DNA Adduct Formation of the Food Carcinogen 2-Amino-3-methylimidazo[4,5-f]quinoline at the C-8 and N2 Atoms of Guanine

Chemical Research in Toxicology

Volumn 7, Issue 6, 1994, Pages 752-761

  Turesky, Robert J ^a   Markovic, Jovanka ^a  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 METHYLIMIDAZO[4,5 F]QUINOLINE; ADENOSINE TRIPHOSPHATE; CARCINOGEN; GUANINE;

ALKALINITY; ARTICLE; CHEMICAL REACTION; DNA ADDUCT; DRUG LABELING; DRUG METABOLISM; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUTAGENESIS; RADIOACTIVITY;

ANIMAL; CARBON; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; FOOD; LIVER; MALE; NITROGEN; QUINOLINES; RATS; RATS, SPRAGUE-DAWLEY;

EID: 0027948365     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00042a007     Document Type: Article

References (52)

1. Felton, J. S., Knize, M. G., Shen, N. H., Andresen, B. D., Bjeldanes, L. F., and Hatch, F. T. (1986) Identification of the mutagens in cooked beef. Environ. Health Perspect. 67, 17-24.
2. Felton, J. S., and Knize, M. G. (1990) Heterocyclic amine mutagens/carcinogens in foods. In Handbook of Experimental Pharmacology (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 471-502, Springer-Verlag, Berlin and Heidelberg.
3. Sugimura, T. (1986) Studies on environmental chemical carcinogenesis in Japan. Science 233, 312-318.
4. Sugimura, T. (1988) Successful use of short-term tests for academic purposes: their use in identification of new environmental carcinogens with possible risk for humans. Mutat. Res. 205, 33-39.
5. Weisburger, J. H. (1987) Mechanisms of nutritional carcinogenesis associated with specific human cancers. ISI Atlas Sci.: Pharmacol. 1, 162-167.
6. Adamson, R. H., Thorgeirsson, U. P., Snyderwine, E. G., Reeves, J., Dalgard, D. W., Takayama, S., and Sugimura, T. (1990) Carcinogenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in nonhuman primates: induction of tumors in 3 macaques. Jpn. J. Cancer Res. 81, 10-14.
7. Miller, J. A. (1970) Carcinogenesis by chemicals: An overview. Cancer Res. 30, 559-576.
8. Yamazoe, Y., Shimada, M. Shinohara, A., Saito, K. Kamataki, T., and Kato, R. (1983) Microsomal activation of 2-amino-3-methylimidazo[4,5-f]quinoline, a pyrolysate of sardine and beef extracts, to a mutagenic intermediate. Cancer Res. 43, 5768-5774.
9. Shimada, T., Iwasaki, M., Martin, M. V., and Guengerich, F. P. (1989) Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA1535/pSk1002. Cancer Res. 49, 3218-3228.
10. Butler, M. A., Iwasaki, M., Guengerich, F. P., and Kadlubar, F. F. (1989) Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc. Natl. Acad. Sci. U.S.A. 86, 7696-7700.
11. Kato, R. (1986) Metabolic activation of mutagenic heterocyclic amines from protein pyrolysates. CRC Crit. Rev. Toxicol. 16, 308-347.
12. Turesky, R. J., Lang, N. P., Butler, M. A., Teitel, C. H., and Kadlubar, F. F. (1991) Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis 12, 1839-1845.
13. Snyderwine, E. G., Roller, P. P., Adamson, R. H., Sato, S., and Thorgeirsson, S. S. (1988) Reaction of the N-hydroxylamine and N-acetoxy derivatives of 2-amino-3-methylimidazo[4,5-f]quinoline with DNA. Synthesis and identification of AT-(deoxyguanosin-8-yl)-IQ. Carcinogenesis 9, 1061-1065.
14. Hashimoto, Y., Shudo, K. and Okamoto, T. (1982) Modification of DNA with potent mutacarcinogenic 2-amino-6-methyldipyrido-[1,2-α:3′,2′-d]imidazole isolated from a glutamic acid pyrolysate: structure of the modified nucleic acid base and initial chemical event caused by the mutagen. J. Am. Chem. Soc. 104, 7635-7640.
15. Hashimoto, Y., Shudo, K., and Okamoto, T. (1980) Activation of a mutagen, 3-amino-1-methyl-5H-pyrido[4,5-b]indole. Identification of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole and its reaction with DNA. Biochem. Biophys. Res. Commun. 96, 355-362.
16. Frandsen, H., Grivas, S., Andersson, R., Dragsted, L., and Larsen, J. C. (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.
17. Lin, D., Kaderlik, K. R., Turesky, R. J., Miller, D. W., Lay, J. O., Jr., and Kadlubar, F. F. (1992) Identification of N-(deoxyguanosin-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.
18. Turesky, R. J., Rossi, S. C., Welti, D. H., Lay, J. O., Jr., and Kadlubar, F. F. (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.
19. Nagaoka, H., Wakabayashi, K., Kim, S.-B., Kim, I.-S., Tanaka, Y., Ochiai, M., Tada, A., Nukaya, H., Sugimura, T., and Nagao, M. (1992) Adduct formation at C-8 of guanine on in vitro reaction of the ultimate form of 2-amino-1-methyl-6-phenylimidazo[4,5-f]pyridine with 2′-deoxyguanosine and its phosphate esters. Jpn. J. Cancer Res. 83, 1025-1029.
20. Sarrif, A. M., White, W. E., and DiVito, N. (1978) Photolysis of 2-azidofluorene in situ as a probe in chemical carcinogenesis; bypass of requirement for metabolic activation. Biochem. Biophys. Res. Commun. 83, 506-512.
21. Wild, D., Fasshauer, I., and Henschler, D. (1989) Photolysis of arylazides and generation of highly electrophilic DNA-binding and mutagenic intermediates. Carcinogenesis 10, 335-341.
22. Kerdar, R. S., Fabhauer, I., Probst, M., Blum, M., Meyer, U. A., and Wild, D. (1993) 32P-Postlabelling studies on the DNA adducts of the food mutagens/carcinogens IQ and PhIP adduct formation in a chemical system, and by rat and human metabolism. In Postlabelling Methods for Detection of DNA Adducts (Phillips, D. H., Castegnaro, M., and Bartsch, H., Eds.) pp 173-179, International Agency for Research on Cancer, Lyon.
23. Randerath, K, E. Randerath, Agrawal, H. P., Gupta, R. C., Schurdak, M. E., and Reddy, M. V. (1985) Postlabeling methods for carcinogen-DNA adduct analysis. Envrion. Health Perspect. 62, 57-65.
24. Schut, H. A. J., Putman, K., 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.
25. Zu, H.-X., and Schut, H. A. J. (1991) Formation and persistence of DNA adducts of 2-amino-3-methylimidazo[4,5-f]quinoline in Male Fischer-344 rats. Cancer Res. 51, 5636-5641.
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-methylimidazo[4,5-f]quinoline in the Fischer 344 rat, CDF1 mouse, cynomolgus monkey and Salmonella typhimurium. Carcinogenesis 12, 931-934.
27. Snyderwine, E. G., Davis, C. D., Nouso, K., Roller, P. P., and Schut, H. A. J. (1993) 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 14, 1389-1395.
28. Grivas, S. (1988) Synthesis of 3,8-dimethyl-2-nitro-3H-imidazo-[4,5-f]quinoxaline, the 2-nitro analogue of the food carcinogen MeIQx. J. Chem. Res. (S), 84.
29. Turesky, R. J., Bracco-Hammer, I., Markovic, J., Richli, U., Kappeler, A. M., and Welti, D. H. (1990) The contribution of N-oxidation to the metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in rat hepatocytes. Chem. Res. Toxicol. 3, 524-535
30. Reddy, M. V., and Randerath, K. (1986) Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7, 1543-1551.
31. Randerath, E., Agrawal, H. P., Weaver, J. A., Bordelon, C. B., and Randerath, K. (1985) 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]anthracene. Carcinogenesis 6, 1117-1126.
32. Hall, M., Shé, 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.
33. Pfau, W., O'Hare, M. J., Grover, P. L., and Phillips, D. H. (1992) Metabolic activation of the food mutagens 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) to DNA binding species in human mammary epithelial cells. Carcinogenesis 13, 907-909.
34. Peluso, M., Castegnaro, M., Malaveille, C., Talaska, G., Vineis, P., Kadlubar, F., and Bartsch, H. (1990) 32P-Postlabeling analysis of DNA adducted with urinary mutagens from smokers of black tobacco. Carcinogenesis 11, 1307-1311.
35. Peluso, M., Castegnaro, M., Malaveille, C., Friesen, M., Garren, L., Hautefeuille, A., Vineis, P., Kadlubar, F., and Bartsch, H. (1991) 32Postlabeling 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.
36. Bemardi, G. (1971) Spleen acid deoxyribonuclease. In The Enzymes (Boyer, P. D., Ed.) Vol. IV, pp 271-287, Academic Press, New York and London.
37. Anfinsen, C. B., Cuatrecasas, P., and Taniuchi, H. (1971) Staphylococcal nuclease, chemical properties and catalysis. In The Enzymes (Boyer, P. D., Ed.) Vol. IV, pp 177-204, Academic Press, New York and London.
38. Gupta, R. C. (1985) Enhanced senstivity of 32P-postlabeling analysis of aromatic carcinogen DNA adducts. Cancer Res. 45, 5656-5662
39. Ochiai, M., Nagaoka, H., Wakabayashi, K., Tanaka, Y., Kim, S.-B., Tada, A., Nukaya, H., Sugimura, T., and Nagao, M. (1993) Identification of N2-(dexoyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline 3′,5′-diphosphate, a major DNA adduct, detected by nuclease P1 modification of the 32P-postlabeling method, in the liver of rats fed MeIQx. Carcinogenesis 14, 2165-2170.
40. Pei, G. K., and Moschel., R. C. (1990) Arylalkylation of 2′-deoxyguanosine: Medium effects on sites of reaction with 7-(bromomethyl) benz[a]anthracene. Chem. Res. Toxicol. 3, 292-295.
41. Kriek, E. (1979) Effect of pH on the ratio of substitution products in DNA after reaction with the carcinogen N-acetoxy-2-acetylaminofluorene. Cancer Lett. 7, 141-146.
42. Kadlubar, F. F., and Beland, F. A. (1985) Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. In Polycyclic Hydrocarbons and Carcinogenesis (Harvey, R. G., Ed.) ACS Symposium Series 283, pp 331-370, American Chemical Society, Washington, D.C.
43. Evans, F. E., Miller, D. W., and Beland, F. A. (1980) Sensitivity of the conformation of deoxyguanosine to binding at the C-8 position by N-acetylated and unacetylated 2-aminofluorene. Carcinogenesis 1, 955-959.
44. Westra, J. G., Kriek, E., and Hittenhausen, H. (1976) Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivo. Chem.-Biol. Interact. 15, 149-164.
45. Beland, F. A., Dooley, K. L., and Jackson, C. D. (1982) Persistence of DNA adducts in rat liver and kidney after multiple doses of the carcinogen N-hydoxy-2-acetylaminofluorene (1982). Cancer Res. 42, 1348-1354.
46. Gupta, R. C. (1988) 32P-Adduct assay: Short-and long-term persistence of 2-acetylaminofluorene-DNA adducts and other applications of the assay. Cell Biol. Toxicol. 4, 467-474.
47. Yamasaki, H., Pulkrabek, P., Grunberger, D., and Weinstein, I. B. (1977) Differential excision from DNA of the C-8 and N2 guanosine adducts of N-acetyl-2-aminofluorene by single strandspecific endonucleases. Cancer Res. 37, 3756-3760.
48. Moore, P. D., Rabkin, S. D., Osborn, A. L., King, C. M., and Strauss, B. S. (1982) Effect of acetylated and deacetylated 2-aminofluorene adducts on in vitro DNA synthesis. Proc. Natl. Acad. Sci. U.S.A. 79, 7166-7170.
49. Bichara, M., and Fuchs, R. P. P. (1985) DNA binding and mutation spectra of the carcinogen N-2-aminofluorene in Escherichia coli. A correlation between conformation of the premutagenic lesion and the mutation specificity. J. Mol. Biol. 183, 341-351.
50. Pierce, J. R., Case, R., and Tang, M.-S. (1989) Recognition and repair of 2-aminofluorene-and 2-(acetylamino)fluorene-DNA adducts by UVRABC nuclease. Biochemistry 28, 5821-5826.
51. Beland, F. A., and Kadlubar, F. F. (1985) Formation and persistence of arylamine DNA adducts in vivo. Environ. Health Perspect. 62, 19-30.
52. Poirier, 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.