title: Chemical oxidation of N-hydroxyguanidine compounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation.
abstract: N omega-Hydroxy-L-arginine was found to cause vasodilation in arginine-depleted rabbit aorta. It is, therefore, likely to be a biosynthetic intermediate in the conversion of arginine to nitric oxide in this tissue. N-Hydroxyalkylguanidine compounds, including N omega-hydroxy-L-arginine were oxidized with various oxidizing agents and examined for their ability to release nitric oxide. All oxidizing agents tested were capable of oxidizing the N-hydroxyguanidine function but only lead tetra-acetate (Pb(OAc)4) and potassium ferricyanide/hydrogen peroxide (K3FeCN6/H2O2) were capable of generating significant amounts of nitric oxide. Oxidation with K3FeCN6, lead oxide (PbO2) and silver carbonate (Ag2CO3) resulted instead in the release of nitrous oxide (N2O) presumably through the initial release of nitroxyl (HNO).
authors.affiliation: Department of Pharmacology, UCLA School of Medicine 90024-1735.
authors.forename: J M
authors.initials: JM
authors.lastname: Fukuto
authors.forename: G C
authors.initials: GC
authors.lastname: Wallace
authors.forename: R
authors.initials: R
authors.lastname: Hszieh
authors.forename: G
authors.initials: G
authors.lastname: Chaudhuri
mesh_terms: D000818:Animals; D001011:Aorta / Q000378:metabolism; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry*; D006898:Hydroxylamines; D066298:In Vitro Techniques; D008956:Models, Chemical; D009569:Nitric Oxide / Q000032:analysis* / Q000378:metabolism; D009589:Nitrogen Oxides / Q000032:analysis*; D009609:Nitrous Oxide / Q000032:analysis*; D016877:Oxidants; D010084:Oxidation-Reduction; D011817:Rabbits
chemical_list: D006146:Guanidines; D006898:Hydroxylamines; D009589:Nitrogen Oxides; D016877:Oxidants; D009569:Nitric Oxide; C029604:hydroxyguanidine; C039900:nitroxyl; D009609:Nitrous Oxide