title: Efficient nitrosation of glutathione by nitric oxide.
abstract: Nitrosothiols are increasingly regarded as important participants in a range of physiological processes, yet little is known about their biological generation. Nitrosothiols can be formed from the corresponding thiols by nitric oxide in a reaction that requires the presence of oxygen and is mediated by reactive intermediates (NO₂ or N₂O₃) formed in the course of NO autoxidation. Because the autoxidation of NO is second order in NO, it is extremely slow at submicromolar NO concentrations, casting doubt on its physiological relevance. In this paper we present evidence that at submicromolar NO concentrations the aerobic nitrosation of glutathione does not involve NO autoxidation but a reaction that is first order in NO. We show that this reaction produces nitrosoglutathione efficiently in a reaction that is strongly stimulated by physiological concentrations of Mg(2+). These observations suggest that direct aerobic nitrosation may represent a physiologically relevant pathway of nitrosothiol formation.
authors: Department of Pharmacology & Toxicology, Karl-Franzens-Universität Graz, A-8010 Graz, Austria.
authors: Bernd
authors: B
authors: Kolesnik
authors: Knut
authors: K
authors: Palten
authors: Astrid
authors: A
authors: Schrammel
authors: Heike
authors: H
authors: Stessel
authors: Kurt
authors: K
authors: Schmidt
authors: Bernd
authors: B
authors: Mayer
authors: Antonius C F
authors: AC
authors: Gorren
mesh_terms: D000332:Aerobiosis; D005978:Glutathione / Q000378:metabolism*; D006801:Humans; D009569:Nitric Oxide / Q000378:metabolism*; D020030:Nitric Oxide Donors / Q000378:metabolism; D015538:Nitrosation; D009603:Nitroso Compounds / Q000378:metabolism; D010100:Oxygen / Q000378:metabolism*; D026422:S-Nitrosoglutathione / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000378:metabolism
chemical_list: D020030:Nitric Oxide Donors; D009603:Nitroso Compounds; D013438:Sulfhydryl Compounds; D009569:Nitric Oxide; D026422:S-Nitrosoglutathione; D005978:Glutathione; D010100:Oxygen
keywords: 2,3-diaminonaphthalene; DAN; DEA/NO; DNIC; DTPA; DTT; Free radicals; GSNO; N-acetylcysteine; NAC; Nitric oxide; Nitrosoglutathione; PROLI/NO; S-nitrosation; S-nitrosoglutathione; SOD; TEA; diethylamine NONOate (diethylammonium (Z)-1-(N,N-diethylamino)diazen-1-ium-1,2-diolate); diethylenetriaminepentaacetic acid; dinitrosyl–iron complex; dithiothreitol; met-Hb; methemoglobin; oxy-Hb; oxyhemoglobin; proline NONOate (1-(hydroxyl-N,N,O-azoxy)-l-proline, disodium salt); superoxide dismutase; triethanolamine; β-ME; β-mercaptoethanol
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