Sulfur signaling is widely accepted as a critical process in mammalian physiology. However, whether it is the sulfide or persulfide species that is the “active” component is a debatable subject. The lack of chemical tools to afford “pure” persulfide hinders studies in this area. Among all the reactive sulfur species (RSS), glutathione persulfide (GSSH) is the most abundant species. However, because of its unstable nature, the detail chemical and biological functions of GSSH are still unclear. Although others and we have developed some persulfide delivery systems, no existing methods can deliver unprotected GSSH. In this work, we describe a new strategy of delivering a “pure” GSSH through the use of an esterase-sensitive prodrug. The release profile was studied by direct trapping of GSSH with 1-fluoro-2,4-dinitrobenzene (DNFB) and monitoring the formation of a side product. The donor was examined for its inhibitory effect toward glyceraldehyde 3-phosphate dehydrogenase (GAPDH). Under highly oxidative conditions, the donor also show cytoprotective effects in H9c2 cardiomyocytes.

Delivering glutathione persulfide by an esterase-sensitive donor

2019 Spring National Meeting

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