Guo-Rong Chen

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Name: 陈国荣; Chen, GuoRong

Organization: East China University of Science and Technology , China

Department: Key Laboratory for Advanced Materials & Institute of Fine Chemicals

Title: Professor(PhD)

Chemicals
References

‘Pungent’ Copper Surface Resists Acid Corrosion in Strong HCl Solutions

Co-reporter:Liang Cai;Qing Fu;Rongwei Shi;Guixia Liu;Yi-Tao Long;Yun Tang;Xiao-Peng He;Yu Jin;Kaixian Chen

Industrial & Engineering Chemistry Research January 8, 2014 Volume 53(Issue 1) pp:64-69

Publication Date(Web):Publication Date (Web): December 16, 2013

DOI:10.1021/ie402609g

Extensive efforts have been devoted to the qualification of plant extracts as green corrosion inhibitors for industrial metals, but studies that demonstrate the active component(s) of these extracts remain scarce. We report here that piperine, the major pungent component of peppers, has the best corrosion inhibitive efficiency for copper in HCl among four analogous amide alkaloids isolated from a traditional Chinese medicine. This compound inhibited HCl corrosion more efficiently than cysteine, and did not exhibit markedly decreased efficiency under several harsh experimental conditions. Electrochemical and microscopic analyses suggested that piperine could form a protective layer on the metal surface via both physisorption and chemisorption, reducing the corrosion rate. The adsorption energies of all the test compounds were calculated using a hybrid density functional theory.

Fluorescent glycoprobes: a sweet addition for improved sensing

Co-reporter:Xiao-Peng He;Yi Zang;Tony D. James;Jia Li;Juan Xie

Chemical Communications 2017 vol. 53(Issue 1) pp:82-90

Publication Date(Web):2016/12/20

DOI:10.1039/C6CC06875H

The development of small-molecule fluorescent probes for the detection of ions and biomacromolecules and for cellular and in vivo imaging has been a very active research area. Nevertheless, many problems exist for traditional probes including their poor water solubility, toxicity and the inability to target specific tissues. Because of the enhanced water solubility, biocompatibility and targeting ability for specific cells, there has been an emerging movement to use carbohydrates as either the backbone or as a warhead to decorate conventional fluorescent probes, producing “glycoprobes” with enhanced properties. This feature article provides an overview of recently developed glycoprobes for ion and protein detection as well as targeted (receptor targeting) cellular imaging and theranostics. Here, we summarise the tactics for preparing small molecular glycoprobes and their supramolecular 2D material composites.

Probing Mannose-Binding Proteins That Express on Live Cells and Pathogens with a Diffusion-to-Surface Ratiometric Graphene Electrosensor

Co-reporter:Donghao Xie, Xue-Qing Feng, Xi-Le Hu, Lin Liu, Zhihong Ye, Jun Cao, Guo-Rong Chen, Xiao-Peng He, and Yi-Tao Long

ACS Applied Materials & Interfaces 2016 Volume 8(Issue 38) pp:25137

Publication Date(Web):September 2, 2016

DOI:10.1021/acsami.6b08566

This paper describes the development of a “diffusion-to-surface” ratiometric graphene electrosensor for the selective detection of live cells and pathogens that highly express mannose-binding proteins (MBPs). MBPs have been implicated in many pathological processes and are identified on specific types of bacteria. Consequently, MBPs are a promising biomarker for targeted disease diagnosis and therapy. Here, we develop a unique electrosensor that features a ratiometric voltammetric signal for the selective probing of MBPs. Self-assembly of mannosyl anthraquinone (AQ) to a graphene oxide-decorated screen-printed electrode produces the sensor with an inherent surface-controlled voltammetric signal. Subsequently, addition of a redox probe (RP) imparts the system with a diffusion-controlled current, thus enabling a ratiometric sensing rationale for which AQ serves as a reference. While the reference current is hardly compromised by adding analytes, RP exhibits a concentration-dependent current quenching on addition of mannose-selective lectins over other proteins. Importantly, this ratiometric electrosensor has proven to be applicable for the ratiometric probing of alternatively activated macrophages and a Gram-negative bacterium highly expressing MBPs, but shows minimal response to a series of control live cells and bacteria without mannose receptor expression.Keywords: anthraquinone; bacteria; cell; electrochemistry; graphene; sensor

Supramolecular Ensembles Formed between Charged Conjugated Polymers and Glycoprobes for the Fluorogenic Recognition of Receptor Proteins

Co-reporter:Wei-Tao Dou, Ya-Li Zeng, Ying Lv, Jiatao Wu, Xiao-Peng He, Guo-Rong Chen, and Chunyan Tan

ACS Applied Materials & Interfaces 2016 Volume 8(Issue 21) pp:13601-13606

Publication Date(Web):May 9, 2016

DOI:10.1021/acsami.6b03223

This paper describes the simple construction of a unique class of supramolecular ensembles formed by electrostatic self-assembly between charged conjugated polymers and fluorophore-coupled glycoligands (glycoprobes) for the selective fluorogenic detection of receptor proteins at both the molecular and cellular levels. We show that positively and negatively charged diazobenzene-containing poly(p-phenylethynylenes) (PPEs) can be used to form stable fluorogenic probes with fluorescein-based (negatively charged) and rhodamine B based (positively charged) glycoprobes by electrostatic interaction. The structures of the ensembles have been characterized by spectroscopic and microscopic techniques. The supramolecular probes formed show quenched fluorescence in an aqueous buffer solution, which can be specifically recovered, in a concentration-dependent manner, through competitive complexation with a selective protein receptor, over a range of other unselective proteins. The ensembles also show selective fluorescence enhancement with a live cell that expresses the glycoligand receptor but not a control cell without receptor expression.

Carbohydrate CuAAC click chemistry for therapy and diagnosis

Co-reporter:Xiao-Peng He, Ya-Li Zeng, Yi Zang, Jia Li, Robert A. Field, Guo-Rong Chen

Carbohydrate Research 2016 Volume 429() pp:1-22

Publication Date(Web):24 June 2016

DOI:10.1016/j.carres.2016.03.022

Carbohydrates are important as signaling molecules and for cellular recognition events, therefore offering scope for the development of carbohydrate-mimetic diagnostics and drug candidates. As a consequence, the construction of carbohydrate-based bioactive compounds and sensors has become an active research area. While the advent of click chemistry has greatly accelerated the progress of medicinal chemistry and chemical biology, recent literature has seen an extensive use of such approaches to construct functionally diverse carbohydrate derivatives. Here we summarize some of the progress, covering the period 2010 to mid-2015, in CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition CuAAC “click chemistry” of carbohydrate derivatives, in the context of potential therapeutic and diagnostic tool development.Figure optionsDownload full-size imageDownload as PowerPoint slideWe summarize the impressive progress since 2010 made in CuAAC-based carbohydrate click chemistry for therapy and diagnosis.

Probing disease-related proteins with fluorogenic composite materials

Co-reporter:Xiao-Peng He, Yi Zang, Tony D. James, Jia Li and Guo-Rong Chen

Chemical Society Reviews 2015 vol. 44(Issue 13) pp:4239-4248

Publication Date(Web):04 Dec 2014

DOI:10.1039/C4CS00252K

Construction of composite materials based on the self-assembly of fluorescently labeled biomolecules with a variety of micro- or nano-quenching materials (by the Förster Resonance Energy Transfer mechanism) for the fluorogenic recognition of disease-related proteins has become a dynamic research topic in the field of fluorescence recognition. Here we summarize the recent progress on the composition of fluorescence dye-labeled biomolecules including sugars, peptides and nucleotides with organic (graphene and carbon nanotubes) and inorganic (gold nanoparticles) materials. Their application in the fluorescence detection of proteins and enzymes on both the molecular and cellular levels is discussed. Perspectives are proposed with respect to the future directions of employing these composite materials in the recognition of pathological proteins.

An insight into graphene oxide associated fluorogenic sensing of glycodye–lectin interactions

Co-reporter:Ding-Kun Ji, Yue Zhang, Xiao-Peng He and Guo-Rong Chen

Journal of Materials Chemistry A 2015 vol. 3(Issue 32) pp:6656-6661

Publication Date(Web):15 Jul 2015

DOI:10.1039/C5TB01162K

Recently, there has been increasing interest in the construction of graphene oxide (GO) based fluorogenic composite materials (FCMs) for the detection of ligand–protein recognitions, which modulate numerous physiological and pathological processes in nature. In the sensing systems developed, GO has been used as a platform to assemble, and thus quench the fluorescence of dye-labelled ligands for the fluorogenic (fluorescence off–on) detection of proteins through the competitive formation of ligand–protein complexes, disassembling the GO composite. Here we show that the size, structure and loading concentration of GO may largely impact the sensing performance of GO-based FCMs. We synthesized four glycodyes that incorporate diverse natural glycoligands (as recognition groups) coupled with fluorescent dyes (as both the graphene binding and signal reporting group) with different emission wavelengths for comparison with GOs with different sizes. We determined that with the increase of size, the quenching ability of GO for the glycodyes increased, whereas the GO with a moderate size showed the best sensing performance for lectins (proteins that recognize glycoligands). The plausible mechanism of action was proposed. This research suggests that judicious quality control of GO is crucial for the construction of GO-based FCMs as biosensors.

“Clicked” galactosyl anthraquinone on graphene electrodes for the label-free impedance detection of live cancer cells

Co-reporter:Lei Cui, Bi-Wen Zhu, Song Qu, Xiao-Peng He, Guo-Rong Chen

Dyes and Pigments 2015 Volume 121() pp:312-315

Publication Date(Web):October 2015

DOI:10.1016/j.dyepig.2015.05.034

•Anthraquinonyl galactoside (AG) was synthesized by CuAAC.•AG could self-assemble to a graphene electrode for impedance detection of lectins.•AG@graphene electrode could probe receptor-rich cancer cells in a label-free manner.•Knockdown of the receptor led to decreased detection signal.Detection of live cells has been difficult with conventional biochemical techniques that require the lysis of cells to release a biomarker. This study describes the simple construction of a galactosyl anthraquinone dye for the label-free impedance detection of live cancer cells. A click dipolar reaction of an alkynyl anthraquinone with azido galactoside yields the anthraquinone probe which can be subsequently employed to bind to a graphene-coated screen printed electrode by self-assembly. By taking advantage of selective sugar-receptor recognitions, live cancer cells without being labeled, can be captured by the electrode, producing a sensitive impedance signal. Knockdown of the receptor leads to a sharp decrease of the impedance signal, suggesting the suitability of the electrode system for the direct live cell capture based on ligand-receptor recognitions.

Ratiometric glyco-probe for transient determination of thiophenol in full aqueous solution and river water

Co-reporter:Kai-Bin Li, Dan Zhou, Xiao-Peng He, Guo-Rong Chen

Dyes and Pigments 2015 Volume 116() pp:52-57

Publication Date(Web):May 2015

DOI:10.1016/j.dyepig.2015.01.013

•Glyco-naphthalimide probe is developed for thiolphenol (Tp).•The probe shows ratiometric response to Tp.•The detection is transient in full aqueous solution.•Tp in real river water samples can be accurately quantified.Although being widely used in organic synthesis, thiophenol (Tp) is toxic to the human body. We report here the preparation of a ratiometric fluorescence probe for the selective, transient determination of Tp in full aqueous solution. The probe was synthesized by a click reaction coupling between an alkynyl naphthalimide-dansyl dyad and an azido galactoside which increases the water solubility. Fluorescence spectroscopic analyses showed that the probe had a specific ratiometric response to Tp transiently in a full aqueous solution, over a range of other species. The probe has also proven suitable for the quantification of Tp in environmental water samples, and possesses superior properties to previous Tp fluorescence probes in terms of water solubility and sensitivity.

Recent progress in quantum dot based sensors

Co-reporter:Lei Cui, Xiao-Peng He and Guo-Rong Chen

RSC Advances 2015 vol. 5(Issue 34) pp:26644-26653

Publication Date(Web):06 Mar 2015

DOI:10.1039/C5RA01950H

This review summarizes the recent progress in quantum dot (QD) based sensors used for the photoluminescent detection of a variety of species in vitro and in vivo. New trends in using these nanomaterials for sensing applications are highlighted.

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

Co-reporter:Kai-Bin Li, Huan Wang, Yi Zang, Xiao-Peng He, Jia Li, Guo-Rong Chen, and He Tian

ACS Applied Materials & Interfaces 2014 Volume 6(Issue 22) pp:19600

Publication Date(Web):November 7, 2014

DOI:10.1021/am505435s

This study describes the exploitation of click chemistry in the one-step molecular engineering of an unqualified rhodamine probe, leading to its considerable functional enhancement in terms of water solubility, ion selectivity, and usefulness in detecting biological and environmental samples. A dipropargyl rhodamine dye previously identified as an unselective and poorly water-soluble mercury(II) probe was used to couple with an azido polyethylene glycol (PEG) by the Cu(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition click reaction in almost quantitative yield. The simple click-engineered rhodamine probe shows, remarkably, better water solubility and mercury(II) selectivity comparing to the raw counterpart, and can be used to sensitively image mercury ions internalized by live cells and to accurately quantify the ion spiked in river water specimens. This study provides insights into the simple functional improvement of unqualified molecular dye probes via the efficient “click engineering”.Keywords: cell imaging; click chemistry; PEG; probe; rhodamine; triazole

Fluorogenic supramolecular complexes formed between pyrenyl-β-cyclodextrin and glyco-rhodamine for the selective detection of lectins

Co-reporter:Xiao-Peng He, Ri-Hui Li, Stéphane Maisonneuve, Yibin Ruan, Guo-Rong Chen and Juan Xie

Chemical Communications 2014 vol. 50(Issue 91) pp:14141-14144

Publication Date(Web):24 Sep 2014

DOI:10.1039/C4CC06356B

Fluorogenic supramolecular complexes formed between tubular-shaped pyrenyl-β-cyclodextrins and glyco-rhodamine are determined to respond to a selective lectin with ‘turn-on’ fluorescence with excellent selectivity over a range of competing species.

A per-acetyl glycosyl rhodamine as a novel fluorescent ratiometric probe for mercury (II)

Co-reporter:Kai-Bin Li, Hai-Lin Zhang, Bin Zhu, Xiao-Peng He, Juan Xie, Guo-Rong Chen

Dyes and Pigments 2014 Volume 102() pp:273-277

Publication Date(Web):March 2014

DOI:10.1016/j.dyepig.2013.11.014

•A per-acetyl glycosyl rhodamine probe detects Hg2+ in a ratiometric manner.•The fluorescent acetyl glycosyl moiety of the probe serves as a FRET donor.•The probe is highly specific for Hg2+ in an 80% aqueous solution.•A plausible mechanism for the detection is proposed.This paper describes the identification of a per-acetyl glycosyl rhodamine B (RB) derivative, KB2, simply prepared by a click reaction, as a novel fluorescent ratiometric probe for mercury (II). In an 80% aqueous solution, KB2 responded to Hg2+ in a ratiometric manner with a good selectivity over a range of metal cations. Upon formation of a 1:1 probe-ion complex, the blue fluorescence of the per-acetyl glycosyl moiety of KB2 is quenched, along with the emergence of a bright red fluorescence attributable to the lactam ring-opening form of RB. This is probably caused by a fluorescence resonance energy transfer from the acetyl glycoside as a donor to the acceptor RB–Hg2+ motif. This study provides unique insight into the design of ratiometric chemoprobes for heavy metals based on the simple coupling of per-acetyl glycosides with fluorogenic dyes.

Bis-triazolyl indoleamines as unique “off–approach–on” chemosensors for copper and fluorine

Co-reporter:De-Tai Shi, Bin Zhang, Ya-Xi Yang, Chu-Chu Guan, Xiao-Peng He, Yuan-Chao Li, Guo-Rong Chen and Kaixian Chen

Analyst 2013 vol. 138(Issue 10) pp:2808-2811

Publication Date(Web):15 Mar 2013

DOI:10.1039/C3AN00030C

Bis-triazolyl indoleamine-based chemosensors that respond to copper, and then fluorine as presumably facilitated by the high-affinity interaction between F− and the NH-proton of indole, are reported. Remarkable fluorimetric as well as colorimetric alternations upon the specific ligand–ion recognitions were observed.

Identification of diverse 1,2,3-triazole-connected benzyl glycoside-serine/threonine conjugates as potent corrosion inhibitors for mild steel in HCl

Co-reporter:Qiong Deng, Na-Na Ding, Xiao-Li Wei, Liang Cai, Xiao-Peng He, Yi-Tao Long, Guo-Rong Chen, Kaixian Chen

Corrosion Science 2012 Volume 64() pp:64-73

Publication Date(Web):November 2012

DOI:10.1016/j.corsci.2012.07.001

The corrosion inhibitive efficiency of diverse 1,2,3-triazolyl benzyl glucoside-, galactoside- and mannoside-serine/threonine conjugates readily synthesized via CuI-catalyzed azide–alkyne cycloaddition reaction (Cue-AAC) for mild steel in HCl was examined via electrochemical impedance spectroscopy. The results indicate that these compounds are potent corrosion inhibitors even in highly concentrated HCl solutions. The potential mechanism of three inhibitors was characterized in detail via polarization and isotherm calculations. This study implies that benzyl glycoside-amino acid hybrids effectively constructed via the Cue-AAC between the highly biocompatible sugars and amino acids may represent a new class of promising and potentially green corrosion inhibitors.Graphical abstractHighlights► Triazolyl benzyl glycoside-amino acid conjugates as new corrosion inhibitors. ► They inhibit HCl corrosion for mild steel at low concentrations. ► Mechanism of inhibitors 7, 10, and 12 investigated in detail. ► They obey Langmuir isotherm and adopt dominantly chemisorption.

TMDS as a Dual-Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers

Co-reporter:Yin-Jie Zhang;Wissam Dayoub;Marc Lemaire

European Journal of Organic Chemistry 2012 Volume 2012( Issue 10) pp:1960-1966

Publication Date(Web):

DOI:10.1002/ejoc.201101682

Abstract

1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)₂ or AlCl₃ to afford the corresponding primary and secondary ethers. Its application to the concise synthesis of carbohydrate-based surfactants is highlighted.

Concise CuI-Catalyzed Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction Ligation Remarkably Enhances the Corrosion Inhibitive Potency of Natural Amino Acids for Mild Steel in HCl

Co-reporter:Qiong Deng, Xiao-Peng He, Hong-Wei Shi, Bao-Qin Chen, Guixia Liu, Yun Tang, Yi-Tao Long, Guo-Rong Chen, and Kaixian Chen

Industrial & Engineering Chemistry Research 2012 Volume 51(Issue 21) pp:7160-7169

Publication Date(Web):May 15, 2012

DOI:10.1021/ie3004557

Despite natural amino acids having been proposed as the green surrogate of currently used corrosion inhibitors that are generally toxic to both nature and human body during the everyday industrial processing of metallic equipments, their structural simplicity yet lowers the inhibitive potency, thereby hampering their further industrialization. We disclose here that a concise chemical ligation (CuI-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction [Cue-AAC]) between two l-amino acids that are weak or noncorrosion inhibitors may result in their largely improved protective effect for mild steel in HCl. A series of 1,4-disubstituted 1,2,3-triazolyl bis-amino acid derivatives constituted by l-serine, l-threonine, l-phenylalanine, and l-tyrosine were efficiently synthesized via Cue-AAC and deprotection reactions in high yields. Subsequently performed electrochemical impedance spectroscopy (EIS) evidenced that the inhibitive effect of these compounds for mild steel in 1 M HCl is markedly better than that of their natural amino acid counterparts. The inhibitive modality of the most potent inhibitor was interpreted in detail by potentiodynamic polarization and thermodynamic calculations. Furthermore, quantum chemical calculations suggest that the triazole ring formed by the Cue-AAC has contribution to their metal surface adsorption. This study would offer unique insights into the facile development of potency-enhanced green corrosion inhibitors based on the concise Cue-AAC ligation of natural amino acids.

The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

Co-reporter:Shao-Xing Song, Ming-Li Wu, Xiao-Peng He, Yu-Bo Zhou, Li Sheng, Jia Li, Guo-Rong Chen

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 5) pp:2030-2032

Publication Date(Web):1 March 2012

DOI:10.1016/j.bmcl.2012.01.069

The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.

Research on the structure–surface adsorptive activity relationships of triazolyl glycolipid derivatives for mild steel in HCl

Co-reporter:Hai-Lin Zhang, Xiao-Peng He, Qiong Deng, Yi-Tao Long, Guo-Rong Chen, Kaixian Chen

Carbohydrate Research 2012 Volume 354() pp:32-39

Publication Date(Web):1 June 2012

DOI:10.1016/j.carres.2012.03.006

Triazolyl glycolipid derivatives constructed via CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC) represent a new range of carbohydrate-based scaffolds for use in many fields of the chemical research. Here the surface adsorptive ability of series of our previously prepared C1- or C6-triazole linked gluco- and galactolipid derivatives for mild steel in 1 M HCl was studied via electrochemical impedance spectroscopy (EIS). Results indicated that these monosaccharide–fatty acid conjugates are weak inhibitors against HCl corrosion for mild steel. Moreover, some newly synthesized triazolyl disaccharide (maltose)–fatty alcohol conjugates failed to display enhanced activity, meaning that the structural enlargement of the sugar moiety does not favor the iron surface adsorption. However, a bis-triazolyl glycolipid derivative, which was realized by introducing a benzenesulfonamide group via Cue-AAC to the C6-position of a C1-triazolyl glucolipid analog, eventually showed significantly improved adsorptive potency compared to that of its former counterparts. The corrosion inhibitive modality of this compound for mild steel in HCl was subsequently studied via potentiodynamic polarization and thermodynamic calculations.Graphical abstractHighlights► Triazolyl monosaccharide–fatty acid derivatives show weak adsorptive efficiency for mild steel in HCl. ► Triazolyl disaccharide–fatty alcohol conjugates fail to exhibit improved potency. ► Bis-triazolyl glycolipid derivative 31 is much more potent than all counterparts. ► The inhibitive modality of 31 was studied by polarization.

Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

Co-reporter:Jia-Lu Xue, Xiao-Peng He, Jin-Wei Yang, De-Tai Shi, Chao-Ying Cheng, Juan Xie, Guo-Rong Chen, Kaixian Chen

Carbohydrate Research 2012 Volume 363() pp:38-42

Publication Date(Web):1 December 2012

DOI:10.1016/j.carres.2012.10.001

Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (∼70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media.

Pyrene Excimer-based Bis-triazolyl Pyranoglycoligands as Specific Mercury Sensors

Co-reporter:Xiaopeng He;Juan Xie;Guorong Chen;Kaixian Chen

Chinese Journal of Chemistry 2012 Volume 30( Issue 12) pp:2874-2878

Publication Date(Web):

DOI:10.1002/cjoc.201200978

Abstract

New C3,4-disubstituted bis-triazolyl glycoligands that feature a glucosyl or galactosyl scaffold incorporating two pyrenyl groups were synthesized via the Cu^I-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC). These compounds exert a major emission band corresponding to that of pyrene excimer and respond specifically to mercury with a markedly quenched fluorescence. The epimeric nature of the pyranoglycosyl scaffold is determined influential toward the selectivity of the sensors.

Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone

Co-reporter:Yin-Jie Zhang, Xiao-Peng He, Min Hu, Zhen Li, Xiao-Xin Shi, Guo-Rong Chen

Dyes and Pigments 2011 Volume 88(Issue 3) pp:391-395

Publication Date(Web):March 2011

DOI:10.1016/j.dyepig.2010.08.010

A novel triazole-linked acetyl-β-N-glucosyl anthraquinone 1 was conveniently synthesized through one-step click chemistry. The functionalized glycoconjugate (1) exhibited a remarkable blue shift absorption and quenching fluorescence in the presence of trace amounts of Cu2+, presumably attributable to intramolecular charge transfer (ICT), which also displayed high selectivity over a series of other metal cations tested in acetonitrile. The result yielded by fluorescence spectroscopy titration suggested a 2:1 ligand-to-metal complex which was further demonstrated by NMR spectroscopy titration. Moreover, the addition of Cu2+ to 1 also significantly altered its electrochemical behavior which was reflected via differential pulse voltammetry (DPV) measurements. Such optically and electrochemically detectable metal-mediated sugar derivatives could be further used as biosensors for the recognition of multivalent carbohydrate-protein interactions.

Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: Novel construction of PTP1B inhibitors on a sugar scaffold

Co-reporter:Cui Li, Xiao-Peng He, Yin-Jie Zhang, Zhen Li, Li-Xin Gao, Xiao-Xin Shi, Juan Xie, Jia Li, Guo-Rong Chen, Yun Tang

European Journal of Medicinal Chemistry 2011 Volume 46(Issue 9) pp:4212-4218

Publication Date(Web):September 2011

DOI:10.1016/j.ejmech.2011.06.025

With an aim of developing novel protein tyrosine phosphatase (PTP) 1B inhibitors based on sugar scaffolds, a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides was efficiently constructed via the modular and selective Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddtion (click chemistry). These glycoconjugates bearing alkyl chain length-varied bridges between the sugar and (hydroxy)-benzoic moieties were identified as new PTP1B inhibitors with selectivity over T-Cell PTP (TCPTP), SH2-Containing PTP-1 (SHP-1), SHP-2 and Leukocyte Antigen-Related Tyrosine Phosphatase (LAR). Molecular docking study sequentially elaborated the plausible binding modes of the structurally diverse sugar-based inhibitors with PTP1B.Novel PTP1B inhibitors based on a sugar scaffold were efficiently constructed via click chemistry. Molecular docking study sequentially elaborated their plausible binding modes with PTP1B.Highlights► Novel PTP1B inhibitors based on a glucosyl scaffold were developed. ► Click chemistry was employed to modularly construct the focused library. ► The inhibitors were identified with high selectivity on PTP1B over others. ► Plausible PTP1B inhibitor interactions were suggested by molecular docking.

Facile fabrication of promising protein tyrosine phosphatase (PTP) inhibitor entities based on ‘clicked’ serine/threonine–monosaccharide hybrids

Co-reporter:Xiao-Peng He, Qiong Deng, Li-Xin Gao, Cui Li, Wei Zhang, Yu-Bo Zhou, Yun Tang, Xiao-Xin Shi, Juan Xie, Jia Li, Guo-Rong Chen, Kaixian Chen

Bioorganic & Medicinal Chemistry 2011 Volume 19(Issue 13) pp:3892-3900

Publication Date(Web):1 July 2011

DOI:10.1016/j.bmc.2011.05.049

Protein tyrosine phosphatases (PTPs) are well-validated therapeutic targets for many human major diseases. The development of their potent inhibitors has therefore become a main focus of both academia and the pharmaceutical industry. We report herein a facile strategy toward the fabrication of new and competent PTP inhibitor entities by simply ’clicking’ alkynyl amino acids onto diverse azido sugar templates. Triazolyl glucosyl, galactosyl, and mannosyl serine and threonine derivatives were efficiently synthesized via click reaction, which were then identified as potent CDC25B and PTP1B inhibitors selective over a panel of homologous PTPs tested. Their inhibitory activity and selectivity were found to largely lie on the structurally and configurationally diversified monosaccharide moieties whereon serinyl and threoninyl residues were introduced. In addition, MTT assay revealed the triazole-connected sugar-amino acid hybrids may also inhibit the growth of several human cancer cell lines including A549, Hela, and especially HCT-116. On the basis of such compelling evidence, we consider that this compound series could furnish promising chemical entities serving as new CDC25B and PTP1B inhibitors with potential cellular activity. Furthermore, the ‘click’ strategy starting from easily accessible and biocompatible amino acids and sugar templates would allow the modular fabrication of a rich library of new PTP inhibitors efficaciously and productively.

A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on ‘clicked’ pseudo-glycopeptides

Co-reporter:Jin-Wei Yang, Xiao-Peng He, Cui Li, Li-Xin Gao, Li Sheng, Juan Xie, Xiao-Xin Shi, Yun Tang, Jia Li, Guo-Rong Chen

Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 4) pp:1092-1096

Publication Date(Web):15 February 2011

DOI:10.1016/j.bmcl.2010.12.126

There has been considerable interest in the development of protein tyrosine phosphatase (PTP) inhibitors since many of the PTP members are tightly associated with major human diseases including autoimmune disorders, diabetes and cancer. We report here a unique and rapid approach toward the development of novel PTP inhibitor entities based on triazolyl pseudo-glycopeptides. By employing microwave-accelerated Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC or ‘click reaction’), a series of triazole-linked serinyl, threoninyl, phenylalaninyl and tyrosinyl 1-O-gluco- or galactosides have been efficiently synthesized in high yields within only ∼30 min. Successive biological assay identified these glycopeptidotriazoles as favorable PTP1B and CDC25B inhibitors with selectivity over TCPTP, LAR, SHP-1 and SHP-2. Both the structural diversity of the amino acid (Ser, Thr, Phe and Tyr) introduced and the epimeric identity (Glc or Gal) on monosaccharide scaffold were determined to impact the corresponding inhibitory activity and selectivity. In addition, the benzylated sugar scaffold was demonstrated to act as a crucial role for enhancing the binding affinity of the inhibitors with the targeted PTP. Docking simulation was eventually conducted to propose plausible binding modes of this compound series with PTP1B and CDC25B. Our approach readily realized from naturally abundant raw materials (sugar and amino acid) and via facile, regioselective and expeditious synthetic method (microwave-assisted click reaction) might provide new insights toward the ‘click’ fabrication of structurally diverse PTP inhibitors.We report the ‘click’ fabrication of triazolyl glycopeptidomimetics as novel PTP1B and CDC25B inhibitors and their plausible binding modes with the targeted PTP via docking simulation.

TMDS–Pd/C: a convenient system for the reduction of acetals to ethers

Co-reporter:Yan Shi, Wissam Dayoub, Guo-Rong Chen, Marc Lemaire

Tetrahedron Letters 2011 Volume 52(Issue 12) pp:1281-1283

Publication Date(Web):23 March 2011

DOI:10.1016/j.tetlet.2011.01.038

A simple and practical procedure for the reduction of acetals to ethers is described. It is based on the use of a 1,1,3,3-tetramethyldisiloxane (TMDS)–Pd/C system in the presence of a Brønsted acid as the co-catalyst. The reaction occurs under mild conditions and ethers are obtained in high yields.A simple and practical procedure for the reduction of acetals to ethers is described. It is based on the use of a 1,1,3,3-tetramethyldisiloxane (TMDS)–Pd/C system in the presence of a Brønsted acid as the co-catalyst. The reaction occurs under mild conditions and ethers are obtained in high yields.

‘Click’ to bidentate bis-triazolyl sugar derivatives with promising biological and optical features

Co-reporter:Zhuo Song, Xiao-Peng He, Xiao-Ping Jin, Li-Xin Gao, Li Sheng, Yu-Bo Zhou, Jia Li, Guo-Rong Chen

Tetrahedron Letters 2011 Volume 52(Issue 8) pp:894-898

Publication Date(Web):23 February 2011

DOI:10.1016/j.tetlet.2010.12.055

Bidentate 1-O-methyl-α-d-pyranoglucosides bearing two triazolyl α-ketoester groups on the 2,6- or 3,4-positions of sugar scaffold were efficiently synthesized via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click reaction) in good yields. These newly featured sugar derivatives displayed favorable inhibitory activity on protein tyrosine phosphatase 1B (PTP1B) and unexpected selective fluorescence quenching in the presence of Ni2+.

Preparation of triazole-linked glycosylated α-ketocarboxylic acid derivatives as new PTP1B inhibitors

Co-reporter:Zhuo Song, Xiao-Peng He, Cui Li, Li-Xin Gao, Zhao-Xia Wang, Yun Tang, Juan Xie, Jia Li, Guo-Rong Chen

Carbohydrate Research 2011 Volume 346(Issue 1) pp:140-145

Publication Date(Web):3 January 2011

DOI:10.1016/j.carres.2010.10.023

The synthesis of triazole-linked glycosyl acetophenone, benzoic acid, and α-ketocarboxylic acid derivatives was readily achieved via Cu(I)-catalyzed azide–alkyne cycloaddition (‘click’ reaction) in excellent yields of 93–97%. Among the synthesized glycoconjugates, the triazolyl α-ketocarboxylic acids were identified as the most potent protein tyrosine phosphatase 1B (PTP1B) inhibitors with micromole-ranged IC50 values and moderate-to-good selectivity over a panel of homologous PTPs including TCPTP (4.6-fold), LAR (>30-fold), SHP-1 (>30-fold) and SHP-2 (>30-fold). Moreover, a docking simulation was conducted to propose a plausible binding mode of the glucosyl α-ketocarboxylic acid triazole with the enzymatic target.Triazole-linked glycosyl acetophenone, benzoic acid and α-ketocarboxylic acid derivatives have been efficiently synthesized by click chemistry. Glycosyl α-ketocarboxylic acids exhibited micromolar inhibition towards PTP1B. Docking simulation was conducted to propose a plausible binding mode with the enzyme.

Disclosing the distinct interfacial behaviors of structurally and configurationally diverse triazologlycolipids

Co-reporter:Xiao-Peng He, Xiaolian Xu, Hai-Lin Zhang, Guo-Rong Chen, Shouhong Xu, Honglai Liu

Carbohydrate Research 2011 Volume 346(Issue 11) pp:1320-1326

Publication Date(Web):16 August 2011

DOI:10.1016/j.carres.2011.04.038

1- or 6-Triazologluco- and galactolipid derivatives bearing a lipid chain length of 16 carbons were efficiently constructed via click chemistry. The differentiation in their surface pressure-molecular area (π–A) isotherms first implies that these structurally and configurationally diverse amphiphiles adopt different distribution manner at air–water interfaces. The Langmuir–Blodgett (LB) films of the synthesized glycoconjugates on mica surface were subsequently prepared and visualized via atomic force microscopy (AFM), which exhibited diverse topographies and possess different contact angles with water. These data further suggest that the structural variation as well as epimeric identity of triazologlycolipids may result in their distinct interfacial behaviors at the air–solid interface. Furthermore, the addition of increasing amounts of 1-triazologalactolipid 2 to poly-diacetylene (PDA) was determined to impact the π–A isotherm of the latter, prompting us to further fabricate new colorimetrically detectable mixed-type vesicles containing triazologlycolipids for biochemical studies.

Synthesis of Triazole-Linked Amino Acid-Aryl C-Glycoside Hybrids via Click Chemistry as Novel PTP1B Inhibitors

Co-reporter:Jia Wang;Xiaopeng He;Lixin Gao;Li Sheng;Xiaoxin Shi;Jia Li;Guorong Chen

Chinese Journal of Chemistry 2011 Volume 29( Issue 6) pp:1227-1232

Publication Date(Web):

DOI:10.1002/cjoc.201190228

Abstract

Triazolyl phenylalanine and tyrosine-aryl C-glycoside hybrids were readily synthesized via microwave-assisted Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition in high yields. Successive enzymatic assay identified the synthesized glycoconjugates as novel PTP1B inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other homologous PTPs tested. In addition, the benzyl groups on glucosyl moiety were found crucial toward PTP1B inhibition.

Creation of 3,4-bis-triazolocoumarin–sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media

Co-reporter:Xiao-Peng He, Zhuo Song, Zhi-Zhou Wang, Xiao-Xin Shi, Kaixian Chen, Guo-Rong Chen

Tetrahedron 2011 67(19) pp: 3343-3347

Publication Date(Web):

DOI:10.1016/j.tet.2011.03.068

Discovering the distinct inhibitory effects between C4-epimeric glycosyl amino acids: new insight into the development of protein tyrosine phosphatase inhibitors

Co-reporter:Xiao-Peng He;Cui Li;Zhi-Zhou Wang;Li-Xin Gao;Xiao-Xin Shi

Glycoconjugate Journal 2011 Volume 28( Issue 7) pp:

Publication Date(Web):2011/10/01

DOI:10.1007/s10719-011-9347-0

There has been increasing interest in the development of drug candidates based on sugar templates that possess rich structural and, especially, configurational diversities. We disclose herein that the epimeric identity between methyl 3,4-bis-phenylalanyl/tyrosinyl triazolyl-alpha-D-galactopyranoside and glucopyranoside may lead to their distinct inhibitory effects on specific protein tyrosine phosphatases (PTPs). Subsequently performed molecular docking study elucidated the plausible binding behaviors of the more potent galactosyl inhibitors with their primary PTP target, i.e. Cell Division Cycle 25B (CDC25B) phosphatase.

Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments

Co-reporter:Hai-Lin Zhang;Xiao-Peng He;Li Sheng;Yuan Yao;Wei Zhang

Molecular Diversity 2011 Volume 15( Issue 4) pp:889-900

Publication Date(Web):2011 November

DOI:10.1007/s11030-011-9318-1

Series of novel 6-triazole-linked galacto- or glucolipids were efficiently synthesized from O-benzylated sugar azides and various lipid alkynes via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click chemistry) followed by hydrogenolysis with PdCl2/H2. Subsequent MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay toward a panel of human cancer cell lines revealed that these triazologlycolipids possess low-to-modest toxicity on A549 (lung), MCF-7 (breast), HeLa (cervix), and HepG2 (liver). Furthermore, both the carbon chain length at the lipid end and the epimeric identity of the glycosyl moiety were determined to impact their corresponding bioactivity.

Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments

Co-reporter:Shao-Xing Song, Hai-Lin Zhang, Chol-Guk Kim, Li Sheng, Xiao-Peng He, Yi-Tao Long, Jia Li, Guo-Rong Chen

Tetrahedron 2010 66(52) pp: 9974-9980

Publication Date(Web):

DOI:10.1016/j.tet.2010.10.033

C-D-Glucopyranosyl Derivatives of Tocopherols Synthesis and Evaluation as Amphiphilic Antioxidants

Co-reporter:Li He;Stéphanie Gall;Claire Dufour;Olivier Dangles;Bernard Fenet;Jean-Pierre Praly

European Journal of Organic Chemistry 2008 Volume 2008( Issue 11) pp:

Publication Date(Web):

DOI:10.1002/ejoc.200700885

Abstract

Treatment of dimethylhydroquinone dimethyl ethers (ortho and meta isomers) with glycopyranose pentaacetates (D-gluco, D-galacto) in the presence of SnCl₄ and F₃CCO₂Ag selectively afforded the corresponding C-β-D-glycosyl derivatives by aromatic electrophilic substitution. Oxidation of the dimethoxybenzene moiety with ceric ammonium nitrate delivered C-β-D-glycosyl-dimethylbenzoquinones, which were reduced with Na₂S₂O₄ to the corresponding C-β-D-glycosyl-dimethylhydroquinones. ZnCl₂-catalyzed cyclization either with methylbut-2-en-1-ol (prenyl alcohol) or with all-racemic phytol led to acetyl-protected C-β-D-glycosyl chromanols or C-β-D-glycosyl tocopherols, the sugar residues of which were deacetylated under base catalysis conditions. These new molecules were evaluated as antioxidants in terms of their ability to inhibit the peroxidation of linoleic acid in SDS micelles. The position of the C-glucosyl moiety on the phenolic nucleus emerges as the critical structural determinant of their activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B

Co-reporter:Li Lin, Qiang Shen, Guo-Rong Chen, Juan Xie

Bioorganic & Medicinal Chemistry 2008 Volume 16(Issue 22) pp:9757-9763

Publication Date(Web):15 November 2008

DOI:10.1016/j.bmc.2008.09.066

Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated β-C-d-glucosyl and β-C-d-galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding β-C-d-glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated β-C-d-glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62–0.88 μM), with no significant difference between gluco and galacto derivatives.

β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors

Co-reporter:Li Lin, Qiang Shen, Guo-Rong Chen, Juan Xie

Bioorganic & Medicinal Chemistry Letters 2008 Volume 18(Issue 24) pp:6348-6351

Publication Date(Web):15 December 2008

DOI:10.1016/j.bmcl.2008.10.091

β-C-Glycosiduronic acid quinones and β-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl β-C-glycosyl compounds (18, 22, 23 and 34) showed IC50 values of 0.77–5.27 μM against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent.Benzoyl protected β-C-glycosyl compounds inhibitent PTP1B with IC50 in micromolar range.

Synthesis of β-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity

Co-reporter:Li Lin, Xiao-Peng He, Qing Xu, Guo-Rong Chen, Juan Xie

Carbohydrate Research 2008 Volume 343(Issue 4) pp:773-779

Publication Date(Web):17 March 2008

DOI:10.1016/j.carres.2007.12.017

β-C-Glucosyl and β-C-galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F3CCO2Ag/SnCl4 promoted Friedel–Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding β-C-glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line.

Fluorescent glycoprobes: a sweet addition for improved sensing

Co-reporter:Xiao-Peng He, Yi Zang, Tony D. James, Jia Li, Guo-Rong Chen and Juan Xie

Chemical Communications 2017 - vol. 53(Issue 1) pp:NaN90-90

Publication Date(Web):2016/10/04

DOI:10.1039/C6CC06875H

An insight into graphene oxide associated fluorogenic sensing of glycodye–lectin interactions

Co-reporter:Ding-Kun Ji, Yue Zhang, Xiao-Peng He and Guo-Rong Chen

Journal of Materials Chemistry A 2015 - vol. 3(Issue 32) pp:NaN6661-6661

Publication Date(Web):2015/07/15

DOI:10.1039/C5TB01162K

Probing disease-related proteins with fluorogenic composite materials

Co-reporter:Xiao-Peng He, Yi Zang, Tony D. James, Jia Li and Guo-Rong Chen