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Food & Nutrition Science

Metal-catalyzed oxidation of 2-alkenals generates genotoxic 4-oxo-2-alkenals during lipid peroxidation

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Pages 2007-2013 | Received 14 Apr 2016, Accepted 09 May 2016, Published online: 07 Jun 2016

References

  • Sander CS, Hamm F, Elsner P, et al. Oxidative stress in malignant melanoma and non-melanoma skin cancer. Br. J. Dermatol. 2003;148:913–922.10.1046/j.1365-2133.2003.05303.x
  • Gonenc A, Ozkan Y, Torun M, et al. Plasma malondialdehyde (MDA) levels in breast and lung cancer patients. J. Clin. Pharm. Ther. 2001;26:141–144.10.1046/j.1365-2710.2001.00334.x
  • Shichiri M. The role of lipid peroxidation in neurological disorders. J. Clin. Biochem. Nutr. 2014;54:151–160.10.3164/jcbn.14-10
  • Kawai Y, Takeda S, Terao J. Lipidomic analysis for lipid peroxidation-derived aldehydes using gas chromatography-mass spectrometry. Chem. Res. Toxicol. 2007;20:99–107.10.1021/tx060199e
  • Gueraud F, Atalay M, Bresgen N, et al. Chemistry and biochemistry of lipid peroxidation products. Free Radic. Res. 2010;44:1098–1124.10.3109/10715762.2010.498477
  • Winczura A, Zdzalik D, Tudek B. Damage of DNA and proteins by major lipid peroxidation products in genome stability. Free Radic. Res. 2012;46:442–459.10.3109/10715762.2012.658516
  • Catala A. Lipid peroxidation of membrane phospholipids generates hydroxy-alkenals and oxidized phospholipids active in physiological and/or pathological conditions. Chem. Phys. Lipids. 2009;157:1–11.10.1016/j.chemphyslip.2008.09.004
  • Guichardant M, Bacot S, Moliere P, et al. Hydroxy-alkenals from the peroxidation of n-3 and n-6 fatty acids and urinary metabolites. Prostaglandins, Leukot. Essent. Fatty Acids. 2006;75:179–182.10.1016/j.plefa.2006.05.006
  • Chung FL, Chen HJ, Nath RG. Lipid peroxidation as a potential endogenous source for the formation of exocyclic DNA adducts. Carcinogenesis. 1996;17:2105–2111.10.1093/carcin/17.10.2105
  • Petrova kV, Jalluri RS, Kozekov ID, et al. Mechanism of 1, N2-etheno-2′-deoxyguanosine formation from epoxyaldehydes. Chem. Res. Toxicol. 2007;20:1685–1692.10.1021/tx7001433
  • Burcham PC. Genotoxic lipid peroxidation products: their DNA damaging properties and role in formation of endogenous DNA adducts. Mutagenesis. 1998;13:287–305.10.1093/mutage/13.3.287
  • Voulgaridou GP, Anestopoulos I, Franco R, et al. DNA damage induced by endogenous aldehydes: current state of knowledge. Mutat. Res. 2011;711:13–27.10.1016/j.mrfmmm.2011.03.006
  • Nair U, Bartsch H, Nair J. Lipid peroxidation-induced DNA damage in cancer-prone inflammatory diseases: a review of published adduct types and levels in humans. Free Radic. Biol. Med. 2007;43:1109–1120.10.1016/j.freeradbiomed.2007.07.012
  • Chou PH, Kageyama S, Matsuda S, et al. Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues. Chem. Res. Toxicol. 2010;23:1442–1448.10.1021/tx100047d
  • Matsuda T, Tao H, Goto M, et al. Lipid peroxidation-induced DNA adducts in human gastric mucosa. Carcinogenesis. 2013;34:121–127.10.1093/carcin/bgs327
  • Kawai Y, Uchida K, Osawa T. 2′-deoxycytidine in free nucleosides and double-stranded dna as the major target of lipid peroxidation products. Free Radic. Biol. Med. 2004;36:529–541.10.1016/j.freeradbiomed.2003.12.006
  • Hecht SS, Young-Sciame R, Chung FL. Reaction of alpha-acetoxy-N-nitrosopiperidine with deoxyguanosine: oxygen-dependent formation of 4-oxo-2-pentenal and a 1, N2-ethenodeoxyguanosine adduct. Chem. Res. Toxicol. 1992;5:706–712.10.1021/tx00029a018
  • Rindgen D, Nakajima M, Wehrli S, et al. Covalent modifications to 2′-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation. Chem. Res. Toxicol. 1999;12:1195–1204.10.1021/tx990034o
  • Berdyshev EV, Goya J, Gorshkova I, et al. Characterization of sphingosine-1-phosphate lyase activity by electrospray ionization-liquid chromatography/tandem mass spectrometry quantitation of (2E)-hexadecenal. Anal. Biochem. 2011;408:12–18.10.1016/j.ab.2010.08.026
  • Kasai H, Kawai K. 4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation: occurrence, detection and adduct formation. Mutat. Res. 2008;659:56–59.10.1016/j.mrrev.2008.02.003
  • Chen HJ, Chung FL. Epoxidation of trans -4-Hydroxy-2-nonenal by fatty acid hydroperoxides and hydrogen peroxide. Chem. Res. Toxicol. 1996;9:306–312.10.1021/tx9501389
  • Lee SH, Blair IA. Characterization of 4-Oxo-2-nonenal as a novel product of lipid peroxidation. Chem. Res. Toxicol. 2000;13:698–702.10.1021/tx000101a
  • Blair IA. Lipid hydroperoxide-mediated DNA damage. Exp. Gerontol. 2001;36:1473–1481.10.1016/S0531-5565(01)00133-4
  • Esterbauer H, Schaur RJ, Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 1991;11:81–128.10.1016/0891-5849(91)90192-6
  • Wu T, Sempos CT, Freudenheim JL, et al. Serum iron, copper and zinc concentrations and risk of cancer mortality in US adults. Ann. Epidemiol. 2004;14:195–201.10.1016/S1047-2797(03)00119-4
  • Yamaguchi K, Mandai M, Toyokuni S, et al. Contents of endometriotic cysts, especially the high concentration of free iron, are a possible cause of carcinogenesis in the cysts through the iron-induced persistent oxidative stress. Clin. Cancer Res. 2008;14:32–40.10.1158/1078-0432.CCR-07-1614
  • Kato J, Kobune M, Nakamura T, et al. Normalization of elevated hepatic 8-hydroxy-2’-deoxyguanosine levels in chronic hepatitis C patients by phlebotomy and low iron diet. Cancer Res. 2001;61:8697–8702.
  • Torti SV, Torti FM. Iron and cancer: more ore to be mined. Nat. Rev. Cancer. 2013;13:342–355.10.1038/nrc3495
  • Nair J, Sone H, Nagao M, et al. Copper-dependent formation of miscoding etheno-DNA adducts in the liver of Long Evans cinnamon (LEC) rats developing hereditary hepatitis and hepatocellular carcinoma. Cancer Res. 1996;56:1267–1271.
  • Toyokuni S, Sagripanti JL. Iron-mediated DNA damage: sensitive detection of DNA strand breakage catalyzed by iron. J. Inorg. Biochem. 1992;47:241–248.10.1016/0162-0134(92)84069-Y

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