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Metabolism of the food carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in isolated rat liver cells. 1989

H Wallin, and J A Holme, and G Becher, and J Alexander
National Institute of Public Health, Department of Toxicology, Oslo, Norway.

2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) was transformed to at least 10 metabolites in suspensions of hepatocytes isolated from Aroclor 1254 treated rats. Combining biochemical data such as effects on MeIQx metabolism of metabolic modulators and incorporation of radioisotopic sulfur with UV, mass and 1H-NMR spectroscopy, we elucidated the structures of six metabolites. About 40% of the MeIQx was transformed to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxalin-4(or5)-yl sulfate. Other oxygenated metabolites were 2-amino-8-hydroxymethyl-3-methylimidazo[4,5-f]quinoxalin-4(or 5)-yl sulfate and 2-amino-4(or5)-beta-D-glucuronopyranosyloxy-3,8-dimethyli midazo[4,5-f] quinoxaline. Evidence was obtained that a glutathione conjugate was formed. This metabolite, and the other oxygenated metabolites were probably formed in P-450 catalyzed reactions. Two metabolites, 2-beta-D-glucuronopyranosylamino-3,8-dimethylimidazo[4,5-f]q uinoxaline and the N-(3,8-dimethylimidazo[4,5-f]quinoxaline-2-yl) sulfamate, were direct conjugates of MeIQx.

UI MeSH Term Description Entries
D008099 Liver A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances. Livers
D008297 Male Males
D008862 Microsomes, Liver Closed vesicles of fragmented endoplasmic reticulum created when liver cells or tissue are disrupted by homogenization. They may be smooth or rough. Liver Microsomes,Liver Microsome,Microsome, Liver
D011810 Quinoxalines Quinoxaline
D011919 Rats, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding. August Rats,Inbred Rat Strains,Inbred Strain of Rat,Inbred Strain of Rats,Inbred Strains of Rats,Rat, Inbred Strain,August Rat,Inbred Rat Strain,Inbred Strain Rat,Inbred Strain Rats,Inbred Strains Rat,Inbred Strains Rats,Rat Inbred Strain,Rat Inbred Strains,Rat Strain, Inbred,Rat Strains, Inbred,Rat, August,Rat, Inbred Strains,Rats Inbred Strain,Rats Inbred Strains,Rats, August,Rats, Inbred Strain,Strain Rat, Inbred,Strain Rats, Inbred,Strain, Inbred Rat,Strains, Inbred Rat
D002273 Carcinogens Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. Carcinogen,Oncogen,Oncogens,Tumor Initiator,Tumor Initiators,Tumor Promoter,Tumor Promoters,Initiator, Tumor,Initiators, Tumor,Promoter, Tumor,Promoters, Tumor
D002478 Cells, Cultured Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others. Cultured Cells,Cell, Cultured,Cultured Cell
D005502 Food Substances taken in by the body to provide nourishment. Foods
D005965 Glucuronates Derivatives of GLUCURONIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that include the 6-carboxy glucose structure. Glucosiduronates,Glucuronic Acids,Acids, Glucuronic
D005978 Glutathione A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides. Reduced Glutathione,gamma-L-Glu-L-Cys-Gly,gamma-L-Glutamyl-L-Cysteinylglycine,Glutathione, Reduced,gamma L Glu L Cys Gly,gamma L Glutamyl L Cysteinylglycine

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