32P-HPLC analysis of DNA adducts formed in vitro and in vivo by 2- amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,4,8-trimethyl- 3H-imidazo[4,5-f]quinoxaline, utilizing an improved adduct enrichment procedure

Chemical Research in Toxicology

Volumn 9, Issue 6, 1996, Pages 1050-1056

  Wohlin, Pär ^a   Zeisig, Magnus ^a   Gustafsson, Jan Åke ^a   Möller, Lennart ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; 2 AMINO 3,4 DIMETHYLIMIDAZO[4,5 F]QUINOLINE; DNA; 2 AMINO 1 METHYL 6 PHENYLIMIDAZO(4,5 B)PYRIDINE; 2-AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE; 3,4,8 TRIMETHYLIMIDAZO(4,5 F)QUINOXALIN 2 AMINE; 3,4,8-TRIMETHYLIMIDAZO(4,5-F)QUINOXALIN-2-AMINE; BUTANOL; CARCINOGEN; IMIDAZOLE DERIVATIVE; MUTAGENIC AGENT; PHOSPHORUS; QUINOXALINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CANCER; CHEMICAL CARCINOGENESIS; COOKING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; MUTAGENESIS; NONHUMAN; PROTEIN INTAKE; RAT; ANIMAL; DNA ADDUCT; ISOLATION AND PURIFICATION; ISOTOPE LABELING; METHODOLOGY; THIN LAYER CHROMATOGRAPHY; WISTAR RAT;

ANIMALS; BUTANOLS; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; DNA ADDUCTS; IMIDAZOLES; ISOTOPE LABELING; MALE; MUTAGENS; PHOSPHORUS RADIOISOTOPES; QUINOXALINES; RATS; RATS, WISTAR;

EID: 0029658546     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960050a     Document Type: Article

References (42)

1. Johansson, M. A. E., and Jägerstad, M. (1994) Occurrence of mutagenic/carcinogenic heterocyclic amines in meat and fish products, including pan residues, prepared under domestic conditions. Carcinogenesis 15, 1511-1518.
2. Wakabayashi, K., Nagao, M., Esumi, H., and Sugimura, T. (1992) Pood-derived mutagens and carcinogens. Cancer Res. (suppl.), 52, 2092-2098.
3. Wakabayashi, K., Ushiyama, H., Takahashi, M., Nukaya, H., Kim, S.-B., Hirose, M., Ochiai, M., Sugimura, T., and Nagao, M. (1993) Exposure to heterocyclic amines. Environ. Health Perspect. 99, 129-133.
4. Goldbohm, R. A., van den Brandt, P. A., van't Veer, P., Brants, H. A. M., Dorant, E., Sturmans, F., and Hermus, R. (1994) A prospective cohort study on the relation between meat consumption and the risk of colon cancer. Cancer Res. 54, 718-723.
5. Ushiyama, H., Wakabayashi, K., Hirose, M., Itoh, H., Sugimura, T., and Nagao, M. (1991) Presence of carcinogenic heterocyclic amines in urine of healthy volunteers eating normal diet, but not of inpatients receiving parental alimentation. Carcinogenesis 12, 1417-1422.
6. Edwards, R., Murray, B., Murray, S., Schulz, T., Neubert, D., Gant, T., Thorgeirsson, S. S., Boobis, A., and Davies, D. (1994) Contribution of CYP1A1 and CYP1A2 to the activation of heterocyclic amines in monkeys and human. Carcinogenesis 15, 829-836.
7. Boobis, A. R., Lynch, A. M., Murray, S., de la Torre, R., Solans, A., Farré, M., Segura, J., Gooderham, N. J., and Davies, D. S. (1994) CYP1A2-catalyzed conversion of dietary heterocyclic amines to their proximate carcinogens is their major route of metabolism in humans. Cancer Res. 54, 89-94.
8. Lin, D. X., Lang, N. P., and Kadlubar, F. F. (1995) Species differences in the biotransformation of the food-borne carcinogen 2-amino-I-methyl-6-phenylimidazo[4,5-b]pyridine by hepatic microsomes and cytosols from humans, rats and mice. Drug Metab. Dispos. 23, 518-524.
9. Fan, L., Schut, H. A., and Snyderwine, E. G. (1995) Cytotoxicity, DNA adduct formation and DNA repair induced by 2-hydroxyamino-3-methylimidazo[4,5-f]quinoline and 2-hydroxyamino-l-methyl-6-phenylimidazo[4,5-b]pyridine in cultured human mammary epithelial cells. Carcinogenesis 16, 775-779.
10. 32P-postlabeling. Chem. Res. Toxicol. 7, 733-739.
11. 2(deoxyguanosine-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (dG-C8-MeIQx) in human tissues. Carcinogenesis 17, 1029-1034.
12. Miller, E. C., and Miller, J. A. (1966) Mechanisms of chemical carcinogenesis: nature of proximate carcinogens and interactions with macromolecules. Pharm. Rev. 18, 805-838.
13. Poirer, M. C., and Beland, F. A. (1992) DNA adduct measurements and tumor incidence during chronic carcinogen exposure in animal models: implications for DNA adduct based human cancer risk assessment. Chem. Res. Toxicol. 5, 749-755.
14. Cui, X.-S., Torndal, U.-B., Eriksson, L. C., and Möller, L. (1995) Early formation of DNA adducts compared to tumor formation in a long term tumor study in rats after administration of 2-nitrofluorene. Carcinogenesis 16, 2135-2141.
15. 32P-postlabeling. Cancer Res. 53, 1522-1528.
16. 32P-postlabeling assay. Carcinogenesis 13, 1053-1074.
17. Takayama, K., Yamashita, K., Wakabayashi, K., Sugimura, T., and Nagao, M. (1989) DNA-modification by 2-amino-l-methyl-6-phenylimidazo(4,5-b)pyridine in rats. Jpn. J. Cancer Res. 80, 1145-1148.
18. Hasegawa, R., Takahashi, S., Shirai, T., Iwasaki, S., Kim, D. J., Ochiai, M., Nagao, M., Sugimura, T., and Ito, N. (1992) Dosedependent formation of preneoplastic foci and DNA adducts in rat liver with MeA-alpha-C and PhIP. Carcinogenesis 13, 1427-1431.
19. 32P-postlabeling analysis of IQ, MeIQx and PhIP adducts formed in vitro in DNA and polynucleotides and found in vivo in hepatic DNA from IQ-, MeIQx- and PhIP-treated monkeys. Carcinogenesis 13, 1389-1395.
20. Schut, H. A. J., Putman, K. L., and Randerath, K. (1988) DNA adduct formation of the carcinogen 2-amino-3-methylimidazo(4,5-f)quinoline in target tissues of the F-344 rat. Cancer Lett. 41, 345-352.
21. Hall, M., She, M. N., Wild, D., Fasshauer, I., Hewer, A., and Phillips, D. H. (1990) Tissue distribution of DNA adducts in CDF1 mice fed 2-amino-3-methylimidazo(4,5-f)-quinoline (IQ) and 2-amino-3,4-dimethylimidazo(4,5-f)-quinoline (MeIQ). Carcinogenesis 11, 1005-1011.
22. Cummings, D. A., and Schut, H. A. J. (1994) Removal of DNA adducts of 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the male Fisher-344 rat. Carcinogenesis 15, 2623-2628.
23. Övervik, E., Ochiai, M., Hirose, M., Sugimura, T., and Nagao, M. (1991) The formation of heart DNA adducts in F344 rats following dietary administration of heterocyclic amines. Mutat. Res. 256, 37-43.
24. Snyderwine, E. G., Roller, P. P., Adamson, R. H., Sato, S., and Thorgeirsson, S. S. (1988) Reaction of N-hydroxylamine and N-acetoxy derivatives of 2-amino-3-methylimidazolo(4,5-f)quinoline with DNA. Synthesis and identification of N-(deoxyguanosin-8-yl)-IQ. Carcinogenesis 9, 1061-1065.
25. 32P-postlabeling method to detect DNA adducts of 2-amino-3-methylimidazolo(4,5-f)quinoline (IQ) in monkeys fed IQ: identification of the N-(deoxyguanosin-8-yl)-IQ adduct. Carcinogenesis 9, 1739-1743.
26. Schut, H. A. J., Snyderwine, E. G., Zu, H.-X., and Thorgeirsson, S. S. (1991) Similar patterns of DNA adduct formation of 2-amino-3-methylimidazolo(4,5-f)-quinoline in the Fisher 344 rat, CDF1 mouse, Cynomolgus monkey and Salmonella typhimurium. Carcinogenesis 12, 931-934.
27. Yamashita, K., Adachi, M., Kato, S., Nakagama, H., Ochiai, M., Wakabayashi, K., Sato, S., Nagao, M., and Sugimura, T. (1990) DNA adducts formed by 2-amino-3,8-dimethylimidazo(4,5-f)-quinoxaline in rat liver: dose-response on chronic administration. Jpn. J. Cancer Res. 81, 470-476.
28. 32P-Postlabeling analysis of DNA adducts formed in vivo by the parent amines and in vitro by their hydroxyamino derivatives. Mutagenesis 3, 515-520.
29. 2-(2′deoxyguanosin-8-yl)-4,8-diMeIQx adduct. Carcinogenesis 15, 2553-2558.
30. Turesky, R. J., and Markovic, J. (1995) DNA adduct formation of the food carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in liver, kidney and colo-rectum of rats. Carcinogenesis 16, 2275-279.
31. 32P-HPLC. Carcinogenesis 14, 53-59.
32. 32P-postlabeled DNA adducts. Carcinogenesis 14, 1343-1348.
33. 32P-HPLC suitable for characterization of DNA adducts formed in vitro by polycyclic aromatic hydrocarbons and derivatives. Carcinogenesis 16, 1-9.
34. 32P-postlabeling analysis of aromatic carcinogen-DNA adducts. Cancer Res. 45, 5656-5662.
35. 32P-postlabeling analysis of DNA adducts persisting for up to 42 weeks in the skin, epidermis and dermis of mice treated topically with 7, 12-dimethylbenz[a]an-thracene. Carcinogenesis 6, 1117-1126.
36. 32P-postlabeling analysis of DNA adducts formed by food-derived heterocyclic amines: evidence for incomplete hydrolysis and a procedure for adduct pattern simplification. Carcinogenesis 15, 877-882.
37. 32P-postlabeling method. Jpn. J. Cancer Res. 85, 113-117.
38. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543-1551.
39. 32P-postlabeling analysis of urinary mutagens from smokers of black tobacco implicates 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) as a major DNA-damaging agent. Carcinogenesis 12, 713-717.
40. 32P-postlabeling method, in the liver of rats fed MeIQx. Carcinogenesis 14, 2165-2170.
41. Lin, D., Kaderlik, K. R., Turesky, R. J., Miller, D. W., Lay, J. O., and Kadlubar, F. F. (1992) Identification of N-(deoxyguanosine-8-yl)2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-l-methyl-6-phenylimidazo[4, 5-b]pyridine, with DNA. Chem. Res. Toxicol. 5, 691-697.
42. Dragsted, L. O., Frandsen, H., Reistad, R., Alexander, J., and Larsen, J. C. (1995) DNA-binding and disposition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat. Carcinogenesis 16, 2785-2793.