Sensors and Actuators, B: Chemical
Sensors and Actuators, B: Chemical
5 years ago

A coumarin-based “off-on” sensor for fluorescence selectivily discriminating GSH from Cys/Hcy and its bioimaging in living cells

A coumarin-based “off-on” sensor for fluorescence selectivily discriminating GSH from Cys/Hcy and its bioimaging in living cells
Glutathione (GSH) is the most abundant intracellular thiol with the concentration in the millimolar range. It has also been reported that GSH plays a crucial role in human pathologies, so it is meaningful to develop an effective probe for GSH. In this work, we report a coumarin-chlorine malononitrile “off-on” sensor for highly selective fluorescence detection of GSH over Cys/Hcy. The chlorine of the probe can be rapidly replaced by thiolates of biothiols through thiol-halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted compound. Subsequently, an intramolecular Michael addition between the α,β-unsaturated malonitrile and thiol group may occur. However, GSH only forms thiol-substituted compound. The significantly different mechanisms enable the discrimination of GSH over Cys/Hcy through fluorescence response. Finally, fluorescence imaging of A549 cells indicated that probe 1 could be used for monitoring GSH in living cells. It would be a useful tool to understand the mechanisms of many related diseases.

Publisher URL: www.sciencedirect.com/science

DOI: S0925400517311395

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