Amino-3-methylimidazo-4,5-quinoline

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.)...

When 2-amino-4-methylimidazo[4,5-/]quinoline (R = Me, R = H) was alkylated with methyl iodide in K2CO3-DMSO, a mixture of both 1//-1,4-dimethyl- and 3//-3,4-dimethyl derivatives was obtained (80CL1391). In the case of DMF-DMA or its bis-trideuterio analogue, methylation in the ratio 8 1 in favor of the 3//-isomer is preferred (88SC973). 

R. Edenharder, 1. von Petersdorff, and R. Rauscher, Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo(4,5-f quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res. 287 261 (1993). 

Amino-3-methylimidazo[4,5-/]quinoline (30 IQ) is formed at modest yields by heating creatinine together with an amino acid (glycine, serine, phenylalanine) at 200 °C200. 

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)... 

From grilled sun-dried sardines, two mutagenic fractions were obtained with high performance liquid chromatography using pBondapak Cie. Their structures were determined, by 270 MHz 1H-NMR and low- and high-resolution mass spectra, to be 2-amino-3-methylimidazo[4,5-/]quinoline (IQ) and 2-amino-3,4-dimethyl-imidazo[4,5-/]quinoline (MelQ) (12,13,14). The structures of these new compounds were confirmed by chemical synthesis. 

M. J. Barnes and J. H. Weisburger, In vitro binding of the food mutagen 2-amino-3-methylimidazo(4,5-f)quinoline to dietary fiber,./. Natl. Cancer Inst., 1983, 70, 757-760. 

Edenharder, R., Kurz, P., John, K., Burgard, S. and Seeger, K. (1 994) In vitro effect of vegetable and fruit juices on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-fjquinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. Food and Chemical Toxicology 32(5), 443 159. 

Liew, C., Schut, H. A. J., Chin, S. F., Pariza, M. W., and Dashwood, R. H. 1995. Protection of conjugated linoleic acids against 2-amino-3-methylimidazo[4,5-f]quinoline-induced colon carcinogenesis in F344 rat a study of inhibitory mechanisms. Carcinogenesis, 16, 3037-3043. 

Hasaniya, N., Youn, K., Xu, M., et al., Inhibitory activity of green and black tea in a free radical-generating system using 2-amino-3-methylimidazo[4,5-f]-quinoline as substrate, J. Jpn. Cancer Res., 88, 553-558, 1997. 

Figure 6 Metabolic activation and deactivation of IQ. IQ, 2-amino-3-methylimidazo-(4,S-f)quinoline.

IQ 2-amino-3-methylimidazo[4,5-/]quinoline MelQx 2-amino-3,8-dimethylimizado[4,5-/]quinoline PhIP 2-amino-l-methyl-6-phenylimizado[4,5-h]pyridine... 

Adamson, R.H. et al., Induction of hepatocellular carcinoma in nonhuman primates by the food mutagen 2-amino-3-methylimidazo-[4,5-/ quinoline, Environ. Health Perspect., 102, 190, 1994. 

PHAs identified in cooked foods that are of concern to human health include 2-amino-3-methylimidazo[4,5-/Iquinoline (IQ), 2-amino-3,4-dimethyl-3H-imidazo[4,5-/ quinoline (MelQ), 2-amino-3,8-dimethylimidazo[4,5-/Iquinoxaline (MelQx), 2-amino-2,4,8 (or 3,7,8)-trimethylimidazo[4,5-/Iquinoxaline (diMelQx), 2-amino-iV-methyl-5-phenylimidazopyridine (PhIP), 3-amino-l,4-dimethyl-5/f-pyrido[4,3-fe]indole (Trp-P-1), 3-amino-l-methyl-5H-... 

C. E., Stover, J.S., Rizzo, C.J., and Stone, M.P. (2006) Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5 /] quinoline in the recognition sequence of the Narl restriction enzyme, a hotspot for -2 bp deletions. J. Am. 

Bol, S.A., Horlbeck, J., Markovic, J., de Boer, J.G., Turesky, R.J., and Constable, A. (2000) Mutational analysis of the liver, colon and kidney of Big Blue rats treated with 2-amino-3-methylimidazo 4,5-/ quinoline. Carcinogenesis, 21,1-6. 

Moller, P., Wallin, H., Vogel, U., Autrup, H., Risom, L., Hald, M.T., Daneshvar, B., Dragsted, L.O., Poulsen, H.E., and Loft, S. (2002) Mutagenidty of 2-amino-3-methylimidazo[4,5 /] quinoline in colon and liver of Big Blue rats role of DNA adduds, strand breaks, DNA repair and oxidative stress. Carcinogenesis, 23,1379-1385. 

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