Macromolecular adduct formation and metabolism of heterocyclic amines in humans and rodents at low doses

Cancer Letters

Volumn 143, Issue 2, 1999, Pages 149-155

  Turteltaub, Kenneth W ^a   Dingley, Karen H ^a   Curtis, Kellie D ^a   Malfatti, Michael A ^a   Turesky, Robert J ^b   Colin Garner, R ^c   Felton, James S ^a   Lang, Nicholas P ^d  

^a LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

^c UNIVERSITY OF YORK   (United Kingdom)

^d UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

2 Amino 1 methyl 6 phenylimidazo 4,5 b pyridine; 2 Amino 3,8 dimethylimidazo 4,5 f quinoxaline; Accelerator mass spectrometry; Dosimetry; Human; Rodent

Indexed keywords

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

ANIMAL EXPERIMENT; ARTICLE; BIOAVAILABILITY; CLINICAL ARTICLE; COOKING; DETOXIFICATION; DNA ADDUCT; DRUG METABOLISM; ENZYME POLYMORPHISM; FISH; HUMAN; MEAT; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; RODENT; TOXICOKINETICS;

ANIMALS; CARCINOGENS; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; IMIDAZOLES; MACROMOLECULAR SUBSTANCES; MICE; QUINOXALINES; RATS;

ANIMALIA; RODENTIA;

EID: 0032782320     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(99)00116-0     Document Type: Article

References (36)

1. Sugimura T., Nagao M., Kawachi T., Honda M., Yahagi T., Seino Y., Sato S., Matsukura N., Matsushima T., Shirai A., Sawamura M., Matsumoto H. Mutagen-carcinogens in foods with special reference to highly mutagenic pyrolytic products in broiled foods. Hiatt H.H., Watson J.D., Winsten J.A. Origins of Human Cancer. 1977;1561 Cold Spring Harbor, New York.
2. Felton J.S., Malfatti M.A., Knize M.G., Salmon C.P., Hopmans E.C., Wu R.W. Health risks of heterocyclic amines. Mutat. Res. 376:1997;37-41.
3. Wakabayashi K., Nagao M., Esumi H., Sugimura T. Food-derived mutagens and carcinogens. Cancer Res. 52(Suppl.):1992;2092s-2098s.
4. Wakabayashi K., Ushiyama H., Takahashi M., Nukaya H., Kim S.B., Hirose M., Ochiai M., Sugimura T. Exposure to heterocyclic amines. Environ. Health Perspect. 99:1993;129-134.
5. Lynch A.M., Knize M.G., Boobis A.R., Gooderham N.J., Davies D.S., Murray S. Intra- and interindividual variability in systemic exposure in humans to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, carcinogens present in cooked beef. Cancer Res. 52:1992;6216-6223.
6. Schiffman M.H., Felton J.S. Letters to the Editor: re 'Fried foods and the risk of colon cancer'. Am. J. Epidemiol. 131:1990;376-387.
7. Gerhardsson de Verdier M., Hagman U., Peters R.K., Steineck G., Övervik E. Meat cooking methods and colorectal cancer: a case-referent study in Stockholm. Int. J. Cancer. 49:1991;520-525.
8. Muscat J.E., Wynder E.L. The consumption of well-done red meat and the risk of colorectal cancer. Am. J. Public Health. 84:1994;856-858.
9. Lang N.P., Butler M.A., Massengill J., Lawaon M., Stotts R.C., Hauer-Jenmsen M., Kadlubar F.F. Rapid metabolic phenotypes for acetyltransferases and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidemiol. Biomarkers Prev. 3:1994;675-682.
10. DeStefani 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. 6:1997;573-581.
11. Ronco J.E., De Stefani E., Mendilaharsu M., Deneo-Pelligrini H. Meat, fat and risk of breast cancer: a case-control study from Uruguay. Int. J. Cancer. 65:1996;328-331.
12. Ambrosone C.B., Freudenheim J.L., Sinha R., Graham S., Marshall J.R., Vena J.E., Laughlin R., Nemoto T., Shields P.G. Breast cancer risk, meat consumption and N-acetyltransferase (NAT2) genetic polymorphisms. Int. J. Cancer. 75:1998;825-830.
13. Layton D.W., Bogen K.T., Knize M.G., Hatch F.T., Johnson V.M., Felton J.S., ancer C. of heterocyclic amines in cooked foods: an analysis and implications for research. Carcinogenesis. 16:1995;39-52.
14. Kadlubar F., Kaderlik R.K., Mulder G.J., Lin D., Butler M.A., Teitel C.H., Minchin R.F., Ilett K.F., Friesen M.D., Bartsch H., et al. Metabolic activation and DNA adduct detection of PhIP in dogs, rats, and humans in relation to urinary bladder and colon carcinogenesis. Princess Takamatsu Symp. 23:1995;207-213.
15. Boobis A.R., Gooderham N.J., Rich K.J., Zhao K., Edwaards R.J., Murray B.P., Lynch A.M., Murray S., Davies D.S. Enzymatic studies of the activation of heterocyclic food mutagens in man. Adamson R.H. Heterocyclic amines in cooked foods: possible human carcinogens, Proceeding of the 23rd International Symposium of the Princess Takamatsu Cancer Research Fund. 1995;134 Princeton Scientific Publishing, Princeton, NJ.
16. Turesky R.J., Lang N.P., Butler M.A., Teitel C.H., Kadlubar F.F. Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis. 12:1991;1839-1845.
17. Chou H.C., Lang N.P., Kadlubar F.F. Metabolic activation of N-hydroxyarylamines and N-hydroxyheterocyclic amines by human sulfotransferases. Cancer Res. 55:1995;525-529.
18. Tannenbaum S.R., Stillwell W.G., Ji H., Skipper P.L., Yu M.C., Ross R.K., Henderson B.E., Turesky R.J., Gross G.A. MeIQx (2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline): metabolism in humans and urinary metabolites in human populations. Princess Takamatsu Symp. 23:1995;197-206.
19. Tada A., Ochiai M., Wakabayashi K., Nukaya H., Sugimura T., Nagao M. Identification of N-(deoxyguanosin-8-yl)-2-amino-3,4-dimethylimidazo[4,5-f]quinoline (dG-C8-MeIQ) as a major adduct formed by MeIQ with nucleotides in vitro with DNA in vivo. Carcinogenesis. 15:1994;1275-1278.
20. K.W. Turteltaub, J.S. Vogel, Applications of Accelerator Mass Spectrometry in Toxicology: a highly sensitive tool for low-level isotope measurements, in: A.L.B.S.A.C. (Eds.) Mass Spectrometry in the Biological Sciences, Humana Press, Totowa, NJ, 1996, pp. 477-497.
21. Turteltaub K.W., Felton J.S., Gledhill B.L., Vogel J.S., Southon J.R., Caffee M.W., Finkel R.C., Nelson D.E., Proctor I.D., Davis J.C. Accelerator mass spectrometry in biomedical dosimetry: relationship between low-level exposure and covalent binding of heterocyclic amine carcinogens to DNA. Proc. Natl. Acad. Sci. USA. 87:1990;5288-5292.
22. Vogel J.S., Turteltaub K.W., Finkel R., Nelson D.E. Accelerator mass spectrometry - isotope quantification at attomole sensitivity. Anal. Chem. 67:1995;A353-A359.
23. Frantz C.E., Bangerter C., Fultz E., Mayer K.M., Vogel J.S., Turteltaub K.W. Dose-response studies of MeIQx in rat liver and liver DNA at low doses. Carcinogenesis. 16:1995;367-373.
24. Turteltaub K.W., Knize M.G., Healy S.K., Tucker J.D., Felton J.S. The metabolic disposition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in the induced mouse. Food Chem. Toxicol. 27:1989;667-673.
25. Turteltaub K.W., Vogel J.S., Frantz C.E., Shen N. Fate and distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in mice at a human dietary equivalent dose. Cancer Res. 52:1992;4682-4687.
26. R.J. Mauthe, K.H. Dingley, S.H. Leveson, J.S. Vogel, R.C. Garner, K.W. Turteltaub, Detection of colonic DNA adducts in humans exposed to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline using accelerator mass spectrometry, Int. J. Cancer (in press).
27. Dingley K.H., Curtis K.D., Turteltaub K.W. Distribution and DNA adduct formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in F344 rats: a comparison of males and females. Proc. Am. Assoc. Cancer Res. 39:1998;635.
28. Dingley K.H., Freeman S., Nelson D.O., Garner R.C., Turteltaub K.W. Covalent binding of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline to albumin and hemoglobin at environmentally relevant doses: comparison of human subjects and F344 rats. Drug Metab. Dispos. 26:1998;825-828.
29. Turesky R.J., Garner R.C., Welti D.H., Richoz J., Leveson S.H., Dingley K.H., Turteltaub K.W., Fay L.B. Metabolism of the food-borne mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in humans, Chem. Res. Toxicol. 11:1998;217-225.
30. 14C]2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine metabolites in humans, Carcinogenesis (in press).
31. Turteltaub K.W., Mauthe R.J., Dingley K.H., Vogel J.S., Frantz C.E., Garner R.C., Shen N. MeIQx-DNA adduct formation in rodent and human tissues at low doses. Mutat. Res. Fundam. Mol. Mech. Mutagen. 376:1997;243-252.
32. Hayatsu H., Kasai H., Yokoyama S., Miyazawa T., Yamaizumi Z., Sato S., Nishimura S., Arimoto S., Hayatasu T., Ohara Y. Mutagenic metabolites in urine and feces of rats fed with 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, a carcinogenic mutagen present in cooked meat. Cancer Res. 47:1987;791-794.
33. Turesky R.J., Aeschbacher H.U., Würzner H.P., Skipper P.L., Tannenbaum S.R. Major routes of metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in the rat. Carcinogenesis. 10:1988;1043-1048.
34. Sjödin P., Wallin H., Alexander J.A., Jägerstad M. Disposition and metabolism of the food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in rats. Carcinogenesis. 10:1989;1269-1275.
35. Kaderlik K.R., Minchin R.F., Mulder G.J., Ilett K.F., Daugaard-Jenson M., Teitel C.H., Kadlubar F.F. 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. 15:1994;1703-1709.
36. Connors M.S., Malfatti M.A., Felton J.S. The metabolism and DNA binding of the cooked-food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in precision-cut rat liver slices. Chem.-Biol. Interact. 96:1995;185-202.