Long Yi

A new H2S-specific near-infrared fluorescence-enhanced probe that can visualize the H2S level in colorectal cancer cells in mice

Co-reporter:Kun Zhang;Jie Zhang;Zhen Xi;Lu-Yuan Li;Xiangxiang Gu;Qiang-Zhe Zhang

Chemical Science (2010-Present) 2017 vol. 8(Issue 4) pp:2776-2781

Publication Date(Web):2017/03/28

DOI:10.1039/C6SC05646F

Near-infrared (NIR) fluorescence-based sensors capable of selective detection of H2S in vivo would be useful tools to understand the mechanisms of diseases. A new NIR fluorescence probe 1 was developed for the detection of endogenous H2S in colorectal cancer cells in mice. 1 displayed an 87-fold fluorescence enhancement at 796 nm (with excitation at 730 nm) when reacted with H2S in a buffer (pH 7.4). 1 was water-soluble, cell-membrane-permeable, had low cytotoxicity and high selectivity and sensitivity for H2S. The properties of 1 enable its use in monitoring endogenous H2S in living cells, tissues, and mice. The bioimaging results indicated that (1) D-Cys could induce endogenous H2S production in living cells and stimulate angiogenesis; (2) tail intravenous injection of 1 into mice generated strong fluorescence in the liver while intraperitoneal injection of D-Cys could further enhance fluorescence in the liver in vivo; (3) importantly, endogenous H2S in colorectal cancer cells (HCT116, HT29) in vitro and in murine tumor models could be quickly and selectively detected by intratumoral injection of 1. These results indicated that our new probe could serve as an efficient tool for the detection of cellular H2S in living animals and even for cancer diagnosis.

Thiolysis of NBD-based dyes for colorimetric and fluorescence detection of H2S and biothiols: design and biological applications

Co-reporter:Long Yi;Zhen Xi

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 18) pp:3828-3839

Publication Date(Web):2017/05/10

DOI:10.1039/C7OB00332C

Hydrogen sulfide (H2S) is an important endogenous signaling molecule with multiple biological functions. The development of colorimetric and fluorescent probes for the visualization of H2S is useful for studying H2S biology. This review details up-to-date research on H2S probes based on thiolysis reactions of NBD (7-nitro-1,2,3-benzoxadiazole) amines or ethers (thioethers). The reactivity and selectivity of NBD-based dyes are discussed. The design principles of NBD-based probes are highlighted. The advantages and disadvantages of NBD-based probes are compared, and their biological applications are discussed.

Design and synthesis of NBD-S-dye dyads for fluorescently discriminative detection of biothiols and Cys/Hcy

Co-reporter:Changyu Zhang, Shuai Wu, Zhen Xi, Long Yi

Tetrahedron 2017 Volume 73, Issue 47(Issue 47) pp:

Publication Date(Web):23 November 2017

DOI:10.1016/j.tet.2017.10.020

Based on thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) thioether, we designed and synthesized fast-response fluorescent probes for discriminative detection of biothiols and Cys/Hcy. Probes treated with GSH/H2S could only release one emission; while reactions with Cys/Hcy generated two. Compared with probe 1, probe 2 exhibited good stability and high sensitivity toward Cys/Hcy in PBS buffer. Moreover, 2 could eliminate the effect of probe consumption by GSH/H2S when used to selectively detect Cys/Hcy and was applied for selective bioimaging of Cys in living mammalian cells successfully.Thiolysis of the NBD thioether was employed to develop highly sensitive and selective fluorescent probes for discriminative detection of biothiols and Cys/Hcy. The probe could eliminate the effect of probe consuption by GSH when used to detect Cys in PBS buffer and in living cells.Download high-res image (127KB)Download full-size image

Design and synthesis of near-infrared fluorescence-enhancement probes for the cancer-specific enzyme hNQO1

Co-reporter:Changyu Zhang, Bei-Bei Zhai, Tao Peng, Zelin Zhong, Lianbin Xu, Qiang-Zhe Zhang, Lu-Yuan Li, Long Yi, Zhen Xi

Dyes and Pigments 2017 Volume 143(Volume 143) pp:

Publication Date(Web):1 August 2017

DOI:10.1016/j.dyepig.2017.04.043

Near-infrared (NIR) fluorescence-based sensors capable of selective detection of cancer biomarkers in vivo would be useful tools for early cancer detection. Two new NIR fluorescent probes were developed for detection of cancer-specific enzyme hNQO1 in colorectal cancer cells (HT29) in mice. Probe 1 was based on cleavage of ester and intramolecular charge transfer (ICT) effect, which showed fast-response property toward hNQO1 for real-time enzymatic assay in vitro. Probe 2 was based on cleavage of amide and photo-induced energy transfer (PET) effect, which was stable, cell-membrance-permeable, low cytotoxic, and highly selective and sensitive for hNQO1. The properties of 2 enabled its use in differentiating hNQO1-positive HT29 cancer cells and hNQO1-negative human breast cancer cells in vitro and bioimaging of HT29 cells in living mice, implying that our new probe could serve as potentially efficient tools for detection of endogenous hNQO1 in living animals.Two new near-infrared fluorescent-enhanced probes 1 and 2 were developed for detection of hNQO1 activity in vitro and in mice. 2 was successfully used in differentiating hNQO1-positive HT29 cancer cells and hNQO1-negative human breast cancer cells in vitro and bioimaging of HT29 cells in living mice.Download high-res image (148KB)Download full-size image

o,o-Difluorination of aromatic azide yields a fast-response fluorescent probe for H2S detection and for improved bioorthogonal reactions

Co-reporter:Jie Zhang;Yasi Gao;Xueying Kang;Zhentao Zhu;Zhiqian Wang;Zhen Xi

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 19) pp:4212-4217

Publication Date(Web):2017/05/16

DOI:10.1039/C7OB00830A

The development of efficient bioorthogonal reactions for sensing of endogenous biomolecules and for bioconjugation should be of paramount importance in the field of chemical biology. In this work, the o,o′-difluorinated aromatic azide was firstly employed to develop a new fast-response fluorescent probe 1 for H2S detection and for bioorthogonal reactions. Compared with non- and mono-fluorinated probes, 1 showed faster reaction toward H2S, the third gasotransmitter, in buffer (pH 7.4), implying that the reaction rate could be enhanced by the dual-fluorine groups. Furthermore, such enhanced reaction rates of 1 were also observed in the Staudinger reaction and strain-promoted azide–alkyne cycloaddition (SPAAC) based on the comparison studies of the non-fluorinated probe. Our results firstly highlight that the o,o′-difluorinated aromatic azide group should be useful for fast bioorthogonal reactions and H2S detection.

Synthesis and characterizations of a highly sensitive and selective fluorescent probe for hydrogen sulfide

Co-reporter:Yan Huang, Changyu Zhang, Zhen Xi, Long Yi

Tetrahedron Letters 2016 Volume 57(Issue 10) pp:1187-1191

Publication Date(Web):9 March 2016

DOI:10.1016/j.tetlet.2016.02.017

Hydrogen sulfide (H2S) is an important endogenous signaling molecule with a variety of biological functions. To detect H2S in living biological systems, herein we developed a new fluorescent probe for highly sensitive and selective sensing of H2S in cells. The probe is based on coumarin–triazole as the fluorophore and thiolysis of the NBD (7-nitro-1,2,3-benzoxadiazole) amine as the receptor. Bioimaging experiments indicated that this probe could be used to monitor H2O2-induced H2S biosynthesis in yeast cells. Our results show that such thiolysis of the NBD amine can be used for the development of fluorescent H2S probes.Thiolysis of the NBD amine was employed for the development of a highly sensitive and selective fluorescent H2S probe, which could be used to detect H2S in buffer and in cells.

Dual-Reactable Fluorescent Probes for Highly Selective and Sensitive Detection of Biological H2S

Co-reporter:Chao Wei;Runyu Wang;Changyu Zhang;Guoce Xu;Yanyan Li;Qiang-Zhe Zhang;Dr. Lu-Yuan Li;Dr. Long Yi;Dr. Zhen Xi

Chemistry – An Asian Journal 2016 Volume 11( Issue 9) pp:1376-1381

Publication Date(Web):

DOI:10.1002/asia.201600262

Abstract

Hydrogen sulfide (H₂S) is an important endogenous signaling molecule with a variety of biological functions. Development of fluorescent probes for highly selective and sensitive detection of H₂S is necessary. We show here that dual-reactable fluorescent H₂S probes could react with higher selectivity than single-reactable probes. One of the dual-reactable probes gives more than 4000-fold turn-on response when reacting with H₂S, the largest response among fluorescent H₂S probes reported thus far. In addition, the probe could be used for high-throughput enzymatic assays and for the detection of Cys-induced H₂S in cells and in zebrafish. These dual-reactable probes hold potential for highly selective and sensitive detection of H₂S in biological systems.

Fast-Response Turn-on Fluorescent Probes Based on Thiolysis of NBD Amine for H2S Bioimaging

Co-reporter:Runyu Wang;Zhifei Li;Changyu Zhang;Yanyan Li;Guoce Xu;Qiang-Zhe Zhang;Dr. Lu-Yuan Li;Dr. Zhen Xi

ChemBioChem 2016 Volume 17( Issue 10) pp:962-968

Publication Date(Web):

DOI:10.1002/cbic.201600060

Abstract

Hydrogen sulfide (H₂S) is an important endogenous signaling molecule with multiple biological functions. New selective fluorescent turn-on probes based on fast thiolyling of NBD (7-nitro-1,2,3-benzoxadiazole) amine were explored for sensing H₂S in aqueous buffer and in living cells. The syntheses of both probes are simple and quite straightforward. The probes are highly sensitive and selective toward H₂S over other biologically relevant species. The fluorescein-NBD-based probe showed 65-fold green fluorescent increase upon H₂S activation. The rhodamine-NBD-based probe reacted rapidly with H₂S (t_1/2≈1 min) to give a 4.5-fold increase in red fluorescence. Moreover, both probes were successfully used for monitoring H₂S in living cells and in mice. Based on such probe-based tools, we could observe H₂O₂-induced H₂S biogenesis in a concentration-dependent and time-dependent fashion in living cells.

A highly selective and fast-response fluorescent probe for visualization of enzymatic H2S production in vitro and in living cells

Co-reporter:Lv Wei, Zhentao Zhu, Yanyan Li, Long Yi and Zhen Xi

Chemical Communications 2015 vol. 51(Issue 52) pp:10463-10466

Publication Date(Web):19 May 2015

DOI:10.1039/C5CC03707G

An o-fluorinated-azido-capped rhodamine probe can react with H2S efficiently and selectively to give large off–on fluorescence enhancement. The probe was used to develop an assay for cystathionine β-synthase acitivity and for in situ visualization of endogenously produced H2S in living cells.

A FRET–ICT dual-quenching fluorescent probe with large off–on response for H2S: synthesis, spectra and bioimaging

Co-reporter:Changyu Zhang, Lv Wei, Chao Wei, Jie Zhang, Runyu Wang, Zhen Xi and Long Yi

Chemical Communications 2015 vol. 51(Issue 35) pp:7505-7508

Publication Date(Web):24 Mar 2015

DOI:10.1039/C5CC01184A

A FRET–ICT dual-quenching probe with large off–on fluorescent response upon H2S treatment is reported. The probe can be used for bioimaging of endogenous H2S in living cells.

A highly selective and sensitive fluorescent thiol probe through dual-reactive and dual-quenching groups

Co-reporter:Huatang Zhang, Changyu Zhang, Ruochuan Liu, Long Yi and Hongyan Sun

Chemical Communications 2015 vol. 51(Issue 11) pp:2029-2032

Publication Date(Web):21 Nov 2014

DOI:10.1039/C4CC08156K

A new fluorescent probe installed with dual-reactive and dual-quenching groups was rationally designed for highly selective and sensitive sensing of biothiols. The sensitivity of the probe toward thiols was significantly improved by dual-quenching effects. Furthermore the selectivity of the probe was also greatly enhanced by installation of dual-reactive groups.

Protein tetrazinylation via diazonium coupling for covalent and catalyst-free bioconjugation

Co-reporter:Jie Zhang, Yuwen Men, Shanshan Lv, Long Yi and Jian-Feng Chen

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 47) pp:11422-11425

Publication Date(Web):30 Oct 2015

DOI:10.1039/C5OB02053K

An efficient and bench-stable reagent was synthesized for direct and covalent introduction of tetrazines onto target protein or virus surfaces, which can be further modified based on tetrazine–ene ligation to achieve fluorescence labelling or PEGylation under mild conditions.

Rational design and synthesis of fast-response NBD-based fluorescent probes for biothiols

Co-reporter:Yuwen Men, Zhifei Li, Jie Zhang, Zizheng Tong, Zhen Xi, Xianbo Qiu, Long Yi

Tetrahedron Letters 2015 Volume 56(Issue 42) pp:5781-5786

Publication Date(Web):14 October 2015

DOI:10.1016/j.tetlet.2015.08.073

Small-molecule thiols are essential for maintaining the cellular redox homeostasis and play important roles in regulating various cellular functions. New reaction-based fluorescent turn-on probes based on fast thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole)ether were rationally designed for sensing of biothiols in physiological buffer and in cells. The blue-light-excited probes were based on a new developed excited-state intramolecular proton transfer (ESIPT) fluorophore. The combination use of ESIPT fluorophore and electron-withdrawing effect in the probe design led to fast-response fluorescent probes toward cysteine (Cys) with reaction rate (k2) up to 616.7 M−1 s−1. The probes were highly selective toward biothiols over other amino acids and could be used for bioimaging in cells.Fluorescent turn-on probes based on fast thiolysis of NBD ether were designed rationally and were explored for selective detection of biothiols.

New NBD-based fluorescent probes for biological thiols

Co-reporter:Zhentao Zhu, Wei Liu, Longhuai Cheng, Zhifei Li, Zhen Xi, Long Yi

Tetrahedron Letters 2015 Volume 56(Issue 25) pp:3909-3912

Publication Date(Web):17 June 2015

DOI:10.1016/j.tetlet.2015.04.117

Biothiols including cysteine (Cys), reduced glutathione (GSH), and hydrogen sulfide (H2S) play critical roles in living organisms. New reaction-based fluorescent turn-on probes based on fast thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) ether were explored for sensing of biothiols in aqueous buffer. The probes showed fast response toward biothiols with more than 100-fold off–on signal enhancement. Moreover, the probes were highly selective toward thiols over other amino acids and could be used for bioimaging in mammalian cells.Fluorescent turn-on probes based on fast thiolysis of NBD ether were explored for selective sensing of biothiols.

A FRET-based ratiometric fluorescent probe for visualizing H2S in lysosomes

Co-reporter:Jie Zhang, Runyu Wang, Zhentao Zhu, Long Yi, Zhen Xi

Tetrahedron 2015 Volume 71(Issue 45) pp:8572-8576

Publication Date(Web):11 November 2015

DOI:10.1016/j.tet.2015.09.028

Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. In order to detect the biological H2S, here a new FRET-based ratiomatric fluorescent probe was designed and synthesized for visualization of H2S in lysosomes. The probe displays good solubility, a marked yellow to blue emission color change in response of H2S and high H2S selectivity. Moreover, the probe could be used to detect of H2S in lysosomes with good biocompatibility.

A Dual-Response Fluorescent Probe Reveals the H2O2-Induced H2S Biogenesis through a Cystathionine -Synthase Pathway

Co-reporter:Dr. Long Yi;Lv Wei;Runyu Wang;Changyu Zhang;Jie Zhang;Dr. Tianwei Tan;Dr. Zhen Xi

Chemistry - A European Journal 2015 Volume 21( Issue 43) pp:15167-15172

Publication Date(Web):

DOI:10.1002/chem.201502832

Abstract

The two signaling molecules H₂S and H₂O₂ play key roles in maintaining intracellular redox homeostasis. The biological relationship between H₂O₂ and H₂S remains largely unknown in redox biology. In this study, we rationally designed and synthesized single- and dual-response fluorescent probes for detecting both H₂O₂ and H₂S in living cells. The dual-response probe was shown to be capable of mono- and dual-detection of H₂O₂ and H₂S selectively and sensitively. Detailed bioimaging studies based on the probes revealed that both exogenous and endogenous H₂O₂ could induce H₂S biogenesis in living cells. By using gene-knockdown techniques with bioimaging, the H₂S biogenesis was found to be majorly cystathionine β-synthase (CBS)-dependent. Our finding shows the first direct evidence on the biological communication between H₂O₂ (ROS) and H₂S (RSS) in vivo.

Self-assembled controllable virus-like nanorods as templates for construction of one-dimensional organic–inorganic nanocomposites

Co-reporter:Dejun Ma, Yonghui Xie, Jie Zhang, Di Ouyang, Long Yi and Zhen Xi

Chemical Communications 2014 vol. 50(Issue 98) pp:15581-15584

Publication Date(Web):27 Oct 2014

DOI:10.1039/C4CC07057G

Virus-like assemblies with controllable size and surface groups can be used as efficient templates for the controllable synthesis of CdS nanorods, which represents a new strategy for controllable preparation of one-dimensional (1D) organic–inorganic nanocomposites.

An efficient reagent for covalent introduction of alkynes into proteins

Co-reporter:Jie Zhang, Dejun Ma, Dawei Du, Zhen Xi and Long Yi

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 47) pp:9528-9531

Publication Date(Web):16 Oct 2014

DOI:10.1039/C4OB01873G

A cheap and bench-stable reagent was synthesized for direct and covalent introduction of alkynes into tyrosine of target proteins, which can be further modified based on click reaction to achieve fluorescence labelling or PEGylation. This reagent should be a generally useful toolbox for chemical biology and biomaterials.

NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide

Co-reporter:Chao Wei, Qing Zhu, Weiwei Liu, Wenbin Chen, Zhen Xi and Long Yi

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 3) pp:479-485

Publication Date(Web):29 Oct 2013

DOI:10.1039/C3OB41870G

Hydrogen sulfide (H2S) is an important endogenous signalling molecule and also an important environmental target for detection. New reaction-based colorimetric and fluorescent turn-on probes based on selective thiolyling of NBD (7-nitro-1,2,3-benzoxadiazole) ether were explored for sensing of H2S in aqueous buffer. The syntheses of both probes are simple and quite straightforward. The probes are highly sensitive and selective toward H2S over other biologically relevant species. Probe 1 can be used to directly visualize H2S by the naked eye and shows more than 1000-fold fluorescence increase upon reaction with H2S. Probe 2 is a near-infrared fluorescent sensor for H2S at physiological pH.

Terminal dual-labeling of a transcribed RNA

Co-reporter:Shibo Li, Dejun Ma, Long Yi, Shiyue Mei, Di Ouyang, Zhen Xi

Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 23) pp:6304-6306

Publication Date(Web):1 December 2013

DOI:10.1016/j.bmcl.2013.09.079

We report here a site-specific terminal dual-labeling strategy for a transcribed RNA. The combination of 5′-thiophosphoryl and 3′-amino functionalities enables efficient RNA dual labeling with different fluorophores at both 5′- and 3′-terminal positions specifically. This dual-labeling strategy is applied to pre-miRNA for construction of molecular beacons. The RNA beacons in their native hairpin formation bring the fluorophore and quencher groups into close proximity, leading to fluorescence quenching by FRET effect. Ribonuclease (dicer enzyme or micrococcal nuclease) can efficiently cleave RNA beacons leading to concentration- and time-dependent fluorescence increase. The dual-labeling strategy for transcribed RNAs involves only commercially available reagents, enzymes and native RNA, making it more accessible for general applications.

A FRET-based fluorescent probe for imaging H2S in living cells

Co-reporter:Chao Wei, Lv Wei, Zhen Xi, Long Yi

Tetrahedron Letters 2013 Volume 54(Issue 50) pp:6937-6939

Publication Date(Web):11 December 2013

DOI:10.1016/j.tetlet.2013.10.049

A FRET-based fluorescence probe was developed for selective detection of H2S in aqueous buffer and inside living cells. For this probe, the FRET probe could be cleaved by H2S, and the fluorescence of FRET donor is released. The probe is highly selective to H2S over other biologically relevant species to give color change for naked eye observation. Confocal imaging indicated that the probe could monitor intracellular H2S level changes.

A highly selective and fast-response fluorescent probe for visualization of enzymatic H2S production in vitro and in living cells

Co-reporter:Lv Wei, Zhentao Zhu, Yanyan Li, Long Yi and Zhen Xi

Chemical Communications 2015 - vol. 51(Issue 52) pp:NaN10466-10466

Publication Date(Web):2015/05/19

DOI:10.1039/C5CC03707G

An o-fluorinated-azido-capped rhodamine probe can react with H2S efficiently and selectively to give large off–on fluorescence enhancement. The probe was used to develop an assay for cystathionine β-synthase acitivity and for in situ visualization of endogenously produced H2S in living cells.

Protein tetrazinylation via diazonium coupling for covalent and catalyst-free bioconjugation

Co-reporter:Jie Zhang, Yuwen Men, Shanshan Lv, Long Yi and Jian-Feng Chen

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 47) pp:NaN11425-11425

Publication Date(Web):2015/10/30

DOI:10.1039/C5OB02053K

An efficient and bench-stable reagent was synthesized for direct and covalent introduction of tetrazines onto target protein or virus surfaces, which can be further modified based on tetrazine–ene ligation to achieve fluorescence labelling or PEGylation under mild conditions.

o,o-Difluorination of aromatic azide yields a fast-response fluorescent probe for H2S detection and for improved bioorthogonal reactions

Co-reporter:Jie Zhang, Yasi Gao, Xueying Kang, Zhentao Zhu, Zhiqian Wang, Zhen Xi and Long Yi

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 19) pp:NaN4217-4217

Publication Date(Web):2017/04/21

DOI:10.1039/C7OB00830A

The development of efficient bioorthogonal reactions for sensing of endogenous biomolecules and for bioconjugation should be of paramount importance in the field of chemical biology. In this work, the o,o′-difluorinated aromatic azide was firstly employed to develop a new fast-response fluorescent probe 1 for H2S detection and for bioorthogonal reactions. Compared with non- and mono-fluorinated probes, 1 showed faster reaction toward H2S, the third gasotransmitter, in buffer (pH 7.4), implying that the reaction rate could be enhanced by the dual-fluorine groups. Furthermore, such enhanced reaction rates of 1 were also observed in the Staudinger reaction and strain-promoted azide–alkyne cycloaddition (SPAAC) based on the comparison studies of the non-fluorinated probe. Our results firstly highlight that the o,o′-difluorinated aromatic azide group should be useful for fast bioorthogonal reactions and H2S detection.

Self-assembled controllable virus-like nanorods as templates for construction of one-dimensional organic–inorganic nanocomposites

Co-reporter:Dejun Ma, Yonghui Xie, Jie Zhang, Di Ouyang, Long Yi and Zhen Xi

Chemical Communications 2014 - vol. 50(Issue 98) pp:NaN15584-15584

Publication Date(Web):2014/10/27

DOI:10.1039/C4CC07057G

Virus-like assemblies with controllable size and surface groups can be used as efficient templates for the controllable synthesis of CdS nanorods, which represents a new strategy for controllable preparation of one-dimensional (1D) organic–inorganic nanocomposites.

A highly selective and sensitive fluorescent thiol probe through dual-reactive and dual-quenching groups

Co-reporter:Huatang Zhang, Changyu Zhang, Ruochuan Liu, Long Yi and Hongyan Sun

Chemical Communications 2015 - vol. 51(Issue 11) pp:NaN2032-2032

Publication Date(Web):2014/11/21

DOI:10.1039/C4CC08156K

A new fluorescent probe installed with dual-reactive and dual-quenching groups was rationally designed for highly selective and sensitive sensing of biothiols. The sensitivity of the probe toward thiols was significantly improved by dual-quenching effects. Furthermore the selectivity of the probe was also greatly enhanced by installation of dual-reactive groups.

NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide

Co-reporter:Chao Wei, Qing Zhu, Weiwei Liu, Wenbin Chen, Zhen Xi and Long Yi

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 3) pp:NaN485-485

Publication Date(Web):2013/10/29

DOI:10.1039/C3OB41870G

Hydrogen sulfide (H2S) is an important endogenous signalling molecule and also an important environmental target for detection. New reaction-based colorimetric and fluorescent turn-on probes based on selective thiolyling of NBD (7-nitro-1,2,3-benzoxadiazole) ether were explored for sensing of H2S in aqueous buffer. The syntheses of both probes are simple and quite straightforward. The probes are highly sensitive and selective toward H2S over other biologically relevant species. Probe 1 can be used to directly visualize H2S by the naked eye and shows more than 1000-fold fluorescence increase upon reaction with H2S. Probe 2 is a near-infrared fluorescent sensor for H2S at physiological pH.

A FRET–ICT dual-quenching fluorescent probe with large off–on response for H2S: synthesis, spectra and bioimaging

Co-reporter:Changyu Zhang, Lv Wei, Chao Wei, Jie Zhang, Runyu Wang, Zhen Xi and Long Yi

Chemical Communications 2015 - vol. 51(Issue 35) pp:NaN7508-7508

Publication Date(Web):2015/03/24

DOI:10.1039/C5CC01184A

A FRET–ICT dual-quenching probe with large off–on fluorescent response upon H2S treatment is reported. The probe can be used for bioimaging of endogenous H2S in living cells.

An efficient reagent for covalent introduction of alkynes into proteins

Co-reporter:Jie Zhang, Dejun Ma, Dawei Du, Zhen Xi and Long Yi

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 47) pp:NaN9531-9531

Publication Date(Web):2014/10/16

DOI:10.1039/C4OB01873G

A cheap and bench-stable reagent was synthesized for direct and covalent introduction of alkynes into tyrosine of target proteins, which can be further modified based on click reaction to achieve fluorescence labelling or PEGylation. This reagent should be a generally useful toolbox for chemical biology and biomaterials.

Thiolysis of NBD-based dyes for colorimetric and fluorescence detection of H2S and biothiols: design and biological applications

Co-reporter:Long Yi and Zhen Xi

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 18) pp:NaN3839-3839

Publication Date(Web):2017/03/21

DOI:10.1039/C7OB00332C

Hydrogen sulfide (H2S) is an important endogenous signaling molecule with multiple biological functions. The development of colorimetric and fluorescent probes for the visualization of H2S is useful for studying H2S biology. This review details up-to-date research on H2S probes based on thiolysis reactions of NBD (7-nitro-1,2,3-benzoxadiazole) amines or ethers (thioethers). The reactivity and selectivity of NBD-based dyes are discussed. The design principles of NBD-based probes are highlighted. The advantages and disadvantages of NBD-based probes are compared, and their biological applications are discussed.

A new H2S-specific near-infrared fluorescence-enhanced probe that can visualize the H2S level in colorectal cancer cells in mice

Co-reporter:Kun Zhang, Jie Zhang, Zhen Xi, Lu-Yuan Li, Xiangxiang Gu, Qiang-Zhe Zhang and Long Yi

Chemical Science (2010-Present) 2017 - vol. 8(Issue 4) pp:NaN2781-2781

Publication Date(Web):2017/01/17

DOI:10.1039/C6SC05646F

Near-infrared (NIR) fluorescence-based sensors capable of selective detection of H2S in vivo would be useful tools to understand the mechanisms of diseases. A new NIR fluorescence probe 1 was developed for the detection of endogenous H2S in colorectal cancer cells in mice. 1 displayed an 87-fold fluorescence enhancement at 796 nm (with excitation at 730 nm) when reacted with H2S in a buffer (pH 7.4). 1 was water-soluble, cell-membrane-permeable, had low cytotoxicity and high selectivity and sensitivity for H2S. The properties of 1 enable its use in monitoring endogenous H2S in living cells, tissues, and mice. The bioimaging results indicated that (1) D-Cys could induce endogenous H2S production in living cells and stimulate angiogenesis; (2) tail intravenous injection of 1 into mice generated strong fluorescence in the liver while intraperitoneal injection of D-Cys could further enhance fluorescence in the liver in vivo; (3) importantly, endogenous H2S in colorectal cancer cells (HCT116, HT29) in vitro and in murine tumor models could be quickly and selectively detected by intratumoral injection of 1. These results indicated that our new probe could serve as an efficient tool for the detection of cellular H2S in living animals and even for cancer diagnosis.

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Abstract