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

He, Xiao‐Peng; Song, Zhuo; Wang, Zhi-Zhou; Shi, Xiao‐Xin; Chen, Kaixian; Chen, Guorong

doi:10.1016/j.tet.2011.03.068

Cited by 56 publications

(25 citation statements)

References 40 publications

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“…1, we have determined in a previous study that a C3,4-disubstituted bis-triazolyl coumarin glucoside ( DT3 ) showed selective and remarkable FL quenching upon coordination with Ag + in water15. The present study initiated with the interrogation of the metal-ion sensibility of two other structurally analogous coumarin glucosides, DT1 and DT2 , synthesized by a microwave-assisted twofold Cue-AAC35.…”

Section: Resultsmentioning

confidence: 91%

“…1), quenched sharply in water15. Since the only structural distinction between DT1 / DT2 and DT3 lies in the substitution pattern of the bis-triazolyl coumarin moieties upon the glucosyl platform, we deduced that they probably adopt different complexation modes with the ion leading to the reversed FL variations observed.…”

Section: Resultsmentioning

confidence: 93%

“…We recently reported that Cue-AAC is also a promisingly suitable tool for fabrication of FGs81524252627. By a twofold Cue-AAC between two azido fluorophores and a di-alkynyl glycoside, the resulting bis-triazolyl FGs exhibited distinct ion sensibilities in terms of the different fluorophores introduced10242526.…”

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confidence: 99%

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Substitution Pattern Reverses the Fluorescence Response of Coumarin Glycoligands upon Coordination with Silver (I)

Shi

Wei

Sheng

et al. 2014

Sci Rep

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Development of sugar-based fluorescence (FL) chemo-probes is of much interest since sugars are biocompatible, water-soluble and structurally rigid natural starting materials. We report here that fluorescent glycoligands with two triazolyl coumarin moieties installed onto the different positions of an identical glucosyl nucleus exert completely reversed optical response to a metal ion. C3,4-, C2,3- and C4,6-di-substituted coumarin glucosides synthesized by a click reaction similarly showed a selective FL variation in the presence of silver (I) among a range of metal cations in an aqueous solution. However, the variation was determined to be converse: the FL of the C3,4-ligand was quenched whereas that of the C2,3/C4,6-ligand tangibly enhanced. FL and NMR titrations suggested that this divergence was due to the distinct complexation modes of the conformationally constrained ligands with the ion. The optimal motifs of the ligand-ion complexation were predicted by a computational simulation. Finally, the C2,3-ligand was determined to be of low cytotoxicity and applicable in the FL imaging of silver ions internalized by live cells.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 93%

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Substitution Pattern Reverses the Fluorescence Response of Coumarin Glycoligands upon Coordination with Silver (I)

Shi

Wei

Sheng

et al. 2014

Sci Rep

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“…By a microwave-assisted dual click reaction, fluorogenic 3-azidocoumarin can be rapidly introduced onto a 3,4-dipropargylglucoor galactosyl scaffold with restored fluorescence. Subsequent desilylation leads to water soluble sugar-bis-triazolocoumarin conjugates which are applicable toward selective Ag + detection in aqueous media via fluorescence spectroscopy (X.-P. He et al, 2011). Huang, 2002).…”

Section: Coumarin-derived Fluorescent Chemosensors For Metal Ionsmentioning

confidence: 99%

Coumarin-Derived Fluorescent Chemosensors

Li¹,

Cai²,

Chen³

2012

Advances in Chemical Sensors

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“…We are currently interested in the construction of functional triazologlycomimetics [9][10][11][12] via the modular and regioselective Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition [13,14] (the best example of click chemistry) [15], which has proven to be very efficacious for the construction Electronic supplementary material The online version of this article (doi:10.1007/s10719-011-9347-0) contains supplementary material, which is available to authorized users. of bioactive compounds [16,17].…”

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confidence: 99%

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

Cui

Wang

et al. 2011

Glycoconj J

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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.

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

Cited by 56 publications

References 40 publications

Substitution Pattern Reverses the Fluorescence Response of Coumarin Glycoligands upon Coordination with Silver (I)

Substitution Pattern Reverses the Fluorescence Response of Coumarin Glycoligands upon Coordination with Silver (I)

Coumarin-Derived Fluorescent Chemosensors

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

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