Mutagenic activation of betel quid-specific N-nitrosamines catalyzed by human cytochrome P450 coexpressed with NADPH-cytochrome P450 reductase in Salmonella typhimurium YG7108

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 581, Issue 1-2, 2005, Pages 165-171

  Miyazaki, Masafumi ^a   Sugawara, Eika ^a   Yoshimura, Teruki ^b   Yamazaki, Hiroshi ^a   Kamataki, Tetsuya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

3 (N Nitrosomethylamino)propionaldehyde; 3 (N Nitrosomethylamino)propionitrile; Areca nut; Betel leaf; Genetically engineered S. typhimurium; Metabolic activation; N Nitrosoguvacoline

Indexed keywords

ALDEHYDE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 2A; CYTOCHROME P450 2A6; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 CYP2A13; NITRILE; NITROSAMINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; BETEL NUT; CATALYSIS; CONCENTRATION (PARAMETERS); GENETIC ENGINEERING; GENOTOXICITY; LABORATORY; MUTAGENIC ACTIVITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; SALMONELLA TYPHIMURIUM;

ARECA CATECHU; PIPER BETEL; SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 13844256200     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2004.12.002     Document Type: Article

References (36)

1. IARC. Tobacco habits other than smoking; betel-quid and areca-nut chewing; and some related nitrosamines, in: IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans, vol. 37, IARC Scientific Publications, Lyon, 1985, pp. 141-202.
2. L.D. Sanghvi Cancer epidemiology: the Indian scene J. Cancer Res. Clin. Oncol. 99 1981 1 14
3. D. Hoffmann, K.D. Brunnemann, B. Prokopczyk, and M.V. Djordjevic Tobacco-specific N-nitrosamines and areca-derived N-nitrosamines: chemistry, biochemistry, carcinogenicity, and relevance to humans J. Toxicol. Environ. Health 41 1994 1 52
4. A. Nishikawa, B. Prokopczyk, A. Rivenson, E. Zang, and D. Hoffmann A study of betel quid carcinogenesis VIII, Carcinogenicity of 3- (methylnitrosamino)propionaldehyde in F344 rats Carcinogenesis 13 1992 369 372
5. B. Prokopczyk, A. Rivenson, P. Bertinato, K.D. Brunnemann, and D. Hoffmann 3-(Methylnitrosamino) propionitrile: occurrence in saliva of betel quid chewers, carcinogenicity, and DNA methylation in F344 rats Cancer Res. 47 1987 467 471
6. G. Wenke, K.D. Brunnemann, D. Hoffmann, and S.V. Bhide A study of betel quid carcinogenesis. IV. Analysis of the saliva of betel chewers: a preliminary report J. Cancer Res. Clin. Oncol. 108 1984 110 113
7. A. Rivenson, D. Hoffmann, B. Prokopczyk, S. Amin, and S.S. Hecht Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines Cancer Res. 48 1988 6912 6917
8. G. Wenke, A. Rivenson, and D. Hoffmann A study of betel quid carcinogenesis. 3. 3-(Methylnitrosamino)-propionitrile, a powerful carcinogen in F344 rats Carcinogenesis 5 1984 1137 1140
9. H. Bartsch, and R. Montesano Relevance of nitrosamines to human cancer Carcinogenesis 5 1984 1381 1393
10. H. Bartsch, S. Petruzzelli, S.D. Flora, E. Hietanen, and A.M. Camus Carcinogen metabolism and DNA adducts in human lung tissues as affected by tobacco smoking or metabolic phenotype: a case-control study on lung cancer patients Mutat. Res. 250 1991 103 114
11. 6 position of guanine in DNA is the most likely initiating event in carcinogenesis by methylating agents Cancer Invest. 2 1984 223 231
12. 6 of guanine is only one of many chemical events that may initiate carcinogenesis Cancer Invest. 2 1984 233 238
13. D.R. Nelson, L. Koymans, T. Kamataki, J.J. Stegeman, R. Feyereisen, D.J. Waxman, M.R. Waterman, O. Gotoh, M.J. Coon, R.W. stabrook, I.C. Gunsalus, and D.W. Nebert P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature Pharmacogenetics 6 1996 1 42
14. F.P. Guengerich Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem. Res. Toxicol. 14 2001 611 650
15. K. Fujita, K. Nakayama, Y. Yamazaki, K. Tsuruma, M. Yamada, T. Nohmi, and T. Kamataki Construction of Salmonella typhimurium YG7108 strains, each coexpressing a form of human cytochrome P450 with NADPH-cytochrome P450 reductase Environ. Mol. Mutagen. 38 2001 329 338
16. K. Fujita, and T. Kamataki Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase Environ. Mol. Mutagen. 38 2001 339 346
17. K. Nunoya, T. Yokoi, K. Kimura, K. Inoue, T. Kodama, M. Funayama, K. Nagashima, Y. Funae, C. Green, M. Kinoshita, and T. Kamataki A new deleted allele in the human cytochrome P4502A6 (CYP2A6) gene found in individuals showing poor metabolic capacity to coumarin and (+)-cis-3,5-dimethyl-2-(3- pyridyl)thiazolidin-4-one hydrochloride (SM-12502) Pharmacogenetics 8 1998 239 249
18. M. Miyamoto, Y. Umetsu, H. Dosaka-Akita, Y. Sawamura, J. Yokota, H. Kunitoh, N. Nemoto, K. Sato, N. Ariyoshi, and T. Kamataki CYP2A6 gene deletion reduces susceptibility to lung cancer Biochem. Biophys. Res. Commun. 261 1999 658 660
19. N. Ariyoshi, M. Miyamoto, Y. Umetsu, H. Kunitoh, H. Dosaka-Akita, Y. Sawamura, J. Yokota, N. Nemoto, K. Sato, and T. Kamataki Genetic polymorphism of CYP2A6 gene and tobacco-induced lung cancer risk in male smokers Cancer Epidemiol. Biomarkers Prev. 11 2002 890 894
20. Z. Topcu, I. Chiba, M. Fujieda, T. Shibata, N. Ariyoshi, H.Y. amazaki, F. Sevgican, M. Muthumala, H. Kobayashi, and T. Kamataki CYP2A6 gene deletion reduces oral cancer risk in betel quid chewers in Sri Lanka Carcinogenesis 23 2002 595 598
21. K. Fujita, and T. Kamataki Role of human cytochrome P450 (CYP) in the metabolic activation of N-alkylnitrosamines: application of genetically engineered Salmonella typhimurium YG7108 expressing each form of CYP together with human NADPH-cytochrome P450 reductase Mutat. Res. 483 2001 35 41
22. T.K. Rao, A.A. Hardigree, J.A. Young, W. Lijinsky, and J.L. Epler Mutagenicity of N-nitrosopiperidines with Salmonella typhimiruim/microsomal activation system Mutat. Res. 56 1977 131 145
23. G. Wenke, and D. Hoffmann A study of betel quid carcinogenesis. 1. On the in vitro N-nitrosation of arecoline Carcinogenesis 4 1983 169 172
24. H. Kushida, K. Fujita, A. Suzuki, M. Yamada, T. Nohmi, and T. Kamataki Development of a Salmonella tester strain sensitive to promutagenic N-nitrosamines: expression of recombinant CYP2A6 and human NADPH-cytochrome P450 reductase in S. typhimurium YG7108 Mutat. Res. 471 2000 135 143
25. T. Omura, and R. Sato The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J. Biol. Chem. 239 1964 2370 2378
26. A.H. Phillips, and R.G. Langdon Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies J. Biol. Chem. 237 1962 2652 2660
27. Y. Yamazaki, K. Fujita, K. Nakayama, A. Suzuki, K. Nakamura, H. Yamazaki, and T. Kamataki Establishment of ten strains of genetically engineered Salmonella typhimurium TA1538 each co-expressing a form of human cytochrome P450 with NADPH-cytochrome P450 reductase sensitive to various promutagens Mutat. Res. 562 2004 151 162
28. A. Singh, and A.R. Rao Modulatory influence of arecanut on the mouse hepatic xenobiotic detoxication system and skin papillomagenesis Teratog. Carcinogenesis Mutagen. 15 1995 135 146
29. M. Vondracek, Z. Xi, P. Larsson, V. Baker, K. Mace, A. Pfe ifer, H. Tjalve, M.J. Gomez-Lechon, and R.C. Grafstrom Cytochrome P450 expression and related metabolism in human buccal mucosa Carcinogenesis 22 2001 481 488
30. J.R. Jalas, X. Ding, and S.E. Murphy Comparative metabolism of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol by rat cytochrome P4502A3 and human cytochrome P4502A13 Drug Metab. Dispos. 31 2003 1199 1202
31. M. Fujieda, H. Yamazaki, K. Kiyotani, A. Muroi, H. Kunitoh, H. Dosaka-Akita, Y. Sawamura, and T. Kamataki Eighteen novel polymorphisms of the CYP2A13 gene in Japanese Drug Metab. Pharmacokinet. 18 2003 86 90
32. B. Prokopczyk, P. Bertinato, and D. Hoffmann Cyanoethylation of DNA in vivo by 3-(methylnitrosamino)propionitrile, an areca-derived carcinogen Cancer Res. 48 1988 6780 6784
33. 2-propanodeoxyguanosine adducts in DNA upon reaction with 3-(N-carbethoxy-N-nitrosamino)propionaldehyde Chem. Res. Toxicol. 7 1994 62 67
34. T. Su, J.J. Sheng, T.W. Lipinskas, and X. Ding Expression of CYP2A genes in rodent and human nasal mucosa Drug Metab. Disposition 24 1996 884 890
35. W. Lijinsky, and H.W. Taylor Carcinogenicity test of two unsaturated derivatives of N-nitrosopiperdine in Sprague-Dawley rats J. Natl. Cancer Inst. 57 1976 1315 1317
36. C.K. Wang, and C.H. Peng The mutagenicities of alkaloids and N-nitrosoguvacoline from betel quid Mutat. Res. 360 1996 165 171