Assessing human risk to heterocyclic amines

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 376, Issue 1-2, 1997, Pages 53-60

  Gooderham, N J ^a   Murray, S ^a   Lynch, A M ^a   Yadollahi Farsani, M ^a   Zhao, K ^a   Rich, K ^a   Boobis, A R ^a   Davies, D S ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Bioavailability; Carcinogenicity; CYP1A2; DiMeIQx; Heterocyclic amine; MeIQx; Metabolism; Mutagenicity; PhIP

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; 2 AMINO 3,8 DIMETHYLIMIDAZO[4,5 F]QUINOXALINE; CYTOCHROME P450 ISOENZYME; FURAFYLLINE; HETEROCYCLIC AMINE;

ANIMAL TISSUE; ARTICLE; BIOAVAILABILITY; CARCINOGENICITY; CONTROLLED STUDY; ENZYME INHIBITION; HUMAN; HUMAN EXPERIMENT; HYDROXYLATION; MEAT; MUTAGENICITY; NORMAL HUMAN; PRIORITY JOURNAL; RISK ASSESSMENT; XENOBIOTIC METABOLISM;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COOKERY; CYTOCHROME P-450 CYP1A2; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; MEAT; MICROSOMES, LIVER; MUTAGENICITY TESTS; MUTAGENS; QUINOLINES; RABBITS; RISK; THEOPHYLLINE;

ALOCASIA MACRORRHIZOS; ANIMALIA; BACTERIA (MICROORGANISMS); MAMMALIA;

EID: 0031011355     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00025-0     Document Type: Article

References (40)

1. Adamson, R.H., E.G. Snyderwine, U.P. Thorgeirsson, H.A. Schut, R.J. Turesky, S.S. Thorgeirsson, S. Takayama and T. Sugimura (1995) Metabolic processing and carcinogenicity of heterocyclic amines in nonhuman primates, Int. Symp. Princess Takamatsu Cancer Research Fund, 21, 289-301.
2. Boobis, A.R., A.M. Lynch, S. Murray, R. de la Torre, A. Solans, M. Farre, J. Segura, N.J. Gooderham and D.S. Davies. (1994) CYP1A2 catalysed conversion of dietary heterocyclic amines to their proximate carcinogens is their major route of metabolism in humans, Cancer Res., 54, 89-94.
3. Brooks, R.A., N.J. Gooderham, K. Zhao, R.J. Edwards, L.A. Howard, A.R. Boobis and D.J. Winton (1994) 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is a potent mutagen in the mouse small intestine, Cancer Res., 54, 1665-1667.
4. Buonarati, M.H., K.W. Turtletaub, N.H. Shen and J.R. Felton (1990) Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind to DNA, Mutat. Res., 245, 185-190.
5. Chen, R.H., V.M. Maher, J. Brouwer, P. Van de Putte and J.J. McCormick (1992) Preferential repair and strand-specific repair of benzo[a]pyrene diol epoxide adducts in the hgprt gene of diploid human fibroblasts, Proc. Natl. Acad. Sci. USA, 89, 5413-5417.
6. Commoner, B., A.J. Vithayathil, P. Dolara, S. Nair, P. Madyastha and G.C. Cuca (1978) Formation of mutagens in beef and beef extract during cooking, Science, 201, 913-916.
7. Doll, R. and R. Peto (1981) The Causes of Cancer, Oxford Medical Publications, Oxford University Press, Oxford, pp. 1226-1235.
8. Dooley, K.L., L.S. Von Tunglen, T. Bucci, P.P. Fu and F.F. Kadlubar (1992) Comparative carcinogencity of 4-amino-biphenyl and the food pyrolysates, Glu-P-1, IQ, PhIP, and MeIQx in the neonatal B6C3F1 male mouse, Cancer Lett., 62, 205-209.
9. Edwards, R.J., B.P. Murray, S. Murray, T. Schultz, D. Neubert, T.W. Gant, S.S. Thorgeirsson, A.R. Boobis and D.S. Davies. (1994) Contribution of CYP1A1 and CYP1A2 to the activation of heterocyclic amines in monkeys and human, Carcinogenesis, 15, 829-836.
10. 1 mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, Jpn. J. Cancer Res., 80, 1176-1178.
11. Felton, J.S., M.G. Knize, N.H. Shen, B.D. Andresen, L.F. Bjeldanes and F.T. Hatch (1986) Identification of the mutagens in cooked beef, Environ. Health Persp., 67, 17-24.
12. Frandsen, H., S. Grivas, R. Andersson, L. Dragsted, J.C. Larsen (1992) Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) with 2′-deoxyguanosine and DNA. Synthesis and identification of N2-(2′-deoxyguanosin-8-yl)-PhIP, Carcinogenesis, 13, 629-635.
13. Gerhardsson de Verdier M., U. Hagman, R.K. Peters, G. Steineck and E. Overvik (1991) Meat, cooking methods and colorectal cancer: A case-referent study in Stockholm, Int. J. Cancer, 49, 520-525.
14. 14C]amino-3,8-dimethylimidazo[4,5-f]quinoxaline in mice. Analysis by whole animal autoradiography, Hum. Exp. Toxicol., 10, 337-345.
15. Gooderham, N.J., D. Watson, J.C. Rice, S. Murray, G.W. Taylor and D.S. Davies (1987) Metabolism of the mutagen MeIQx in vivo: metabolite screening by liquid chromatography-thermospray mass spectrometry, Biochem. Biophys. Res. Commun., 148, 1377-1382.
16. Ito, N., R. Hasegawa, M. Sano, S. Tamano, H. Esumi, S. Takayama and T. Sugimura (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.
17. Kadlubar, F.F., M.A. Butler, K.R. Kaderlik, H.C. Chou, N.P. Lang (1992) Polymorphisms for aromatic amine metabolism in humans: relevance for human carcinogenesis, Environ. Health. Perspect., 98, 69-74.
18. Kakiuchi, H., M. Watanabe, T. Ushijima, M. Toyota, K. Imai, J.H. Weisburger, T. Sugimura and M. Nagao (1995) Specific 5′-GGGA-3′ 5′-GGA-3′ mutation of the APC gene in rat colon tumours induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, Proc. Natl. Acad. Sci. USA, 92, 910-914.
19. Kato, T., H. Ohgaki, H. Hasegawa, S. Sato, S. Takayama and T. Sugimura (1988) Induction of tumours in the Zymbal gland, oral cavity, colon, skin and mammary gland of F344 rats by a mutagenic compound 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, Carcinogenesis, 9, 71-73.
20. Lin, D., K.R. Kaderlik, R.J. Turesky, D.W. Miller, J.O. Lay and F.F. Kadlubar (1992) Identification of N-[deoxyguanosine-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. Lynch, A.M., M.G. Knize, A.R. Boobis, N.J. Gooderham, D.S. Davies and S. Murray (1992) Intra- and inter-individual variability in systemic exposure in man to MeIQx and PhIP, carcinogens present in cooked beef, Cancer Res., 52, 6216-6223.
22. Morgenthaler, P.M. and D. Holzhauser (1995) Analysis of mutations induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in human lymphoblastoid cells, Carcinogenesis, 16, 713-718.
23. Murray, S., A.M. Lynch, M.G. Knize, N.J. Gooderham (1993a) Quantification of the carcinogens 2-amino-3,8-dimethyl- and 2-amino-3,4,8-trimethylimidazo[4,5-f] quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in food using a combined assay based on gas chromatography-negative ion mass spectrometry, J. Chromatogr., 616, 211-219.
24. Murray, B.P., R.J. Edwards, S. Murray, A.M. Singleton, D.S. Davies and A.R. Boobis (1993b) Human hepatic CYPIA1 and CYPIA2 content, determined with specific anti-peptide antibodies, correlates with the mutagenic activation of PhIP, Carcinogenesis, 14, 585-592.
25. Ohgaki, H., S. Takayama and T. Sugimura (1991) Carcinogenicities of heterocyclic amines in cooked food, Mutat. Res., 259, 399-410.
26. Rich, K., B.P. Murray, I. Lewis, N. Rendell, D.S. Davies, N.J. Gooderham and A.R. Boobis (1992) N-Hydroxy-MeIQx is the major microsomal oxidation product of the dietary carcinogen MeIQx with human liver, Carcinogenesis, 13, 2221-2226.
27. Rich, K.J., K. Zhao, D.S. Davies, A.R. Boobis and N.J. Gooderham (1996) Developmental changes in hepatic activation of 2-amino-3,8-dimethyl[4,5-f]quinoxaline in rabbit, Carcinogenesis, 17, 555-558.
28. Sesardic, D., A.R. Boobis, B.P. Murray, S. Murray, J. Segura, R. De La Torre and D.S. Davies (1990) Furafylline is a potent and selective inhibitor of cytochrome P4501A2 in man, Br. J. Clin. Pharmacol., 29, 651-663.
29. Sjodin, P., H. Wallin, J. Alexander and M. Jagerstad (1989) Disposition and metabolism of the food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in rats, Carcinogenesis, 10, 1269-1275.
30. Skog, K. (1993) Cooking procedures and food mutagens: a literature review, Fd. Chem. Toxic., 31, 655-675.
31. Sugimura, T. and S. Sato (1983) Mutagens - Carcinogens in foods, Cancer Res. [Suppl.], 43, 2415s-2421s.
32. Thompson, L.H., J.D. Tucker, S.A. Stewart, M.L. Christensen, E.P. Salazar, A.V. Carrano and J.S. Felton (1987) Genotoxicity of compounds from cooked beef in repair-deficient CHO cells versus Salmonella mutagenicity, Mutagenesis, 2, 483-487.
33. Turesky, R.J., J. Markovic, I. Bracco-Hammer and L.B. Fay (1991) The effect of dose and cytochrome P450 induction on the metabolism and disposition of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in the rat, Carcinogenesis, 12, 1847-1855.
34. Turesky, R.J., S.C. Rossi, D.H. Welti, J.O. Lay Jr, F.F. Kadlubar (1992) 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., 5, 479-490.
35. Turteltaub, K.W., M.G. Knize, S.K. Healy, J.D. Tucker and J.S. Felton (1989) The metabolic disposition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in the induced mouse, Food Chem. Toxicol., 27, 667-673.
36. Watkins, B.E., M. Susuki, H. Wallin, K. Wakabayashi, J. Alexander, M. Vanderlaan, T. Sugimura and H. Esumi (1991) The effect of dose and enzyme inducers on the metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rats, Carcinogenesis, 12, 2291-2295.
37. Winton, D.J., N.J. Gooderham, A.R. Boobis, D.S. Davies and B.A.J. Ponder (1990) The putative dietary carcinogen MeIQx is not mutagenic in mouse intestine in vivo as determined by the DIb-1 specific locus test, Cancer Res., 50, 7992-7996.
38. Wolfel, C., B. Heinrich-Hirsch, T. Schulz-Schalge, A. Seidel, H. Frank, U. Ramp, F. Wachter, F.J. Wiebel, F. Gonzalez, H. Greim and J. Doehmer (1992) Genetically engineered V79 Chinese hamster cells for stable expression of human cytochrome P450IA2, Eur. J. Pharmacol., 228, 95-102.
39. Yadollahi-Farsani, M., N.J. Gooderham, D.S. Davies and A.R. Boobis (1996) Mutational spectra of the dietary carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) at the Chinese hamster hprt locus, Carcinogenesis, 17, 617-624.
40. Zhao, K., S. Murray, D.S. Davies, A.R. Boobis and N.J. Gooderham (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.