59
Views
12
CrossRef citations to date
0
Altmetric
Research Article

DNA adduct formation of 14 heterocyclic aromatic amines in mouse tissue after oral administration and characterization of the DNA adduct formed by 2-amino-9H-pyrido[2,3-b]indole (AαC), analysed by 32 P-HPLC

, &
Pages 243-257 | Received 19 May 2004, Accepted 02 Aug 2004, Published online: 04 Oct 2008

References

  • AUGUSTSSON, K, SKOG, K, JAGERSTAD, M. and STEINECK, G. 1997, Assessment of the human exposure to heterocyclic amines. Carcinogenesis, 18, 1931–1935.
  • BARANCZEWSKI, P. and MOILER, L. 2004, Relationship between content and activity of cytochrome P450 and induction of heterocyclic amine DNA adducts in human liver samples in vivo and in vitro. Cancer Epidemiology and Biomarkers Prey., 13, 1071–1078.
  • BOGEN, K T and KEATING, G. A. 2001, U.S. dietary exposures to heterocyclic amine. Journal of Experimental and Analytical Environmental Epidemiology, 11, 155–168.
  • BUTLER, L M., SINHA, R, MILLLKAN, R C., MARTIN, C. F., NEWMAN, B., GAMMON, M. D., AMMERMAN, A. S. and SANDLER, R. S. 2003, Heterocyclic amines, meat intake, and association with colon cancer in a population-based study. American Journal of Epidemology, 57, 434–445.
  • Cul, X. S., TORNDAI-, U. B., ERIKSSON, L C. and MOILER, L 1995, Early formation of DNA adducts compared with tumor formation in a long-term tumor study in rats after administration of 2-nitrofluorene. Carcinogenesis, 16, 2135–2141.
  • DAVIS, C. D., DAcQuEL, E. J., ScHur, H. A. J., THORGEIRSSON, S. S. and SNYDERWINE, E. G. 1996, In vivo mutagenicity and DNA adduct levels of heterocyclic amines in Muta®Mice and c-mycllacZ double transgenic mice. Mutation Research, 356, 287–296.
  • EISENBRAND, G. and TANG, W. 1993, Food-borne heterocyclic amines, chemistry, formation, occurrence and biological activities. A literature review. Toxicology, 84, 1–82.
  • FREDERIKSEN, H. and FRANDSEN, H. 2003, Impact of five cytochrome P450 enzymes on the metabolism of two heterocyclic aromatic amines, 2-amino-9H-pyrido[2,3-b]indole (AaC) and 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAaC). Pharmacology and Toxicology, 92, 246–248.
  • FREDERIKSEN, H., FRANDSEN, H. and PFAU W. 2004, Syntheses of DNA-adducts of two heterocyclic amines, 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAocC) and 2-amino-9H-pyrido [2,3-b]in-dole (AocC) and identification of DNA-adducts in organs from rats dosed with MeAocC. Carcinogenesis, 25, 1525–1533.
  • FRIESEN, M. D., KADERLI KK, LIN, D., GARREN, L., BARTSCH, H., LANG, N. P. and KADLUBAR, F. F. 1994, Analysis of DNA adducts of 2-amino-1-methyl-6-phenylimidazo4,5-b]pyridine in rat and human tissues by alkaline hydrolysis and gas chromatography/electron capture mass spectrometry: validation by comparison with 32P-postlabeling. Chemical Research in Toxicology, 7, 733–739.
  • GRIVA SS. 1988, Synthesis of 3,8-dimethy1-2-nitro-3H-imidazo [4,54] quinoxaline, the 2-nitro analogue of the food carcinogen MeIQx. Journal of Chemical Research, 84, 515–520.
  • HASHIMOTO, Y., SHUDO, K and OKAMOTO, T. 1982, Modification of DNA with potent mutacarcino-genic Glu-P-1 isolated from a glutamic acid pyrolysate: structure of the modified nucleic base and initial chemical event caused by the mutagen. Journal of the American Chemical Society, 104, 7636–7640.
  • HIROSE, M., WAKABAYASHI, K., OCHIAI, M., KUSHIDA, H., SATO, H., STJGIMTJRA, T. and NAGAO, M. 1995, Formation and removal of DNA adducts in the liver of rats chronically fed the food-borne carcinogen, 2-amino-3,8-dimethylimidazo [4,54] quinozaline. Japanese Journal of Cancer Research, 86, 516–522.
  • JOHANSSON, M. A. E. and JAGERSTAD, M. 1994, Occurrence of mutagenic/carcinogenic heterocyclic amines in meat and fish products, including pan residues, prepared under domestic conditions. Carcinogenesis, 15, 1511–1518.
  • LANG, N. P., BUTLER, M. A., MASSENGILL, J., LAWSON, M., STOTT'S, R C., HALTER-JENSEN, M. and KADLUBAR, F. F. 1994, Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidemiology and Biomarkers Prey., 3, 675–682.
  • LAYTON, D. W, BOGEN, K T., KNIZE, M. G., HATCH, F. T., JOHNSON, V. M. and FELTON, J. S. 1995, Cancer risk of heterocyclic amines in cooked foods: an analysis and implications for research. Carcinogenesis, 16, 39–52.
  • MAJER, B. J., KASSIE, F., SASAKI, Y., PFAU, W., GLATT, H., MEINL, W., DARROUDI, F. and KNASMTJLIER, S. 2004, Investigation of the genotoxic effects of 2-amino-9H-pyrido[2,3-b]indole in different organs of rodents and in human derived cells. Journal of Chromatography B, 802, 167–173.
  • MATSUMOTO, T., YOSHIDA, D. and ToNum, H. 1981, Determination of mutagens, amino-alpha-carbolines in grilled foods and cigarette smoke condensate. Cancer Letters, 12, 105–110.
  • MOLLER, L, ZEISIG, M. and VODICKA, P. 1993, Optimization of an HPLC method for analyses of 32P-postlabeled DNA adducts. Carcinogenesis, 7, 1343–1348.
  • NAGAO, M. 1999, A new approach to risk estimation of food-borne carcinogens-heterocyclic amines-based on molecular information. Mutation Research, 431, 3–12.
  • NAGAO, M., UsHipmA, T., TOYOTA, M., INOUE, R. and SUGIMURA, T. 1997, Genetic changes induced by heterocyclic amines. Mutation Research, 376, 161–167.
  • OHE, T. 1997, Quantification of mutagenic/carcinogenic heterocyclic amines, MeIQx, Trp-P-1, Trp-P-2 and PhIP, contributing highly to gentoxicity of river water. Mutation Research, 393, 73–79.
  • OHGAKI, H., MATSUKURA, N., MORINO, K, KAWACHI, T., SUGIMURA, T. and TAKAYAMA, S. 1984, Carcinogenicity in mice of mutagenic compounds from glutamic acid and soybean globulin pyrolysates. Carcinogenesis, 5, 815–819.
  • PFAU, W., SCHULZE, CH., SHIRM, T., HASEGAWA, R. and BROCKSTEDT, U. 1997, Identification of the major hepatic DNA adduct formed by the food mutagen 2-amino-9H-pyrido[2,3-b]indole (AalphaC). Chemical Research in Toxicology, 10, 1192–1197.
  • POWELL, S. M., ZILZ, N., BEAZER-BARCLAY, Y., BRYAN, T. M., HAMILTON, S. R., THIBODEAU, S. N., VOGELSTEIN, B. and KINZLER, K W. 1992, APC mutations occur early during colorectal tumorigenesis. Nature, 359, 235–237.
  • RAZA, H., KING, R. S., SQUIRES, R B., GUENGERICH, F. P., MILLER, D. W., FREEMAN, J. P., LANG, N. P. and KADLUBAR, F. F. 1996, Metabolism of 2-amino-alpha-carboline a food-borne heterocyclic amine mutagen and carcinogen by human and rodent liver microsomes and by human cytochrome P4501A2. Drug Metabolism and Disposition, 24, 395–400.
  • ROHRMANN, S., LLNSEISEN, J., BECKER, N., NORAT, T., SINHA, R., SKEIE, G., LUND, E., MARTINEZ, C., BARRICARTE, A., MATTISSON, I., BERGLUND, G., WELCH, A., DAVEY, G., OVERVAD, K., TJONNELAND, A., CLAVEL-CHAPELON, F., KESSE, E., LOTZE, G., KLIPSTEIN-GROBTJSCH, K., VASILOPOULOU, E., POLYCHRONOPOULOS, E., PALA, V., CELENTANO, E., BUENO-DE-MESQUITA, H. B., PEETERS, P. H., RIBOLI, E., SLIMANI, N. AND EUROPEAN PROSPECTIVE INVESTIGATION INTO CANCER AND NurRrrioN, 2002, Cooking of meat ad fish in Europe - results from the European Prospective Investigation into Cancer and Nutrition (EPIC), European Journal of Clinical Nutrition, 12, 1216–1230.
  • TOTSUKA, Y, Fuxu-romE, K., TAKAHASHI, M., TAKAHASHI, S., TADA, A., SUGIMURA, T. and WAKABAYASHI, K 1996, Presence of N2-(deoxyguanosin-8-y1)-2-amino-3,8-dimethylimidazo [4,54] quino-xaline (dG-C8-MeIQx) in human tissues. Carcinogenesis, 17, 1029–1034.
  • TURESKY, R J. 2002, Heterocyclic aromatic amine metabolism, adduct formation, mutagenesis, and carcinogenesis. Drug Metabolism Reviews, 34, 625–650.
  • TURESKY, R J. and VOUROS, P. 2004, Formation and analysis of heterocyclic aromatic amine-DNA adducts in vitro and in vivo. Journal of Chromatography B, 802, 155–166.
  • TURTELTAUB, K, MAUTHE, R. J., DINGEY, K H., VOGEL, J. S., FRANTZ, CH. E., GARNER, R C. and SHE NN. 1997, MeIQx-DNA adduct formation in rodent and human tissues at low doses. Mutation Research, 376, 243–252.
  • WAKABAYASHI, K, KIM, I. S., KUROSAKA, R, YAMAIZUMI, Z., USHIYAMA, H., TAKAHASHI, M., KOYOTA, S., TADA, A., NUKAYA, H. and GOTO, S. 1995, Identification of new mutagenic heterocyclic amines and quantification of know heterocyclic amines. Princess Takamatsu Symposia, 23, 39–49.
  • WOMAN, P., ZEISIG, M., GISTAFSSON, J. A. and MOLLER, L. 1996, 32-P-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-trimethy1-3H-imidazo [4,54] quinoxaline, utilizing an improved adduct enrichment procedure. Chemical Research in Toxicology, 9, 1050–1056.
  • YAmAsHrrA, K, TAKAYAMA, S., NAGAO, M., SATO, S. and SUGIMURA, T. 1986, Amino-methyl-alpha-carboline-induced DNA modification in rat salivary glands and pancreas detected by 32P-postlabeling method. Proceedings of the Japanese Academy, 62, 45–48.
  • YOSHIDA, D., MATSUMOTO, T, YOSHIMURA, R. and MATSUZAKI, T. 1978, Mutagenicity of amino-alpha-carborlines in pyrolysis products of soybean globulin. Biochemical and Biophysical Research Communications, 83, 915–920.
  • ZEISIG, M. and MoLLER, L. 1995, 32P-HPLC suitable for characterization of DNA adducts formed in vitro by polycyclic aromatic hydrocarbons and derivatives. Carcinogenesis, 16, 1–9.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.