2-Amino-6-phenylimidazo pyridine

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.)...

NAGAO M (1995) Specific 5 -GGGA-3 - 5 -GGA-3 mutation of the Ape gene in rat colon tumours induced by 2-amino-1 -methyl-6-phenylimidazo [4,5-b]pyridine , Proc Nat Acad Sci, 92 910-14. 

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).

Y. Ueyama, Y. Monden, X. B. He, C. X. Lin, M. A. Momen, S. Mimura and A. Umemoto, Effects of bile acids on 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine-induced aberrant crypt foci and DNA adduct formation in the rat colon, J. Exp. Clin. Cancer Res., 2002, 21, 577. 

Z-aminO 1 -methy 1 6 phenylimidazo [4,5-b]-pyridine 2 aminO 3,7,8 trimethylimidazo[4,5 f]quinoxaline 2 aminO 3,4,7,8 tetramethyl 3H imidazO [4,5 f]quinoxaline inoxaline 3 aminO l,4 dimethyl SH pyrid [4,3 b] indole (Trp P I) and 3 aminO l methyl 5H pyrido [4,3 b]indole induced mutagenesis. Metabolic activation was required for positive results b... 

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. 

Frandsen H, Alexander J (2000) N-Acetyltransferase-dependant activation of 2-hydroxyamino-l-methyl-6-phenylimidazo[4,5-b]pyridine formation of 2-amino-l-methyl-6-(5-hydroxy)phenylimidazo[4,5-b]pyridine, a possible biomarker for the reactive dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Carcinogenesis 21 1197-1203... 

Kobayashi, M., Hanaoka, T., et al. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) level in human hair as biomarkers for dietary grilled/stir-fried meat and fish intake. Mutat. Res. 588(2), 136-142, 2005. 

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. 

The potential of a natural anthocyanin with purple corn color (PCC) has been tested against colorectal carcinogenesis, using male F344/DuCrj rats that were initially treated with 1,2-dimethylhydrazine (DMH). 2-Amino-l-melhyl-6-phenylimidazo [4,5-fc] pyridine (PhIP) exerted promoting effects on... 

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... 

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.

Knize, M. G., Felton, J. S. The synthesis of the cooked-beef mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and its 3-methyl isomer. Heterocycles 1986, 24, 1815-1819. 

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... 

---