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Issue 10, 2019
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A novel turn-on fluorescent probe for selective sensing and imaging of glutathione in live cells and organisms

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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.

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

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Publication details

The article was received on 18 Jan 2019, accepted on 25 Mar 2019 and first published on 28 Mar 2019


Article type: Paper
DOI: 10.1039/C9AN00115H
Analyst, 2019,144, 3260-3266

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

    X. Zhang, Z. Wang, Z. Guo, N. He, P. Liu, D. Xia, X. Yan and Z. Zhang, Analyst, 2019, 144, 3260
    DOI: 10.1039/C9AN00115H

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