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

Xue, Jialu; He, Xiao‐Peng; Yang, Jinwei; Shi, De-Tai; Cheng, Chaoying; Xie, Juan; Chen, Guorong; Chen, Kaixian

doi:10.1016/j.carres.2012.10.001

Cited by 16 publications

(3 citation statements)

References 49 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. The only structural divergence is that two same triazolyl coumarin moieties were substituted on the different positions of the glucosyl platform to display these functional groups in diversely constrained manners58102829.…”

Section: Resultsmentioning

confidence: 91%

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%

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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“…Here, we use the CuAAC click reaction to simply couple 1 with a water-soluble PEG tail to enhance the water solubility. In addition, since the as-formed bis-triazolyl motif is envisioned to chelate more strongly and selectively a metal ion, − a monotriazolyl PEG rhodamine derivative was synthesized for analyzing the structure activity relationship.…”

Section: Resultsmentioning

confidence: 99%

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

Wang

Zang

et al. 2014

ACS Appl. Mater. Interfaces

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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".

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“… 15 Because of their optical properties, triazoles have been used as fluorescent linkers between two or more molecular fragments, showing an ambipolar behavior, depending on the substitution position. 16 The 1,2,3-triazole ring has been incorporated as a 3-, 4-, 5- and 7-substituent into the coumarin heterocycle, acting as a linker between coumarin and other heterocycles, 17–19 glycosides, 20,21 polymeric chains; 22 or a phenyl ring. 23,24 All these SO conjugates share the non-planarity as a common feature through the incorporation of C(sp 3 ) or O(sp 3 ) atoms as part of the linker to improve solubility.…”

Section: Introductionmentioning

confidence: 99%

3-(4-Formylphenyl)-triazole functionalized coumarins as violet-blue luminophores and n-type semiconductors: synthesis, photophysical, electrochemical and thermal properties

et al. 2022

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

Cited by 16 publications

References 49 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)

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

3-(4-Formylphenyl)-triazole functionalized coumarins as violet-blue luminophores and n-type semiconductors: synthesis, photophysical, electrochemical and thermal properties

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