2-Amino-l-methyl-6-phenylimidazo

HUBER W W, MCDANIEL L P, KADERLIK K R, TEITEL C H, LANG N P and KADLUBAR F F (1997) Chemoprotection against the formation of colon DNA adducts from the food-bome carcinogen 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhlP) in the rat , Mutat Res, 376 115-22. 

Aoki, H. et al., Inhibitory effect of anthocyanin colors on mutagenicity induced by 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), Foods Food Ingred. J. Jpn., 209, 240, 2004. 

P. Pavek, G. Merino, E. Wagenaar, E. Bolscher, M. Novotna, J.W. Jonker, and A.H. Schinkel. Human breast cancer resistance protein Interactions with steroid drugs, hormones, the dietary carcinogen 2-amino-l-methyl-6-phenylimidazo(4,5-b)pyridine, and transport of cimetidine. J Pharmacol Exp Ther. 312 144—152... 

Figure 13.8 Mutagenic and carcinogenic heterocyclic amines (a) IQ (2-amino-3-methylimidazo[4,5-/ quinoline), (b) IQx (2-amino-3-methylimidazo[4,5-/ quinoxaline), (c) PhIP, (2-amino-l-methyl-6-phenylimidazo[4,5- ] pyridine), (d) 1,5,6-TMIP (2-amino-l,5,6-trimethylimidazo[4,5-6] p5ridine).

Amino-2-methylanthraquinone 2-Amino-3-methylimidazo[4,5-/]quinoline (see IQ) 2-Amino-6-methyldipyrido[l,2-a 3, 2 -fil]imidazole (see Glu-P-1) 2-Amino-l-methyl-6-phenylimidazo[4,5-6]pyridine (see PhIP)... 

Boyce A, Doehmer J, Gooderham NJ. 2004. Phytoalexin resveratrol attenuates the mutagenicity of the heterocyclic amines 2-amino-l-methyl-6-phenylimidazo [4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. J Chromatogr B Analyt Technol Biomed Life Sci 802 217-223. 

L. M. Tikkanen, T. M. Sauri, and K. J. Latva-Kala, Screening of heat-processed Finnish foods for the mutagens 2-amino-3,4,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, and 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyri-dine, Food Chem. Toxic., 1993, 31, 717-721. 

Strickland, P. T., Qian, Z., Friesen, M. D., Rothman, N., and Sinha, R. Metabolites of 2-amino-l-methyl-6-phenylimidazo(4,5,-b)pyridine (PhIP) in human urine after consumption of charbroiled or fried beef. Mutat. Res. 2002.163-173, 506-507. 

AMINO-3-METHYLPENTANOIC ACID see IKXOOO 2-AMINO-4-METHYLPENTANOIC ACID see LESOOO 2-AMINO-l-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE see AKZ200... 

Figure 11.4. Structures of various heterocyclic amines. IQ is 2-amino-3-methylimidazo-quinoline. MelQx is 2-amino-3,8-dimethylLtnidazo-quinoxalme. 4,8-DiMelQx is 2-amino-3,4,8-trimethylimidazo-quinoxaline. PhIP is 2-amino-l-methyl-6-phenylimidazo-pyridine. These and other related compounds can be found in fried or broil beef, fish, and chicken, but can also be created by cooking mixtures of creatinine, amino acids, and glucose. Microwave cooking, or cooking in aluminum foil, reduces the formation of heterocyclic amines. (From Sugimura, 1997.)...

Ito, N., Flasegawa, R., Sano, M., Tamano, S., Esumi, H., Takayama, S., and Sugimura, T. (1991). A new colon and mammary carcinogen in cooked food, 2-amino-l-methyl-6-phenylimidazo[4,5-p]pyridine (PhIP). Carcinogenesis 12,1503-1506. 

Figure 14.10 Structures of four of the most abundant HAA in cooked food. PhIP is 2-amino-l-methyl-6-phenylimidazo[4,5-6]pyridine, AocC is 2-amino-9/f-pyrido[2,3-Z)]indole, MelQx is 2-amino-3,8-dimethylimidazo[4,5-/]quinoxaline, and IFP is 2-amino-l,6-dimethylfuro[3,2-e]imidazo[4,5-6]pyridine.

While the HCA concentration is low, at the ppb level, the carcinogenicity may be enhanced by polyunsaturated oils. Since high-fat western diets may promote aryl amine cancer, considerable importance is attached to the roles of HCAs and the related food-derived PhIP, or 2-amino-l-methyl-6-phenylimidazo[4,5-ft]pyridine (57), in the etiology of cancer. The mechanisms are similar to those encountered with other tumor-forming... 

Phosphorescence lifetimes of 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyri-dine and benzo[f]quinoline increase with decreasing temperature in glucose glasses. A series of articles has addressed the properties of the excited triplet state of 4H-l-benzopyrane-4-thione in perfluoroalkane solvents.Delayed S2-S0 fluorescence arises via triplet-triplet annihilation. 

Dietrich, C.G., de Waart, D.R., Ottenhoff, R., Bootsma, A.H., van Germip, A.H., and Elferink, R.P. (2001) Mrp2-deficiency in the rat impairs biliary and intestinal excretion and influences metabolism and disposition of the food-derived carcinogen 2-amino-l-methyl-6-phenylimidazo. Carcinogenesis, 22 (5), 805-811. 

Shioya M., Wakabayashi K., Sato S., Nagao M. and Sugimura T. Formation of a mutagen, 2-amino-l-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP) in cooked beef by heating a mixture containing creatinine, phenylalanine and glucose. Mutation Research. 191,133. 1987... 

Doi, K., Wanibuchi, H., Salim, E. I., Morimura, K., Kinoshita, A., Kudoh, S., Hirata, K., Yoshikawa, J., and Fukushima, S. (2005). Lack of large intestinal carcinogenicity of 2-amino-l-methyl-6-phenylimidazo[4,5-i)]pyridine at low doses in rats initiated with azoxymethane. Int J Cancer 115, 870-878. 

Activation of amino-a-carboline, 2-amino-l -methyl-6-phenylimidazo[4,5-fcjpyridine, and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes. Cancer Res., 51, 5284-5291. 

Lewis, A.)., Walle, U.K., King, R.S., Kadlubar, F.F., Falany, C.N., and Walle, T. (1998) Bioadivation of the cooked food mutagen N-hydroxy-2-amino-l-methyl-6-phenylimidazo[4,5-i>] pyridine by estrogen sulfotransferase in cultured human mammary epithelial cells. Carcinogenesis, 19, 2049-2053. 

Frandsen, H., Grivas, S., Andersson, R., Dragsted, L., and Larsen, J.C. (1992) Reaction of the N2-acetoxy derivative of 2-amino-l-methyl-6-phenylimidazo[4,5-fcjpyridine (PhIP) with 2 -deoxyguanos-ine and DNA. Synthesis and identification of N2-(2 -deoxyguanosin-8-yl)-PhIP. Carcinogenesis, 13, 629-635. 

Styczynski, P.B., Blackmon, R.C., Groopman, J.D., and Kensler, T.W. (1993) The direct glucuronidation of 2-amino-l-methyl-6-phenylimidazo[4,5-fe]pyridine (PhIP) by human and rabbit liver microsomes. Chem. Res. Toxicol.,... 

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