Garlic-inspired trisulfide linkers for thiol-stimulated H2S release. Issue 57 (3rd July 2017)

• Record Type: Journal Article
• Authors: Ercole, Francesca; Whittaker, Michael R.; Halls, Michelle L.; Boyd, Ben J.; Davis, Thomas P.; Quinn, John F.
• Is Part Of: Chemical communications. Volume 53:Issue 57(2017)
• Page Start: 8030
• Page End: 8033
• Publication Date: 2017-07-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc03820h
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Garlic-inspired cholesterol-mPEG conjugates incorporating a trisulfide linkage have the ability to cleave upon exposure to thiols with a concomitant release of H2 S. Abstract : Garlic-derived polysulfides ( e.g., diallyl trisulfide, DATS) act as potent donors of the cell-signalling mediator H2 S when exposed to endogenous thiols. Inspired by this chemistry, we incorporated a trisulfide linkage into a conjugate comprising an mPEG tail and a cholesteryl head via thiol-mediated fragmentation chemistry. The synthesized conjugate releases H2 S upon exposure to thiol even at intracellular levels.