Abstract
2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) is a heterocyclic aromatic amine formed during cooking of fish and meat (1). It is mutagenic and carcinogenic in different animal species and is suspected to play a role in the etiology of human cancer (2). Studies performed in animals and with purified human enzymes demonstrated that MeIQx is metabolized by cytochrome P450 (CYP) 1A2 in the liver and CYP1A1 and 1BI in extrahepatic tissues (3). However the metabolic pathways of MeIQx remain incompletely elucidated in humans.
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Wakabayashi, K., Ushiyama, H., Takahashi, M., Nukaya, H., Kim, S. B., Hirose, M., Ochiai, M., Sugimura, T., and Nagao, M. Exposure to heterocyclic amines, Environ Health Perspect. 99: 129–34, 1993.
Muscat, J. E. and Wynder, E. L. The consumption of well-done red meat and the risk of colorectal cancer, Am J Public Health. 84: 856–8, 1994.
Turesky, R. J., Constable, A., Richoz, J., Varga, N., Markovic, J., Martin, M. V., and 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. 11: 925–36, 1998.
Kato, T., Ohgaki, H., Hasegawa, H., Sato, S., Takayama, S., and Sugimura, T. Carcinogenicity in rats of a mutagenic compound, 2-amino-3,8- dimethylimidazo[4,5 f]quinoxaline, Carcinogenesis. 9: 71–3, 1988.
Guillouzo, A., Morel, F., Langouet, S., Maheo, K., and Rissel, M. Use of hepatocyte cultures for the study of hepatotoxic compounds, J Hepatol. 26: 73–80, 1997.
Guguen-Guillouzo, C., Campion, J. P., Brissot, P., Glaise, D., Launois, B., Bourel, M., and Guillouzo, A. High yield preparation of isolated human adult hepatocytes by enzymatic perfusion of the liver, Cell Biol Int Rep. 6: 625–8, 1982.
Burke, M. D. and Mayer, R. T. Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal metabolism and cytochrome P-450- binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresorufins), Chem Biol Interact. 45: 243–58, 1983.
Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal Biochem. 72: 248–54, 1976.
Langouet, S., Welti, D. H., Kerriguy, N., Fay, L. B., Markovic, J., Guengerich, F. P., Guillouzo, A., and Turesky, R. J. Metabolism of 2-amino-3,8-dimethylimidazo[4,5- f ]quinoxaline in human hepatocytes: 2-amino-3,8-dimethylimidazo[4,5- f ]quinoxaline-8-carboxylic acid is a major detoxication pathway catalysed by cytochrome P450 1A2, Chem Res Toxicol. 14: 211–221, 2001.
Turesky, R. J., Garner, R. C., Welti, D. H., Richoz, J., Leveson, S. H., Dingley, K. H., Turteltaub, K. W., and Fay, L. B. Metabolism of the food-borne mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in humans, Chem Res Toxicol. 11: 217–25, 1998.
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Langouët, S. et al. (2001). Metabolism of the Food Mutagen 2-Amino-3,8-Dimethylimidazo[4,5-f]Quinoxaline in Human Hepatocytes. In: Dansette, P.M., et al. Biological Reactive Intermediates VI. Advances in Experimental Medicine and Biology, vol 500. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-0667-6_69
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DOI: https://doi.org/10.1007/978-1-4615-0667-6_69
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