Nucleic acid alkylation by free radical metabolites of ethanol. Formation of 8-(1-hydroxyethyl)guanine and 8-(2-hydroxyethyl)guanine adducts

Chemical Research in Toxicology

Volumn 11, Issue 8, 1998, Pages 888-894

  Nakao, Lia S ^a   Augusto, Ohara ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

8 (1 HYDROXYETHYL)GUANINE; 8 (2 HYDROXYETHYL)GUANINE; FREE RADICAL; NUCLEIC ACID; UNCLASSIFIED DRUG;

ALCOHOL CONSUMPTION; ALKYLATION; ARTICLE; CANCER RISK; ELECTRON SPIN RESONANCE; IMMUNE RESPONSE; NUCLEIC ACID METABOLISM; PROTON NUCLEAR MAGNETIC RESONANCE; SPIN TRAPPING;

ALKYLATION; DNA; ETHANOL; FREE RADICALS; GUANINE; OXIDATION-REDUCTION; RNA;

EID: 0031819230     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9800351     Document Type: Article

References (52)

1. Seitz, H., and Pöschl, G. (1997) Alcohol and gastrointesinal cancer: pathogenic mechanisms. Addit. Biol. 2, 19-33.
2. Brooks, P. J. (1997) DNA damage, DNA repair and alcohol toxicity-a review. Alcohol Clin. Exp. Res. 21, 1073-1082.
3. Kurose, I., Higuchi, H., Kato, S., Miura, S., and Ishii, H. (1996) Ethanol-induced oxidative stress in the liver. Alcohol. Clin. Exp. Res. 20, 77A-85A.
4. Rajasinghe, H., Jayatilleke, E., and Shaw, S. (1990) DNA cleavage during ethanol metabolism: role of Superoxide radicals and catalytic iron. Life Sci. 47, 807-814.
5. Renis, M., Calabrese, V., Russo, A., Calderone, A., Barcellona, M. L., and Rizza, V. (1996) Nuclear DNA strand breaks during ethanol-induced oxidative stress in rat brain. FEBS Lett. 390, 153-156.
6. Reinke, L. A., Lai, K., DuBose, C. M., and McCay, P. B. (1987) Reactive free radical generation in vivo in heart and liver of ethanol-fed rats: correlation with free radical formation in vitro. Proc. Natl. Acad. Sci. U.S.A. 84, 9223-9227.
7. Albano, E., Tomasi, A., Goria-Gatti, L., and Dianzani, M. U. (1988) Spin-trapping of free radical species produced during microsomal metabolism of ethanol. Chem.-Biol. Interact. 65, 223-234.
8. Knecht, K. T., Bradford, B. U., and Mason, R. P. (1990) In vivo formation of a free radical metabolite of ethanol. Mol. Pharmacol. 38, 26-30.
9. Rao, D. N. R., Yang, M.-X., Lasker, J. M., and Cederbaum, A I. (1996) 1-Hydroxyethyl radical formation during NADPH- and NADH-dependent oxidation of ethanol by human liver microsomes. Mol. Pharmacol. 49, 814-821.
10. Reinke, L. A., Moore, D. R., and McCay, P. B. (1997) Mechanisms for metabolism of ethanol to 1-hydroxyethyl radicals in rat liver microsomes. Arch. Biochem. Biophys. 348, 9-14.
11. Moncada, C., Torres, V., Varghese, G. Albano, E., and Israel, Y. (1994) Ethanol-derived immunoreactive species formed by free radical mechanisms. Mol. Pharmacol. 46, 786-791.
12. Clot, P., Bellomo, G., Tabone, M., Aricó, S., and Albano, E. (1995) Detection of antibodies against protein modified by hydroxyethyl free radicals in patients with alcoholic cirrhosis. Gastroenterology 108, 201-207.
13. Clot, P., Albano, E., Eliasson, E., Tabone, M., Aricó, S., Israel, Y., Moncada, C., and Ingelman-Sundberg, M. (1996) Cytochrome P4502E1 hydroxyethyl radical adducts as the major antigen in autoantibody formation among alcoholics. Gastroenterology 111, 206-216.
14. Augusto, O. (1993) Alkylation and cleavage of DNA by carboncentered free radical metabolites. Free Radic. Biol. Med. 15, 329-336.
15. Salomon, J., and Elad, D. (1973) Photochemical reactions of nucleic acid constituents. Peroxide-initiated reactions of purines with alcohols. J. Org. Chem. 38, 3420-3421.
16. Livneh, Z., Livneh, E., and Sperling, J. (1980). Specific photoalkylation of poly U and poly A with 2-propanol and their messenger properties. Photochem. Photobiol. 32, 131-135.
17. Livneh, E., Elad, D., and Sperling, J. (1982) Light-induced free reactions of purines and pyrimidines in deoxyribonucleic acid. Effect of structure and base sequence on reactivity. Biochemistry 21, 3698-3703.
18. Augusto, O., Cavalieri, E. L., Rogan, E. G., Ramakrishna, N. V. S., and Kolar, C. (1990) Formation of 8-methylguanine as a result of DNA alkylation by methyl radicals generated during horseradish peroxidase-catalyzed oxidation of methylhydrazine. J. Biol. Chem. 265, 22093-22096.
19. Netto, L. E. S., Ramakrishna, N. V. S., Kolar, C. Cavalieri, E. L., Rogan, E. G., Lawson, T. A., and Augusto, O. (1992) Identification of C8-methyl guanine in the hydrolysates of DNA from rats administered 1,2-dimethylhydrazine. Evidence for in vivo DNA alkylation by methyl radicals. J. Biol. Chem. 267, 21524-21527.
20. Hix, S., Morais, M. S., and Augusto, O. (1995) DNA methylation by tert-butylhydroperoxide-iron(II). Free Radic. Biol. Med. 19, 293-301.
21. Kikugawa, K, Kato, T., and Kojima, K. (1992) Substitution of p and o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic diazoquinone compounds. Mutat. Res. 268, 105-114.
22. Gannet, P. M., Lawson, T., Miller, D. D., Thakkar, J. W., Lord, W.-M., Yau, and Toth, B. (1996) 8-Arylguanine adducts from arenediazonium ions and DNA. Chem.-Biol. Interact. 101, 149-164.
23. Kohda, K., Tsunomoto, H., Minoura, Y., Tanabe, K., and Shibutani, S. (1996) Synthesis, miscoding specifity, and thermodynamic stability of oligodeoxynucleotide containing 8-methyl-2′-deoxyguanosine. Chem. Res. Toxicol. 9, 1278-1284.
24. Kohda, K., Tsunomoto, H., Kasamatsu, T., Sawamura, F., Terashima, I., and Shibutani, S. (1997) Synthesis and miscoding specifity of oligodeoxynucleotide containing 8-phenyl-2′-deoxyguanosine. Chem. Res. Toxicol. 10, 1351-1358.
25. Kaur, H., Leung, K. H. W., and Perkins, M. J. (1981) A watersoluble, nitroso-aromatic spin-trap. J. Chem. Soc., Chem. Commun., 142-143.
26. North, J. A., Spectro, A. A., and Buettner, G. (1992) Detection of lipid radicals by electron paramagnetic resonance spin trapping using intact cells enriched with polyunsaturated acids. J. Biol. Chem. 267, 5743-5746.
27. Sambrook, J., Fritsch, E. F., and Maniatis, T., Eds. (1989) Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY.
28. Maeda, M., Nushi, K., and Kawazoe, Y. (1974) Studies on chemical alterations of nucleic acid and their components-VII C-alkylation of purine bases through free radical process catalyzed by ferrous ion. Tetrahedron 30, 2677-2682.
29. Barrows, L. R., and Shank, R. C. (1981) Aberrant methylation of liver DNA during hepatotoxicity. Toxicol. Appl. Pharmacol. 60, 334-345.
30. Kang, J. O., Gallargher, K. S., and Cohen, G. (1993) Methylation of RNA purine bases by methyl radicals. Arch. Biochem. Biophys. 306, 178-182.
31. 23-ethenoguanine using liquid chromatography/electrospray ionization mass spectrometry. J. Mass Spectrom. 31, 1271-1276.
32. Gomes, L. F., Netto, L. E. S., and Augusto, O. (1995) Electrochemical detection of C8-methylguanine: a potential marker for monitoring DNA alkylation by methyl radicals. In The Oxygen Paradox (Davies, K. J. A., and Ursini, F., Eds.) pp 149-156, CLEUP Press, Padova, Italy.
33. Park, J.-W., Cundy, K. C., and Ames, B. N. (1989) Detection of DNA adducts by high-performance liquid chromatography with electrochemical detection. Carcinogenesis 10, 827-832.
34. Ozawa, T., an Hanaki, A. (1987) Spin-trapping of alkyl radicals by a water-soluble nitroso aromatic spin-trap, 3,5-dibromo-4-nitrosobenzenesulfonate. Bull. Chem. Soc. Jpn. 60, 2304-2306.
35. Smith, P., and Robertson, J. S. (1988) Electron paramagnetic resonance study of the reactions of the spin trap 3,5-dibromo-4-nitrosobenzenesulfonate. Can. J. Chem. 66, 1153-1158.
36. Gatti, R. M., Alvarez, B., Vasquez-Vivar, J., Radi, R., and Augusto, O. (1998) Formation of spin trap adducts during the decomposition of peroxynitrite. Arch. Biochem. Biophys. 349, 36-46.
37. Dizdaroglu, M., Rao, G., Halliwell, B., and Gajewski, E. (1991) Damage to the DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch. Biochem. Biophys. 285, 317-324.
38. Cadet, J. (1994) DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralens. In DNA adducts: Identification and biological significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) pp 245-276, IARC Scientific Publications, Lyon, France.
39. Henle, E. S., Luo, Y., Gassmann, W., and Linn, S. (1996) Oxidative damage to DNA constituents by iron-mediated Fenton reactions. The deoxyguanosine family. J. Biol. Chem. 271, 21177-21186.
40. 3+, and oxygen react with DNA-derived radicals formed during iron-mediated Fenton reactions. Biochemistry 35, 12212-12219.
41. Uppu, R. M., Cueto, R., Squadrito, G. L., Salgo, M. G., and Pryor, W. A. (1996) Competitive reactions of peroxynitrite with 2′-deoxyguanosine and 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-ox-odG): relevance to the formation of 8-oxodG in DNA exposed to peroxynitrite. Free Radic. Biol. Med. 21, 407-411.
42. Halliwell, B., and Gutteridge, J. M. C. (1989) Free Radicals in Biology and Medicine, Clarendon Press: Oxford, England.
43. Augusto, O. (1989) Spin-trapping studies of xenobiotic mediated toxicity. In CRC Handbook of Biomedicine of Free Radicals and Antioxidants (Miquel, J., Ed.) Vol. III, pp 193-208, CRC Press, Boca Raton, FL.
44. Motley, C., and Mason, R. P. (1989) Nitroxide radical adducts in biology: chemistry, applications and pitfalls. In Biological Magnetic Resonance (Berliner, L. J., and Reuben, J., Eds.) Vol. 8, pp 489-546, Plenum, New York.
45. Netto, L. E. S., Ferreira, A. M. C., and Augusto, O. (1991) DNAiron(III): complex formation and catalytic activity in the oxidation of hydrazine derivatives. Chem.-Biol. Interact. 79, 1-14.
46. Voet, D., and Voet, J. G. (1990) Biochemistry, John Wiley & Sons, New York.
47. Asmus, K.-D., Mockel, H., and Henglein, A. (1973) Pulse radiolytic study of the site of OH radical attack on aliphatic alcohols in aqueous solution. J. Phys. Chem. 77, 1218-1221.
48. Rush, J. D., Maskos, Z., and Koppenol, W. H. (1990) Distinction between hydroxyl radical and ferryl species. Methods Enzymol. 186, 148-156.
49. Walling, C. (1975) Fenton's reagent revisited. Acc. Chem. Res. 8, 125-150.
50. Frankel-Conrat, H., and Singer, B. (1988) Nucleoside adducts are formed by cooperative reaction of acetaldehyde and alcohols: Possible mechanism for the role of ethanol in carcinogenesis. Proc. Natl. Acad. Sci. U.S.A. 85, 3758-3761.
51. Fang, J.-L., and Vaca, C. E. (1997) Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 18, 627-632.
52. Joenje, H. (1989) Genetic toxicology of oxygen. Mutat. Res. 219, 193-208.