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American Health Foundation, Naylor Dana Institute for Disease Prevention, Valhalla, New York 10595
New metabolites of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), a potent mutagen and carcinogen formed during cooking of meat or fish, have been identified and quantitated in the urine and bile of rats. Administration was either by a pulse gavage dose of 40 mg/kg [2-14C]IQ or by dietary intake of 300 ppm IQ for 6 weeks. The metabolites were isolated by high-performance liquid chromatography and quantitated by radioactivity. They were then characterized by their resistance or sensitivity to hydrolytic enzymes or acid hydrolysis, by nuclear magnetic resonance and mass spectrometry, or coinjection with a synthetic sample. A minor metabolite was the IQ N-glucuronide. A major metabolite was formed by hydroxylation of IQ at the 5-position; it was present in urine and bile and was conjugated as the glucuronide or sulfate ester, which together accounted for about 40% of urinary or biliary metabolites. The unconjugated compound partially adsorbs onto the high-performance liquid chromatographic columns used. The amounts of 5-OH-IQ present as conjugates in urine or bile were similar, irrespective of mode of administration. Thus, hydroxylation of IQ on carbon 5 followed by type II conjugation reactions yields quantitatively important metabolic products.
1 This work was supported by USPHS Grant CA-42381 awarded by the National Cancer Institute, and BRSG Grant S07 RR-05775 from the Division of Research Resources, NIH, Department of Health and Human Services.
2 To whom requests for reprints should be addressed, at American Health Foundation, Valhalla, NY 10595.
Received 2/ 8/89. Revised 5/ 8/89. Accepted 5/15/89.
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