Glucuronidation of catechol estrogens by expressed human UDP- glucuronosyltransferases (UGTs) 1A1, 1A3, and 2B7

Toxicological Sciences

Volumn 45, Issue 1, 1998, Pages 52-57

  Cheng, Ziqiang ^a   Rios, Gladys R ^a   King, Christopher D ^a   Coffman, Birgit L ^a   Green, Mitchell D ^a   Mojarrabi, Behnaz ^b   Mackenzie, Peter I ^b   Tephly, Thomas R ^a  

^a UNIVERSITY OF IOWA   (United States)

^b FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL ESTROGEN; FLUNITRAZEPAM; GLUCURONOSYLTRANSFERASE; XENOBIOTIC AGENT;

ARTICLE; CARCINOGENESIS; CATECHOLAMINE METABOLISM; CELL NUCLEUS MEMBRANE; COMPETITIVE INHIBITION; ENDOPLASMIC RETICULUM; EXON; GLUCURONIDATION; HUMAN; HUMAN TISSUE; HYDROPHILICITY; MOLECULAR CLONING; MULTIGENE FAMILY; PROTEIN EXPRESSION;

MAMMALIA;

EID: 0031784886     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1006/toxs.1998.2494     Document Type: Article

References (27)

1. Battaglia, E., Senay, C., Fournel-Gigleux, S., Herber, R., Siest, G., and Magdalou, J. (1994). The chemical modification of human liver UDP-glucuronosyltransferase UGT1*6 reveals the involvement of a carboxyl group in catalysis. FEBS Lett. 346, 146-150.
2. Chen, C., and Okayama, H. (1988). Calcium phosphate-mediated gene transfer: A highly efficient system for stably transforming cells with plasmid DNA. Biotechniques 6, 632-638.
3. Ciotti, M., and Owens, I. S. (1996). Evidence for overlapping active sites for 17α-ethynlestradiol and bilirubin in the human major bilirubin UDP-glucuronosyltransferase. Biochemistry 35, 10119-10124.
4. Coffman, B. L., King, C. D., Rios, G. R., and Tephly, T. R. (1998). The glucuronidation of opioids, other xenobiotics and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab. Dispos. 26, 73-77.
5. Coffman, B. L., Rios, G. R., King, C. D., and Tephly, T. R. (1997). Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab. Dispos. 25, 1-4.
6. Dutton, G. J. (1980). Glucuronidation of Drugs and Other Compounds. CRC Press, Boca Raton, FL.
7. Ebner, T., and Burchell, B. (1993). Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family. Drug Metab. Dispos. 21, 50-55.
8. Green, M. D., King, C. D., Mojarrabi, B., Mackenzie, P. I., and Tephly, T. R. (1998). Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab. Dispos. 26, 507-512.
9. Green, M. D., Oturo, E. M., and Tephly, T. R. (1994). Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug Metab. Dispos. 22, 799-805.
10. Green, M. D., and Tephly, T. R. (1996). Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug Metab. Dispos. 24, 356-363.
11. Haque, S. J., Peterson, D. D., Nebert, D. W., and Mackenzie, P. I. (1991). Isolation, sequence, and developmental expression of rat UGT2B2: The gene encoding a constitutive UDP-glucuronosyltransferase that metabolizes etiocholanolone and androsterone. DNA Cell Biol. 10, 515-524.
12. Jin, C., Miners, J. O., Lillywhite, K. J., and Mackenzie, P. I. (1993). Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J. Pharmacol. Exp. Ther. 264, 475-479.
13. King, C. D., Green, M. D., Rios, G. R., Coffman, B. L., Owens, I. S., Bishop, W. P., and Tephly, T. R. (1996). The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1. Arch. Biochem. Biophys. 332, 92-100.
14. Liehr, J. G. (1998). Catecholestrogens in the induction of tumors in the kidney of the syrian hamster. In Advances in Pharmacology (D. S. Goldstein, G. Eisenhofer, and R. McCarty, Eds.), Vol. 42, pp. 824-828. Academic Press, San Diego.
15. Liehr, J. G., and Ricci, M. J. (1996). 4-Hydroxylation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. USA 93, 3294-3296.
16. Mojarrabi, B., Butler, R., and Machenzie, P. I. (1996). cDNA cloning and characterization of the human UDP-glucuronosyltransferases, UGT1A3. Biochem. Biophys. Res. Commun. 225, 785-790.
17. Matern, H., Heinemann, H., and Matern, S. (1994). Radioassay of UDP-glucuronosyltransferase activities toward endogenous substrates using labeled UDP-glucuronic acid and an organic solvent extraction procedure. Anal. Biochem. 219, 182-188.
18. Merriam, G. R., and Lipsett, M. B. (Eds.). (1983). Catechol Estrogens. Raven Press, New York.
19. Mackenzie, P. I., Owens, I. S., Burchell, B., Bock, K. W., Bairoch, A., Bélanger, A., Fournel-Gigleux, S., Green, M. D., Hum, D. W., Iyanagi, T., Lancet, D., Louisot, P., Magdalou, J., Chowdhury, J. R., Ritter, J. K., Schachter, H., Tephly, T. R., Tipton, K. F., and Nebert, D. W. (1997). The UDP-glucuronosyltransferase gene superfamily: Recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7, 255-269.
20. r-2, gene and characterization of its promoter. J. Biol. Chem. 265, 11328-11332.
21. Puig, J. F., and Tephly, T. R. (1986). Isolation and purification of rat liver morphine UDP-glucuronosyltransferase. Mol. Pharmacol. 30, 558-565.
22. Ritter, J. K., Chen, F., Sheen, Y. Y., Lubet, R. A., and Owens, I. S. (1992a). Two human liver cDNAs encode UDP-glucuronosyltransferases with 2 log differences in activity toward parallel substrates including hyodeoxycholic acid and certain estrogen derivatives. Biochemistry 31, 3409-3414.
23. Ritter, J. K., Chen, F., Sheen, Y. Y., Tran, H. M., Kimura, S., Yeatman, M. T., and Owens, I. S. (1992b). A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isoenzymes with identical carboxyl termini. J. Biol. Chem. 267, 3257-3261.
24. Ritter, J. K., Crawford, J. M., and Owens, I. S. (1991). Cloning of two human liver bilirubin UDP-glucuronosyltransferase cDNAs with expression in COS-1 cells. J. Biol. Chem. 266, 1043-1047.
25. Ritter, J. K., Sheen, Y. Y., and Owens, I. S. (1990). Cloning and expression of human liver UDP-glucuronosyltransferase in COS-1 cells. J. Biol. Chem. 265, 7900-7906.
26. Senafi, S. B., Clarke, D. J., and Burchell, B. (1994). Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem. J. 303, 233-240.
27. 3H]flunitrazepam. Mol. Pharmacol. 38, 294-298.