Mechanism of oxidative DNA damage induced by a heterocyclic amine, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline

Japanese Journal of Cancer Research

Volumn 90, Issue 3, 1999, Pages 268-275

  Murata, Mariko ^a   Kobayashi, Mikiko ^a   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Copper; Heterocyclic amine; MeIQx; NADH; Oxidative DNA damage

Indexed keywords

2 AMINO 3,8 DIMETHYLIMIDAZO[4,5 F]QUINOXALINE; CATALASE; CHELATING AGENT; COPPER ION; CYTOSINE; DNA; GUANOSINE DERIVATIVE; HETEROCYCLIC AMINE; PHOSPHORUS 32; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; THYMINE;

ARTICLE; AUTOOXIDATION; CHEMICAL CARCINOGENESIS; CONTROLLED STUDY; DNA ADDUCT; DNA CLEAVAGE; DNA DAMAGE; ELECTROCHEMICAL DETECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLITE; OXIDATIVE STRESS; PRIORITY JOURNAL; REDUCTION; ULTRAVIOLET SPECTROSCOPY;

EID: 0032954014     PISSN: 09105050     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1349-7006.1999.tb00743.x     Document Type: Article

References (40)

1. Ames, B. N. Dietary carcinogens and anticarcinogens. Science, 221, 1256-1264 (1983).
2. Sugimura, T. and Sato, S. Mutagens-carcinogens in foods. Cancer Res., 43(Suppl.), 2415-2421 (1983).
3. Kasai, H., Yamaizumi, Z., Shiomi, T., Yokoyama, S., Miyazawa, T., Wakabayashi, K., Nagao, M., Sugimura, T. and Nishimura, S. Structure of a potent mutagen isolated from fried beef. Chem. Lett., 485-488 (1981).
4. IARC Working Group. Some naturally occurring substances: food items and constituents, heterocyclic aromatic amines and mycotoxins. In "IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans," vol. 56, pp. 211-228 (1993). IARC, Lyon.
5. Sugimura, T. Carcinogenicity of mutagenic heterocyclic amines formed during cooking process. Mutat. Res., 150, 33-41 (1985).
6. Ohgaki, H., Hasegawa, H., Suenaga, M., Sato, S., Takayama, S. and Sugimura, T. Carcinogenicity in mice of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) from cooked foods. Carcinogenesis, 8, 665-668 (1987).
7. Dooley, K. L., Von Tungeln, L. S., Bucci, T., Fu, P. P. and Kadlubar, F. F. Comparative carcinogenicity of 4-aminobiphenyl and the food pyrolysates, Glu-P-1, IQ, PhIP, and MeIQx in the neonatal B6C3F1 male mouse. Cancer Lett., 62, 205-209 (1992).
8. Kato, T., Ohgaki, H., Hasegawa, H., Sato, S., Takayama, S. and Sugimura, T. Carcinogenicity in rats of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. Carcinogenesis, 9, 71-73 (1988).
9. Kushida, H., Wakabayashi, K., Sato, H., Katami, M., Kurosaka, R. and Nagao, M. Dose-response study of MeIQx carcinogenicity in F344 male rats. Cancer Lett., 83, 31-35 (1994).
10. Turesky, R. J., Lang, N. P., Butler, M. A., Teitel, C. H. and Kadlubar, F. F. Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis, 10, 1839-1845 (1991).
11. Yanagawa, Y., Sawada, M., Deguchi, T., Gonzalez, F. J. and Kamataki, T. Stable expression of human CYP1A2 and N-acetyltransferases in Chinese hamster CHL cells: mutagenic activation of 2-amino-3-methylimidazo[4,5-f]quinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. Cancer Res., 54, 3422-3427 (1994).
12. 32P-Postlabeling analysis of IQ, MeIQx and PhIP adducts formed in vitro in DNA and polynucleotides and found in vivo in hepatic DNA from IQ-, MeIQx- and PhIP-treated monkeys. Carcinogenesis, 14, 1389-1395 (1993).
13. Hirose, M., Iwata, S., Ito, E., Nihro, Y., Takahashi, S., Mizoguchi, Y., MiKi, T., Satoh, T., Ito, N. and Shirai, T. Strong anti-mutagenic activity of novel lipophilic anti-oxidant 1-O-hexyl-2,3,5-trimethylhydroquinone against heterocyclic amine-induced mutagenesis in the Ames assay and its effect on metabolic activation of 2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1). Carcinogenesis, 16, 2227-2232 (1995).
14. Hirose, M., Futakuchi, M., Tanaka, H., Orita, S. I., Ito, T., Miki, T. and Shirai, T. Prevention by antioxidants of heterocyclic amine-induced carcinogenesis in a rat medium-term liver bioassay: results of extended and combination treatment experiments. Eur. J. Cancer Prev., 7, 61-67 (1998).
15. Hirose, M., Hasegawa, R., Kimura, J., Akagi, K., Yoshida, Y., Tanaka, H., Miki, T., Satoh, T., Wakabayashi, K. and Ito, N. Inhibitory effects of 1-O-hexyl-2,3,5-trimethylhydroquinone (HTHQ), green tea catechins and other anti-oxidants on 2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole (Glu-P-1)-induced rat hepatocarcinogenesis and dose-dependent inhibition by HTHQ of lesion induction by Glu-P-1 or 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). Carcinogenesis, 16, 3049-3055 (1995).
16. Kato, T., Hasegawa, R., Nakae, D., Hirose, M., Yaono, M., Cui, L., Kobayashi, Y., Konishi, Y., Ito, N. and Shirai, T. Dose-dependent induction of 8-hydroxyguanine and preneoplastic foci in rat liver by a food-derived carcinogen, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, at low dose levels. Jpn. J. Cancer Res., 87, 127-133 (1996).
17. Wakata, A., Oka, N., Hiramoto, K., Yoshioka, Y., Negishi, K., Wataya, Y. and Hayatsu, H. DNA strand cleavage in vitro by 3-hydroxyamino-1-methyl-5H-pyrido-[4,3-b]indole, a direct-acting mutagen formed in the metabolism of carcinogenic 3-amino-1-methyl-5H-pyrido[4,3-b]indole. Cancer Res., 45, 5867-5871 (1985).
18. Wataya, Y., Yamane, K., Hiramoto, K., Ohtsuka, Y., Okubata, Y., Negishi, K. and Hayatsu, H. Generation of intracellular active oxygens in mouse FM3A cells by 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole, the activated Trp-P-2. Jpn. J. Cancer Res. (Gann), 79, 576-579 (1988).
19. Chumakov, P. EMBL Data Library, accession number X54156 (1990).
20. Yamashita, N., Murata, M., Inoue, S., Hiraku, Y., Yoshinaga, T. and Kawanishi, S. Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat. Res., 39, 191-201 (1998).
21. Capon, D. J., Chen, E. Y., Levinson, A. D., Seeburg, P. H. and Goeddel, D. V. Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature, 302, 33-37 (1983).
22. Yamamoto, K. and Kawanishi, S. Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper(II) ion and hydrogen peroxide. J. Biol. Chem., 264, 15435-15440 (1989).
23. Kawanishi, S., Inoue S. and Kawanishi, M. Human DNA damage induced by 1,2,4-benzenetriol, a benzene metabolite. Cancer Res., 49, 164-168 (1989).
24. Maxam, A. M. and Gilbert, W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol., 65, 499-560 (1980).
25. Ito, K., Inoue, S., Yamamoto, K. and Kawanishi, S. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: non-Fenton-type hydroxyl radical formation. J. Biol. Chem., 268, 13221-13227 (1993).
26. Levine, A. J., Momand, J. and Finlay, C. A. The p53 tumor suppressor gene. Nature, 351, 453-456 (1991).
27. Youngman, R. J. and Elstner, E. F. Oxygen species in paraquat toxicity: the crypto-OH radical. FEBS Lett., 129, 265-268 (1981).
28. Pryor, W. A. and Tang, R. H. Ethylene formation from methional. Biochem. Biophys. Res. Commun., 81, 498-503 (1978).
29. Oikawa, S. and Kawanishi, S. Site-specific DNA damage induced by NADH in the presence of copper(II): role of active oxygen species. Biochemistry, 35, 4584-4590 (1996).
30. Hiraku, Y. and Kawanishi, S. Oxidative DNA damage and apoptosis induced by benzene metabolites. Cancer Res., 56, 5172-5178 (1996).
31. Murata, M., Imada, M., Inoue, S. and Kawanishi, S. Metal-mediated DNA damage induced by diabetogenic alloxan in the presence of NADH. Free Radic. Biol. Med., 25, 586-595 (1998).
32. Fujii, H., Koscielniak, J., Kakinuma, K. and Berliner, L. J. Biological reduction of aromatic nitroso compounds: evidence for the involvement of superoxide anions. Free Radic. Res., 21, 235-243 (1994).
33. Sato, K., Akaike, T., Kojima, Y., Ando, M., Nagao, M. and Maeda, H. Evidence of direct generation of oxygen free radicals from heterocyclic amines by NADH/cytochrome P-450 reductase in vitro. Jpn. J. Cancer Res., 83, 1204-1209 (1992).
34. Maeda, H., Sato, K. and Akaike, T. Superoxide radical generation from heterocyclic amines. Proc. 23rd Int. Symp. Princess Takamatsu Cancer Res. Fund, 103-112 (1995).
35. Malaisse, W. J., Hutton, J. C., Kawazu, S., Herchuelz, A., Valverde, I. and Sener, A. The stimulus-secretion coupling of glucose-induced insulin release. Diabetologia, 16, 331-341 (1979).
36. Kukielka, E. and Cederbaum, A. I. Ferritin stimulation of hydroxy radical production by rat liver nuclei. Arch. Biochem. Biophys., 308, 70-77 (1994).
37. Burkitt, M. J. Copper-DNA adducts. Methods Enzymol., 234, 66-79 (1994).
38. Li, Y. and Trush, M. A. 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 (1993).
39. Savoye, C., Sabattier, R, Charlier, M. and Spotheim-Maurizot, M. Sequence-modulated radiosensitization of DNA by copper ions. Int. J. Radiat. Biol., 70, 189-198 (1996).
40. Ushijima, T., Makino, H., Kakiuchi, H., Inoue, R., Sugimura, T. and Nagao, M. Genetic alterations in HCA-induced tumors. Proc. 23rd Int. Symp. Princess Takamatsu Cancer Res. Fund, 281-291 (1995).