DNA cleavage induced by oxyl radicals generated in the photosensitized decomposition of fatty ester hydroperoxides derived from oleic and linoleic acid

Archives of Biochemistry and Biophysics
W AdamC R Saha-Möller

Abstract

The xanthone-sensitized photodecomposition of the fatty ester hydroperoxides 1 and 2 in the presence of pBR 322 DNA was investigated as a chemical model system to assess whether this process may cause DNA damage through oxyl radicals. Unequivocally, oxyl radicals are formed in the xanthone-sensitized photodecomposition of the hydroperoxides 1 and 2, as confirmed by EPR studies. Indeed, both hydroperoxides 1 and 2 induce DNA single-strand breaks upon uv-A irradiation in the presence of the exogenous sensitizer xanthone. Under similar reaction conditions, the corresponding alcohol 3 of the hydroperoxide 1 was ineffective. Mannitol as radical scavenger inhibited significantly the formation of DNA single-strand breaks in the xanthone-sensitized decomposition of the hydroperoxides 1 and 2. Irradiation of xanthone alone or the hydroperoxides 1 and 2 without sensitizer did not cause any detectable DNA single-strand breaks. These results confirm that photosensitization of the fatty ester hydroperoxides 1 and 2 induces DNA modifications by oxyl radicals. We suspect that the combination of endogenous photosensitizers, solar uv radiation, and lipid hydroperoxides may damage cellular DNA through oxyl radicals.

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Citations

Jun 9, 2005·Natural Product Research·Birija S PatroSubrata Chattopadhyay
Aug 13, 2003·Biological & Pharmaceutical Bulletin·Kazuyuki HiramotoKiyomi Kikugawa
Jul 11, 2009·Journal of Clinical Biochemistry and Nutrition·Hiroko Mori, Hideo Iwahashi
Dec 12, 2007·Bioscience, Biotechnology, and Biochemistry·Hiroko Mori, Hideo Iwahashi
Feb 26, 2004·Bioorganic & Medicinal Chemistry·Mahesh SubramanianSubrata Chattopadhyay
Oct 15, 2010·Free Radical Research·Graziella E RonseinPaolo Di Mascio
Jan 24, 2002·Journal of Agricultural and Food Chemistry·Tetsuya SuzukiKunimoto Hotta
Aug 18, 2005·Journal of Agricultural and Food Chemistry·Birija S PatroSubrata Chattopadhyay
Sep 2, 2010·Bioorganic & Medicinal Chemistry·Birija S PatroSubrata Chattopadhyay

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