Garlic-inspired trisulfide linkers for thiol-stimulated H2S release

Francesca Ercole; Michael R. Whittaker; Michelle L. Halls; Ben J. Boyd; Thomas P. Davis; John F. Quinn

doi:10.1039/C7CC03820H

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Garlic-inspired trisulfide linkers for thiol-stimulated H₂S release†

Francesca Ercole,^a Michael R. Whittaker,

^a Michelle L. Halls,^b Ben J. Boyd,^a Thomas P. Davis

*^ac and John F. Quinn

*^a

Author affiliations

* Corresponding authors

^a ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Drug Delivery, Disposition and Dynamics Theme, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, Australia
E-mail: thomas.p.davis@monash.edu, john.f.quinn@monash.edu

^b Drug Discovery Biology Theme, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville, Australia

^c Department of Chemistry, University of Warwick, Coventry, UK

Abstract

Garlic-derived polysulfides (e.g., diallyl trisulfide, DATS) act as potent donors of the cell-signalling mediator H₂S 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 H₂S upon exposure to thiol even at intracellular levels.

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Article information

DOI: https://doi.org/10.1039/C7CC03820H
Article type: Communication
Submitted: 17 May 2017
Accepted: 24 Jun 2017
First published: 03 Jul 2017

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Chem. Commun., 2017,53, 8030-8033

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Garlic-inspired trisulfide linkers for thiol-stimulated H₂S release

F. Ercole, M. R. Whittaker, M. L. Halls, B. J. Boyd, T. P. Davis and J. F. Quinn, Chem. Commun., 2017, 53, 8030 DOI: 10.1039/C7CC03820H

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