HETEROCYCLIC AROMATIC AMINE METABOLISM, DNA ADDUCT FORMATION, MUTAGENESIS, AND CARCINOGENESIS

REFERENCES

• Sugimura T. Past, Present, and Future of Mutagens in Cooked Foods. Environ. Health Perspect. 1986; 5–10
   PubMed Web of Science ®Google Scholar
• Felton J.S., Jagerstad M., Knize M.G., Skog K., Wakabayashi K. Contents in Foods, Beverages and Tobacco. Food Borne Carcinogens Heterocyclic Amines, M. Nagao, T. Sugimura. John Wiley & Sons Ltd., West Sussex 2000; 31–71
   Google Scholar
• Felton J.S., Knize M.G. Heterocyclic Amine Mutagens/Carcinogens in Foods. Handbook of Experimental Pharmacology, C.S. Cooper, P.L. Grover. Springer-Verlag, Berlin 1990; 471–502
   Google Scholar
• Sinha R., Rothman N., Brown E.D., Salmon C.P., Knize M.G., Swanson C.S., Rossi S.C., Mark S.D., Levander O.A., Felton J.S. High Concentrations of the Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Occur in Chicken But Are Dependent on the Cooking Method. Cancer Res. 1995; 55(20)4516–4519
   PubMed Web of Science ®Google Scholar
• Manabe S., Suzuki H., Wada O., Ueki A. Detection of the Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in Beer and Wine. Carcinogenesis 1993; 14(5)899–901
   PubMed Web of Science ®Google Scholar
• Manabe S., Tohyama K., Wada O., Aramaki T. Detection of a Carcinogen, 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, in Cigarette Smoke Condensate. Carcinogenesis 1991; 12(10)1945–1947
   PubMed Web of Science ®Google Scholar
• Jagerstad M., Skog K., Grivas S., Olsson K. Formation of Heterocyclic Amines Using Model Systems. Mutat. Res. 1991; 259(3–4)219–233
   PubMed Web of Science ®Google Scholar
• Sugimura T., Nagao N., Kawachi T., Honda M., Yahagi T., Seino Y., Stao S., Matsukura N., Matsushima T., Shirai A., Sawamura M., Matsumoto H. Mutagen–Carcinogens in Food, with Special Reference to Highly Mutagenic Pyrolytic Products in Broiled Foods. Origins of Human Cancer, Book C, H.H. Hiatt, J.D. Watson, J.A. Winstein. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY 1977; 1561–1577
   Google Scholar
• Nagao M., Sugimura T. Carcinogenic Factors in Food with Relevance to Colon Cancer Development. Mutat. Res. 1993; 290(1)43–51
   PubMed Web of Science ®Google Scholar
• Sugimura T. Overview of Carcinogenic Heterocyclic Amines. Mutat. Res. 1997; 376(1–2)211–219
   PubMed Web of Science ®Google Scholar
• Potter J.D. Nutrition and Colorectal Cancer. Cancer Causes Control 1996; 7(1)127–146
   PubMed Web of Science ®Google Scholar
• Willet W.C., Stamfer M.J., Graham M.J., Colditz G.A., Rosner B.A., Speizer F.E. Relation of Meat, Fat, and Fiber Intake to the Risk of Colon Cancer in a Prospective Study Amongst Women. N. Engl. J. Med. 1990; 323(24)1664–1672
   PubMed Web of Science ®Google Scholar
• Willett W.C. Diet, Nutrition, and Avoidable Cancer. Environ. Health Perspect. 1995; 103(Suppl. 8)165–170
   PubMed Web of Science ®Google Scholar
• Lang N.P., Butler M.A., Massengill J.P., Lawson M., Stotts R.C., Hauer-Jensen M., Kadlubar F.F. 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 Epidemiol. Biomark. Prev. 1994; 3(8)675–682
   PubMed Web of Science ®Google Scholar
• Shirai T., Sano M., Tamano S., Takahashi S., Hirose M., Futakuchi M., Hasegawa R., Imaida K., Matsumoto K., Wakabayashi K., Sugimura T., Ito N. The Prostate: A Target for Carcinogenicity of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Derived from Cooked Foods. Cancer Res. 1997; 57(2)195–198
   PubMed Web of Science ®Google Scholar
• Snyderwine E.G. Some Perspectives on the Nutritional Aspects of Breast Cancer Research. Food-Derived Heterocyclic Amines as Etiologic Agents in Human Mammary Cancer. Cancer 1994; 74(3)1070–1077
   PubMed Web of Science ®Google Scholar
• Ronco A., De Stefani E., Mendilaharsu M., Deneo-Pellegrini H. Meat, Fat and Risk of Breast Cancer: A Case-Control Study from Uruguay. Int. J. Cancer 1996; 65(3)328–331
   PubMed Web of Science ®Google Scholar
• Gaylor D.W., Kadlubar F.F. Quantitative Risk Assessments of Heterocyclic Amines in Cooked Foods. Mutagens in Foods: Detection and Prevention, H. Hayatsu. CRC Press, Boca Raton, FL 1991; 229–236
   Google Scholar
• Lutz W.K., Schlatter J. Chemical Carcinogens and Overnutrition in Diet-Related Cancer. Carcinogenesis 1992; 13(12)2211–2216
   PubMed Web of Science ®Google Scholar
• Sugimura T., Nagao M., Wakabayashi K. How We Should Deal with Unavoidable Exposure of Man to Environmental Mutagens: Cooked Food Mutagen Discovery, Facts and Lessons for Cancer Prevention. Mutat. Res. 2000; 447(1)15–25
   PubMed Web of Science ®Google Scholar
• Guengerich F.P. Comparisons of Catalytic Selectivity of Cytochrome P450 Subfamily Members from Different Species. Chem.–Biol. Interact. 1997; 106(3)161–182
   PubMed Web of Science ®Google Scholar
• MacLeod S., Nowell S., Lang N.P. Genetic Polymorphisms. Food Borne Carcinogens Heterocyclic Amines, M. Nagao, T. Sugimura. John Wiley & Sons Ltd., West Sussex 2000; 112–130
   Google Scholar
• Wattenberg L.W. An Overview of Chemoprevention: Current Status and Future Prospects. Proc. Soc. Exp. Biol. Med. 1997; 216(2)133–141
   PubMed Web of Science ®Google Scholar
• Reddy B.S., Rivenson A. Inhibitory Effect of Bifidobacterium longum on Colon, Mammary, and Liver Carcinogenesis Induced by 2-Amino-3-methylimidazo[4,5-f]quinoline, a Food Mutagen. Cancer Res. 1993; 53(17)3914–3918
   PubMed Web of Science ®Google Scholar
• Lin D.-X., Meyer D.J., Caterer B., Lang N.P., Kadlubar F.F. Effects of Human and Rat Glutathione-S-transferase on the Covalent Binding of the N-Acetoxy Derivatives of Heterocyclic Amine Carcinogens In Vitro: A Possible Mechanism of Organ Specificity in Their Carcinogenesis. Cancer Res. 1994; 54(18)4920–4926
   PubMed Web of Science ®Google Scholar
• Dashwood R., Guo D. Protective Properties of Chlorophylls Against the Covalent Binding of Heterocyclic Amines to DNA In Vitro and In Vivo. Heterocyclic Amines in Cooked Foods: Possible Human Carcinogens, R.H. Adamson, J.-A. Gustafsson, N. Ito, M. Nagao, T. Sugimura, K. Wakabayashi, Y. Yamazoe. Princeton Scientific Publishing Co., Inc., Princeton, NJ 1995; 181–189
   Google Scholar
• Turesky R.J., Constable A., Richoz J., Varga N., Markovic J., Martin M.V., Guengerich F.P. Activation of Heterocyclic Aromatic Amines by Rat and Human Liver Microsomes and by Purified Rat and Human Cytochrome P450 1A2. Chem. Res. Toxicol. 1998; 11(8)925–936
   PubMed Web of Science ®Google Scholar
• Sinha R., Rothman N., Brown E.D., Mark S.D., Hoover R.N., Caporaso N.E., Levander O.A., Knize M.G., Lang N.P., Kadlubar F.F. Pan-Fried Meat Containing High Levels of Heterocyclic Aromatic Amines but Low Levels of Polycyclic Aromatic Hydrocarbons Induces Cytochrome P4501A2 Activity in Humans. Cancer Res. 1994; 54(23)6154–6159
   PubMed Web of Science ®Google Scholar
• Schut H.A., Snyderwine E.G. DNA Adducts of Heterocyclic Amine Food Mutagens: Implications for Mutagenesis and Carcinogenesis. Carcinogenesis 1999; 20(3)353–368
   PubMed Web of Science ®Google Scholar
• Food Borne Carcinogens Heterocyclic Amines, H.U. Aeschbacher. John Wiley & Sons Ltd., West Sussex 2000
   Google Scholar
• Heterocyclic Amines in Cooked Foods: Possible Human Carcinogens, H.U. Aeschbacher. Princeton Scientific Publishing Co., Princeton, NJ 1995
   Google Scholar
• Mutagenic/Carcinogenic N-Substituted Aryl Compounds, H.U. Aeschbacher. Elsevier, Amsterdam 1997
   Google Scholar
• The 7th International Conference on Carcinogenic and Mutagenic N-Substituted Aryl Compounds, H.U. Aeschbacher. Elsevier Science Ireland Ltd., NagoyaJapan 1999
   Google Scholar
• Potential Carcinogens in the Diet, H.U. Aeschbacher. Elsevier Science Publishers B.V., Amsterdam 1991
   Google Scholar
• King R.S., Kadlubar F.F., Turesky R.J. In Vivo Metabolism of Heterocyclic Amines. Food Borne Carcinogens: Heterocyclic Amines, M. Nagao, T. Sugimura. John Wiley & Sons, Ltd., West Sussex 2000; 90–111
   Google Scholar
• Langouët S., Welti D.H., Kerriguy N., Fay L.B., Huynh-Ba T., Markovic J., Guengerich F.P., Guillouzo A., Turesky R.J. Metabolism of 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline in Human Hepatocytes: 2-Amino-3-methylimidazo[4,5-f]quinoxaline-8-Carboxylic Acid Is a Major Detoxification Pathway Catalyzed by Cytochrome P450 1A2. Chem. Res. Toxicol. 2001; 14(2)211–221
   PubMed Web of Science ®Google Scholar
• Boobis A.R., Lynch A.M., Murray S., de la Torre R., Solans A., Farré M., Segura J., Gooderham N.J., Davies D.S. CYP1A2-Catalyzed Conversion of Dietary Heterocyclic Amines to Their Proximate Carcinogens Is Their Major Route of Metabolism in Humans. Cancer Res. 1994; 54(1)89–94
   PubMed Web of Science ®Google Scholar
• Shimada T., Hayes C.L., Yamazaki H., Amin S., Hecht S.S., Guengerich F.P., Sutter T.R. Activation of Chemically Diverse Procarcinogens by Human Cytochrome P-450 1B1. Cancer Res. 1996; 56(13)2979–2984
   PubMed Web of Science ®Google Scholar
• Josephy P.D. The Role of Peroxidase-Catalyzed Activation of Aromatic Amines in Breast Cancer. Mutagenesis 1996; 11(1)3–7
   PubMed Web of Science ®Google Scholar
• Kato R., Yamazoe Y. Metabolic Activation and Covalent Binding to Nucleic Acids of Carcinogenic Heterocyclic Amines from Cooked Foods and Amino Acid Pyrolysates. Jpn. J. Cancer Res. 1987; 78(4)297–311
   PubMedGoogle Scholar
• Turesky R.J. DNA Adducts of Heterocyclic Aromatic Amines, Arylazides and 4-Nitroquinoline 1-Oxide. DNA Adducts: Identification and Biological Significance, K. Hemminki, A. Dipple, D.E.G. Shuker, F.F. Kadlubar, D. Segerbäck, H. Bartsch. International Agency for Research on Cancer, Lyon 1994; 217–228
   Google Scholar
• Snyderwine E.G., Roller P.P., Adamson R.H., Sato S., Thorgeirsson S.S. Reaction of the N-Hydroxylamine and N-Acetoxy Derivatives of 2-Amino-3-methylimidazo[4,5-f]quinoline with DNA. Synthesis and Identification of N-(Deoxyguanosin-8-yl)-IQ. Carcinogenesis 1988; 9(6)1061–1065
   PubMed Web of Science ®Google Scholar
• Frandsen H., Grivas S., Andersson R., Dragsted L., Larsen J.C. 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 1992; 13(4)629–635
   PubMed Web of Science ®Google Scholar
• Santella R.M., Grunberger D. Induction of the Base Displacement or Z Conformation in DNA by N-2-Acetylaminofluorene Modification. Environ. Health Perspect. 1983; 49: 107–115
   PubMed Web of Science ®Google Scholar
• Beland F.A., Kadlubar F.F. Formation and Persistence of Arylamine DNA Adducts In Vivo. Environ. Health Perspect. 1985; 62: 19–30
   PubMed Web of Science ®Google Scholar
• Bichara M., Fuchs R.P. DNA Binding and Mutation Spectra of the Carcinogen N-2-Aminofluorene in Escherichia coli. A Correlation Between the Conformation of the Premutagenic Lesion and the Mutation Specificity. J. Mol. Biol. 1985; 183(3)341–351
   PubMed Web of Science ®Google Scholar
• Shibutani S., Fernandes A., Suzuki N., Zhou L., Johnson F., Grollman A.P. Mutagenesis of the N-(Deoxyguanosin-8-yl)-2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine DNA Adduct in Mammalian Cells. Sequence Context Effects. J. Biol. Chem. 1999; 274(39)27433–27438
   PubMed Web of Science ®Google Scholar
• Garcia A., Lambert I.B., Fuchs R.P. DNA Adduct-Induced Stabilization of Slipped Frameshift Intermediates Within Repetitive Sequences: Implications for Mutagenesis. Proc. Natl Acad. Sci. USA 1993; 90(13)5989–5993
   PubMed Web of Science ®Google Scholar
• Lambert I.B., Napolitano R.L., Fuchs R.P. Carcinogen-Induced Frameshift Mutagenesis in Repetitive Sequences. Proc. Natl Acad. Sci. USA 1992; 89(4)1310–1314
   PubMed Web of Science ®Google Scholar
• Brown K., Hingerty B.E., Guenther E.A., Krishnan V.V., Broyde S., Turteltaub K.W., Cosman M. Solution Structure of the 2-Amino-1-Methyl-6-phenylimidazo[4,5-b]pyridine C8-Deoxyguanosine Adduct in Duplex DNA. Proc. Natl Acad. Sci. USA 2001; 98(15)8507–8512
   PubMed Web of Science ®Google Scholar
• Turesky R.J., Rossi S.C., Welti D.H., Lay J.O., Jr., Kadlubar F.F. 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. 1992; 5(4)479–490
   PubMed Web of Science ®Google Scholar
• Turesky R.J., Box R.M., Markovic J., Gremaud E., Snyderwine E.G. Formation and Persistence of DNA Adducts of 2-Amino-3-methylimidazo[4,5-f]quinoline in the Rat and Nonhuman Primates. Mutat. Res. 1997; 376(1–2)235–241
   PubMed Web of Science ®Google Scholar
• Miller E.C. Some Current Perspectives on Chemical Carcinogenesis in Humans and Experimental Animals: Presidential Address. Cancer Res. 1978; 38(6)1479–1496
   PubMed Web of Science ®Google Scholar
• Poirier M.C., Beland F.A. 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. 1992; 5(6)749–755
   PubMed Web of Science ®Google Scholar
• Hemminki K. DNA Adducts, Mutations and Cancer. Carcinogenesis 1993; 14(10)2007–2012
   PubMed Web of Science ®Google Scholar
• Phillips D.H. Detection of DNA Modifications by the 32P-Postlabeling Assay. Mutat. Res. 1997; 378(1–2)1–12
   PubMed Web of Science ®Google Scholar
• Beach A.C., Gupta R.C. Human Biomonitoring and the 32P-Postlabeling Assay. Carcinogenesis 1992; 13(7)1053–1074
   PubMed Web of Science ®Google Scholar
• Davis C.D., Schut H.A.J., Snyderwine E.G. Enzymatic Phase II Activation of the N-Hydroxylamines of IQ, MeIQx and PhIP by Various Organs of Monkeys and Rats. Carcinogenesis 1993; 14(10)2091–2096
   PubMed Web of Science ®Google Scholar
• Turesky R.J., Markovic J. DNA Adduct Formation of the Food Carcinogen 2-Amino-3-methylimidazo[4,5-f]quinoline at the C-8 and N2 Atoms of Guanine. Chem. Res. Toxicol. 1994; 7(6)752–761
   PubMed Web of Science ®Google Scholar
• Pfau W., Brockstedt U., Sohren K.D., Marquardt H. 32P-Post-Labelling Analysis of DNA Adducts Formed by Food-Derived Heterocyclic Amines: Evidence for Incomplete Hydrolysis and a Procedure for Adduct Pattern Simplification. Carcinogenesis 1994; 15(5)877–882
   PubMed Web of Science ®Google Scholar
• Paehler A., Richoz J., Vouros P., Turesky R.J. Analysis and Quantification DNA Adducts of 2-Amino-3,8-dimethylimidazo [4,5-f] Quinoxaline in Liver of Rats by Liquid Chromatography/Electrospray Tandem Mass Spectrometry. Chem. Res. Toxicol. 2002; 15: 551–561
   PubMed Web of Science ®Google Scholar
• Turesky R.J., Gremaud E., Markovic J., Snyderwine E.G. DNA Adduct Formation of the Food-Derived Mutagen 2-Amino-3-methylimidazo[4,5-f]quinoline in Nonhuman Primates Undergoing Carcinogen Bioassay. Chem. Res. Toxicol. 1996; 9(2)403–408
   PubMed Web of Science ®Google Scholar
• Nagao N., Wakabayashi K., Ushijima U., Toyota M., Totsuka Y., Sugimura T. Human Exposure to Carcinogenic Heterocyclic Amines and Their Mutational Fingerprints in Animals. Environ. Health Perspect. 1996; 104(Suppl. 3)497–501
   PubMedGoogle Scholar
• Friesen M.D., Kaderlik K., Lin D., Garren L., Bartsch H., Lang N.P., Kadlubar F.F. Analysis of DNA Adducts of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Rat and Human Tissues by Alkaline Hydrolysis and Gas Chromatography/Electron Capture Mass Spectrometry: Validation by Comparison with 32P-Postlabeling. Chem. Res. Toxicol. 1994; 7(6)733–739
   PubMed Web of Science ®Google Scholar
• Vogel J.S., Turteltaub K.W., Finkel R., Nelson D.E. Accelerator Mass Spectrometry. Anal. Chem. 1995; 67(11)353A–359A
   PubMed Web of Science ®Google Scholar
• 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 1990; 87(14)5288–5292
   PubMed Web of Science ®Google Scholar
• 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. 1997; 376(1–2)243–252
   PubMed Web of Science ®Google Scholar
• 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. 1992; 52(17)4682–4687
   PubMed Web of Science ®Google Scholar
• Dingley K.H., Freeman S.P., 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. 1998; 26(8)825–828
   PubMed Web of Science ®Google Scholar
• Dingley K.H., Curtis K.D., Nowell S., Felton J.S., Lang N.P., Turteltaub K.W. DNA and Protein Adduct Formation in the Colon and Blood of Humans After Exposure to a Dietary-Relevant Dose of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Cancer Epidemiol. Biomark. Prev. 1999; 8(6)507–512
   PubMed Web of Science ®Google Scholar
• Leclercq L., Laurent C., De Pauw E. High-Performance Liquid Chromatography/Electrospray Mass Spectrometry of the Analysis of Modified Bases in DNA: 7-(2-Hydroxyethyl)-guanine, the Major Ethylene Oxide–DNA Sequence Adduct. Anal. Chem. 1997; 69(10)1952–1955
   PubMed Web of Science ®Google Scholar
• Gangl E.T., Turesky R.J., Vouros P. Detection of In Vivo Formed DNA Adducts at the Part-Per-Billion Level by Capillary Liquid Chromatography/Microelectrospray Mass Spectrometry. Anal. Chem. 2001; 73(11)2397–2404
   PubMed Web of Science ®Google Scholar
• Soglia J.R., Turesky R.J., Paehler A., Vouros P. Quantification of the Heterocyclic Aromatic Amine DNA Adduct N-(Deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-f]quinoline in Livers of Rats Using Capillary Liquid Chromatography/Microelectrospray Mass Spectrometry: A Dose–Response Study. Anal. Chem. 2001; 73(13)2819–2827
   PubMed Web of Science ®Google Scholar
• Singh G., Gutierrez A., Xu K., Blair I.A. Liquid Chromatography/Electron Capture Atmospheric Pressure Chemical Ionization/Mass Spectrometry: Analysis of Pentafluorobenzyl Derivatives of Biomolecules and Drugs in the Attomole Range. Anal. Chem. 2000; 72(14)3007–3013
   PubMed Web of Science ®Google Scholar
• Ochiai M., Nagaoka H., Wakabayashi K., Tanaka Y., Kim S.-B., Tada A., Nukaya H., Sugimura T., Nagao N. Identification of N2-(Deoxyguanosin-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 1993; 24(10)2165–2170
   Google Scholar
• Rindgen D., Turesky R.J., Vouros P. Determination of In Vitro Formed DNA Adducts of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine Using Capillary Liquid Chromatography/Electrospray Ionization/Tandem Mass Spectrometry. Chem. Res. Toxicol. 1995; 8(8)1005–1013
   PubMed Web of Science ®Google Scholar
• Crosbie S.J., Murray S., Boobis A.R., Gooderham M.J. Mass Spectrometric Detection and Measurement of N2-(2′-Deoxyguanosin-8-yl)PhIP Adducts in DNA. J. Chromatogr. B. Biomed. Sci. Appl. 2000; 744(1)55–64
   PubMedGoogle Scholar
• Sugimura T., Sato S. Mutagens–Carcinogens in Foods. Cancer Res. 1983; 43(5 Suppl.)2415s–2421s
   PubMed Web of Science ®Google Scholar
• Felton J.S., Knize M.G., Dolbeare F.A., Wu R. Mutagenic Activity of Heterocyclic Amines in Cooked Foods. Environ. Health Perspect. 1994; 102(Suppl. 6)201–204
   PubMedGoogle Scholar
• Fuscoe J.C., Wu R., Shen N.H., Healy S.K., Felton J.S. Base-Change Analysis of Revertants of the hisD3052 Allele in Salmonella typhimurium. Mutat. Res. 1988; 201(1)241–251
   PubMed Web of Science ®Google Scholar
• McCoy E.C., Anders M., Rosenkranz H.S. The Basis of the Insensitivity of Salmonella typhimurium Strain TA98/1,8-DNP6 to the Mutagenic Action of Nitroarenes. Mutat. Res. 1983; 121(1)17–23
   PubMed Web of Science ®Google Scholar
• Watanabe M., Ishidate M., Jr., Nohmi T. Sensitive Method for the Detection of Mutagenic Nitroarenes and Aromatic Amines: New Derivatives of Salmonella typhimurium Tester Strains Possessing Elevated O-Acetyltransferase Levels. Mutat. Res. 1990; 234(5)337–348
   PubMed Web of Science ®Google Scholar
• Kosakarn P., Halliday J.A., Glickman B.W., Josephy P.D. Mutational Specificity of 2-Nitro-3,4-dimethylimidazo[4,5-f]quinoline in the lacI Gene of Escherichia coli. Carcinogenesis 1993; 14(3)511–517
   PubMed Web of Science ®Google Scholar
• Watanabe M., Ohta T. Analysis of Mutational Specificity Induced by Heterocyclic Amines in the lacZ Gene of Escherichia coli. Carcinogenesis 1993; 14(6)1149–1153
   PubMed Web of Science ®Google Scholar
• Solomon M.S., Leong Morgenthaler P.-M., Turesky R.J., Essigmann J.M. Mutational and DNA Binding Specificity of the Carcinogen 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline. J. Biol. Chem. 1996; 271(31)18368–18374
   PubMed Web of Science ®Google Scholar
• Josephy P.D., Evans D.H., Parikh A., Guengerich F.P. Metabolic Activation of Aromatic Amine Mutagens by Simultaneous Expression of Human Cytochrome P450 1A2, NADPH-Cytochrome P450 Reductase, and N-Acetyltransferase in Escherichia coli. Chem. Res. Toxicol. 1998; 11(1)70–74
   PubMed Web of Science ®Google Scholar
• Josephy P.D., Gruz P., Nohmi T. Recent Advances in the Construction of Bacterial Genotoxicity Assays. Mutat. Res. 1997; 386(1)1–23
   PubMed Web of Science ®Google Scholar
• Oda Y., Yamazaki H., Watanabe M., Nohmi T., Shimada T. Development of High Sensitive umu Test System: Rapid Detection of Genotoxicity of Promutagenic Aromatic Amines by Salmonella typhimurium Strain NM2009 Possessing High O-Acetyltransferase Activity. Mutat. Res. 1995; 334(2)145–156
   PubMed Web of Science ®Google Scholar
• Oda Y., Aryal P., Terashita T., Gillam E.M., Guengerich F.P., Shimada T. Metabolic Activation of Heterocyclic Amines and Other Procarcinogens in Salmonella typhimurium umu Tester Strains Expressing Human Cytochrome P4501A1, 1A2, 1B1, 2C9, 2D6, 2E1, and 3A4 and Human NADPH-P450 Reductase and Bacterial O-Acetyltransferase. Mutat. Res. 2001; 492(1–2)81–90
   PubMed Web of Science ®Google Scholar
• Thompson L.H., Carrano A.V., Salazar E., Felton J.S., Hatch F.T. Comparative Genotoxic Effects of the Cooked-Food-Related Mutagens Trp-P-2 and IQ in Bacteria and Cultured Mammalian Cells. Mutat. Res. 1983; 117(3–4)243–257
   PubMed Web of Science ®Google Scholar
• Thompson L.H., Tucker J.D., Stewart S.A., Christensen M.L., Salazar E.P., Carrano A.V., Felton J.S. Genotoxicity of Compounds from Cooked Beef in Repair-Deficient CHO Cells Versus Salmonella Mutagenicity. Mutagenesis 1987; 2(6)483–487
   PubMed Web of Science ®Google Scholar
• Aeschbacher H.U., Ruch E. Effect of Heterocyclic Amines and Beef Extract on Chromosome Aberrations and Sister Chromatid Exchanges in Cultured Human Lymphocytes. Carcinogenesis 1989; 10(3)429–433
   PubMed Web of Science ®Google Scholar
• Tohda H., Oikawa A., Kawachi T., Sugimura T. Induction of Sister-Chromatid Exchanges by Mutagens from Amino Acid and Protein Pyrolysates. Mutat. Res. 1980; 77(1)65–69
   PubMed Web of Science ®Google Scholar
• Aeschbacher H.U., Turesky R.J. Mammalian Cell Mutagenicity and Metabolism of Heterocyclic Aromatic Amines. Mutat. Res. 1991; 259(3–4)235–250
   PubMed Web of Science ®Google Scholar
• Morgenthaler P.M., Holzhauser D. Analysis of Mutations Induced by 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in Human Lymphoblastoid Cells. Carcinogenesis 1995; 16(4)713–718
   PubMed Web of Science ®Google Scholar
• Carothers A.M., Yuan W., Hingerty B.E., Broyde S., Grunberger D., Snyderwine E.G. Mutation and Repair Induced by the Carcinogen 2-(Hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (N–OH–PhIP) in the Dihydrofolate Reductase Gene of Chinese Hamster Ovary Cells and Conformational Modeling of the dG-C8-PhIP Adduct in DNA. Chem. Res. Toxicol. 1994; 7(2)209–218
   PubMed Web of Science ®Google Scholar
• Wu R.W., Wu E.M., Thompson L.H., Felton J.S. Identification of Aprt Gene Mutations Induced in Repair-Deficient and P450-Expressing CHO Cells by the Food-Related Mutagen/Carcinogen, PhIP. Carcinogenesis 1995; 16(5)1207–1213
   PubMed Web of Science ®Google Scholar
• Yadollahi-Farsani M., Gooderham N.J., Davies D.S., Boobis A.R. Mutational Spectra of the Dietary Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) at the Chinese Hamsters Hprt Locus. Carcinogenesis 1996; 17(4)617–624
   PubMed Web of Science ®Google Scholar
• Kakiuchi H., Watanabe M., Ushijima T., Toyota M., Imai K., Weisburger J.H., Sugimura T., Nagao N. Specific 5′‐GGGA‐3′→5′‐GGA‐3′ Mutation of the APC Gene in Rat Colon Tumors Induced by 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Proc. Natl Acad. Sci. USA 1995; 92(3)910–914
   PubMed Web of Science ®Google Scholar
• Leong-Morgenthaler P.M., Op H.V., Jaccaud E., Turesky R.J. Mutagenicity of 2-Amino-3-methylimidazo[4,5-f]quinoline in Human Lymphoblastoid Cells. Carcinogenesis 1998; 19(10)1749–1754
   PubMed Web of Science ®Google Scholar
• Nagao M., Ushijima T., Toyota M., Inoue R., Sugimura T. Genetic Changes Induced by Heterocyclic Amines. Mutat. Res. 1997; 376(1–2)161–167
   PubMed Web of Science ®Google Scholar
• Nagao M., Sugimura T. Carcinogenic Factors in Food with Relevance to Colon Cancer Development. Mutat. Res. 1993; 290(1)43–51
   PubMed Web of Science ®Google Scholar
• Fujimoto Y., Hampton L.L., Snyderwine E.G., Nagao M., Sugimura T., Adamson R.H., Thorgeirsson S.S. p53 Gene Mutation in Hepatocellular Carcinoma Induced by 2-Amino-3-methylimidazo[4,5-f]quinoline in Nonhuman Primates. Jpn. J. Cancer Res. 1994; 85(5)506–509
   PubMedGoogle Scholar
• Powell S.M., Zilz N., Beazer-Barclay Y., Bryan T.M., Hamilton S.R., Thibodeau S.N., Vogelstein B., Kinzler K.W. APC Mutations Occur Early During Colorectal Tumorigenesis. Nature 1992; 359(6392)235–237
   PubMed Web of Science ®Google Scholar
• Burnouf D., Miturski R., Nagao M., Nakagama H., Nothisen M., Wagner J., Fuchs R.P. Early Detection of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine(PhIP)-induced Mutations Within the Apc Gene of Rat Colon. Carcinogenesis 2001; 22(2)329–335
   PubMed Web of Science ®Google Scholar
• Dashwood R.H., Suzui M., Nakagama H., Sugimura T., Nagao M. High Frequency of Beta-Catenin (ctnnb1) Mutations in the Colon Tumors Induced by Two Heterocyclic Amines in the F344 Rat. Cancer Res. 1998; 58(6)1127–1129
   PubMed Web of Science ®Google Scholar
• Snyderwine E.G. Mammary Gland. Food Borne Carcinogens Heterocyclic Aromatic Amines, M. Nagao, T. Sugimura. John Wiley & Sons Ltd., West Sussex 2000; 241–255
   Google Scholar
• Ushijima T., Kakiuchi H., Makino H., Hasegawa R., Ishizaka Y., Hirai H., Yazaki Y., Ito N., Sugimura T., Nagao M. Infrequent Mutation of Ha-ras and p53 in Rat Mammary Carcinomas Induced by 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Mol. Carcinog. 1994; 10(1)38–44
   PubMed Web of Science ®Google Scholar
• Okonogi H., Ushijima T., Zhang X.B., Heddle J.A., Suzuki T., Sofuni T., Felton J.S., Tucker J.D., Sugimura T., Nagao M. Agreement of Mutational Characteristics of Heterocyclic Amines in lacI of the Big Blue Mouse with Those in Tumor Related Genes in Rodents. Carcinogenesis 1997; 18(4)745–748
   PubMed Web of Science ®Google Scholar
• Okonogi H., Stuart G.R., Okochi E., Ushijima T., Sugimura T., Glickman B.W., Nagao M. Effects of Gender and Species on Spectra of Mutation Induced by 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in the lacI Transgene. Mutat. Res. 1997; 395(2–3)93–99
   PubMed Web of Science ®Google Scholar
• Okochi E., Watanabe N., Shimada Y., Takahashi S., Wakazono K., Shirai T., Sugimura T., Nagao M., Ushijima T. Preferential Induction of Guanine Deletion at 5′-GGGA-3′ in Rat Mammary Glands by 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Carcinogenesis 1999; 20(10)1933–1938
   PubMed Web of Science ®Google Scholar
• Stuart G.R., Holcroft J., de Boer J.G., Glickman B.W. Prostate Mutations in Rats Induced by the Suspected Human Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Cancer Res. 2000; 60(2)266–268
   PubMed Web of Science ®Google Scholar
• Nagao M., Ochiai M., Okochi E., Ushijima T., Sugimura T. LacI Transgenic Animal Study: Relationships Among DNA-Adduct Levels, Mutant Frequencies and Cancer Incidences. Mutat. Res. 2001; 477(1–2)119–124
   PubMed Web of Science ®Google Scholar
• Bol S.A., Horlbeck J., Markovic J., de Boer J.G., Turesky R.J., Constable A. Mutational Analysis of the Liver, Colon and Kidney of Big Blue Rats Treated with 2-Amino-3-methylimidazo[4,5-f]quinoline. Carcinogenesis 2000; 21(1)1–6
   PubMed Web of Science ®Google Scholar
• Brooks R.A., Gooderham N.J., Zhao K., Edwards R.J., Howard L.A., Boobis A.R., Winton D.J. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine Is a Potent Mutagen in the Mouse Small Intestine. Cancer Res. 1994; 54(7)1665–1671
   PubMed Web of Science ®Google Scholar
• Andreassen A., Vikse R., Steffensen I.L., Paulsen J.E., Alexander J. Intestinal Tumours Induced by the Food Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Multiple Intestinal Neoplasia Mice Have Truncation Mutations as Well as Loss of the Wild-Type Apc+ Allele. Mutagenesis 2001; 16(4)309–315
   PubMed Web of Science ®Google Scholar
• Davis C.D., Dacquel E.J., Schut H.A., Thorgeirsson S.S., Snyderwine E.G. In Vivo Mutagenicity and DNA Adduct Levels of Heterocyclic Amines in Muta Mice and c-myc/lacZ Double Transgenic Mice. Mutat. Res. 1996; 356(2)287–296
   PubMed Web of Science ®Google Scholar
• Thorgeirsson S.S., Factor V.M., Snyderwine E.G. Transgenic Mouse Models in Carcinogenesis Research and Testing. Toxicol. Lett. 2000; 112–113: 553–555
   PubMed Web of Science ®Google Scholar
• Hasegawa R., Yoshimura I., Imaida K., Ito N., Shirai T. Analysis of Synergism in Hepatocarcinogenesis Based on Preneoplastic Foci Induction by 10 Heterocyclic Amines in the Rat. Jpn. J. Cancer Res. 1996; 87(11)1125–1133
   PubMedGoogle Scholar
• Hasegawa R., Tanaka H., Tamano S., Shirai T., Nagao M., Sugimura T., Ito N. Synergistic Enhancement of Small and Large Intestinal Carcinogenesis by Combined Treatment of Rats with Five Heterocyclic Amines in a Medium-Term Multi-Organ Bioassay. Carcinogenesis 1994; 15(5)2567–2573
   PubMedGoogle Scholar
• Adamson R.H. Carcinogenicity in Animals and Specific Organs. Food Borne Carcinogens Heterocyclic Amines, M. Nagao, T. Sugimura. John Wiley & Sons Ltd., West Sussex 2000; 229–240
   Google Scholar
• Snyderwine E.G., Turesky R.J., Turteltaub K.W., Davis C.D., Sadrieh N., Schut H.A., Nagao M., Sugimura T., Thorgeirsson U.P., Adamson R.H., Thorgeirsson S.S. Metabolism of Food-Derived Heterocyclic Amines in Nonhuman Primates. Mutat. Res. 1997; 376(1–2)203–210
   PubMed Web of Science ®Google Scholar
• Skipper P.L., Tannenbaum S.R. Protein Adducts in the Molecular Dosimetry of Chemical Carcinnnnogens. Carcinogenesis 1990; 11(4)507–518
   PubMed Web of Science ®Google Scholar