Oxidation of eugenol to form DNA adducts and 8-hydroxy-2'-deoxyguanosine: Role of quinone methide derivative in DNA adduct formation

Carcinogenesis

Volumn 19, Issue 3, 1998, Pages 437-443

  Bodell, William J ^a   Ye, Qiuping ^a   Pathak, Deena N ^a   Pongracz, Krisztina ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; CATALASE; COPPER SULFATE; DEOXYGUANOSINE PHOSPHATE; DNA; EUGENOL; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; MYELOPEROXIDASE; QUINONE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CARCINOGEN DNA INTERACTION; CELL STRAIN HL 60; CONTROLLED STUDY; DNA ADDUCT; HUMAN; HUMAN CELL; OXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL;

AUTORADIOGRAPHY; COPPER SULFATE; DEOXYGUANOSINE; DNA ADDUCTS; EUGENOL; HL-60 CELLS; HORSERADISH PEROXIDASE; HUMANS; HYDROGEN PEROXIDE; INDOLEQUINONES; INDOLES; OXIDATION-REDUCTION; PEROXIDASE; QUINONES;

EID: 0031878397     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/19.3.437     Document Type: Article

References (45)

1. IARC Monographs (1985) Eugenol, Vol. 36. International Agency for Research on Cancer, Lyon, France, pp. 75-97.
2. Council on Scientific Affairs American Medical Association (1988) Evaluation of the health hazards of clove cigarettes. Proceedings of the House of Delegates, pp. 319-325.
3. Miller, E.C., Swanson, A.B., Phillips, D.H., Fletcher, T.L. and Miller, J.A. (1983) Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res., 43, 1124-1134.
4. NTP (1983) Carcinogenic studies of eugenol (CAS No. 97-53-0) in F344/N rats and B6C3F1 mice (Feed Studies)(NTP/TR No. 223, NIH No. 84-1779), US Department of Health and Human Services, Washington, DC, pp. 159-171.
5. Illnesses possibly associated with smoking clove cigarettes (1985) Morbid. Mortal. Weekly Rep., 34, 297-299.
6. .LaVoie, E.J., Adams, J.D., Reinhardt, J. and Hoffmann, D. (1986) Toxicity studies on cigarette smoke and constituents of clove: determination of the LD50 of eugenol by intratracheal instillation in rats and hamsters. Arch. Toxicol., 59, 78-81.
7. Thompson, D., Constantin, T.D., Egestad, B., Mickos, H. and Moldeus, P. (1990) Formation of glutathione conjugates during oxidation of eugenol by microsomal fraction of rat liver and lung. Biochem. Pharmacol., 39, 1587-1595.
8. Thompson, D.C., Constantin, T.D. and Moldeus, P. (1991) Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem.-Biol. Interactions, 77, 137-147.
9. Thompson, D., Norbeck, K., Olsson, L.I., Constantin, T.D., Van der Zee, J. and Moldeus, P. (1989) Peroxidase-catalysed oxidation of eugenol: Formation of a cytotoxic metabolite(s). J Biol Chem., 264, 1016-1021.
10. Thompson, D.C., Constantin, T.D., Norbeck, K., Svensson, B. and Moldeus, P. (1989) Metabolic activation of eugenol by myeloperoxidase and polymorphonuclear leukocytes. Chem. Res. Toxicol., 2, 186-192.
11. Bolton, J.L., Comeau, E. and Vukomanovic, V. (1995) The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended π-conjugation dramatically stabilizes the quinonc methide formed from eugenol. Chem.-Biol. Interactions, 95, 279-290.
12. O'Brien, P.J. (1988) Radical formation during the peroxidase catalyzed metabolism of carcinogens and xenobiotics: the reactivity of these radicals with GSH, DNA and unsaturated lipid. Free Rad. Biol. Med., 4, 169-183.
13. Markey, C.M., Alward, A., Weller, P.E. and Marnett, L.J. (1987) Quantitative studies of hydroperoxide reduction by prostaglandin H synthase: Reducing substrate specificity and the relationship of peroxidase and cylooxygenase activities. J. Biol. Chem., 262, 6266-6279.
14. Eling, T.E., Thompson, D.C., Foureman, G.L., Curtis J.F. and Hughes, M.F. (1990) Prostaglandin H synthase and xenobiotic oxidation. Ann. Rev. Pharmacol. Toxicol., 30, 1-45.
15. Bodell, W.J., Levay, G., Pongracz, K. and Pathak, D.N. (1994) DNA adducts formed by peroxidase activation of benzene metabolites. Polycyclic Aromat. Comp., 6. 1-8.
16. 32P-postlabeling. Carcinogenesis, 12, 1181-1191.
17. Levay, G. and Bodell, W.J. (1992) Potentiation of DNA adduct formation in HL-60 cells by combination of benzene metabolites. Proc. Natl Acad. Sci. USA, 89, 7105-7109.
18. Levay, G., Ross, D. and Bodell, W.J. (1993) Peroxidase activation of hydroquinone results in the formation of DNA adducts in HL-60 cells, mouse bone marrow macrophages and human bone marrow. Carcinogenesis, 14, 2329-2334.
19. Horvath, E., Levay, G., Pongracz, K. and Bodell, W.J. (1992) Peroxidative activation of o-phenyIhydroquinone leads to the formation of DNA adducts in HL-60 cells. Carcinogenesis, 13, 1937-1939.
20. Pathak, D.N., Levay, G. and Bodell, W.J. (1995) DNA adduct formation in the bone marrow of B6C3F1 mice treated with benzene. Carcinogenesis, 16, 1803-1808.
21. Gillette, J.R., Watland, D. and Kalnitsky, G. (1955) Some properties of the manganese and copper catalyzed oxidation of catechol and some other ortho-dihydroxybenzene derivatives. Biochem. Biophys. Acta, 16, 51-57.
22. Miller, D.M., Buettner, G.R. and Aust, S.D. (1990) Transition metals as catalysts of autoxidation reactions. Free Radical Biol. Med., 8, 95-108.
23. Li, Y. and Trush, M.A. (1993) DNA damage resulting from the oxidation of hydroquinone by copper: role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation. Carcinogenesis, 14, 1303-1311.
24. Li, Y. and Trush, M.A. (1994) Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res., 54(Suppl.), 1895s-1898s.
25. Inoue, S., Yammamoto, K. and Kawanishi, S. (1990) DNA damage induced by metabolites of o-phenylphenol in the presence of copper (II) ion. Chem. Res. Toxicol., 3, 144-149.
26. 32P-post-labeling of DNA reacted with p-benzoquinone. Carcinogenesis, 11, 1469-1472.
27. 32P-post-labeling of DNA reacted with p-benzoquinone. Chem. Res. Toxicol., 4, 199-202.
28. Pongracz, K., Pathak, D.N., Nakamura, T., Burlingame, A.L. and Bodell, W.J. (1995) Activation of the tamoxifen derivative metabolite E to form DNA adducts: Comparison with the adducts formed by microsomal activation of tamoxifen. Cancer Res., 55, 3012-3015.
29. Moorthy, B., Sriram, P., Pathak, D.N., Bodell, W.J. and Randerath, K. (1996) Tamoxifen metabolic activation: Comparison of DNA adducts formed by microsomal; and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adducts formed in vivo. Cancer Res., 56, 53-57.
30. Subrahmanyam, V.V., Ross, D., Eastmond, D.A. and Smith, M.T. (1991) Potential role of free radicals in benzene-induced myelotoxicity and leukemia. Free Rad. Biol. Med., 11, 495-515.
31. Dizdaroglu, M. (1992) Oxidative damage to DNA in mammalian chromatin. Mutat. Res., 275, 331-342.
32. Zanorotti, A. (1985) Synthesis and reactivity of vinyl quinone methide. J. Org. Chem., 50, 941-945.
33. Bodell, W.J. and Banerjee, M.R. (1976) Reduced DNA repair in mouse satellite DNA after treatment with methyl-methanesulfonate and N-methyl-N-nitrosourea. Nucl. Acids Res., 3, 1689-1701.
34. Shatkin, A.J. (1969) Colorimetric reactions for DNA, RNA and protein determinations. In K.Habel and N.O.Salzman (eds) Fundamental Techniques in Virology. Academic Press, New York, pp. 231-236.
35. Ye, Q. and Bodell, W.J. (1996) Production of 8-hydroxy-2′deoxyguanosine in DNA by microsomal activation of tamoxifen and 4-hydroxytamoxifen. Carcinogenesis, 17, 1747-1750.
36. Kasai, H. and Nishimura, S. (1984) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucl. Acid Res., 12, 2137-2145.
37. Levay, G. and Bodell, W.J. (1996) Role of hydrogen peroxide in the formation of DNA adducts in HL-60 cells treated with benzene metabolites. Biochem. Biophys. Res. Commun., 222, 44-49.
38. Hollenberg, P.F. (1992) Mechanisms of cytochrome P450 and peroxidase-catalyzed xenobiotic metabolism. FASEB J., 6, 686-694.
39. Thompson, D.C., Thompson, J.A., Sugumaran, M. and Moldeus, P. (1992) Biological and toxicological consequences of quinone methide formation. Chem.-Biol. Interactions, 86, 129-162.
40. Rahman, A., Shahabudddin, Hadi, S.M., Parish, J.H. and Ainley, K. (1989) Strand scission in DNA induced by quercetin and Cu(II): role of Cu(I) and oxygen free radicals. Carcinogenesis, 10, 1833-1839.
41. Prütz, W.A. (1993) Cu(II)-induced oxidation of catechols, ascorbate and o-phenylenediamine is promoted by DNA. Z. Naturforsch., 48C, 872-878.
42. Li, Y., Kuppusamy, P., Zweier, J.L. and Trush, M.A. (1995) ESR evidence for the generation of reactive oxygen species from the copper mediated oxidation of the benzene metabolite, hydroquinone: role in DNA damage. Chem.-Biol. Interactions, 94, 101-120.
43. Dizdaroglu, M., Rao, G., Halliwell, B. and Gajewski, E. (1991) Damage to DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Archiv. Biochem. Biophys., 285, 317-324.
44. Makrigiorgos, G.M., Bump, E., Huang, C., Baranowska-Kortylewicz, J. and Kassis, A.I. (1995) A fluorimetric method for the detection of copper-mediated hydroxyl free radicals in the immediate proximity of DNA. Free Rad. Biol. Med., 18, 669-678.
45. Phillips, D.H. (1990) Further evidence that eugenol does not bind to DNA in vivo. Mutat. Res, 245, 23-26.