71 which is valuable for studying acidic organelles in living cells.•This probe exhibits excellent membrane-permeable and low cytotoxicity.•This probe was successfully used to monitor lysosomal pH changes in HeLa cells.We designed and synthesized a new pH fluorescent probe, RCE, based on structural changes of rhodamine dye at different pH values. The probe exhibits high selectivity, high sensitivity and quick response to acidic pH, as well as low cytotoxicity, excellent photostability, reversibility and cell membrane permeability. Fluorescence intensity at 584 nm was increased more than 150-fold within pH range 7.51–3.53. This probe has pKa value 4.71, which is valuable for studying acidic organelles. Because of its long absorption and emission wavelengths, RCE can avoid associated cell damage. The probe can selectively stain lysosomes and monitor lysosomal pH changes in living cells.A rhodamine B-based pH fluorescent probe can selectively stain lysosomes and monitor lysosomal pH changes in living cells.
Co-reporter:Sheng-Qing Wang, Qing-Hua Wu, Hao-Yan Wang, Xiao-Xin Zheng, Shi-Li Shen, Yan-Ru Zhang, Jun-Ying Miao and Bao-Xiang Zhao
Analyst 2013 vol. 138(Issue 23) pp:7169-7174
Publication Date(Web):19 Sep 2013
DOI:10.1039/C3AN01440A
A new fluorescent probe, N-(4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-2,4-dinitrobenzenesulfonamide (probe 3), was designed and synthesized as a highly sensitive and selective fluorescent probe for recognizing and detecting glutathione among biological thiols in aqueous media. Probe 3 is a nonfluorescent compound. On being mixed with biothiols under neutral aqueous conditions, the 2,4-dinitrobenzenesulfoyl moiety can be cleaved off by glutathione, and the blue emission of the pyrazoline at 464 nm is switched on, with a fluorescence enhancement of 488-fold for glutathione. Furthermore, probe 3 was highly selective for glutathione without interference from some biologically relevant analytes. The detection limit of glutathione was 4.11 × 10−7 M. The emission of the probe is pH independent in the physiological pH range. Moreover, the probe can be used for fluorescent imaging of cellular glutathione and can be used for detecting glutathione in calf serum.
Co-reporter:Fei Ge, Hui Ye, He Zhang, Bao-Xiang Zhao
Dyes and Pigments 2013 Volume 99(Issue 3) pp:661-665
Publication Date(Web):December 2013
DOI:10.1016/j.dyepig.2013.06.024
•Probe L, a new ratiometric fluorescence probe for Fe3+ was firstly synthetized based on rhodamine B and coumarin.•Probe L upon addition of Fe3+ generated two fluorescence peaks at 580 nm and 460 nm.•Probe L was a novelty design of ratiometric probe of Fe3+, due to CHEF process generated along with the PET process suppressed simultaneously.We have developed a new ratiometric fluorescence probe based on rhodamine B and coumarin to monitor the Fe3+ with high sensitivity and selectivity. Upon addition of Fe3+ to aqueous solution of the probe, two fluorescence peaks at 580 nm and 460 nm were observed, which belong to rhodamine B and coumarin, respectively. This is a novelty design of ratiometric probe of Fe3+, due to CHEF process generated along with the PET process suppressed simultaneously. The fluorescence intensity at 580 nm was significantly increased about 120-fold with 5 equiv. of Fe3+ added in aqueous solution.
Co-reporter:Shi-Li Shen, Jin-Hui Shao, Ji-Zhuang Luo, Jin-Ting Liu, Jun-Ying Miao, Bao-Xiang Zhao
European Journal of Medicinal Chemistry 2013 Volume 63() pp:256-268
Publication Date(Web):May 2013
DOI:10.1016/j.ejmech.2013.02.016
A series of novel 2-ferrocenyl-7-hydroxy-5-phenethyl-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one derivatives with optical activity (2) was synthesized in the microwave-assisted condition and characterized by means of IR, 1H NMR and mass spectroscopy, and furthermore confirmed by X-ray analysis of a representative compound (R)-2a. Preliminary biological evaluation showed that some compounds could suppress the growth of A549, H322 and H1299 lung cancer cells. Among the tested compounds, 2b–d were more effective and might perform their action through cell cycle arrest for A549 cell. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis. The anti-tumor activities of these compounds were related to the nature of substituents in benzene moiety. In addition, the results indicated also that compounds 2b–d possessed notable cytotoxicity and selectivity for A549 vs H1299 and H322 lung cancer cells.Graphical abstractA series of novel ferrocenyl pyrazole derivatives was synthesized. Some compounds could suppress the growth of A549, H322 and H1299 cells through cell cycle arrest or inducing apoptosis.Highlights► Synthesis of ferrocenyl pyrazole-containing chiral diazepin derivatives by microwave. ► Compounds could suppress the growth of A549, H322 and H1299 lung cancer cells. ► Compounds 2b–d might perform their action through cell cycle arrest or apoptosis.
Co-reporter:Hui Ye, Fei Ge, Xiao-Cui Chen, Yan Li, He Zhang, Bao-Xiang Zhao, Jun-Ying Miao
Sensors and Actuators B: Chemical 2013 Volume 182() pp:273-279
Publication Date(Web):June 2013
DOI:10.1016/j.snb.2013.03.015
We developed a new probe based on rhodamine B and 5-ferrocenyl-1,3,4-thiadiazole. The probe can be used to sensitive and selective fluorescent recognition of Hg2+ with good quantum yield. The fluorescence intensity was remarkably increased upon the addition of Hg2+ within 1 or 2 min with about 27 fold enhancement. Additionally, the turn-on fluorescent probe with good membrane-permeable property was successfully applied to microscopic imaging for the detection of Hg2+ in HeLa cells. The probe facilitates also naked-eye detection of Cu2+ in aqueous solution.
Co-reporter:Hui Ye, Fei Ge, Yi-Ming Zhou, Jin-Ting Liu, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013 Volume 112() pp:132-138
Publication Date(Web):August 2013
DOI:10.1016/j.saa.2013.03.093
•Probe L for Cu2+ was firstly synthesized based on ferrocenyl-1,3,4-thiadiazol.•Probe L was a multichannel chemosensor with electrochemical and optical properties.•Probe L was applied to monitor the intracellular Cu2+ level in Hela cells.A novel probe based on ferrocenyl-1,3,4-thiadiazol-containing Schiff base was synthesized by the reaction of 5-ferrocenyl-1,3,4-thiadiazol-2-amine and 4-(diethylamino)salicylaldehyde, and characterized by IR, NMR, HRMS and X-ray analysis. UV–vis spectral and fluorescence property of the probe were investigated. The probe can be used to colorimetric sensitive and selective fluorescent recognition of Cu2+ in buffer solution. Moreover, the probe can detect Cu2+ by electrochemical method. Additionally, the Schiff base was successfully used as a selective and sensitive fluorescent probe for monitoring Cu2+ ions in living cells.Graphical abstract
Co-reporter:Di Ge;Xiangqian Kong;Weiyong Liu;Jing Zhao;Le Su;Shangli Zhang;Yun Zhang
Apoptosis 2013 Volume 18( Issue 9) pp:1120-1131
Publication Date(Web):2013 September
DOI:10.1007/s10495-013-0860-4
Integrin β4 and its Y-1494 phosphorylation play an important role in cell signaling. We found a small molecule, ethyl1-(3-(4-chlorophenoxy)-2-hydroxypropyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (ECPC), that could elevate the levels of KIT ligand (KITLG), interleukin 8 (IL-8), prostaglandin-endoperoxide synthase 2 (PTGS2) and activating transcription factor 3 (ATF3) and promote apoptosis in vascular endothelial cells (VECs) through integrin β4. We investigated the underlying mechanism of integrin β4 participating in this process. ECPC treatment increased the phosphorylation of Y-1494 in the integrin β4 cytoplasmic domain via a well-known receptor tyrosine kinase, fibroblast growth factor receptor 1 (FGFR1), and integrin β4 translocated from the cytoplasm to nucleus. With suppression of Y-1494 phosphorylation by FGF-2 or siRNA of FGFR1, ECPC failed to promote integrin β4 nuclear translocation and could not increase the expression of KITLG, IL-8, PTGS2 or ATF3. Y-1494 phosphorylation and nuclear translocation of integrin β4 may be important during ECPC-induced apoptosis in VECs.
Co-reporter:Fei Ge, Hui Ye, Ji-Zhuang Luo, Sheng Wang, Ya-Jing Sun, Bao-Xiang Zhao, Jun-Ying Miao
Sensors and Actuators B: Chemical 2013 Volume 181() pp:215-220
Publication Date(Web):May 2013
DOI:10.1016/j.snb.2013.01.048
We report the development of a new fluorescence probe based on rhodamine hydrazone and ferrocene unit to monitor the intracellular Cu2+ level in living cells. The fluorescent probe exhibits a fluorescence response toward Cu2+ under physiological conditions with high sensitivity and selectivity and facilitates naked-eye detection of Cu2+. The fluorescence intensity was significantly increased about 40-fold with 5 equiv. of Cu2+ added.
Co-reporter:Sheng-Qing Wang, Ying Gao, Hao-Yan Wang, Xiao-Xin Zheng, Shi-Li Shen, Yan-Ru Zhang, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013 Volume 106() pp:110-117
Publication Date(Web):April 2013
DOI:10.1016/j.saa.2012.12.062
A series of novel 1,3,5-triarylpyrazoline derivatives was synthesized by the reaction of chalcone and 5-aryl-2-hydrazinyl-1,3,4-thiadiazole in 43.3–84.7% yields. The structures of compounds were characterized using IR, 1H NMR and HRMS spectroscopy and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane, toluene, acetonitrile, N,N-dimethylformamide and tetrahydrofuran. The results showed that the absorption maxima of the compounds vary from 366 to 370 nm depending on the group bound to benzene rings. The maximum emission spectra of the compounds in dichloromethane were dependent on nature of groups in benzene ring. Furthermore, the compound 3b can be used to determine Cu2+ ion with high selectivity and a low detection limit in the DMF:H2O = 1:1 (v/v) solution.Graphical abstractA series of 1,3,5-triarylpyrazoline derivatives were synthesized. These derivatives exhibited large Stokes shifts. The compound 3b can be used to determine Cu2+ ion. The sensor is very sensitive with fluorometric detection limit of 2.46 × 10−8 M.Highlights► A series of 1,3,5-triarylpyrazoline derivatives were synthesized. ► These derivatives exhibited large Stokes shifts. ► The compound 3b can be used to determine Cu2+ ion. ► The sensor is very sensitive with fluorometric detection limit of 2.46 × 10−8 M.
Co-reporter:Meng-Meng Li;Wen-Bo Zhao;Ting-Ting Zhang;Wei-Liu Fan;Yu Xu
Journal of Fluorescence 2013 Volume 23( Issue 6) pp:1263-1269
Publication Date(Web):2013 November
DOI:10.1007/s10895-013-1259-x
A new thiophenyl pyrazoline probe for Cu2+ in aqueous solution was synthesized and characterized by IR, NMR, HRMS and X-ray analysis. The probe displays remarkably high selectivity and sensitivity for Cu2+ with a detection limit of 1.919 × 10−7 M in aqueous solution (EtOH:HEPES = 1:1, v/v, 0.02 M, pH = 7.2). In addition, the probe is further successfully used to image Cu2+ in living cells and the probe possesses good reversibility.
Co-reporter:Zhe Zhang, Fang-Wu Wang, Sheng-Qing Wang, Fei Ge, Bao-Xiang Zhao and Jun-Ying Miao
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 43) pp:8640-8644
Publication Date(Web):12 Sep 2012
DOI:10.1039/C2OB26375K
We develop a pyrazoline-based fluorescent sensor for biological Zn2+ detection. The sensor shows good binding selectivity for Zn2+ over competing metal with 40-fold fluorescence enhancement in response to Zn2+. The new probe is cell-permeable and can be used to detect intracellular zinc ions in living neuron cells.
Co-reporter:Shi-Li Shen, Jian Zhu, Meng Li, Bao-Xiang Zhao, Jun-Ying Miao
European Journal of Medicinal Chemistry 2012 Volume 54() pp:287-294
Publication Date(Web):August 2012
DOI:10.1016/j.ejmech.2012.05.008
A series of novel ethyl 3-ferrocenyl-1-(2-hydroxy-3-(phenylamino)propyl)-1H-pyrazole-5-carboxylate derivatives with optical activity (4) was synthesized by microwave-assisted reaction of substituted aniline and ethyl 3-ferrocenyl-1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylate that was prepared from ethyl 3-ferrocenyl-1H-pyrazole-5-carboxylate and (R)- or (S)-oxiran-2-ylmethyl 4-methylbenzenesulfonate. Structures of the compounds were characterized by means of IR, 1H NMR and mass spectroscopy. Preliminary biological evaluation showed that all of the compounds could suppress the growth of A549 and H322 lung cancer cells. Among all of the tested compounds 4a, 4b and 4d were more effective and might perform their action through cell cycle arrest. Moreover, although the inhibition differences between R and S enantiomers are mostly not so significant, (R)-4b displayed more effective inhibition than (S)-4b.Graphical abstractChiral aminoethanol derivatives were synthesized. All compounds suppressed A549 and H322 cells growth. Compounds 4a, 4b and 4d were more effective and might perform their action through cell cycle arrest.Highlights► Microwave-assisted synthesis of ferrocenyl pyrazole aminoethanol derivatives. ► Suppress A549 and H322 lung cancer cells growth through cell cycle arrest. ► (R)-4b displayed more effective inhibition than (S)-4b.
Co-reporter:Zhong-Liang Gong, Liang-Wen Zheng, Bao-Xiang Zhao
Journal of Luminescence 2012 Volume 132(Issue 2) pp:318-324
Publication Date(Web):February 2012
DOI:10.1016/j.jlumin.2011.08.037
A series of novel bis-pyrazoline derivatives were synthesized by the reaction of chalcone and (sulfonylbis(3,1-phenylene))bis(hydrazine) in 20–34% yields. The structures of the compounds were determined by IR, 1H NMR, HRMS spectra, and a representative compound 3b was confirmed based on the X-ray crystallographic analysis. Absorption and fluorescence spectra of these compounds in dichloromethane solution were investigated. The results showed that the emission maxima varied from 415 to 444 nm mainly depending on C3 substituents of pyrazoline moiety. The compounds had higher quantum yields, when C3 substituent was an electron-withdrawing p-chlorophenyl group. Moreover, absorption spectra and emission spectra exhibited a blue-shift and a red-shift with increasing the polarity of solvents, respectively. Fluorescent molecules happened to collide with each other and resulted in quench of the fluorescence when the concentration increased over to 10−5 M.Highlights► A series of novel diphenyl sulfone-based bis-pyrazoline derivatives were designed and synthesized. ► Their UV–vis absorption and fluorescence emission spectra were investigated. ► The relationship of substituents and the optical properties were discussed. ► With increasing the solvent polarity, fluorescence emission displayed a red-shift and fluorescence quantum yields decreased. ► Fluorescence was quenched when the concentration increased over to 10−5 M.
Co-reporter:Zhen-Ju Jiang, Hong-Shui Lv, Jian Zhu, Bao-Xiang Zhao
Synthetic Metals 2012 Volume 162(Issue 23) pp:2112-2116
Publication Date(Web):December 2012
DOI:10.1016/j.synthmet.2012.09.013
A new fluorescent chemosensor based a coumarin fluorophore and an 8-hydroxyquinoline ionophore was synthesized and characterized by 1H NMR, IR and ESI-HRMS. Its selectivity toward metal ions in acetonitrile (1% water, v/v) was investigated by UV absorption and fluorescence spectroscopy. The results showed that this chemosensor exhibited good selectivity toward Cu2+ over other metal ions by enhancement of fluorescence intensity more than 13-fold, and the fluorescent color change could be observed by naked eyes under the light of 365 nm. The absorption spectra of the sensor (L) toward the concentration of Cu2+ indicated the formation of L–Cu2+ complex, and the complex was 1:1 ratio according to Job plot experiment. Both of photo-induced electron transfer (PET) and intramolecular charge transfer (ICT) mechanisms were considered to be operational for fluorescence enhancement and spectral shift. The detection limit of Cu2+ was determined to be 1.16 μM, a satisfying level to detect Cu2+ in micromolar scale.Graphical abstractHighlights► A new fluorescent chemsensor 3 based on coumarin and 8-hydroxyquinoline was synthesized. ► 3 exhibited good selectivity toward Cu2+ by a strong fluorescence enhancement. ► PET and ICT mechanisms are operational for fluorescence enhancement.
Co-reporter:Ying-Rui Liu, Ji-Zhuang Luo, Pan-Pan Duan, Jing Shao, Bao-Xiang Zhao, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 22) pp:6882-6887
Publication Date(Web):15 November 2012
DOI:10.1016/j.bmcl.2012.09.032
A series of novel pyrazole peptidomimetics was synthesized from 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxylic acid and amino acid ester. Structures of the compounds were characterized by means of IR, 1H NMR and mass spectroscopy. Compounds 5e and 5k suppress effectively the growth of A549 lung cancer cells. Preliminary research on the mechanism of action showed that the inhibition might perform through combination of apoptosis, autophagy and cell cycle arrest.A series of novel pyrazole peptidomimetics was synthesized from 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxylic acid and amino acid ester. Compounds 5e and 5k suppress effectively the growth of A549 lung cancer cells through combination of apoptosis, autophagy and cell cycle arrest.
Co-reporter:Hong-Shui Lv, Xiang-Qian Kong, Qian-Qian Ming, Xing Jin, Jun-Ying Miao, Bao-Xiang Zhao
Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 2) pp:844-849
Publication Date(Web):15 January 2012
DOI:10.1016/j.bmcl.2011.12.049
A series of substituted 5-benzyl-2-phenylpyrazolo[1,5-a]pyrazin-4,6(5H,7H)-dione derivatives was synthesized by one-step reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and N-arylalkyl-2-chloroacetamide. Structures of the compounds were determined by IR, 1H NMR and mass spectroscopy. In addition, a representative single-crystal structure was characterized by using X-ray diffraction analysis. The compound 5j could selectively inhibit the growth of H322 lung cancer cells which contain a mutated p53 gene in a dose-dependent manner through inducing apoptosis of cells.A series of novel 5-benzyl-2-phenylpyrazolo[1,5-a]pyrazin-4,6(5H,7H)-dione derivatives were synthesized and characterized by IR, 1H NMR, HRMS spectroscopy and X-ray analysis. An apoptosis inducer for H322 lung cancer cell was discovered. Hoechst 33258 staining assay showed that the inhibition against H322 cell growth might be attributed to apoptosis.
Co-reporter:Liang-Wen Zheng;Ying-Rui Liu
Journal of Heterocyclic Chemistry 2012 Volume 49( Issue 3) pp:691-695
Publication Date(Web):
DOI:10.1002/jhet.833
A series of 2,6-diphenyl-4H-pyrazolo[5,1-c][1,4]oxazin-4-ones has been synthesized via a lactonization of 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylic acids in the presence of Ac2O at reflux temperature. The products were isolated by simple filtration in excellent yields and were characterized by IR, 1H-NMR, and HRMS. The molecular structure was confirmed by the X-ray crystal analysis of one compound that was prone to crystallization.
Co-reporter:Liang-Wen Zheng;Hong-Zhuan Xuan;Ying-Rui Liu;Jin-Ting Liu;Jun-Ying Miao
Helvetica Chimica Acta 2012 Volume 95( Issue 1) pp:134-143
Publication Date(Web):
DOI:10.1002/hlca.201100249
Abstract
A facile ring-enlargement reaction of 2,6-diphenyl-4H-pyrazolo[5,1-c][1,4]oxazin-4-one is described, generating the pyrazolo[5,1-d][1,2,5]triazepin-4-ones in good yields. Structures of the prepared compounds were determined on the basis of IR, 1H- and 13C-NMR, and HR-MS data. Moreover, the molecular structure was confirmed by the X-ray crystal-structure analysis of one compound that was prone to crystallization. Preliminary biological evaluation showed that the compounds 2e–2h promote the viability and inhibit the apoptosis of vascular endothelial cells at low concentration.
Co-reporter:Zhen-Ju Jiang, Jin-Ting Liu, Hong-Shui Lv, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012 Volume 86() pp:181-186
Publication Date(Web):February 2012
DOI:10.1016/j.saa.2011.10.021
A series of novel 5-(3-aryl-1H-pyrazol-5-yl)-2-(6-methoxy-3-methylbenzofuran-2-yl)-1,3,4-oxadiazole derivatives has been synthesized from 6-methoxy-3-methylbenzofuran-2-carboxylic acid and ethyl 3-aryl-1H-pyrazole-5-carboxylate. The structures of compounds obtained were determined by IR, 1H NMR and HRMS spectra. Typically, the spatial structure of compound 7e was determined by using X-ray diffraction analysis. UV–vis absorption and fluorescence spectral characteristics of the compounds in dichloromethane and acetonitrile were investigated. The results showed that the absorption maxima of the compounds vary from 321 to 339 nm depending on the substituents in N-1 position of pyrazole moiety and para position of benzene moiety. The maximum emission spectra of compounds in two different solvents were mainly dependent on groups in N-1 position of pyrazole moiety. The intensity of absorption and fluorescence was also correlated with substituents on the aryl ring bonded to pyrazole moiety. In addition, the absorption and emission spectra of these compounds change with increasing solvent polarity.Graphical abstractHighlights► Novel 1,3,4-oxadiazole derivatives were prepared and fully characterized. ► X-ray crystal structure of compound 7e was reported. ► UV–vis absorption and fluorescence spectroscopy of all compounds were measured. ► Influence of solvent on UV–vis absorption and fluorescence spectroscopy was examined.
Co-reporter:Wei-Yong Liu, Hai-Ying Li, Hong-Shui Lv, Bao-Xiang Zhao, Jun-Ying Miao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012 Volume 95() pp:658-663
Publication Date(Web):September 2012
DOI:10.1016/j.saa.2012.04.073
We describe the development of a rhodamine chromene-based turn-on fluorescence probe to monitor the intracellular Cu2+ level in living cells. The new fluorescent probe with a chlorine group in chromene moiety exhibits good membrane-permeable property than previous reported because the predicted lipophilicity of present probe 4 is stronger than that of methoxyl substituted probe in our previous work (CLogP of 4: 8.313, CLogP of methoxyl substituted probe: 7.706), and a fluorescence response toward Cu2+ under physiological conditions with high sensitivity and selectivity, and facilitates naked-eye detection of Cu2+. The fluorescence intensity was remarkably increased upon the addition of Cu2+ within 1 or 2 min, while the other sixteen metal ions caused no significant effect.Graphical abstractRhodamine chromene-based “turn-on” fluorescence probe can monitor the intracellular Cu2+ level in living HeLa cells with high sensitivity and selectivity in shorter time.Highlights► A new fluorescence probe was synthesized to improve membrane-permeable property. ► The probe can monitor Cu2+ in living cells with high sensitivity and selectivity. ► The probe can monitor intracellular Cu2+ in HeLa cells in shorter time.
Co-reporter:Ning Liu, Jin-Hua Zhang, Bao-Xiang Zhao, Jing Zhao, Le Su, Wen-Liang Dong, Shang-Li Zhang, Jun-Ying Miao
European Journal of Medicinal Chemistry 2011 Volume 46(Issue 6) pp:2359-2367
Publication Date(Web):June 2011
DOI:10.1016/j.ejmech.2011.03.018
A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives with hydrophilic group was synthesized under general heating condition and microwave-assisted condition. The structures of compounds were determined by IR, 1H NMR and HRMS, moreover, representative crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that some compounds could inhibit the growth of A549, H322 and H1299 cells in dosage dependent manners. The compounds could inhibit growth of A549, H322 and H1299 cells in different mechanism. Compounds 3e–h inhibited growth of A549 cells by inducing a strong G1-phase arrest. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis.Novel pyrazolo[1,5-a]pyrazin-4(5H)-ones was synthesized and biological evaluation showed that compounds 3e–h could suppress A549, H322 and H1299 lung cancer cells growth through cell cycle arrest and apoptosis selectively.Highlights► Microwave-assisted synthesis and characterization of novel pyrazolo[1,5-a]pyrazin-4(5H)-ones. ► Two X-ray crystal structures were reported in this work. ► Compounds 3e–h suppressed A549, H322 and H1299 lung cancer cells growth through cell cycle arrest and apoptosis selectively.
Co-reporter:Liang-Wen Zheng, Jin-Hui Shao, Bao-Xiang Zhao, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 13) pp:3909-3913
Publication Date(Web):1 July 2011
DOI:10.1016/j.bmcl.2011.05.035
A series of substituted pyrazolo[1,5-a]pyrazin-4(5H)-one was synthesized by the reaction of ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-(2-aminoethoxy)ethanol or 2-morpholinoethanamine in the condition of microwave-assisted one-step and solvent-free in a good yield. The structures of the compounds were determined by IR, 1H NMR and mass spectroscopy. In addition, a representative single-crystal structure was characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 and H322 cells in dosage-dependent manners.A series of pyrazolo[1,5-a]pyrazin-4(5H)-ones was synthesized under the condition of microwave-assisted one-step and solvent-free in good yields. Application of microwave irradiation reduces the reaction time dramatically to 4–12 min and the experimental procedure is operationally easy and leads to high yields in short reaction time without using toxic reagents and solvents. In addition, structure of a synthesized compound 3i was determined by X-ray analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 and H322 cells in dosage-dependent manners.
Co-reporter:Maohua Wang;Jingyong Zhang;Xuejun Wu;Xing Jin
Molecular Biology Reports 2011 Volume 38( Issue 3) pp:1491-1497
Publication Date(Web):2011 March
DOI:10.1007/s11033-010-0256-2
Human umbilical cord vascular endothelial cells (HUVECs) cultured without serum and fibroblast growth factor-2 is an in vitro model of ischemic conditions. Our previous study showed that ethyl 3-(o-chlorophenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) could inhibit apoptosis of HUVECs in this model. In this study, we investigated the effect of MPD on angiogenesis and the possible mechanisms. Capillary-like tube formation assay on Matrigel and cell migration assay were performed to investigate the effect of MPD on angiogenesis. The reactive oxygen species (ROS) and interferon-inducible protein 10 (IP-10) levels were respectively evaluated by intracellular ROS assay and western blot analysis. MPD at 5 and 10 μM promoted vascular structure formation and HUVEC migration in an in vitro ischemic model. MPD promoted angiogenesis through elevating ROS levels and depressing IP-10 level. ROS seemed to be necessary for angiogenesis, and a high level of IP-10 inhibited angiogenesis in ischemic state. ROS provide clues for seeking new key factors involved in angiogenesis. IP-10 may become a new target for future therapeutic intervention. MPD is a good tool for investigating the mechanism of angiogenesis, and MPD might be useful in the development of new drugs in therapy of ischemic diseases.
Co-reporter:Zhong-Liang Gong, Fei Ge, Bao-Xiang Zhao
Sensors and Actuators B: Chemical 2011 Volume 159(Issue 1) pp:148-153
Publication Date(Web):28 November 2011
DOI:10.1016/j.snb.2011.06.064
This work describes the preparation of a novel pyrazoline compound and the properties of its UV–vis absorption and fluorescence emission. Moreover, this compound can be used to determine Zn2+ ion with high selectivity and a low detection limit in the HEPES (20 mM HEPES, pH = 7.2, 50% (v/v) CH3CN) buffer solution. This sensor forms a 1:1 complex with Zn2+ and shows a fluorescent enhancement by chelation enhanced fluorescence effect with good tolerance of other metal ions. In addition, this sensor is very sensitive with fluorometric detection limit of 0.12 μM.
Co-reporter:Zhong-Liang Gong, Bao-Xiang Zhao, Wei-Yong Liu, Hong-Shui Lv
Journal of Photochemistry and Photobiology A: Chemistry 2011 Volume 218(Issue 1) pp:6-10
Publication Date(Web):5 February 2011
DOI:10.1016/j.jphotochem.2010.11.014
A novel pyrazoline derivative, 2-(4-chloro-2-(1-(6-chloropyridazin-3-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)phenoxy)acetic acid, was synthesized starting from a chalcone and 3-chloro-6-hydrazinylpyridazine and proposed for the determination of Zn2+ ion with high selectivity and a low detection limit in CH3CN:EtOH (90/10, v/v). This sensor formed a 1:1 complex with Zn2+ and showed a fluorescent enhancement with good tolerance of other metal ions.
Co-reporter:Liang-Wen Zheng, Zhong-Liang Gong, Wen-Long Liu, Ying-Rui Liu, Bao-Xiang Zhao
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011 Volume 81(Issue 1) pp:372-379
Publication Date(Web):15 October 2011
DOI:10.1016/j.saa.2011.06.025
A series of fluorescent compounds, containing pyrazolo[1,5-a]pyrazin-4(5H)-one moiety, were designed and synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylates. The structures of the compounds have been confirmed by IR, 1H NMR, HRMS and X-ray crystal diffraction. The optical properties of the compounds were investigated by UV–vis absorption and fluorescence spectroscopy. The effect of pH on the UV–vis absorption of compound 2a in methanol–H2O solutions was studied and interpreted by theory calculation. The pKa value of compound 2a was determined by the absorption spectra.Graphical abstractA series of fluorescent compounds, containing pyrazolo[1,5-a]pyrazin-4(5H)-one moiety, were designed and synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylates. The structures of the compounds have been confirmed by IR, 1H NMR, HRMS and X-ray crystal diffraction. The optical properties of the compounds were investigated by UV–vis absorption and fluorescence spectroscopy. The effect of pH on the UV–vis absorption of compound 2a in methanol–H2O solutions was studied and interpreted by theory calculation. The pKa value of compound 2a was determined by the absorption spectra.Highlights• Novel pyrazolo[1,5-a]pyrazin-4(5H)-ones were prepared and fully characterized. • X-ray crystal structure of compound 2c was reported. • UV–vis absorption and fluorescence spectroscopy of all compounds were measured. • Influence of pH on the structure of compound 2a in solution was examined. • Ionization constant of compound 2a was determined by spectrophotometric method.
Co-reporter:Yong-Sheng Xie, Hong-Ling Zhao, Hua Su, Bao-Xiang Zhao, Jin-Ting Liu, Ji-Kun Li, Hong-Shui Lv, Bai-Shan Wang, Dong-Soo Shin, Jun-Ying Miao
European Journal of Medicinal Chemistry 2010 Volume 45(Issue 1) pp:210-218
Publication Date(Web):January 2010
DOI:10.1016/j.ejmech.2009.09.046
A series of novel ferrocenyl pyrazolo[1,5–a]pyrazin-4(5H)-one derivatives was synthesized and characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray diffraction analysis. Preliminary evaluation of biological applications showed that the compounds 6c and 6f inhibit the growth of A549 cells in dosage-dependent manners through cell cycle arrest.Novel ferrocenyl pyrazolo[1,5–a]pyrazin-4(5H)-one derivatives were synthesized and characterized by spectroscopy and X-ray diffraction analysis. The compounds 6c and 6f were found to inhibit the growth of A549 cells through cell cycle arrest.
Co-reporter:Liang-Wen Zheng, Jian Zhu, Bao-Xiang Zhao, Yao-Hui Huang, Jun Ding, Jun-Ying Miao
European Journal of Medicinal Chemistry 2010 Volume 45(Issue 12) pp:5792-5799
Publication Date(Web):December 2010
DOI:10.1016/j.ejmech.2010.09.041
A series of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives (4) was synthesized from ethyl 1-(2-oxo-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate derivatives (3) and characterized by means of IR, 1H NMR, HRMS and X-ray crystal diffraction. Structures of 4a, 4d, 4e and 4f were also determined by 13C NMR. Isomeric intermediates, 3a and 5a, were unambiguously confirmed by X-ray crystal structure analysis and successfully differentiated with 1H NMR chemical shifts of methylene bonded to pyrazole ring. Preliminary biological evaluation showed that compounds 4d and 4e could suppress A549 lung cancer cell growth through cell cycle arrest and autophagy.Biological evaluation showed that compounds 4d and 4e could suppress A549 lung cancer cell growth through cell cycle arrest and autophagy.
Co-reporter:ChuanDong Fan, Hua Su, Jing Zhao, BaoXiang Zhao, ShangLi Zhang, JunYing Miao
European Journal of Medicinal Chemistry 2010 Volume 45(Issue 4) pp:1438-1446
Publication Date(Web):April 2010
DOI:10.1016/j.ejmech.2009.12.048
In light of the increased anticancer activities of some reported copper complexes and our previous finding of nine novel anti-proliferative salicylaldehyde pyrazole hydrazone (SPH) derivatives, we prepared copper complexes of these SPH derivatives (Cu-SPHs), which turned out to be stronger growth inhibitors to A549 cells than their corresponding SPHs via inducing apoptosis. Among them, the copper complex of (E)-N′-(2-hydroxybenzylidene)-1-(4-tert-butylbenzyl)-3-phenyl-1H-pyrazole-5-carbohydrazide, termed Cu-16, exhibited an advantage in selectivity and efficacy over the others. Immunofluorescence and Western blot analyses showed an elevated protein level of integrin β4 upon Cu-16 treatment, and knockdown of integrin β4 significantly inhibited Cu-16 induced apoptosis in H322 cells. Taken together, the results indicate that Cu-16 promotes apoptosis in H322 cells through elevating the protein level of integrin β4.Cu-16 promotes apoptosis in H322 cells through elevating the protein level of integrin β4.
Co-reporter:Hong-Shui Lv, Bao-Xiang Zhao, Ji-Kun Li, Yong Xia, Song Lian, Wei-Yong Liu, Zhong-Liang Gong
Dyes and Pigments 2010 Volume 86(Issue 1) pp:25-31
Publication Date(Web):June 2010
DOI:10.1016/j.dyepig.2009.11.003
A series of novel substituted pyrazoly 1,3,4-oxadiazole derivatives were synthesized by the reaction of substituted pyrazole-5-carbohydrazide with substituted benzoic acid in the presence of phosphorus oxychloride. The compounds were characterised using IR, 1H NMR and HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane. The compounds displayed similar absorption, ranging from 267 to 281 nm with a strong absorption band occurring at ∼275 nm. Correlation of the absorption spectra and fluorescence characteristics of the pyrazoly 1,3,4-oxadiazole derivatives with substituent effects on the benzene rings, revealed that a methoxy and a bromine group attached to the benzene ring markedly influenced maximum emission.
Co-reporter:Liang-Wen Zheng, Ying Li, Di Ge, Bao-Xiang Zhao, Ying-Rui Liu, Hong-Shui Lv, Jun Ding, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 16) pp:4766-4770
Publication Date(Web):15 August 2010
DOI:10.1016/j.bmcl.2010.06.121
A series of novel oxime-containing pyrazole derivatives were synthesized by the reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-bromo-1-phenylethanone followed by the reaction with hydroxylamine hydrochloride. The structures were determined by IR, 1H NMR, HRMS, and X-ray analysis. A dose- and time-dependent inhibition of proliferation was observed in A549 lung cancer cell after compound treatment. Inhibition of growth was mainly attributed to the autophagy induction.A series of novel oxime-containing pyrazole derivatives were synthesized and characterized by IR, 1H NMR, HRMS spectroscopy, and X-ray analysis. A dose- and time-dependent inhibition of proliferation was observed in A549 lung cancer cell after compounds treatment. Hoechst 33258 staining assay and Western blot analysis of LC3-II level showed that the inhibition against A549 cell growth might be attributed to apoptosis and autophagy.
Co-reporter:Zhong-Liang Gong, Liang-Wen Zheng, Bao-Xiang Zhao, De-Zhong Yang, Hong-Shui Lv, Wei-Yong Liu, Song Lian
Journal of Photochemistry and Photobiology A: Chemistry 2010 Volume 209(Issue 1) pp:49-55
Publication Date(Web):1 January 2010
DOI:10.1016/j.jphotochem.2009.10.007
A series of novel 1,3,5-triaryl pyrazoline derivatives has been synthesized by the reaction of chalcone and 3-chloro-6-hydrazinylpyridazine in 47–82% yields. The structures of compounds obtained were determined by IR, 1H NMR and HRMS spectra. Representatively, the spatial structure of compound 3d was determined by using X-ray diffraction analysis. Absorption and fluorescence spectral characteristics of the compounds were investigated in CHCl3 by UV–vis absorption and emission spectra. The results showed that the absorption maxima of the compounds vary from 332 to 342 nm depending on the group bonded to benzene rings. The maximum emission spectra of compounds in CHCl3 are dependent on groups in benzene ring in which a strong electron-donating group in benzene ring such as methoxyl group on C3 position of pyrazoline made the emission wavelength of 3e, 3f and 3g red shifted than that of compounds 3b, 3c and 3d with chlorine group. The intensity of absorption and fluorescence was also correlated with substituent on two aryl rings. In addition, the absorption spectra of these compounds change very little with increasing solvent polarity.
Co-reporter:Wei-Yong Liu, Yong-Sheng Xie, Bao-Xiang Zhao, Bai-Shan Wang, Hong-Shui Lv, Zhong-Liang Gong, Song Lian, Liang-Wen Zheng
Journal of Photochemistry and Photobiology A: Chemistry 2010 Volume 214(2–3) pp:135-144
Publication Date(Web):15 August 2010
DOI:10.1016/j.jphotochem.2010.06.017
A series of novel 5-aryl-1-arylthiazolyl-3-ferrocenyl-pyrazoline derivatives has been synthesized by the reaction of ferrocenyl chalcone and thiosemicarbazide followed by the reaction with 2-bromo-1-arylethanone in 48–90% yields. The compounds were characterized using IR, 1H NMR and HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane, chloroform and tetrahydrofuran. The results showed that the absorption maxima of the compounds vary from 316 to 347 nm depending on the group bonded to phenylthiazole rings. The electron-donating methoxyl group in phenylthiazole moiety caused red shifts in dichloromethane solution, and the electron-withdrawing chloro group resulted in blue shifts. The absorption maxima of these compounds in tetrahydrofuran were red shift compared with that in dichloromethane and chloroform. The maximum emission spectra of compounds in tetrahydrofuran were also red shift compared with that in dichloromethane.
Co-reporter:Wei-Yong Liu, Yong-Sheng Xie, Bao-Xiang Zhao, Song Lian, Hong-Shui Lv, Zhong-Liang Gong, Dong-Soo Shin
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2010 Volume 76(Issue 5) pp:531-536
Publication Date(Web):1 September 2010
DOI:10.1016/j.saa.2010.04.019
A series of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and 1H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV–vis absorption and fluorescence spectra were recorded in ethanol and dichloromethane. The results showed that compounds 5a–g display similar absorptions ranging from 300 to 500 nm and maximal emission bands are about 566 nm. The intensity of fluorescence and maximal emission bands are dependent on the groups bonded to triazole rings.
Co-reporter:Hua Su;Ling Su;Qiuxia He;Jing Zhao;Baoxiang Zhao;Shangli Zhang
Frontiers in Biology 2010 Volume 5( Issue 2) pp:180-186
Publication Date(Web):2010 April
DOI:10.1007/s11515-010-0031-8
A fundamental aspect of cancer development is cancer cell proliferation. Seeking for chemical agents that can interfere with cancer cell growth has been of great interest over the years. In our study, we found that a benzoxazine derivative, (6-tert-butyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl) methanol (TBM), could inhibit cell growth and caused significant cell cycle arrest in pulmonary adenocarcinoma A549 and H460 cells with wild-type p53, while not affecting the cell cycle distribution in p53-deleted H1299 lung adenocarcinoma cells. Since P53 plays an important role in regulating cell cycle progression, we analyzed the protein level of p53 by Western blot, and detected a significant elevation of p53 level after TBM treatment in A549 and H460 cells. The data suggested that TBM might specifically inhibit the proliferation of p53 wild-type lung adenocarcinoma cells through a p53-dependent cell cycle control pathway. More interestingly, results indicated that TBM might serve as a useful tool for studying the molecular mechanisms of lung cancer cell growth and cell cycle control, especially for the biologic process regulated by P53.
Co-reporter:Bin Huang, Ning Meng, BaoXiang Zhao, Jing Zhao, Yun Zhang, ShangLi Zhang and JunYing Miao
Chemical Research in Toxicology 2009 Volume 22(Issue 3) pp:471
Publication Date(Web):February 9, 2009
DOI:10.1021/tx8002824
We previously found a butyrolactone derivative, 3-benzyl-5-((2-nitrophenoxy) methyl)-dihydrofuran-2(3H)-one (3BDO), could inhibit vascular endothelial cell (VEC) apoptosis and senescence induced by a deprivation of serum and FGF-2. In this study, we aimed to investigate its actions in VEC autophagy induced by chloroquine (CQ). The measurement on the volume of acidic compartments (VAC) and autophagy analysis by acridine orange (AO) staining and microtubule-associated protein 1 light chain 3 (MAP1LC3) process revealed that 3BDO was an effective inhibitor of autophagic vesicle accumulation (vacuolation) induced by CQ in VECs. 5,5′,6,6′-tetrachloro-1,1′,3,3′-tetraethylbenzimidazolylcarbocyanine iodide (JC-1) was used for mitochondrial membrane potential (MMP) measurement. The results showed that CQ elevated MMP significantly and that 3BDO could significantly inhibit CQ-induced MMP increase. Na+,K+-ATPase activity assay showed that CQ inhibited this enzyme activity significantly and that 3BDO attenuated the alteration of Na+,K+-ATPase activity caused by CQ. We concluded that 3BDO was a promising inhibitor of CQ-induced accumulation of autophagic vesicles in VECs and could weaken the alterations of MMP and Na+,K+-ATPase activity induced by CQ. The data indicate that 3BDO will be a potential tool for investigating the mechanism of autophagy.
Co-reporter:Chuandong Fan, Jing Zhao, Baoxiang Zhao, Shangli Zhang and Junying Miao
Chemical Research in Toxicology 2009 Volume 22(Issue 9) pp:1517
Publication Date(Web):July 22, 2009
DOI:10.1021/tx900111y
To determine apoptosis modulators of human umbilical vein endothelial cells (HUVECs), we prepared 9 novel complexes of copper (Cu) and salicylaldehyde pyrazole hydrazone (SPH) derivatives (Cu−SPHs). The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay revealed that all of the SPHs and Cu−SPHs effectively inhibited cell growth. Six of the 9 Cu−SPHs induced apoptosis in HUVECs. Among the 9 Cu−SPHs, the complex of Cu and (E)-N′-(2-hydroxybenzylidene)-1-benzyl-3-phenyl-1H-pyrazole-5-carbohydrazide, named Cu-15, was one of the most effective apoptosis inducers and inhibited angiogenesis on Matrigel and HUVEC migration in vitro. We further studied the mechanism of Cu-15 action and found that the protein level of integrin β4 increased with 10 μM Cu-15 treatment for 12 or 24 h. Knockdown of integrin β4 by RNA interference significantly inhibited apoptosis induced by Cu-15 in HUVECs. Thus, high level of integrin β4 could promote apoptosis induced by Cu-15. Cu-15 might be a useful tool for further investigating the functions of integrin β4 in regulating angiogenesis and HUVEC apoptosis.
Co-reporter:Wei-Yong Liu, Hai-Ying Li, Bao-Xiang Zhao, Dong-Soo Shin, Song Lian, Jun-Ying Miao
Carbohydrate Research 2009 Volume 344(Issue 11) pp:1270-1275
Publication Date(Web):27 July 2009
DOI:10.1016/j.carres.2009.05.017
A series of novel ribavirin hydrazone derivatives were synthesized by the reaction of ribavirin hydrazone with benzaldehyde or acetophenone derivatives. The structures of the compounds were determined by IR, 1H NMR, and HRESIMS. Preliminary biological evaluation showed that one compound (7h) inhibits the growth of A549 cells at 20 μM.
Co-reporter:Xiao-Ling Ding, Hai-Yan Zhang, Lei Qi, Bao-Xiang Zhao, Song Lian, Hong-Shui Lv, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 18) pp:5325-5328
Publication Date(Web):15 September 2009
DOI:10.1016/j.bmcl.2009.07.131
A series of novel 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxamide derivatives 3a–l, were synthesized by the reaction of 3-aryl-1-arylmethyl-1H-pyrazole-5-carbonyl chloride with substituted amine in excellent yields. The compounds 3e–h could suppress A549 lung cancer cell growth. More interestingly, compounds 3e and 3f might inhibit the A549 cell growth by inducing apoptosis; whereas compounds 3g and 3h with fluorine group might inhibit the A549 cell growth by inducing autophagy.A series of novel 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxamide derivatives 3a–l, were synthesized by the reaction of 3-aryl-1-arylmethyl-1H-pyrazole-5-carbonyl chloride with substituted amine in excellent yields. The compounds 3e–h could suppress A549 lung cancer cell growth. More interestingly, compounds 3e and 3f might inhibit the A549 cell growth by inducing apoptosis; whereas compounds 3g and 3h with fluorine group might inhibit the A549 cell growth by inducing autophagy.
Co-reporter:Liang-Wen Zheng, Ling-Ling Wu, Bao-Xiang Zhao, Wen-Liang Dong, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2009 17(5) pp: 1957-1962
Publication Date(Web):
DOI:10.1016/j.bmc.2009.01.037
Co-reporter:Yong-Sheng Xie, Bao-Xiang Zhao, Hong-Shui Lv, Ji-Kun Li, Bai-Shan Wang, Dong-Soo Shin
Journal of Molecular Structure 2009 930(1–3) pp: 83-87
Publication Date(Web):
DOI:10.1016/j.molstruc.2009.04.042
Co-reporter:Song Lian, Hua Su, Bao-Xiang Zhao, Wei-Yong Liu, Liang-Wen Zheng, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2009 17(20) pp: 7085-7092
Publication Date(Web):
DOI:10.1016/j.bmc.2009.09.004
Co-reporter:Ning Meng;Jing Zhao;BaoXiang Zhao;Yizhe Cheng;Weiwei Wang;Yun Zhang;ShangLi Zhang;JunYing Miao
Journal of Cellular Biochemistry 2008 Volume 104( Issue 6) pp:2123-2130
Publication Date(Web):
DOI:10.1002/jcb.21769
Abstract
We have found that 3-benzyl-5-((2-nitrophenoxy) methyl)–dihydrofuran -2(3H)-one (3BDO), could effectively suppress human umbilical vascular endothelial cell (HUVEC) apoptosis induced by deprivation of fibroblast growth factor-2 and serum. Here, our purpose was to investigate whether 3BDO could modulate angiogenesis and its possible acting mechanism. The effect of 3BDO on angiogenesis was investigated by capillary-like tubule formation and rat aortic ring assay. Proliferation and migration of cells were detected by counting living cell number and scraping cell monolayer, respectively. Na, K-ATPase activity was measured spectrophotometrically. Mitochondrial membrane potential was analyzed using tetramethylrhodamine methylester fluorescence by confocal microscopy. Our results showed that 3BDO inhibited migration and proliferation of vascular smooth muscle cells (VSMCs), but maintained migration and tubule formation of HUVECs. In HUVECs, 3BDO inhibited Na, K-ATPase activity, but had no effect on mitochondria membrane potential. In VSMCs, it did not affect Na, K-ATPase activity, but depressed mitochondria membrane potential obviously. The data showed that 3BDO had selective effects on HUVECs and VSMCs, it might perform its role through the selective effects on the activity of Na, K-ATPase and the mitochondria membrane potential in HUVECs and VSMCs. J. Cell. Biochem. 104: 2123–2130, 2008. © 2008 Wiley-Liss, Inc.
Co-reporter:Xiao-Hong Pan, Xia Liu, Bao-Xiang Zhao, Yong-Sheng Xie, Dong-Soo Shin, Shang-Li Zhang, Jing Zhao, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2008 Volume 16(Issue 20) pp:9093-9100
Publication Date(Web):15 October 2008
DOI:10.1016/j.bmc.2008.09.046
we found that 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives 8d, 8e and 8f could effectively induce apoptosis in A549 lung cancer cells and elevate the levels of integrin β4 and ROS. The data suggested that these compounds might be promising agents for the cancer therapy, and these compounds would be useful tools for further investigate the functions of integrin β4 in regulation of the cancer cell apoptosis.5-Alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives 8d, 8e and 8f induced apoptosis in A549 cancer cells and elevated the levels of integrin β4 and ROS.
Co-reporter:Bao-Xiang Zhao, Lu Zhang, Xing-Shang Zhu, Mao-Sheng Wan, Jing Zhao, Yun Zhang, Shang-Li Zhang, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2008 Volume 16(Issue 9) pp:5171-5180
Publication Date(Web):1 May 2008
DOI:10.1016/j.bmc.2008.03.011
Recently, pyrazole derivatives as high affinity and selective A2A adenosine receptor antagonists have been reported. But, so far, there are no reports about the inhibitory effects of multi-substituted pyrazole derivatives on apoptosis of vascular endothelial cells (VECs). In this study, we synthesized six pyrazole derivatives and characterized the structures of the compounds by IR, 1H NMR, mass spectroscopy, and element analysis. The biology assay showed that a novel pyrazole derivative, ethyl 3-(o-chlorophenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) at low concentration (25 μM) increased VECs viability and inhibited VECs apoptosis induced by deprivation of serum and FGF-2. During this process, the levels of integrin β4, reactive oxygen species (ROS), and p53 were depressed obviously. The data suggested that MPD was a potential inhibitor of apoptosis associated with the signal pathway mediated by integrin β4, ROS, and p53 in VECs.Six novel multi-pyrazole derivatives have been synthesized and characterized by IR, 1H NMR, mass spectroscopy, and element analysis. Ethyl 3-(o-chlorophenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) at low concentration (25 μM) increased VEC viability and inhibited VEC apoptosis through down-regulating the levels of integrin β4, p53, and ROS increased by deprivation of serum and FGF-2 in vascular endothelial cells.
Co-reporter:Jin-Hua Zhang, Chuan-Dong Fan, Bao-Xiang Zhao, Dong-Soo Shin, Wen-Liang Dong, Yong-Sheng Xie, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2008 Volume 16(Issue 24) pp:10165-10171
Publication Date(Web):15 December 2008
DOI:10.1016/j.bmc.2008.10.066
A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives were synthesized by the reaction of ethyl 3-aryl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate and amine in the general heating condition and microwave-assisted condition. The structures of the compounds were determined by IR, 1H NMR and mass spectroscopy, in addition, representative single-crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 cells in dosage- and time-dependent manners. The study on structure-activity relationships showed that compounds with 4-chlorophenyl group at pyrazole moiety, such as 5-benzyl-2-(4-chlorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (3o) had much more inhibitory effects. Compound 3o was the most effective small molecule in inhibiting A549 cell growth and might perform its action through modulating autophagy.A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives were synthesized by the reaction of ethyl 3-aryl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate and amine in the general heating condition and microwave-assisted condition. Representative single-crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 cells in dosage- and time-dependent manners. Compound 3o was the most effective small molecule in inhibiting A549 cell growth and might perform its action through modulating autophagy.
Co-reporter:Chuan-Dong Fan, Bao-Xiang Zhao, Fang Wei, Gai-Hua Zhang, Wen-Liang Dong, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2008 Volume 18(Issue 14) pp:3860-3864
Publication Date(Web):15 July 2008
DOI:10.1016/j.bmcl.2008.06.058
A series of novel 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives were synthesized, and the effects of the compounds on A549 cell growth were investigated. The results showed that all of the 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives 2 could inhibit the growth of A549 cells in dosage- and time-dependent manners. Typically, compound 2a and 2d induced A549 cells to autophagy but did not cause apoptosis and necrosis in the cells, and 2d had the most autophagy inducing effect in H460 cells. More importantly, 2a and 2d did not inhibit the growth of HUVEC cells.A series of novel 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives were synthesized. All of the 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carbohydrazide derivatives 2 could inhibit the growth of A549 cells in dosage- and time-dependent manners. Typically, compounds 2a and 2d induced A549 and H460 cells to autophagy, but did not inhibit the growth of HUVEC cells.
Co-reporter:Yong Xia, Zhi-Wu Dong, Bao-Xiang Zhao, Xiao Ge, Ning Meng, Dong-Soo Shin, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2007 Volume 15(Issue 22) pp:6893-6899
Publication Date(Web):15 November 2007
DOI:10.1016/j.bmc.2007.08.021
A series of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives were synthesized, and the effects of all the compounds on A549 cell growth were investigated. The results showed that all the nine compounds had inhibitory effects on the growth of A549 cells and induced the cell apoptosis. The study on structure–activity relationships and prediction of lipophilicities of compounds showed that compounds with log P values in the range of 3.12–4.94 had more inhibitory effects on the growth of A549 cells.1-Arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives were synthesized, and their effects on A549 cell growth and apoptosis were evaluated. The structure–activity relationships and prediction of lipophilicity of compounds were studied.
Co-reporter:Baoxiang Zhao;Jing Zhao;Bin Huang;Weiwei Wang;Junying Miao;Shangli Zhang;Jing Zhao;Weiwei Wang;Junying Miao;Shangli Zhang;Bin Huang;Baoxiang Zhao
Journal of Cellular Biochemistry 2007 Volume 102(Issue 2) pp:421-428
Publication Date(Web):28 MAR 2007
DOI:10.1002/jcb.21301
To find the key factors that were involved in the survival and vascular endothelial differentiation of chick blatodisc induced by fibroblast growth factor 2 (FGF-2), we built a chick vasculogenesis model in vitro. Subsequently, the activities of phosphatidylcholine-specific phospholipase C (PC-PLC), including Ca2+-dependent and -independent PC-PLC, and the level of reactive oxygen species (ROS) were evaluated during the endothelial differentiation of chick blastodisc. The results showed that Ca2+-indepentent PC-PLC underwent a remarkable increase in 24 h (P < 0.01), then it decreased gradually with the cell differentiation, while the Ca2+-depentent PC-PLC was nearly not changed in the whole process. At the same time, ROS level dramatically decreased during the cell differentiation. To understand the role of PC-PLC and how it performs its function in the vascular endothelial differentiation induced by FGF-2, we suppressed PC-PLC activity by its specific inhibitor D609 (tricyclodecan-9-yl potassium xanthate) at 24 h during the cell differentiation. As a result, the cell differentiation could not progress and the intracellular level of ROS was elevated. The data suggested that PC-PLC and ROS were involved in chicken blastodisc differentiation to vascular endothelial cells. PC-PLC was an important factor in the blastodisc cell survival and differentiation, and it might perform its function associated with ROS. J. Cell. Biochem. 102: 421–428, 2007. © 2007 Wiley-Liss, Inc.
Co-reporter:Qiuxia He, Xingshang Zhu, Mei Shi, Baoxiang Zhao, Jing Zhao, Shangli Zhang, Junying Miao
Bioorganic & Medicinal Chemistry 2007 Volume 15(Issue 11) pp:3889-3895
Publication Date(Web):1 June 2007
DOI:10.1016/j.bmc.2007.03.008
Previously, we found that nine kinds of new morpholin-3-one derivatives could inhibit the growth of A549 lung cancer cells in a dose-dependent manner, but how they performed their function remained unknown. In this paper, we studied the effects of the three more effective morpholin-3-one derivatives {4-(4-chlorophenyl)-6-((4-nitrophenoxy) methyl) morpholin-3-one (1); 6-(4-chlorophenoxy)-4-(4-methoxyphenyl) morpholin-3-one (2); and 6-((4-nitrophenoxy) methyl)-4-phenylmorpholin-3-one (3)} on the cell cycle distribution, apoptosis, and the level of P53 and Fas that are two kinds of important proteins in the regulation of A549 cell growth and apoptosis. According to the results of cell viability, we selected 40 μg/ml of morpholin-3-one derivatives as the most appropriate concentration for the following study. The results showed that the morpholin-3-one derivatives partly blocked the cells at G1 phase, induced apoptosis, and elevated the level of P53 and Fas proteins significantly. The effect of the morpholin-3-one derivates was associated with translocation of P53 and clustering of Fas. Our data suggested that the morpholin-3-one derivates might be promising tools for elucidating the molecular mechanism of lung cancer cell apoptosis and they will be very potential candidates for developing anti-cancer drugs.Morpholin-3-one derivatives arrested cell cycle partly at G1 phase, elevated the levels of P53 and Fas, and induced A549 cell apoptosis.
Co-reporter:Weiwei Wang, Xia Liu, Jing Zhao, Baoxiang Zhao, Shangli Zhang, Junying Miao
Bioorganic & Medicinal Chemistry Letters 2007 Volume 17(Issue 2) pp:482-485
Publication Date(Web):15 January 2007
DOI:10.1016/j.bmcl.2006.10.023
To understand the effects of a novel butyrolactone derivative, 3-benzyl-5-((2-nitrophenoxy) methyl)-dihydrofuran-2(3H)-one (3BDO), on the apoptosis of vascular endothelial cells (VECs), we exposed 3BDO (20–60 μg/ml) to VECs deprived of serum and FGF-2 for 24 and 48 h, respectively. The results showed that 3BDO (20–60 μg/ml) increased VEC viability and inhibited VEC apoptosis induced by deprivation of serum and FGF-2 in a very weak dose-dependent manner. During this process, integrin β4 expression was depressed, but the level of reactive oxygen species (ROS) was not changed. The data suggested that 3BDO (20–60 μg/ml) could inhibit VEC apoptosis and suppress integrin β4 expression, but it could not depress the ROS level induced by deprivation of serum and FGF-2.3-Benzyl-5-((2-nitrophenoxy) methyl)-dihydrofuran-2(3H)-one (3BDO) inhibited VEC apoptosis induced by deprivation of serum and FGF-2 and depressed the expression of integrin β4. ROS were not involved in this process.
Co-reporter:Le Su, BaoXiang Zhao, Xin Lv, Jing Zhao, ShangLi Zhang, JunYing Miao
Bioorganic & Medicinal Chemistry Letters 2007 Volume 17(Issue 11) pp:3167-3171
Publication Date(Web):1 June 2007
DOI:10.1016/j.bmcl.2007.03.032
Previously, we found safrole oxide could promote VEC apoptosis, however, it is not known whether it can induce NSC apoptosis. It is reported that neural stem cells (NSCs) are localized in a vascular niche. But the effects of apoptosis in vascular endothelial cells (VEC) on NSC growth and differentiation are not clear. To answer these questions, in this study, we co-cultured NSCs with VECs in order to imitate the situation in vivo, in which NSCs are associated with the endothelium, and treated the single-cultured NSCs and the co-cultured NSCs with safrole oxide. The results showed that safrole oxide (10–100 μg/mL) had no effects on NSC growth. Based on these results, we treated the co-culture system with this small molecule. The results showed that the NSCs differentiation, into neurons and gliacytes was induced by VECs untreated with safrole oxide. But in the co-culture system treated with safrole oxide, the NSCs underwent apoptosis. The data suggested that when VEC apoptosis occurred in the co-culture system, the NSC survival and differentiation could not be maintained, and NSCs died by apoptosis. Our finding provided a useful tool for investigating the effect of apoptosis in vascular endothelial cells on neural stem cell survival and differentiation in vitro.Safrole oxide has no effect on the growth of mouse neural stem cells. But the apoptotic VECs triggered by safrole oxide induced NSC apoptosis in the co-culture system.
Co-reporter:Chuandong Fan, Weiwei Wang, Baoxiang Zhao, Shangli Zhang, Junying Miao
Bioorganic & Medicinal Chemistry 2006 Volume 14(Issue 9) pp:3218-3222
Publication Date(Web):1 May 2006
DOI:10.1016/j.bmc.2005.12.035
To investigate the effects of chloroquine diphosphate (CQ) on lung cancer cell growth, we treated A549 cells, a lung cancer cell line, with the drug at various concentrations (0.25–128 μM) for 24–72 h. The results showed that, at lower concentrations (from 0.25 to 32 μM), CQ inhibited the growth of A549 cells and, at the same time, it induced vacuolation with increased volume of acidic compartments (VAC). On the other hand, at higher concentrations (64–128 μM), CQ induced apoptosis at 24 h, while its effect of inducing vacuolation declined. The lactate dehydrogenase (LDH) assay showed that with the treatment of CQ 32–64 μM for 72 h or 128 μM for 48 h, CQ induced necrosis of A549 cells. To understand the possible mechanism by which CQ acts in A549 cells, we further incubated the cells with this drug at the concentrations of 32 or 128 μM in the presence of D609, a specific inhibitor of phosphatidylcholine-specific phospholipase C (PC-PLC). The results showed that D609 (50 μM) could inhibit the effects of CQ 32 μM on the viability and VAC, but it could not change the effects of CQ 128 μM on the same. Our data suggested that CQ inhibited A549 lung cancer cell growth at lower concentrations by increasing the volume of lysosomes and that PC-PLC might be involved in this process. The data also indicated that, at higher concentrations, CQ induced apoptosis and necrosis, but at this time its ability to increase the volume of lysosome gradually declined, and PC-PLC might not be implicated in the process.Chloroquine diphosphate (CQ) could inhibit cell growth, elicit cell apoptosis, and induce necrosis in A549 cells at different concentrations. Moreover, the results suggested the involvement of PC-PLC in cell growth inhibition by CQ at lower concentrations.
Co-reporter:AiYing Du, BaoXiang Zhao, JunYing Miao, DeLing Yin, ShangLi Zhang
Bioorganic & Medicinal Chemistry 2006 Volume 14(Issue 7) pp:2438-2445
Publication Date(Web):1 April 2006
DOI:10.1016/j.bmc.2005.11.026
Previously, we found that 3,4-(methylenedioxy)-1-(2′,3′-epoxypropyl)-benzene (safrole oxide) induced a typical apoptosis in A549 human lung cancer cells by activating caspase-3, -8, and -9. In this study, we further investigated which upstream pathways were activated by safrole oxide during the apoptosis. Immunofluorescence assay combined with laser scanning confocal microscopy revealed that both Fas and Fas ligand (FasL) were up-regulated by the small molecule. In addition, Fas protein distribution was altered, showing a clustering distribution instead of a homogeneous one. Subsequently, Western blot analysis confirmed the up-regulations of Fas and its membrane-binding form of FasL (m-FasL), as well as P53 protein. Conversely, safrole oxide hardly affected integrin β4 subunit expression or distribution, which was reflected from the data obtained by immunofluorescence assay combined with laser scanning confocal microscopy. The results suggested that Fas/FasL pathway might be involved in safrole oxide-induced apoptosis of A549 cells, while integrin β4 might be irrelevant to the apoptosis. Nevertheless, we first found the strong expression of integrin β4 in A549 cells. The study first suggested that safrole oxide might be used as a small molecular promoter of Fas/FasL pathway to elicit apoptosis in A549 cells, which would lay the foundation for us to insight into the new strategies for lung cancer therapy.Safrole reacted with 3-chloroperoxybenzoic acid (mCPBA) in chloroform or in benzene to yield 3,4-(methylenedioxy)-1-(2′,3′-epoxypropyl)-benzene (safrole oxide). Safrole oxide induced apoptosis in A549 human lung cancer cells perhaps through Fas/FasL pathway.
Co-reporter:Fang Wei, Bao-Xiang Zhao, Bin Huang, Lu Zhang, Chun-Hui Sun, Wen-Liang Dong, Dong-Soo Shin, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2006 Volume 16(Issue 24) pp:6342-6347
Publication Date(Web):15 December 2006
DOI:10.1016/j.bmcl.2006.09.008
We synthesized a series of novel small molecules, ethyl 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives 3a–3o, by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 2-aryloxymethylepoxide in the presence of potassium carbonate at refluxing in acetonitrile in moderate or excellent yields. We investigated the effects of all the compounds on A549 cell growth. The results showed that 15 compounds could suppress A549 lung cancer cell growth. Among them, compound 3i was the most effective small molecule in inhibiting A549 cell growth. Compound 3f might most effectively induce A549 cell differentiation. Compound 3g remarkably induced cellular vacuolation.A series of ethyl 1-(2′-hydroxy-3′-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate derivatives (15 compounds) was synthesized and the effects of all of the compounds on A549 cell growth were investigated.
Co-reporter:Nan Wang, Xin Lv, Le Su, BaoXiang Zhao, ShangLi Zhang, JunYing Miao
Bioorganic & Medicinal Chemistry Letters 2006 Volume 16(Issue 18) pp:4780-4783
Publication Date(Web):15 September 2006
DOI:10.1016/j.bmcl.2006.06.080
In order to investigate the effects of tricyclodecane-9-yl-xanthogenate (D609) on the survival of neural stem cells (NSCs), which were isolated from rat forebrain, we treated the NSCs with D609 in the presence of basic fibroblast growth factor (bFGF). We found that when NSCs were exposed to 18.76–56.29 μM D609, the viability of the cells remarkably declined and apoptosis occurred. At the same time, the ROS level in NSCs was depressed. The data suggested that D609 was a powerful growth inhibitor and apoptosis inducer in NSCs.D609 could suppress cell survival and induce apoptosis in rat neural stem cells. Moreover, the changes of intracellular ROS level induced by D609 indicated that a modest level of ROS might be indispensable to NSC survival.
Co-reporter:AiYing Du, BaoXiang Zhao, DeLing Yin, ShangLi Zhang, JunYing Miao
Bioorganic & Medicinal Chemistry Letters 2006 Volume 16(Issue 1) pp:81-83
Publication Date(Web):1 January 2006
DOI:10.1016/j.bmcl.2005.09.050
Previously we found that 3,4-(methylenedioxy)-1-(2′,3′-epoxypropyl)-benzene (safrole oxide) induced a typical apoptosis in A549 human lung cancer cells. In this study, we further investigated which caspases were activated by safrole oxide during the apoptosis. The data showed that the activity of caspase-3, -8, and -9 was significantly enhanced by the compound, which suggested that safrole oxide might be used as a caspase promoter to initiate lung cancer cell apoptosis.Safrole reacted with 3-chloroperoxybenzoic acid (mCPBA) in chloroform to yield 3,4-(methylenedioxy)-1-(2′,3′-epoxypropyl)-benzene (safrole oxide). Safrole oxide induced apoptosis in A549 human lung cancer cells by activating caspase-3, -8, and -9.
Co-reporter:Pei-Fu Jiao, Bao-Xiang Zhao, Wei-Wei Wang, Qiu-Xia He, Mao-Sheng Wan, Dong-Soo Shin, Jun-Ying Miao
Bioorganic & Medicinal Chemistry Letters 2006 Volume 16(Issue 11) pp:2862-2867
Publication Date(Web):1 June 2006
DOI:10.1016/j.bmcl.2006.03.013
We synthesized a series of novel small molecules, 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives, by tandem reduction-oxirane opening of 2-nitroaroxymethyloxiranes in moderate or excellent yields. We investigated the effects of all of the compounds on HUVEC apoptosis and A549 cell growth. The results showed that 6,8-dichloro-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine was the most effective small molecule in promoting HUVEC apoptosis and inhibiting A549 cell proliferation, but 6-amino-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine could remarkably inhibit HUVEC apoptosis and might induce the formation of microvessel.A series of 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives (seven compounds) was synthesized and the effects of all of the compounds on HUVEC apoptosis and A549 cell growth were investigated.
Co-reporter:Wei Tan;Mei Shi;Lei Sha;Jun-Ying Miao;Dong-Soo Shin
Chinese Journal of Chemistry 2006 Volume 24(Issue 3) pp:
Publication Date(Web):13 MAR 2006
DOI:10.1002/cjoc.200690076
A series of 4-aryl-6-aryloxymethylmorpholin-3-one derivatives were synthesized very efficiently from readily available starting compounds in two steps. Ring opening reactions of epoxides with aniline compounds on alumina gave corresponding β-aminoalcohols (3). The resulting β-aminoalcohols were reacted with 2-chloroacetyl chloride to yield the desired 4-aryl-6-aryloxymethylmorpholin-3-one derivatives (5). All compounds 5 were assayed for inhibitory activity against A549 lung cancer cell growth, and the inhibitory effect of the novel morpholin-3-ones on cell viability was dose-dependent.
Co-reporter:Bao-Xiang Zhao;Marco Schaudt;Siegfried Blechert
Chinese Journal of Chemistry 2006 Volume 24(Issue 8) pp:
Publication Date(Web):9 AUG 2006
DOI:10.1002/cjoc.200690202
A series of succinate-derived macrocyclic amides 1 were synthezized using ring-closing metathesis in the key step. The substrate scope includes rings of 11 to 14 members. The cyclic dicarboxylic acids 1 represent a family of new model compounds for potential zinc metalloprotease inhibitors. The metathesis precursors were provided by amide coupling of tert-butyl 3-carboxyhex-5-enoate 2 with numerous side chain alkenylated amino acid esters of general type 3 derived from L-tyrosine and L-cysteine.
Co-reporter:Ai-Ying Du, Bao-Xiang Zhao, De-Ling Yin, Shang-Li Zhang, Jun-Ying Miao
Bioorganic & Medicinal Chemistry 2005 Volume 13(Issue 13) pp:4176-4183
Publication Date(Web):1 July 2005
DOI:10.1016/j.bmc.2005.04.031
A novel small molecule, 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol (EOD), was synthesized in our laboratory. Previously, we reported pharmacological properties of EOD, triggering apoptosis in Human umbilical vein endothelial cells (HUVECs). Here, we further investigated the effects of EOD on the growth of A549 human lung cancer cells. EOD treatment induced apoptosis in A549 cells via up-regulating the expression of P53 protein, blocking cell cycle partly at G1 phase, and ultimately activating caspase-3. In contrast, caspase-8 might be irrelevant to EOD-triggered apoptosis. This study indicated that EOD might be a potential chemopreventive agent for lung cancer. The work would encourage us to add more novel compounds to our ‘library’ of small molecules derived through modern synthetic organic chemistry, and would drive us to determine the proteins that the compounds target.3,4-(Methylenedioxy)-1-(2′,3′-epoxypropyl)-benzene reacted with sodium ethoxide in alcohol to yield 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol (EOD). EOD induced apoptosis in A549 human lung cancer cells by up-regulation of P53 protein, blocking cell cycle partly at G1 phase and activation of caspase-3.
Co-reporter:Lu Zhang, Xingshang Zhu, BaoXiang Zhao, Jing Zhao, ... JunYing Miao
Vascular Pharmacology (February–March 2008) Volume 48(Issues 2–3) pp:63-69
Publication Date(Web):1 February 2008
DOI:10.1016/j.vph.2007.11.007
A new derivative of isochroman, 7-(isopropoxymethyl)-5-phenyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromene (ISO-9), was synthesized in our laboratory. In this study, we investigated the effect of ISO-9 on the apoptosis induced by deprivation of serum and fibroblast growth factor-2 (FGF-2) in human umbilical vein vascular endothelial cells (HUVECs). The results of MTT assay showed that 40 µM ISO-9 prevented the reduction of cell viability induced by the deprivation of serum and FGF-2 at 24 h or 48 h, respectively. To further study the correlated mechanism, the levels of integrin β4, p53 and reactive oxygen species (ROS) were analyzed. The results showed that the high levels of integrin β4, p53 and ROS induced by the deprivation of serum and FGF-2 could be inhibited by the treatment of 40 µM ISO-9. The data suggested that ISO-9 was a promising anti-apoptotic agent and could be served as a useful tool to study the molecular mechanism of apoptosis in vascular endothelial cells (VECs).
Co-reporter:Wen-Li Wu, Xuan Zhao, Long-Long Xi, Miao-Fei Huang, Wen-Hui Zeng, Jun-Ying Miao, Bao-Xiang Zhao
Analytica Chimica Acta (15 January 2017) Volume 950() pp:
Publication Date(Web):15 January 2017
DOI:10.1016/j.aca.2016.11.019
•A colorimetric and ratiometric fluorescent probe CPBT for hypochlorite was developed.•CPBT can target mitochondria of cells.•CPBT was designed based on FRET mechanism and displayed larger gap between two emission peaks.•CPBT was applied to detect exogenous and endogenous hypochlorite in living RAW264.7 cells.A mitochondria-targeted fluorescence probe (CPBT) for ratiometric detection of endogenous hypochlorite in the living cells was developed. CPBT could detect hypochlorite with high selectivity and sensitivity in a ratiometric manner based on FRET mechanism. In absence of hypochlorite, when CPBT was excited with absorption maximum wavelength of the donor moiety, it showed the emission of acceptor moiety because of FRET process. However, in the presence of hypochlorite, the reaction of CC double bond with hypochlorite interrupted the conjugation system resulting in the inhibition of FRET process and the emission of the donor moiety. The two well-resolved emission bands can ensure accurate detection of hypochlorite. A good linear relationship between the fluorescence intensity ratios of the two emissions and the ClO− concentrations in the range from 41.8 nM (detection limit) to 12.5 μM was established. Importantly, CPBT could localize mainly in the mitochondria of RAW264.7 cells. CPBT was successfully used to fluorescence ratiometric imaging of endogenous hypochlorite in RAW264.7 cells.
Co-reporter:Shi-Li Shen, Xuan Zhao, Xiao-Fan Zhang, Xuan-Li Liu, Hao Wang, Yi-Ying Dai, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2017 - vol. 5(Issue 2) pp:NaN295-295
Publication Date(Web):2016/11/23
DOI:10.1039/C6TB01992G
A novel ratiometric probe (RCP) for −OCl was developed based on the fluorescence resonance energy transfer (FRET) platform. The probe was constructed by integrating the coumarin moiety (FRET donor) with the rhodamine moiety (FRET acceptor). Upon treatment with −OCl, the coumarin emission at 483 nm decreased and the rhodamine emission at 570 nm increased, enabling the probe to provide accurate detection of −OCl (in the concentration range of 0–50 μM). The probe exhibited brilliant selectivity and sensitivity, rapid response and low cytotoxicity. More importantly, the introduction of the quaternized pyridine moiety can not only manage to increase the solubility, but also achieve mitochondria-targeting. The probe was applied successfully to imaging endogenous −OCl in mitochondria, highlighting its potential applications in bioanalysis.
Co-reporter:Dong-Peng Li, Zhao-Yang Wang, Hao Su, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2017 - vol. 53(Issue 3) pp:NaN580-580
Publication Date(Web):2016/12/02
DOI:10.1039/C6CC06459K
Probe L-HF1, which featured large (pseudo) Stokes shifts and high FRET efficiency, was designed on a new ESIPT enhanced FRET platform for the detection of HSO3−/SO32−. L-HF1 could detect endogenous bisulfite in HepG2 cells but not in L-02 cells, implying the different bisulfite levels in normal and cancer cells of liver.
Co-reporter:Dong-Peng Li, Zhao-Yang Wang, Xiang-Jian Cao, Jie Cui, Xin Wang, Hao-Zhong Cui, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2016 - vol. 52(Issue 13) pp:NaN2763-2763
Publication Date(Web):2016/01/05
DOI:10.1039/C5CC09092J
A new mitochondria-targeted fluorescent probe HCy-D, constructed by dansyl and hemicyanine fluorophores, for SO2 derivatives (HSO3−/SO32−) was presented. This probe was designed based on a new FRET platform. HCy-D showed a ratiometric, sensitive and rapid response to HSO3−/SO32−. Importantly, HCy-D was successfully used for fluorescence imaging of endogenous bisulfite in HepG2 cells, which may benefit cancer diagnosis by discriminating liver cancer cells from normal liver cells.
Co-reporter:Xiao Feng, Tao Zhang, Jin-Ting Liu, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2016 - vol. 52(Issue 15) pp:NaN3134-3134
Publication Date(Web):2016/01/19
DOI:10.1039/C5CC09267A
We have developed a new ratiometric fluorescent probe composed of a coumarin–merocyanine dyad based on the FRET mechanism. The probe showed clear dual-emission signal changes in blue and red spectral windows upon addition of H2S in a dose dependent manner under a single wavelength excitation. The probe targeted mitochondria with high selectivity and sensitivity toward H2S.
Co-reporter:Shi-Li Shen, Xin-Peng Chen, Xiao-Fan Zhang, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2015 - vol. 3(Issue 5) pp:NaN925-925
Publication Date(Web):2014/11/21
DOI:10.1039/C4TB01763C
A novel rhodamine B-based fluorescent probe (RML) for lysosomal pH was developed by integrating a 4-(2-aminoethyl)morpholine moiety, which is a lysosome-targetable group, into a rhodamine B fluorophore, which is associated with rhodamine B dyes possessing spirocyclic (non-fluorescent) and ring-opening (fluorescent) forms with response to pH. The probe responded to acidic pH at low concentration in a short amount of time. In addition, RML showed good membrane permeability and brilliant selectivity among various amino acids and metal cations. RML exhibited an 80-fold increase in fluorescence intensity at 583 nm throughout the pH range of 7.40–4.00 with a pKa of 5.16, which indicates that RML is valuable for studying intracellular acidic organelles. Moreover, RML has been successfully applied in HeLa cells, and the results demonstrated that RML could selectively stain lysosomes in living HeLa cells. Note that RML could be used to detect the pH increase in lysosomes induced by bafilomycin A1 within HeLa cells.
Co-reporter:Fang-Wu Wang, Sheng-Qing Wang, Bao-Xiang Zhao and Jun-Ying Miao
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 19) pp:NaN3070-3070
Publication Date(Web):2014/02/26
DOI:10.1039/C3OB42429D
A series of 2′-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 2–7 possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.
Co-reporter:Zhe Zhang, Fang-Wu Wang, Sheng-Qing Wang, Fei Ge, Bao-Xiang Zhao and Jun-Ying Miao
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 43) pp:NaN8644-8644
Publication Date(Web):2012/09/12
DOI:10.1039/C2OB26375K
We develop a pyrazoline-based fluorescent sensor for biological Zn2+ detection. The sensor shows good binding selectivity for Zn2+ over competing metal with 40-fold fluorescence enhancement in response to Zn2+. The new probe is cell-permeable and can be used to detect intracellular zinc ions in living neuron cells.
Co-reporter:Xiao-Fan Zhang, Tao Zhang, Shi-Li Shen, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2015 - vol. 3(Issue 16) pp:NaN3266-3266
Publication Date(Web):2015/03/04
DOI:10.1039/C4TB02082K
In this study, a novel ratiometric pH probe RNL based on fluorescence resonance energy transfer (FRET) was well developed. It was fabricated by integrating the naphthalimide moiety as an FRET donor with the rhodamine moiety as an FRET acceptor. Meanwhile, 4-(2-aminoethyl)morpholine, which was a lysosome-locating group, was introduced. The sensing mechanism was the integration of PET and FRET processes and the comprehensive effect led to the simultaneous intensity enhancement of naphthalimide and rhodamine along with the pH value decrease. With a pKa of 4.82, the fluorescence intensity ratio (I529/I580) of the probe changed significantly within the pH range from 4.50 to 5.50. The probe showed excellent selectivity among various metal cations, amino acids and ATP. Moreover, RNL has been successfully applied in HeLa cells, and the results demonstrated that it could be used to detect lysosomal pH changes. The probe could also selectively stain lysosome in HeLa cells. Besides, the probe exhibited low cytotoxicity and satisfactory photostability in living HeLa cells.
Co-reporter:Xuan-Xuan Zhao, Jin-Feng Zhang, Wei Liu, Shuai Zhou, Ze-Quan Zhou, Yu-Hao Xiao, Gang Xi, Jun-Ying Miao and Bao-Xiang Zhao
Journal of Materials Chemistry A 2014 - vol. 2(Issue 42) pp:NaN7350-7350
Publication Date(Web):2014/09/08
DOI:10.1039/C4TB01192A
We developed a new dansyl phthalimide-based fluorescent chemosensor for hydrazine detection. Upon a Gabriel type-based hydrazinolysis of dansyl phthalimide (DPI) in the presence of hydrazine in a mixture of HEPES buffer (pH 7.0, 20 mM) and DMSO (1/9, v/v) at room temperature, the chemosensor produces fluorescent dansyl-NH2 with the maximum emission wavelength changed from 475 nm to 512 nm along with a color change from yellow to colorless, allowing colorimetric detection of hydrazine by the naked eye. DPI can selectively detect hydrazine over other environmentally abundant ions. Moreover, DPI coated with silica gel TLC plates could act as a visual and fluorimetric probe for hydrazine vapor at a partial pressure of 5.5 × 10−3 mm Hg over other potentially interfering volatile analytes, including hydrogen peroxide, ethylenediamine, urea, ammonium hydroxide and methylamine. DPI can also be used for the detection of hydrazine in water samples and HeLa cells without appreciable interference from other biologically abundant analytes. The limit of detection is 6.01 ppb (1.88 × 10−7 M), which is well below the accepted limit (10 ppb) for hydrazine set by the U.S. Environmental Protection Agency (EPA).
Co-reporter:Yan-Ru Zhang, Xin-Peng Chen, Jing-Shao, Jia-Yi Zhang, Qiong Yuan, Jun-Ying Miao and Bao-Xiang Zhao
Chemical Communications 2014 - vol. 50(Issue 91) pp:NaN14244-14244
Publication Date(Web):2014/09/25
DOI:10.1039/C4CC05976J
We developed a ratiometric fluorescent probe for sensing HOCl based on coumarin and rhodamine acid that is directly used as a detection moiety. The probe shows high selectivity and sensitivity toward HOCl under best working conditions of myeloperoxidase by which HOCl can be generated from hydrogen peroxide and chloride.
