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Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites : pH stability and synthesis by human and dog liver

Babu, Satram R. ; Lakshmi, Vijaya M. ; Huang, George Pen-Wen ; Zenser, Terry V. ; Davis, Bernard B. ;
  • 초록  

    Abstract Glucuronide conjugates of arylamines are thought to be important in the carcinogenic process. This study investigated the pH stability and synthesis of glucuronide conjugates of 4-aminobiphenyl and its N -hydroxy metabolites by human and dog liver. Both dog and human liver slices incubated with 0.06 mM [ 3 H]-4-aminobiphenyl produced the N -glucuronide of 4-aminobiphenyl as the major product. After 2 hr of incubation, the N -glucuronide of 4-aminobiphenyl represented 52 and 27% of the total radioactivity recovered by HPLC in dog and human, respectively. When 4-aminobiphenyl, N -hydroxy-4-aminobiphenyl, or N -hydroxy- N -acetyl-4-aminobiphenyl was added to human microsomes containing [ 14 C]UDP-glucuronic acid, a new product peak was detected by HPLC. At 0.5 mM, the rate of glucuronidation was N -hydroxy- N -acetyl-4-aminobiphenyl > N -hydroxy-4-aminobiphenyl > 4-aminobiphenyl. The rate of formation of the N -glucuronide of 4-aminobiphenyl was similar to that observed with benzidine and N -acetylbenzidine. The glucuronides of 4-aminobiphenyl and N -hydroxy-4-aminobiphenyl were both acid labile with T12 values of 10.5 and 32 min, respectively, at pH 5.5. The glucuronide of N -hydroxy- N -acetyl-4-aminobiphenyl was not acid labile with T12 values at pH 5.5 and 7.4 of 55 and 68 min, respectively. The glucuronide of 4-aminobiphenyl was the most acid labile conjugate examined. Thus, the glucuronide of 4-aminobiphenyl is a major product of dog and human liver slice metabolism and likely to play an important role in the carcinogenic process.


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  • 주제어

    4-aminobiphenyl .   N-hydroxy-4-aminobiphenyl .   N-hydroxy-N-acetyl-4-aminobiphenyl .   glucuronidation .   N-glucuronides .   acid lability .   liver slices.  

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