5-Methylcytosine attack by hydroxyl free radicals and during carbon tetrachloride promoted liver microsomal lipid peroxidation: Structure of reaction products

Chemico-Biological Interactions

Volumn 99, Issue 1-3, 1996, Pages 289-299

  Castro, Gerardo D ^a   Díaz Gómez, María I ^a   Castro, José A ^a  

^a Instituto de Investigaciones Cientificas y Tecnicas de Las Fuerzas Armadas   (Argentina)

Author keywords

5 Methylcytosine; Carbon tetrachloride; DNA methylation; Free radicals; Lipid peroxidation

Indexed keywords

5 METHYLCYTOSINE; CARBON TETRACHLORIDE; FREE RADICAL; HYDROXYL RADICAL;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DNA METHYLATION; LIPID PEROXIDATION; LIVER MICROSOME; MALE; METABOLIC ACTIVATION; NONHUMAN; RAT;

EID: 0343026425     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-2797(95)03680-6     Document Type: Article

References (41)

1. G.D. Castro, C.J. Stamato and J.A. Castro, 5-Methylcytosine attack by free radicals arising from bromotrichloromethane in a model system. Structures of reaction products, Free Rad. Biol. Med., 17 (1994) 419-428.
2. T.F. Slater, Activation of carbon tetrachloride: chemical principles and biological significance, in: D.C. Mc Brien and T.F. Slater (Eds), Free Radicals, Lipid Peroxidation and Cancer, Academic Press, New York, 1982, pp. 260-264.
3. J.A. Castro, Mechanistical studies and prevention of free radical cell injury, Proceedings of the 9th IUPHAR International Congress on Pharmacology, Vol. 2, 1984, pp. 243-250.
4. M.U. Dianzani, Free radicals in physiology and pathology, Bull. Soc. Ital. Biol. Sper., 68 (1992) 491-511.
5. R.O. Recknagel, E.A. Glende, J.A. Dolak and R.L. Waller, Mechanism of carbon tetrachloride toxicity, Pharmacol. Ther., 43 (1989) 139-154.
6. A.A. Horton and S. Fairhurst, Lipid peroxidation and mechanisms of toxicity, Crit. Rev. Toxicol., 18 (1987) 28-79.
7. K. Sai, A. Tagaki, T. Umemura, R. Hasegawa and Y. Rurokawa, Relation of 8 hydroxy deoxy guanosine formation in rat kidney to lipid peroxidation, glutathione level and relative organ weight after a single administration of potassium bromate, Jpn. J. Cancer Res., 82 (1991) 165-169.
8. A. Hruskewycz and O.S. Bergtold, The hydroxyguanine content of isolated mitochondria increases with lipid peroxidation, Mutat. Res., 244 (1990) 123-128.
9. V.L. Wilson and P.A. Jones, Inhibition of DNA methylation by chemical carcinogenesis in vitro, Cell, 32 (1983) 239-246.
10. P.A. Jones and J.D. Buckley, The role of DNA methylation in cancer. Adv. Cancer Res., 54 (1990) 1-23.
11. R. Holliday and G.W. Grigg, DNA methylation and mutation, Mutat. Res., 285 (1993) 61-67.
12. J.A. Castro, E.V. Cignoli, C.R. de Castro and O.M. de Fenos, Prevention by cystamine of liver necrosis and early biochemical alterations induced by carbon tetrachloride, Biochem. Pharmacol., 21 (1972) 102-114.
13. R.A. Floyd, C.A. Lewis and P.K. Wong, High-pressure liquid chromatography-electrochemical detection of oxygen free radicals, in: Methods in Enzymology, Academic Press, New York, Vol. 105, pp. 231-237.
14. B. Halliwell and O.I. Aruoma, DNA damage by oxygen-derived species, its mechanism and measurement in mammalian systems, FEBS Lett., 281 (1991) 9-19.
15. S.L. Fanelli and J.A. Castro, Carbon tetrachloride promoted malondialdehyde formation in liver microsomal and nuclear preparations from Sprague Dawley or Osborne Mendel male rats, Res. Commun. Chem. Pathol. Pharmacol., 82 (1993) 233-236.
16. M. Dizdaroglu, Gas chromatography-mass spectrometry of free radical-induced products of pyrimidines and purines in DNA, Methods Enzymol., 193 (1990) 842-857.
17. A.P. Breen and J.A. Murphy, Reactions of hydroxyl radicals with DNA, Free Rad. Biol. Med., 18 (1995) 1033-1077.
18. G.D. Castro, J.T. Simpson and J.A. Castro, Interaction of trichloromethyl free radicals with thymine in a model system. A mass spectrometric study, Chem.-Biol. Interact., 90 (1994) 13-22.
19. J.F. Mouret, M. Polverelli, F. Sarrazini and J. Cadet, Ionic and radical oxidations of DNA by hydrogen peroxide, Chem.-Biol. Interact., 77 (1991) 187-201.
20. O.I. Aruoma, B. Halliwell, E. Gajewski and M. Dizdaroglu, Copper-iron-dependent damage to the bases in DNA in the presence of hydrogen peroxide, Biochem. J., 273 (1991) 601-604.
21. R.L.P. Adams, DNA methylation, Biochem. J., 265 (1990) 309-320.
22. L.A. Poirier, Methyl group deficiency in hepatocarcinogenesis, Drug Metab. Rev., 26 (1994) 185-199.
23. C.C. Harris, Chemical and physical carcinogenesis: advances and perspectives for the 1990s, Cancer Res. (Suppl). 51 (1991) 5023-5044.
24. T.J. Slaga, A.J.P. Klein-Szanto, L. Triplett, P. Yotti and J.E. Trosko, Skin tumor promoting activity of benzoyl peroxide, a widely used free radical generating compound, Science 13 (1981) 1023-1025.
25. T.J. Slaga, V. Solanki and M. Logani, Studies on the mechanism of action of antitumor promoting agents: suggestive evidence for the involvement of free radicals in promotion, in: O. F. Nygaard and M.G. Simic (Eds.), Radioprotectors and Anticarcinogens, Academic Press, New York, 1983, pp. 471-485.
26. V. Solanki, R.S. Kana and T.J. Slaga, Diminution of mouse epidermal superoxide dismutase and catalase activities by tumor promoters, Carcinogenesis, 2 (1982) 1141-1146.
27. S. Belman and W. Troll, Hormones, cyclic nucleotides and prostaglandins, in: T.J. Slaga, A. Sivak and R.K. Bontwell (Eds.), Carcinogenesis, Mechanisms of Tumor Promotion and Carcinogenesis, Raven Press, New York, 1978, Vol. 2, pp. 117-134.
28. P. Cerutti, Prooxidant states in tumor or promotion, Science 227 (1985) 375-381.
29. T.W. Kensler and B.G. Taffe, Free radicals in tumor promotion, Adv. Free Rad. Biol. Med., 2 (1986) 347-387.
30. G. Witz, Active oxygen species as factors in multistage carcinogenesis, Proc. Soc. Exp. Biol. Med., 198 (1991) 675-682.
31. M.A. Trusk and T. W. Kensler, An overview of the relationship between oxidative stress and chemical carcinogenesis, Free Rad. Biol. Med., 10 (1991) 201-209.
32. K.Z. Guyton, T.W. Kensler, Oxidative mechanisms in carcinogenesis, Br. Med. J., 49 (1993) 523-544.
33. T. Ganguly and N.J. Duker, Inhibition of DNA polymerase activity by thymine hydrates, Mutat. Res., 293 (1992) 71-77.
34. S.A. Weitzman, P.W. Turk, D.H. Milkouski and K. Kozlowski, Free radical adducts induce alterations in DNA cytosine methylation, Proc. Natl. Acad. Sci. USA, 91 (1994) 1261-1264.
35. M.I. Díaz Gómez and J.A. Castro, Nuclear activation of carbon tetrachloride and chloroform, Res. Commun. Chem. Pathol. Pharmacol., 27 (1980) 191-194.
36. 4 reactive metabolites and liver DNA or nuclear protein fractions, Carcinogenesis, 10 (1989) 289-294.
37. G.D. Castro, M.I. Díaz Gómez and J.A. Castro, Biotransformation of carbon tetrachloride and lipid peroxidation promotion by liver nuclear preparations from different animal species. Cancer Lett., 53 (1990) 9-15.
38. IARC, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Some halogenated hydrocarbons, Lyon, France, Vol. 20, 1979, pp. 371-379.
39. US EPA, Health assessment document for carbon tetrachloride, EPA 600/8é001, 1983.
40. G.D. Castro and J.A. Castro, Cytosine attack by free radicals arising from bromotrichloromethane in the presence of benzoyl peroxide catalyst. A mass spectrometric study, Teratogen. Carcinogen. Mutagen., 13 (1993) 235-245.
41. J. Darnell, H. Lodish and D. Baltimore, Molecular cell biology, Scientific American Books, New York, 1990, pp. 82-85.