Reactions between Nitric Oxide, Superoxide, and Peroxynitrite: Footprints of Peroxynitrite in Vivo

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This chapter examines a number of reaction pathways for nitric oxide, with the emphasis on assessing their biological relevance. Till date, the fastest reaction for nitric oxide with clear toxicological significance is that with superoxide to produce ONOO. Thus, the chemistry and reactivity of ONOO are discussed at length. In addition, the interaction between ONOO and nitric oxide is examined with respect to its effects on nitric oxide half-life as well as effects on peroxynitrite reactivity toward phenol. Reaction mechanisms are proposed to account for the nitrated, hydroxylated, and nitrosated phenolic products available. The primary reactions of nitric oxide are almost exclusively limited to other species possessing unpaired electrons, such as the iron in heme proteins, as well as nonheme iron and superoxide. Nitric oxide does react with molecular oxygen; however, this reaction occurs so slowly at physiological concentrations as to be toxicologically insignificant. Primary reactions of nitric oxide can result in a variety of secondary products ranging from innocuous nitrate (NO−3), nitrite (NO−2) and nitroxyl (NO) to reactive intermediates such as nitrosonium (NO+), peroxynitrite (ONOO), and nitrogen dioxide (NO2). The predominant end products of these reactive intermediates that are stable enough to be measured in biological systems include nitrite, nitrate, nitrotyrosine, and various nitrosothiols.

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