title: [Thionitrites as potent donors of nitric oxide: example of S-nitroso- and S,S'-dinitroso-dihydrolipoic acids].
abstract: Until recently, nitric oxide (NO.) was considered as a toxic radical, but it appears now as an essential messenger implicated in a wide range of biological processes, including immune system, cardiovascular system, and nervous system. An aspect of NO. metabolism in vivo is the formation of a variety of high and low molecular weight nitrosothiols. S-nitrosocysteine and S-nitrosoglutathione are among the biologically derived S-nitrosothiols that are postulated to be carriers of NO.. Although most of the S-nitrosothiols are unstable and spontaneously break down to produce NO. and a disulfide, some of them, including protein thiols, can show significant stability. These molecules are able to convey nitric oxide, that is, to keep, to carry, and then to generate NO. in physiological media, and might display pharmacological effects as potential vasodilators or neuroprotectors. Here, we present the development of new thionitrites R-S-NO having intrinsic antioxidant properties. We report the preparation, the characterization, and the stability studies in aqueous solutions of S-nitroso derivatives of dihydro-alpha-lipoic acid, known for its antioxidant properties.
authors.affiliation: Laboratoire de Synthèse, Physico-Chimie et Radiobiologie-JE 175, Université Paul-Sabatier, Faculté des Sciences Pharmaceutiques, Toulouse, France.
authors.forename: C
authors.initials: C
authors.lastname: Petit
authors.forename: P
authors.initials: P
authors.lastname: Hoffmann
authors.forename: J P
authors.initials: JP
authors.lastname: Souchard
authors.forename: F
authors.initials: F
authors.lastname: Nepveu
authors.forename: S
authors.initials: S
authors.lastname: Labidalle
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis*; D004355:Drug Stability; D004578:Electron Spin Resonance Spectroscopy; D009569:Nitric Oxide; D009603:Nitroso Compounds / Q000138:chemical synthesis*; D008063:Thioctic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000975:Antioxidants; D009603:Nitroso Compounds; C106036:S,S'-dinitrosodihydrolipoic acid; C106037:S-nitrosodihydrolipoic acid; D009569:Nitric Oxide; D008063:Thioctic Acid; C015144:dihydrolipoic acid
vernacular_title: Les thionitries comme agents donneurs potentiels de monoxyde d'azote: exemple des acides S-nitroso- et S,S'-dinitroso-dihydrolipoïque.