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Analyst. 2019 May 13;144(10):3260-3266. doi: 10.1039/c9an00115h.

A novel turn-on fluorescent probe for selective sensing and imaging of glutathione in live cells and organisms.

Author information

1
A State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian, China. zczhang@dlut.edu.cn.

Abstract

We synthesized six 1-oxo-1H-phenalene-2,3-dicarbonitrile (OPD)-based probes with various leaving groups using an arylthioether linker and for the first time identified the probe O-NH2 capable of highly selective detection of glutathione over cysteine/homocysteine in vitro and in vivo based on an aromatic nuclear substitution reaction (SNAr) mechanism. The fluorescence of the probe O-NH2 was quenched because of the photoinduced electron transfer (PET) process, but switched on by a glutathione-triggered specific recognition reaction between the probe O-NH2 and glutathione. The recognition mechanism for glutathione was explored and verified by theoretical calculations and ESI-MS analysis. Using O-NH2 as the probe, the GSH fluorescence images were demonstrated in HeLa cells and the intracellular GSH levels in different imatinib-resistant K562 tumor cells were firstly determined. Further, O-NH2 was utilized to detect glutathione in D. magna and zebrafish embryos. The combined results indicate that O-NH2 can be applied as an effective tool for detecting glutathione in biological investigations.

PMID:
30982838
DOI:
10.1039/c9an00115h

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