Novel donors of nitric oxide derived of S-nitrosocysteine possessing antioxidant activities.
Novel S-nitrosothiols possessing a phenolic function were investigated as nitric oxide (NO) donors. A study of NO release from these derivatives was carried out by electron spin resonance (ESR). All compounds gave rise to a characteristic three-line ESR signal in the presence of the complex [Fe(II)(MGD)2], revealing the formation of the complex [Fe(II)(MGD)2(NO)]. Furthermore, tests based on cytochrome c reduction were performed in order to study the ability of each phenolic disulfide, the final organic decomposition product of S-nitrosothiols, to trap superoxide radical anion (O2-). This study revealed a high reactivity of 1b and 3b towards O2-. For these two compounds, the respective inhibitory concentration (IC) 50 values were 92 microM and 43 microM.
Petit
C
C
Laboratoire de Synthèse, Physico-Chimie et Radiobiologie, Faculté des Sciences Pharmaceutiques, Toulouse, France.
Bernardes-Genisson
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V
Hoffmann
P
P
Souchard
J
J
Labidalle
S
S
D000975:Antioxidants / Q000737:chemistry*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D020030:Nitric Oxide Donors / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D026403:S-Nitrosothiols; D013481:Superoxides / Q000737:chemistry
D000975:Antioxidants; D004220:Disulfides; D020030:Nitric Oxide Donors; D009603:Nitroso Compounds; D026403:S-Nitrosothiols; D013481:Superoxides; C021315:S-nitrosocysteine; D003545:Cysteine