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Chemical Compound Review

PhIP     9-methyl-3-phenyl-5,7,9...

Synonyms: AGN-PC-006AEQ, SureCN151718, ACMC-1BRGI, CCRIS 2954, AG-A-35552, ...
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Disease relevance of PhIP


High impact information on PhIP


Chemical compound and disease context of PhIP


Biological context of PhIP


Anatomical context of PhIP


Associations of PhIP with other chemical compounds


Gene context of PhIP


Analytical, diagnostic and therapeutic context of PhIP


  1. 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, a carcinogen in high-temperature-cooked meat, and breast cancer risk. Sinha, R., Gustafson, D.R., Kulldorff, M., Wen, W.Q., Cerhan, J.R., Zheng, W. J. Natl. Cancer Inst. (2000) [Pubmed]
  2. The prostate: a target for carcinogenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) derived from cooked foods. Shirai, T., Sano, M., Tamano, S., Takahashi, S., Hirose, M., Futakuchi, M., Hasegawa, R., Imaida, K., Matsumoto, K., Wakabayashi, K., Sugimura, T., Ito, N. Cancer Res. (1997) [Pubmed]
  3. Characterization of dysplastic aberrant crypt foci in the rat colon induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Ochiai, M., Ushigome, M., Fujiwara, K., Ubagai, T., Kawamori, T., Sugimura, T., Nagao, M., Nakagama, H. Am. J. Pathol. (2003) [Pubmed]
  4. Influence of biliary cirrhosis on the detoxification and elimination of a food derived carcinogen. Dietrich, C.G., Geier, A., Wasmuth, H.E., Matern, S., Gartung, C., de Waart, D.R., Elferink, R.P. Gut (2004) [Pubmed]
  5. Substances in human urine that strongly inhibit bacterial mutagenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and related heterocyclic amines. Malaveille, C., Hautefeuille, A., Brun, G., Vineis, P., Bartsch, H. Carcinogenesis (1992) [Pubmed]
  6. Consequences of bile duct obstruction on intestinal expression and function of multidrug resistance-associated protein 2. Dietrich, C.G., Geier, A., Salein, N., Lammert, F., Roeb, E., Oude Elferink, R.P., Matern, S., Gartung, C. Gastroenterology (2004) [Pubmed]
  7. Carcinogen-specific induction of genetic instability. Bardelli, A., Cahill, D.P., Lederer, G., Speicher, M.R., Kinzler, K.W., Vogelstein, B., Lengauer, C. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  8. 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. Kakiuchi, H., Watanabe, M., Ushijima, T., Toyota, M., Imai, K., Weisburger, J.H., Sugimura, T., Nagao, M. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  9. The breast cancer resistance protein (Bcrp1/Abcg2) restricts exposure to the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. van Herwaarden, A.E., Jonker, J.W., Wagenaar, E., Brinkhuis, R.F., Schellens, J.H., Beijnen, J.H., Schinkel, A.H. Cancer Res. (2003) [Pubmed]
  10. Deregulation of the cyclin D1/Cdk4 retinoblastoma pathway in rat mammary gland carcinomas induced by the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Qiu, C., Shan, L., Yu, M., Snyderwine, E.G. Cancer Res. (2003) [Pubmed]
  11. Steroid hormone receptor expression and proliferation in rat mammary gland carcinomas induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Qiu, C., Shan, L., Yu, M., Snyderwine, E.G. Carcinogenesis (2005) [Pubmed]
  12. Proliferation and apoptosis in PhIP-induced rat mammary gland carcinomas with elevated phosphotyrosine-STAT5a. Papaconstantinou, A.D., Snyderwine, E.G. FEBS Lett. (2007) [Pubmed]
  13. Dietary nitrosamines, heterocyclic amines, and risk of gastric cancer: a case-control study in Uruguay. De Stefani, E., Boffetta, P., Mendilaharsu, M., Carzoglio, J., Deneo-Pellegrini, H. Nutrition and cancer. (1998) [Pubmed]
  14. Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat. Huber, W.W., McDaniel, L.P., Kaderlik, K.R., Teitel, C.H., Lang, N.P., Kadlubar, F.F. Mutat. Res. (1997) [Pubmed]
  15. Effect of chrysin, a flavonoid compound, on the mutagenic activity of 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) and benzo(a)pyrene (B(a)P) in bacterial and human hepatoma (HepG2) cells. Uhl, M., Ecker, S., Kassie, F., Lhoste, E., Chakraborty, A., Mohn, G., Knasmüller, S. Arch. Toxicol. (2003) [Pubmed]
  16. Single nucleotide instability without microsatellite instability in rat mammary carcinomas. Watanabe, N., Okochi, E., Hirayama, Y., Shimada, Y., Yanagihara, K., Yoshida, M.C., Takahashi, S., Mochizuki, M., Sugimura, T., Nagao, M., Ushijima, T. Cancer Res. (2001) [Pubmed]
  17. The food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine activates S-phase checkpoint and apoptosis, and induces gene mutation in human lymphoblastoid TK6 cells. Zhu, H., Boobis, A.R., Gooderham, N.J. Cancer Res. (2000) [Pubmed]
  18. Immunohistochemical demonstration of carcinogen-DNA adducts in tissues of rats given 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): detection in paraffin-embedded sections and tissue distribution. Takahashi, S., Tamano, S., Hirose, M., Kimoto, N., Ikeda, Y., Sakakibara, M., Tada, M., Kadlubar, F.F., Ito, N., Shirai, T. Cancer Res. (1998) [Pubmed]
  19. Mutagenic specificity of 2-amino-3-methylimidazo[4,5-f]quinoline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in the supF shuttle vector system. Endo, H., Schut, H.A., Snyderwine, E.G. Cancer Res. (1994) [Pubmed]
  20. Susceptibility of rats to mammary gland carcinogenesis by the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) varies with age and is associated with the induction of differential gene expression. Shan, L., Yu, M., Schut, H.A., Snyderwine, E.G. Am. J. Pathol. (2004) [Pubmed]
  21. Activation of amino-alpha-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes. Shimada, T., Guengerich, F.P. Cancer Res. (1991) [Pubmed]
  22. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is a potent mutagen in the mouse small intestine. Brooks, R.A., Gooderham, N.J., Zhao, K., Edwards, R.J., Howard, L.A., Boobis, A.R., Winton, D.J. Cancer Res. (1994) [Pubmed]
  23. Increased bioavailability of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in MRP2-deficient rats. Dietrich, C.G., de Waart, D.R., Ottenhoff, R., Schoots, I.G., Elferink, R.P. Mol. Pharmacol. (2001) [Pubmed]
  24. Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human hepatocytes. Langouët, S., Paehler, A., Welti, D.H., Kerriguy, N., Guillouzo, A., Turesky, R.J. Carcinogenesis (2002) [Pubmed]
  25. Gene expression profiling of chemically induced rat mammary gland cancer. Shan, L., Yu, M., Snyderwine, E.G. Carcinogenesis (2005) [Pubmed]
  26. Comparative tumorigenicity of benzo[a]pyrene, 1-nitropyrene and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine administered by gavage to female CD rats. el-Bayoumy, K., Chae, Y.H., Upadhyaya, P., Rivenson, A., Kurtzke, C., Reddy, B., Hecht, S.S. Carcinogenesis (1995) [Pubmed]
  27. Curcumin modifies Apc(min) apoptosis resistance and inhibits 2-amino 1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) induced tumour formation in Apc(min) mice. Collett, G.P., Robson, C.N., Mathers, J.C., Campbell, F.C. Carcinogenesis (2001) [Pubmed]
  28. Effect of glutathione depletion and inhibition of glucuronidation and sulfation on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) metabolism, PhIP-DNA adduct formation and unscheduled DNA synthesis in primary rat hepatocytes. Kaderlik, K.R., Mulder, G.J., Shaddock, J.G., Casciano, D.A., Teitel, C.H., Kadlubar, F.F. Carcinogenesis (1994) [Pubmed]
  29. Contribution of CYP1A1 and CYP1A2 to the activation of heterocyclic amines in monkeys and human. Edwards, R.J., Murray, B.P., Murray, S., Schulz, T., Neubert, D., Gant, T.W., Thorgeirsson, S.S., Boobis, A.R., Davies, D.S. Carcinogenesis (1994) [Pubmed]
  30. High frequency of beta-catenin (ctnnb1) mutations in the colon tumors induced by two heterocyclic amines in the F344 rat. Dashwood, R.H., Suzui, M., Nakagama, H., Sugimura, T., Nagao, M. Cancer Res. (1998) [Pubmed]
  31. Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by human cytochrome P4501B1. Crofts, F.G., Strickland, P.T., Hayes, C.L., Sutter, T.R. Carcinogenesis (1997) [Pubmed]
  32. Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2. Cheung, C., Ma, X., Krausz, K.W., Kimura, S., Feigenbaum, L., Dalton, T.P., Nebert, D.W., Idle, J.R., Gonzalez, F.J. Chem. Res. Toxicol. (2005) [Pubmed]
  33. Carcinogen and anticancer drug transport by Mrp2 in vivo: studies using Mrp2 (Abcc2) knockout mice. Vlaming, M.L., Mohrmann, K., Wagenaar, E., de Waart, D.R., Elferink, R.P., Lagas, J.S., van Tellingen, O., Vainchtein, L.D., Rosing, H., Beijnen, J.H., Schellens, J.H., Schinkel, A.H. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  34. Possible role of Stat5a in rat mammary gland carcinogenesis. Shan, L., Yu, M., Clark, B.D., Snyderwine, E.G. Breast Cancer Res. Treat. (2004) [Pubmed]
  35. Etiology-specific gene expression profiles in rat mammary carcinomas. Kuramoto, T., Morimura, K., Yamashita, S., Okochi, E., Watanabe, N., Ohta, T., Ohki, M., Fukushima, S., Sugimura, T., Ushijima, T. Cancer Res. (2002) [Pubmed]
  36. Detection of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in beer and wine. Manabe, S., Suzuki, H., Wada, O., Ueki, A. Carcinogenesis (1993) [Pubmed]
  37. Mutagenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the mammary gland of Big Blue rats on high-and low-fat diets. Yu, M., Jones, M.L., Gong, M., Sinha, R., Schut, H.A., Snyderwine, E.G. Carcinogenesis (2002) [Pubmed]
  38. Short-term carcinogenicity testing of a potent murine intestinal mutagen, 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP), in Apc1638N transgenic mice. Sørensen, I.K., Kristiansen, E., Mortensen, A., van Kranen, H., van Kreijl, C., Fodde, R., Thorgeirsson, S.S. Carcinogenesis (1997) [Pubmed]
  39. N-Acetyltransferases, sulfotransferases and heterocyclic amine activation in the breast. Williams, J.A., Stone, E.M., Fakis, G., Johnson, N., Cordell, J.A., Meinl, W., Glatt, H., Sim, E., Phillips, D.H. Pharmacogenetics (2001) [Pubmed]
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