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

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 flu...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2015-10, Vol.6 (10), p.5435-5439
Main Authors: Kim, Youngsam, Mulay, Sandip V, Choi, Minsuk, Yu, Seungyoon B, Jon, Sangyong, Churchill, David G
Format: Article
Language:English
Subjects:
Amino acids
Confocal
Cysteine
Fluorescence
Microscopy
Platforms
Selectivity
Time response
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc02090e