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Issue 10, 2015
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Exceptional time response, stability and selectivity in doubly-activated phenyl selenium-based glutathione-selective platform

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Abstract

A phenyl-selenium-substituted coumarin probe was synthesized for the purpose of achieving highly selective and extremely rapid detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy) without background fluorescence. The fluorescence intensity of the probe with GSH shows a ∼100-fold fluorescent enhancement compared with the signal generated for other closely related amino acids, including Cys and Hcy. Importantly, the substitution reaction with the sulfhydryl group of GSH at the 4-position of the probe, which is doubly-activated by two carbonyl groups, occurs extremely fast, showing subsecond maximum fluorescence intensity attainment; equilibrium was reached within 100 ms (UV-vis). The probe selectivity for GSH was confirmed in Hep3B cells by confocal microscopy imaging.

Graphical abstract: Exceptional time response, stability and selectivity in doubly-activated phenyl selenium-based glutathione-selective platform

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Supplementary files

Article information


Submitted
10 Jun 2015
Accepted
09 Jul 2015
First published
09 Jul 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 5435-5439
Article type
Edge Article
Author version available

Exceptional time response, stability and selectivity in doubly-activated phenyl selenium-based glutathione-selective platform

Y. Kim, S. V. Mulay, M. Choi, S. B. Yu, S. Jon and D. G. Churchill, Chem. Sci., 2015, 6, 5435
DOI: 10.1039/C5SC02090E

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