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Formation of 8-nitroguanine by the reaction of guanine with peroxynitrite in vitro
International Agency for Research on Cancer 150 Cours Albert Thomas, 69372 Lyon Cedex 08
1CNRS-SCA 69390 Vernaison, France
2Visiting Scientist at IARC from: N.N.Petrov Research Institute Leningradskaya st. 68, Pesochny-2 189646, St Petersburg, Russia
3Visiting Scientist at IARC from: Instituto de Investigaciones Biomédicas, Departmento de Genética y Toxicología Ambiental, Apartado Postal 70228, CD Universitaria 04510 México DF, México
4To whom correspondence should be addressed
Nitric oxide and superoxide anion, both formed in inflamed tissues, react rapidly to form the peroxynitrite anion (ONOO–), a strong oxidant which can initiate reactions characteristic of hydroxyl radical (HO•), nitronium ion (NO2+) and nitrogen dioxide radical (NO2•). Peroxynitrite, therefore, may cause DNA or tissue damage, contributing to the multistage carcinogenesis process. We have studied reactions of various bases, nucleosides or deoxynucleosides with peroxynitrite in vitro. Guanine reacted rapidly with peroxynitrite under physiological conditions and formed several substances, two of which were yellow, a characteristic of nitro and nitroso compounds. On the basis of chromatographic and spectral evidence we identified the major compound (which accounts for 
80% of all compounds formed) as 8-nitroguanine. Its formation was maximal at pH 8 and increased dose-dependently with peroxynitrite concentration, but was not dependent on guanine concentration. The presence of ferric ions, which has been shown to catalyse nitration of tyrosine, did not affect nitration of guanine. 8-Nitroguanine could act as a specific marker for DNA damage induced by peroxynitrite in inflamed tissues.
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