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

Persulfides have been considered as potential signaling compounds similar to the H2S 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 tw...

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Published in:Journal of organic chemistry 2019-09, Vol.84 (18), p.11441-11449
Main Authors: Chaudhuri, Amrita, Venkatesh, Yarra, Das, Joyjyoti, Gangopadhyay, Moumita, Maiti, Tapas K, Singh, N. D. Pradeep
Format: Article
Language:English
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Summary:Persulfides have been considered as potential signaling compounds similar to the H2S 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01224