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Issue 9, 2015

Investigating the generation of hydrogen sulfide from the phosphonamidodithioate slow-release donor GYY4137

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Abstract

A combination of NMR spectroscopy, mass spectrometry and chemical synthesis was used to elucidate the two-step hydrolytic decomposition pathway of the slow-release hydrogen sulfide (H2S) donor GYY4137 and the key decomposition product was also prepared by an independent synthetic route. The (dichloromethane-free) sodium salt of the phosphonamidodithioate GYY4137 was also produced as a pharmaceutically more acceptable salt. In contrast with GYY4137 and its sodium salt, the decomposition product did not generate H2S or exert cytoprotective or anti-inflammatory effects in oxidatively stressed human Jurkat T-cells and LPS-treated murine RAW264.7 macrophages. The decomposition product represents a useful control compound for determining the biological and pharmacological effects of H2S generated from GYY4137.

Graphical abstract: Investigating the generation of hydrogen sulfide from the phosphonamidodithioate slow-release donor GYY4137

Supplementary files

Article information


Submitted
21 Apr 2015
Accepted
21 Jul 2015
First published
23 Jul 2015

Med. Chem. Commun., 2015,6, 1649-1655
Article type
Concise Article
Author version available

Investigating the generation of hydrogen sulfide from the phosphonamidodithioate slow-release donor GYY4137

B. E. Alexander, S. J. Coles, B. C. Fox, T. F. Khan, J. Maliszewski, A. Perry, M. B. Pitak, M. Whiteman and M. E. Wood, Med. Chem. Commun., 2015, 6, 1649 DOI: 10.1039/C5MD00170F

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