Nonenzymatic reduction of nitro derivative of a heterocyclic amine IQ by NADH and Cu(II) leads to oxidative DNA damage

Biochemistry

Volumn 38, Issue 24, 1999, Pages 7624-7629

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

^a MIE UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 METHYLIMIDAZO[4,5 F]QUINOLINE; 8 HYDROXYDEOXYGUANOSINE; BATHOCUPROINE; CATALASE; COPPER; CYTOSINE; DEOXYGUANOSINE DERIVATIVE; DNA; HETEROCYCLIC AMINE; NITRO DERIVATIVE; NITROREDUCTASE; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SCAVENGER; THYMINE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARCINOGENESIS; CATTLE; CONTROLLED STUDY; DNA CLEAVAGE; DNA DAMAGE; HUMAN; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL; REDUCTION; THYMUS;

ANIMALS; CATTLE; COPPER; DEOXYGUANOSINE; DNA; DNA DAMAGE; FREE RADICAL SCAVENGERS; HUMANS; MUTAGENS; NAD; OXIDATION-REDUCTION; OXIDATIVE STRESS; PHENANTHROLINES; PHOSPHORUS RADIOISOTOPES; PROTO-ONCOGENE PROTEINS P21(RAS); QUINOLINES; SPECTROPHOTOMETRY, ULTRAVIOLET; TUMOR SUPPRESSOR PROTEIN P53;

ANIMALIA; BOS TAURUS;

EID: 0033564662     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi982906b     Document Type: Article

References (51)

1. Sugimura, T. (1997) Mutat. Res. 376, 211-219.
2. Felton, J. S., Knize, M. G., Wood, C., Wuebbles, B. J., Healy, S. K., Stuermer, D. H., Bjeldanes, L. F., Kimble, B. J., and Hatch, F. T. (1984) Carcinogenesis 5, 95-102.
3. IARC Working Group (1993) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, vol. 56, pp 165-195, IARC, Lyon, France.
4. Yamashita, M., Wakabayashi, K., Nagao, M., Sato, S., Yamaizumi, Z., Takahashi, M., Kinae, N., Tomita, I., and Sugimura, T. (1986) Jpn. J. Cancer Res. 77, 419-422.
5. Fay, L. B., and Turesky, R. J. (1992) Biol. Mass Spectrom. 21, 463-469.
6. Sasagawa, C., Muramatsu, M., and Matsushima, T. (1988) Mutat. Res. 203, 386.
7. Hirose, M., Wakabayashi, K., Grivas, S., De Flora, S., Arakawa, N., Nagao, M., and Sugimura, T. (1990) Carcinogenesis 11, 869-871.
8. Morrison, L. D., Eling, T. E., and Josephy, P. D. (1993) Mutat. Res. 302, 45-52.
9. Dirr, A., and Wild, D. (1988) Mutagenesis 3, 147-152.
10. Asan, E., Fasshauer, I., Wild, D., and Henschler, D. (1987) Carcinogenesis 8, 1589-1593.
11. Graf, U., Wild, D., and Würgler, F. E. (1992) Mutagenesis 7, 145-149.
12. Sawada, S., Daimon, H., Asakura, S., Kawaguchi, T., Yamatsu, K., Furihata, C., and Matsushima, T. (1994) Carcinogenesis 15, 285-290.
13. Snyderwine, E. G., Davis, C. D., Nouso, K., Roller, P. P., and Schut, H. A. J. (1993) Carcinogenesis 14, 1389-1395.
14. Yanagawa, Y., Sawada, M., Deguchi, T., Gonzalez, F. J., and Kamataki, T. (1994) Cancer Res. 54, 3422-3427.
15. Hirose, M., Iwata, S., Ito, E., Nihro, Y., Takahashi, S., Mizoguchi, Y., MiKi, T., Satoh, T., Ito, N., and Shirai, T. (1995) Carcinogenesis 16, 2227-2232.
16. Hirose, M., Futakuchi, M., Tanaka, H., Orita, S.-I., Ito, T., Miki, T., and Shirai, T. (1998) Eur. J. Cancer Prevent. 7, 61-67.
17. Hirose, M., Hasegawa, R., Kimura, J., Akagi, K., Yoshida, Y., Tanaka, H., Miki, T., Satoh, T., Wakabayashi, K., Ito, N., and Shirai, T. (1995) Carcinogenesis 16, 3049-3055.
18. Kato, T., Hasegawa, R., Nakae, D., Hirose, M., Yaono, M., Cui, L., Kobayashi, Y., Konishi, Y., Ito, N., and Shirai, T. (1996) Jpn. J. Cancer Res. 87, 127-133.
19. Wakata, A., Oka, N., Hiramoto, K., Yoshioka, A., Negishi, K., Wataya, Y., and Hayatsu, H. (1985) Cancer Res. 45, 5867-5871.
20. Wataya, Y., Yamane, K., Hiramoto, K., Ohtsuka, Y., Okubata, Y., Negishi, K., and Hayatsu, H. (1988) Jpn. J. Cancer Res. 79, 576-579.
21. Oikawa, S., and Kawanishi, S. (1996) Biochemistry 35, 4584-4590.
22. Hiraku, Y., and Kawanishi, S. (1996) Cancer Res. 56, 5172-5178.
23. Murata, M., Imada, M., Inoue, S., and Kawanishi, S. (1998) Free Radical Biol. Med. 25, 586-595.
24. Krainev, A. G., Williams, T. D., and Bigelow, D. J. (1998) Chem. Res. Toxicol. 11, 495-502.
25. Chumakov, P. (1990) EMBL Data Library, accession number X54156.
26. Yamashita, N., Murata, M., Inoue, S., Hiraku, Y., Yoshinaga, T. and Kawanishi, S. (1998) Mutat. Res. 39, 191-201.
27. Capon, D. J., Chen, E. Y., Levinson, A. D., Seeburg, P. H., and Goeddel, D. V. (1983) Nature 302, 33-37.
28. Yamamoto, K., and Kawanishi, S. (1989) J. Biol. Chem. 264, 15435-15440.
29. Kawanishi, S., Inoue, S., and Kawanishi, M. (1989) Cancer Res. 49, 164-168.
30. Maxam, A. M., and Gilbert, W. (1980) Methods Enzymol. 65, 499-560.
31. Ito, K., Inoue, S., Yamamoto, K., and Kawanishi, S. (1993) J. Biol. Chem. 268, 13221-13227.
32. Levine. A. J, Momand, J., and Finlay, C. A. (1991) Nature 351, 453-456.
33. Wolz, E., Wild, D., and Degen, G. H. (1995) Arch. Toxicol. 69, 171-179.
34. Yamamoto, K., and Kawanishi, S. (1991) J. Biol. Chem. 266, 1509-1515.
35. Pryor, W. A., and Tang, R. H. (1978) Biochem. Biophys. Res. Commun. 81, 498-503.
36. Youngman, R. J., and Elstner, E. F. (1981) FEBS Lett. 129, 265-268.
37. Carlson, B. W., Miller, L. L., Neta, P., and Grodkowski, J. (1984) J. Am. Chem. Soc. 106, 7233-7239.
38. Mason, R. P., and Holtzman, J. L. (1975) Biochemistry 14, 1626-1632.
39. Orna, M. V., and Mason, R. P. (1989) J. Biol. Chem. 264, 12379-12384.
40. Sato, K., Akaike, T., Kojima, Y., Ando, M., Nagao, M., and Maeda, H. (1992) Jpn. J. Cancer Res. 83, 1204-1209.
41. Malaisse, W. J., Hutton, J. C., Kawazu, S., Herchuelz, A., Valverde, I., and Sener, A. (1979) Diabetologia 16, 331-341.
42. Burkitt, M. J. (1994) Methods Enzymol. 234, 66-79.
43. Fujimoto, J., Tran, L., and Sowers L. C. (1997) Chem. Res. Toxicol. 10, 1254-1258.
44. Saito, I., Takayama, M., and Kawanishi, S. (1995) J. Am. Chem. Soc. 117, 5590-5591.
45. Bourdat, A.-G., Gasparutto, D., and Cadet, J. (1999) Nucleic Acids Res. 27, 1015-1024.
46. Kino, K., Saito, I., and Sugiyama, H. (1998) J. Am. Chem. Soc. 120, 7373-7374.
47. Gasparutto, D., Ravanat, J.-L., Gérot, O., and Cadet, J. (1998) J. Am. Chem. Soc. 120, 10283-10286.
48. Adam, W., Sana-Möller, C. R., and Schönberger, A. (1996) J. Am. Chem. Soc. 118, 9233-9238.
49. Dooley, K. L., Von Tungeln, L. S., Bucci, T., Fu, P. P., and Kadlubar, F. F. (1992) Cancer Lett. 62, 205-209.
50. Thorgeisson, U. P., Gomez, D. E., Lindsay, C. K., Sinha, C. C., and Adamson, R. H., (1996) Liver 16, 71-83.
51. Fujimoto, Y., Hampton, L. L., Snyderwine, E. G., Nagao, M., Sugimura, T., Adamson R. H., and Thorgeirsson, S. S., (1994) Jpn. J. Cancer Res. 85, 506-509.