2-Amino-3,8-dimethylimidazo-[4,5-f]quinoxaline-induced DNA adduct formation and mutagenesis in DNA repair-deficient Chinese hamster ovary cells expressing human cytochrome P4501A1 and rapid or slow acetylator N-acetyltransferase 2

Cancer Epidemiology Biomarkers and Prevention

Volumn 16, Issue 7, 2007, Pages 1503-1509

  Bendaly, Jean ^a   Zhao, Shuang ^a   Neale, Jason R ^a   Metry, Kristin J ^a   Doll, Mark A ^a   States, J Christopher ^a   Pierce Jr , William M ^a   Hein, David W ^a  

^a University of Louisville School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3,8 DIMETHYLIMIDAZO [4,5 F]QUINOXALINE; ACYLTRANSFERASE; ARYLAMINE ACETYLTRANSFERASE; CYTOCHROME P450; DEOXYGUANOSINE; HETEROCYCLIC AMINE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; MUTAGENIC AGENT; QUINOXALINE DERIVATIVE; SULFADIMIDINE; UNCLASSIFIED DRUG;

ACETYLATOR PHENOTYPE; ALLELE; ANIMAL CELL; ARTICLE; CATALYSIS; CELL LINE; CHO CELL; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY; DISORDERS OF DNA SYNTHESIS AND REPAIR; DNA ADDUCT; DNA DAMAGE; DOSE RESPONSE; EXCISION REPAIR; GENETIC POLYMORPHISM; GENETIC TRANSFECTION; HUMAN; MUTAGENESIS; MUTANT; NONHUMAN; PRIORITY JOURNAL; STABLE TRANSFECTION;

ACETYLATION; ACETYLTRANSFERASES; ANIMALS; ARYLAMINE N-ACETYLTRANSFERASE; CARCINOGENS; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; CRICETULUS; CYTOCHROME P-450 CYP1A1; DNA ADDUCTS; DNA DAMAGE; DNA REPAIR; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; MUTAGENESIS; MUTATION; QUINOXALINES; TANDEM MASS SPECTROMETRY; TRANSFECTION;

EID: 34447526255     PISSN: 10559965     EISSN: None     Source Type: Journal    
DOI: 10.1158/1055-9965.EPI-07-0305     Document Type: Article

References (40)

1. Keating GA, Bogen KT. Estimates of heterocyclic amine intake in the US population. J Chromatogr B Analyt Technol Biomed Life Sci 2004;802:127-33.
2. Byrne C, Sinha R, Platz EA, et al. Predictors of dietary heterocyclic amine intake in three prospective cohorts. Cancer Epidemiol Biomarkers Prev 1998;7:523-9.
3. National Toxicology Program. Report on carcinogenesis. 11th ed. Triangle Park (NC): US Department of Health and Human Services, Public Health Service, Research; 2005.
4. Ohgaki H, Hasegawa H, Suenaga M, Sato S, Takayama S, Sugimura T. Carcinogenicity in mice of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4, 5-f]quinoxaline (MeIQx) from cooked foods. Carcinogenesis 1987;8:665-8.
5. Kato T, Ohgaki H, Hasegawa H, Sato S, Takayama S, Sugimura T. Carcinogenicity in rats of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4, 5-f]quinoxaline. Carcinogenesis 1988;9:71-3.
6. Sinha R, Kulldorff M, Chow WH, Denobile J, Rothman N. Dietary intake of heterocyclic amines, meat-derived mutagenic activity, and risk of colorectal adenomas. Cancer Epidemiol Biomarkers Prev 2001;10:559-62.
7. Ishibe N, Sinha R, Hein DW, et al. Genetic polymorphisms in heterocyclic amine metabolism and risk of colorectal adenomas. Pharmacogenetics 2002;12:145-50.
8. Sinha R, Kulldorff M, Swanson CA, Curtin J, Brownson RC, Alavanja MC. Dietary heterocyclic amines and the risk of lung cancer among Missouri women. Cancer Res 2000;60:3753-6.
9. De Stefani E, Ronco A, Mendilaharsu M, Guidobono M, Deneo-Pellegrini H. Meat intake, heterocyclic amines, and risk of breast cancer: a case-control study in Uruguay. Cancer Epidemiol Biomarkers Prev 1997;6:573-81.
10. Turesky RJ. The role of genetic polymorphisms in metabolism of carcinogenic heterocyclic aromatic amines. Curr Drug Metab 2004;5:169-80.
11. Turesky RJ. Formation and biochemistry of carcinogenic heterocyclic aromatic amines in cooked meats. Toxicol Lett 2007;168:219-27.
12. Kim D, Guengerich FP. Cytochrome P450 activation of arylamines and heterocyclic amines. Annu Rev Pharmacol Toxicol 2005;45:27-49.
13. Josephy PD, Batty SM, Boverhof DR. Recombinant human P450 forms 1A1, 1A2, and 1B1 catalyze the bioactivation of heterocyclic amine mutagens in Escherichia coli lacZ strains. Environ Mol Mutagen 2001;38:12-8.
14. Wild D, Feser W, Michel S, Lord HL, Josephy PD. Metabolic activation of heterocyclic aromatic amines catalyzed by human arylamine N- acetyltransferase isozymes (NAT1 and NAT2) expressed in Salmonella typhimurium. Carcinogenesis 1995;16:643-8.
15. Hein DW, Fretland AJ, Doll MA. Effects of single nucleotide polymorphisms in human N-acetyltransferase 2 on metabolic activation (O-acetylation) of heterocyclic amine carcinogens. Int J Cancer 2006;119:1208-11.
16. Turesky RJ, Rossi SC, Welti DH, Lay JO, Jr., Kadlubar FF. Characterization of DNA adducts formed in vitro by reaction of N-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine. Chem Res Toxicol 1992;5:479-90.
17. Turteltaub KW, Mauthe RJ, Dingley KH, et al. MeIQx-DNA adduct formation in rodent and human tissues at low doses. Mutat Res 1997;376:243 - 52.
18. Schut HA, Snyderwine EG. DNA adducts of heterocyclic amine food mutagens: implications for mutagenesis and carcinogenesis. Carcinogenesis 1999;20:353-68.
19. Paehler A, Richoz J, Soglia J, Vouros P, Turesky RJ. Analysis and quantification of DNA adducts of 2-amino-3,8-dimethylimidazo[4,5-f] quiinoxaline in liver of rats by liquid chromatography/electrospray tandem mass spectrometry. Chem Res Toxicol 2002;15:551-61.
20. Hein DW. Molecular genetics and function of NAT1 and NAT2: role in aromatic amine metabolism and carcinogenesis. Mutat Res 2002;506-507:65-77.
21. Hein DW. N-acetyltransferase 2 genetic polymorphism: effects of carcinogen and haplotype on urinary bladder cancer risk. Oncogene 2006;25:1649-58.
22. Hein DW, Doll MA, Fretland AJ, et al. Molecular genetics and epidemiology of the NAT1 and NAT2 acetylation polymorphisms. Cancer Epidemiol Biomarkers Prev 2000;9:29-42.
23. Metry KJ, Zhao S, Neale JR, et al. 2-Amino-1-methyl-6-phenylimidazo [4,5-b] pyridine-induced DNA adducts and genotoxicity in chinese hamster ovary (CHO) cells expressing human CYP1A2 and rapid or slow acetylator N-acetyltransferase 2. Mol Carcinog. Epub 2007 Feb 12.
24. States JC, Quan T, Hines RN, Novak RF, Runge-Morris M. Expression of human cytochrome P450 1A1 in DNA repair deficient and proficient human fibroblasts stably transformed with an inducible expression vector. Carcinogenesis 1993;14:1643-9.
25. Leff MA, Epstein PN, Doll MA, et al. Prostate-specific human N-acetyltransferase 2 (NAT2) expression in the mouse. J Pharmacol Exp Ther 1999;290:182-7.
26. Hein DW, Doll MA, Nerland DE, Fretland AJ. Tissue distribution of Nacetyltransferase 1 and 2 catalyzing the N-acetylation of 4-aminobiphenyl and O-acetylation of N-hydroxy-4-aminobiphenyl in the congenic rapid and slow acetylator Syrian hamster. Mol Carcinog 2006;45:230-8.
27. Lang NP, Butler MA, Massengill J, et al. Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to foodborne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidemiol Biomarkers Prev 1994;3:675-82.
28. Le Marchand L, Hankin JH, Wilkens LR, et al. Combined effects of well-done red meat, smoking, and rapid N-acetyltransferase 2 and CYP1A2 phenotypes in increasing colorectal cancer risk. Cancer Epidemiol Biomarkers Prev 2001;10:1259-66.
29. Le Marchand L, Hankin JH, Pierce LM, et al. Well-done red meat, metabolic phenotypes, and colorectal cancer in Hawaii. Mutat Res 2002;506-507:205-14.
30. Lilla C, Verla-Tebit E, Risch A, et al. Effect of NAT1 and NAT2 genetic polymorphisms on colorectal cancer risk associated with exposure to tobacco smoke and meat consumption. Cancer Epidemiol Biomarkers Prev 2006;15:99-107.
31. Ognjanovic S, Yamamoto J, Maskarinec G, Le Marchand L. NAT2, meat consumption, and colorectal cancer incidence: an ecological study among 27 countries. Cancer Causes Control 2006;17:1175-82.
32. Deitz AC, Zheng W, Leff MA, et al. N-acetyltransferase-2 genetic polymorphism, well-done meat intake, and breast cancer risk among postmenopausal women. Cancer Epidemiol Biomarkers Prev 2000;9:905-10.
33. Gallicchio L, McSorley MA, Newschaffer CJ, et al. Flame-broiled food, NAT2 acetylator phenotype, and breast cancer risk among women with benign breast disease. Breast Cancer Res Treat 2006;99:229-33.
34. Chiou HL, Wu MF, Chien WP, et al. NAT2 fast acetylator genotype is associated with an increased risk of lung cancer among never-smoking women in Taiwan. Cancer Lett 2005;223:93-101.
35. Stone EM, Williams JA, Grover PL, Gusterson BA, Phillips DH. Interindividual variation in the metabolic activation of heterocyclic amines and their N-hydroxy derivatives in primary cultures of human mammary epithelial cells. Carcinogenesis 1998;19:873-9.
36. Yanagawa Y, Sawada M, Deguchi T, Gonzalez FJ, 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 1994;54:3422-7.
37. Wu RW, Tucker JD, Sorensen KJ, Thompson LH, Felton JS. Differential effect of acetyltransferase expression on the genotoxicity of heterocyclic amines in CHO cells. Mutat Res 1997;390:93-103.
38. Murtaugh MA, Sweeney C, Ma KN, Caan BJ, Slattery ML. The CYP1A1 genotype may alter the association of meat consumption patterns and preparation with the risk of colorectal cancer in men and women. J Nutr 2005;135:179-86.
39. Totsuka Y, Fukutome K, Takahashi M, et al. Presence of N2-(deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f ]quinoxaline (dG-C8-MeIQx) in human tissues. Carcinogenesis 1996;17:1029-34.
40. Wu RW, Panteleakos FN, Kadkhodayan S, Bolton-Grob R, McManus ME, Felton JS. Genetically modified Chinese hamster ovary cells for investigating sulfotransferase-mediated cytotoxicity and mutation by 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine. Environ Mol Mutagen 2000;35:57-65.