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Issue 9, 2015
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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

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Publication details

The article was received on 21 Apr 2015, accepted on 21 Jul 2015 and first published on 23 Jul 2015


Article type: Concise Article
DOI: 10.1039/C5MD00170F
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Med. Chem. Commun., 2015,6, 1649-1655

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    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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