Formation of 8-nitroguanine by the reaction of guanine with peroxynitrite in vitro

Vladimir Yermilov, Julieta Rubio, Michel Becchi, Marlin D. Friesen, Brigitte Pignatelli, Hiroshi Ohshima

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273 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)2045-2050
Number of pages6
Issue number9
StatePublished - Sep 1995
Externally publishedYes

ASJC Scopus subject areas

  • Cancer Research


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