Effects of oxygen on the reactivity of nitrogen oxide species including peroxynitrite.
This paper describes the O(2)-dependent control of the reactivity of nitrogen oxide species for the production of biologically important nitrated and nitrosated compounds. In this study, the effects of O(2) on the reactivity of NO, NO(2), and ONOO(-)/ONOOH for nitration of tyrosine (Tyr) and nitrosation of glutathione (GSH) and morpholine (MOR) were examined. NO produced S-nitrosoglutathione (GSNO) and N-nitrosomorpholine (NMOR) through the formation of N(2)O(3) under aerobic conditions, and NO(2) produced 3-nitrotyrosine (3-NO(2)Tyr), GSNO, and NMOR. Transnitrosation from GSNO to MOR was observed only in the presence of O(2). Although preformed ONOO(-)/ONOOH produced all the products under aerobic conditions, the formation of 3-NO(2)Tyr and GSNO was markedly reduced and the formation of NMOR was enhanced under anaerobic conditions. The reactivity of the CO(2) adduct of ONOO(-) was similarly dependent on O(2). 3-NO(2)Tyr was produced effectively by reaction with ONOO(-)/ONOOH at the O(2) concentration of 270 microM and by reaction with its CO(2) adduct at O(2) concentrations greater than 5 microM. Generation of.OH from ONOO(-)/ONOOH was suppressed under anaerobic conditions. The reactivity of ONOO(-)/ONOOH and.OH generation from ONOO(-) were reversibly controlled by the O(2) concentration.
Kikugawa
Kiyomi
K
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. kikugawa@ps.toyaku.ac.jp
Hiramoto
Kazuyuki
K
Ohkawa
Takumi
T
D000693:Anaerobiosis; D004578:Electron Spin Resonance Spectroscopy; D005978:Glutathione / Q000737:chemistry; D008981:Molsidomine / Q000031:analogs & derivatives / Q000737:chemistry; D009025:Morpholines / Q000737:chemistry; D009569:Nitric Oxide / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D009602:Nitrosamines / Q000737:chemistry; D009609:Nitrous Oxide / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D030421:Peroxynitrous Acid / Q000737:chemistry*; D026422:S-Nitrosoglutathione / Q000737:chemistry; D012996:Solutions; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
D009025:Morpholines; D009589:Nitrogen Oxides; D009602:Nitrosamines; D012996:Solutions; D030421:Peroxynitrous Acid; D009569:Nitric Oxide; C002744:3-nitrotyrosine; C002741:N-nitrosomorpholine; D014443:Tyrosine; D026422:S-Nitrosoglutathione; C002385:linsidomine; D008981:Molsidomine; D005978:Glutathione; D009609:Nitrous Oxide; D010100:Oxygen