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One- and Two-Photon-Activated Cysteine Persulfide Donors for Biological Targeting.

Authors :
Chaudhuri A
Venkatesh Y
Das J
Gangopadhyay M
Maiti TK
Singh NDP
Source :
The Journal of organic chemistry [J Org Chem] 2019 Sep 20; Vol. 84 (18), pp. 11441-11449. Date of Electronic Publication: 2019 Sep 03.
Publication Year :
2019

Abstract

Persulfides have been considered as potential signaling compounds similar to the H <subscript>2</subscript> S in "S-persulfidation", a sulfur-mediated redox cycle. The research of this sulfur-mediated species is hindered because of the lack of efficient persulfide donors. In this current study, we have developed one- and two-photon-activated persulfide donors based on an o -nitrobenzyl (ONB) phototrigger, which releases the biologically active persulfide ( N -acetyl l-cysteine persulfide, NAC-SSH) in a spatiotemporal manner. Next, we have demonstrated the detection of persulfide release both qualitatively and quantitatively using the well-known "turn on" fluorescence probe, that is, monobromobimane, and the trapping agent, that is, 2,4-dinitrofluorobenzene, respectively. Furthermore, we examined the cytotoxicity of synthesized persulfide donors on HeLa cells and the cytoprotective ability in the highly oxidizing cellular environment.

Details

Language :
English
ISSN :
1520-6904
Volume :
84
Issue :
18
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
31432682
Full Text :
https://doi.org/10.1021/acs.joc.9b01224