Bioactivation of the cooked food mutagen N-hydroxy-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by estrogen sulfotransferase in cultured human mammary epithelial cells

Carcinogenesis

Volumn 19, Issue 11, 1998, Pages 2049-2053

  Lewis, Amy J ^a   Walle, U Kristina ^a   King, Roberta S ^b   Kadlubar, Fred F ^b   Falany, Charles N ^c   Walle, Thomas ^a  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^c University of Alabama at Birmingham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; ADENOSINE 3' PHOSPHATE 5' PHOSPHOSULFATE; DNA; ESTROGEN; ESTRONE; MUTAGENIC AGENT; N HYDROXY 2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; RECOMBINANT ENZYME; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; BREAST EPITHELIUM; CARCINOGEN DNA INTERACTION; CELL CULTURE; CONTROLLED STUDY; COVALENT BOND; DNA ADDUCT; ENZYME ACTIVITY; FOOD; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

EID: 0031753391     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/19.11.2049     Document Type: Article

References (40)

1. American Cancer Society (1997) Cancer Facts and Figures. American Cancer Society, Atlanta, GA.
2. Perera, F.P., Estabrook, A., Hewer, A., Channing, K., Rundle, A., Mooney, L.A., Whyatt, R. and Phillips, D.H. (1995) Carcinogen-DNA adducts in human breast tissue. Cancer Epidemiol. Biomarkers Prev., 4, 233-238.
3. Biggs, P.J., Warren, W., Venitt, S. and Stratton, M.R. (1993) Does a genotoxic carcinogen contribute to human breast cancer? The value of mutational spectra in unravelling the aetiology of cancer. Mutagenesis, 8, 275-283.
4. Layton, D.W., Bogen, K.T., Knize, M.G., Hatch, F.T., Johnson, V.M. and Felton, J.S. (1995) Cancer risk of heterocyclic amines in cooked foods: an analysis and implications for research. Carcinogenesis, 16, 39-52.
5. Ronco, A., De Stefani, E., Mendilaharsu, M. and Deneo-Pellegrini, H. (1996) Meat, fat and risk of breast cancer: a case-control study from Uruguay. Int. J. Cancer, 65, 328-331.
6. Järvinen, R., Knekt, P., Seppänen, R. and Teppo, L. (1997) Diet and breast cancer risk in a cohort of Finnish women. Cancer Lett., 114, 251-253.
7. Gooderham, N.J., Murray, S., Lynch, A.M. et al. (1996) Heterocyclic amines: evaluation of their role in diet associated human cancer. Br. J. Clin. Pharmacol, 42, 91-98.
8. Malfatti, M.A., Shen, N.H., Wu, R.W., Turteltaub, K.W. and Felton, J.S. (1995) A correlation of Salmonella mutagenicity with DNA adducts induced by the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Mutagenesis, 10, 425-431.
9. Thompson, L.H., Tucker, J.D., Stewart, S.A., Christensen, M.L., Salazar, E.P., Carrano, A.V. and Felton, J.S. (1987) Genotoxicity of compounds from cooked beef in repair-deficient CHO cells versus Salmonella mutagenicity. Mutagenesis, 2, 483-487.
10. Yadollahi-Farsani, M., Gooderham, N.J., Davies, D.S. and Boobis, A.R. (1996) Mutational spectra of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) at Chinese hamster hprt locus. Carcinogenesis, 17, 617-624.
11. Ito, N., Hasegawa, R., Sano, M., Tamano, S., Esumi, H., Takayama, S. and Sugimura, T. (1991) A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis, 12, 1503-1506.
12. Imaida, K., Hagiwara, A., Yada, H., Masui, T., Hasegawa, R., Hirose, M., Sugimura, T., Ito, N. and Shirai, T. (1996) Dose-dependent induction of mammary carcinomas in female Sprague-Dawley rats with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Jpn. J. Cancer Res., 87, 1116-1120.
13. Fan, L., Schut, H.A.J. and Snyderwine, E.G. (1995) Cytotoxicity, DNA adduct formation and DNA repair induced by 2-hydroxyamino-3-methyl imidazo[4,5-f]quinoline and 2-hydroxyamino-1-methyl-6-phenylimidazo-[4,5-b]pyridine in cultured human mammary epithelial cells. Carcinogenesis, 16, 775-779.
14. Carmichael, P.L., Stone, E.M., Grover, P.L., Gusterson, B.A. and Phillips, D.H. (1996) Metabolic activation and DNA binding of food mutagens and other environmental carcinogens in human mammary epithelial cells. Carcinogenesis, 17, 1769-1772.
15. Sadrieh, N., Davis, C.D. and Snyderwine, E.G. (1996) N-acetyltransferase expression and metabolic activation of the food-derived heterocyclic amines in the human mammary gland. Cancer Res., 56, 2683-2687.
16. McManus, M.E., Felton, J.S., Knize, M.G., Burgess, W.M., Roberts-Thompson, S., Pond, S.M., Stupans, I. and Veronese, M.E. (1989) Activation of the food-derived mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by rabbit and human liver microsomes and purified forms of cytochrome P-450. Carcinogenesis, 10, 357-363.
17. Zhao, K., Murray, S., Davies, D.S., Boobis, A.R. and Gooderham, N.J. (1994) Metabolism of the food derived mutagen and carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP) by human liver microsomes. Carcinogenesis, 15, 1285-1288.
18. Buonarati, M.H., Turteltaub, K.W., Shen, N.H. and Felton, J.S. (1990) Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind DNA. Mutat. Res., 245, 185-190.
19. Turesky, R.J., Lang, N.P., Butler, M.A., Teitel, C.H. and Kadlubar, F.F. (1991) Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis, 10, 1839-1845.
20. Lin, D., Kaderlik, K.R., Turesky, R.J., Miller, D.W., Lay, J.O.Jr and Kadlubar, F.F. (1992) Identification of N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo[4,5,-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA. Chem. Res. Toxicol., 5, 691-697.
21. Abu-Zeid, M., Yamazoe, Y. and Kato, R. (1992) Sulfotransferase-mediated DNA binding of N-hydroxyarylamines(amides) in liver cytosols from human and experimental animals. Carcinogenesis, 13, 1307-1314.
22. Davis, C.D., Schut, H.A.J. and Snyderwine, E.G. (1993) Enzymatic phase II activation of the N-hydroxylamines of IQ, MeIQx and PhIP by various organs of monkeys and rats. Carcinogenesis, 14, 2091-2096.
23. Malfatti, M.A., Buonarati, M.H., Turteltaub, K.W., Shen, N.H. and Felton, J.S. (1994) The role of sulfation and/or acetylation in the metabolism of the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Salmonella typhimurium and isolated rat hepatocytes. Chem. Res. Toxicol., 7, 139-147.
24. Kaderlik, K.R., Minchin, R.F., Mulder, G.J., Ilett, K.F., Daugaard-Jenson, M., Teitel, C.H. and Kadlubar, F.F. (1994) Metabolic activation pathway for the formation of DNA adducts of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat extrahepatic tissues. Carcinogenesis, 15, 1703-1709.
25. Ozawa, S., Chou, H.-C., Kadlubar, F.F., Nagata, K., Yamazoe, Y. and Kato, R. (1994) Activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine by cDNA-expressed human and rat arylsulfotransferases. Jpn. J. Cancer Res., 85, 1220-1228.
26. Chou, H.-C., Lang, N.P. and Kadlubar, F.F. (1995) Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s). Cancer Res., 55, 525-529.
27. Falany, J.L. and Falany, C.N. (1996) Expression of cytosolic sulfotransferases in normal mammary epithelial cells and breast cancer cell lines. Cancer Res., 56, 1551-1555.
28. Falany, C.N., Krasnykh, V. and Falany, J.L. (1995) Bacterial expression and characterization of a cDNA for human liver estrogen sulfotransferase. J. Steroid Biochem. Mol Biol., 52, 529-539.
29. Enomoto, M., Sato, K., Miller, E.C. and Miller, J.A. (1968) Reactivity of the diacetyl derivative of the carcinogen 4-hydroxyaminoquinoline-1-oxide with DNA, RNA, and other nucleophiles. Life Sci., 7, 1025-1032.
30. Lewis, A.J., Kelly, M.M., Walle, U.K., Eaton, A.E., Falany, C.N. and Walle, T. (1996) Improved bacterial expression of the human P form phenolsulfotransferase. Drug Metab. Dispos., 24, 1180-1185.
31. Hernandez, J.S., Powers, S.P. and Weinshilboum, R.M. (1991) Human liver arylamine N-sulfotransferase activity: thermostable phenol sulfotransferase catalyzes the N-sulfation of 2-naphthylamine. Drug Metab. Dispos., 19, 1071-1079.
32. Snyderwine, E.G., Turesky, R.J., Turteltaub, K.W. et al. (1997) Metabolism of food-derived heterocyclic amines in nonhuman primates. Mutat. Res., 376, 203-210.
33. Ohgaki, H., Takayama, S. and Sugimura, T. (1991) Carcinogenicities of heterocyclic amines in cooked food. Mutat. Res., 259, 399-410.
34. Lee, J., Chung, J., Lai, J., Levy, G. and Weber, W. (1997) Kinetics of arylamine N-acetyltransferase in tissue from human breast cancer. Cancer Lett., 111, 39-50.
35. Huang, Z., Fasco, M.J., Figge, H.L., Keyomarsi, K. and Kaminsky, L.S. (1996) Expression of cytochromes P450 in human breast tissue and tumors. Drug Metab. Dispos., 24, 899-905.
36. Crofts, F.G., Strickland, P.T., Hayes, C.L. and Sutter, T.R. (1997) Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by human cytochrome P4501B1. Carcinogenesis, 18, 1793-1798.
37. Toyota, M., Ushijima, T., Kakiuchi, H., Canzian, F., Watanabe, M., Imai, K., Sugimura, T. and Nagao, M. (1996) Genetic alterations in rat colon tumors induced by heterocyclic amines. Cancer, 77 (suppl.), 1593-1597.
38. Snyderwine, E.G. (1996) The food-derived heterocyclic amines and breast cancer: a 1995 perspective. Recent Results Cancer Res., 140, 17-25.
39. Roberts-Thomson, S.J. and Snyderwine, E.G. (1997) Effect of dietary fat on codon 12 and 13 Ha-ras gene mutations in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced rat mammary gland tumors. Mol. Carcinogen., 20, 348-354.
40. Falany, J.L. and Falany, C.N. (1996) Regulation of estrogen sulfotransferase in human endometrial adenocarcinoma cells by progesterone. Endocrinology, 137, 1395-1401.