4-Hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7

Journal of Biological Chemistry

Volumn 275, Issue 10, 2000, Pages 6908-6914

  Samokyszyn, Victor M ^a   Gall, Walter E ^b   Zawada, Gregory ^b   Freyaldenhoven, Mary Ann ^a   Chen, Guangping ^b   Mackenzie, Peter I ^c   Tephly, Thomas R ^d   Radominska Pandya, Anna ^b  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^c FLINDERS UNIVERSITY   (Australia)

^d UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; GLUCURONOSYLTRANSFERASE; RETINOIC ACID; RETINOIC ACID DERIVATIVE;

ADOLESCENT; ADULT; AEROBIC METABOLISM; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME SUBSTRATE; FEMALE; GLUCURONIDATION; HUMAN; KINETICS; LIVER MICROSOME; MALE; PRIORITY JOURNAL;

ATRA;

EID: 0034629096     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.275.10.6908     Document Type: Article

References (50)

1. Heyman, R. A., Mangelsdorf, D. J., Dyck, J. A., Stein, R. B., Eichele, G., Evans, R. M., and Thaller, C. (1992) Cell 68, 397-406
2. Levin, A. A. (1992) Nature 355, 359-361
3. Kraft, J. C., Schuh, T., Juchau, M., and Kimelman, D. (1994) Proc. Natl. Acad. Sci. U. S. A. 91, 3067-3071
4. Pijnappel, W. W. M., Hendriks, H. F. J., Folkers, G. E., van den Brink, C. E., Dekker, E. J., Edelsenbosch, C., van der Saag, P. T., and Durston, A. J. (1993) Nature 366, 340-344
5. White, J. A., Guo, Y.-D., Baetz, K., Beckett-Jones, B., Bonasoro, J., Hsu, K. E., Dilworth, F. J., Jones, G., and Petkovich, M. (1996) J. Biol. Chem. 271, 29922-29927
6. Fujii, H., Takashi, S., Kaneko, S., Gotoh, O., Fujii-Kuriyama, Y., Osawa, K., Kato, S., and Hamada, H. (1997) EMBO J. 16, 4163-4173
7. White, J. A., Beckett Jones, B., Guo, Y.-D., Dilworth, F. J., Bonasoro, J., Jones, G., and Petkovich, M. (1997) J. Biol. Chem. 272, 18538-18541
8. Ray, W., Bain, G., Yao, M., and Gottleib, D. I. (1997) J. Biol. Chem. 272, 18702-18708
9. Abu-Abed, S. S., Beckett, B. R., Chiba, H., Chithalen, J. V., Jones, G., Metzger, D., Chambon, P., and Petkovich, M. (1998) J. Biol. Chem. 273, 2409-2415
10. Zile, M. H., Schnoes, H. K., and DeLuca, H. F. (1980) Proc. Natl. Acad. Sci. U. S. A. 77, 3230-3233
11. Zile, M. H., Inborn, R. C., and DeLuca, H. F. (1982) J. Biol. Chem. 257, 3537-3543
12. Blaner, W. S., and Olson, J. A. (1994) in The Retinoids: Biology, Chemistry, and Medicine (Sporn, M. B., Roberts, A. B., and Goodman, D. S., eds) 2nd Ed., pp. 229-255, Raven Press, New York
13. Chambon, P. (1994) Semin. Cell Biol. 5, 115-125
14. Mangelsdorf, D. J., Umesono, K., and Evans, R. M. (1994) in The Retinoids (Sporn, M. B., Roberts, A. B., and Goodman, D. S., eds) pp. 319-350, Raven Press, New York
15. Muindi, J. R. F., Frankel, S. R., Huselton, C., DeGrazia, F., Garland, W. A., Young, C. W., and Warrell, R. P. (1992) Cancer Res. 52, 2138-2142
16. Braakhuis, B. J. M., Klaassen, I., vander Leede, B. M., Cloos, J., Brakenhoff, R. H., Copper, M. P., Teerlink, T., Hendriks, H. F. J., van der Saag, P. T., and Snow, G. B. (1997) Br. J. Cancer 76, 189-197
17. van der Leede, B. M., van den Brink, C. E., Pijnappel, W. W. M., Sonneveld, E., van der Saag, P. T., and van der Burg, B. (1997) J. Biol. Chem. 272, 17921-17928
18. Carter, C. A., Pogribny, M., Davidson, A., Jackson, C. D., McGarrity, L. J., and Morris, S. M. (1996) Anticancer Res. 16, 1996
19. Janick-Bruckner, D., Barua, A. B., and Olson, J. A. (1991) FASEB J. 5, 320-325
20. Roberts, A. B., Nichols, M. B., Newton, S. L., and Sporn, M. B. (1979) J. Biol. Chem. 254, 6296-6302
21. Abbot, F. V., and Palmour, R. M. (1988) Life Sci. 43, 1685-1695
22. Oelberg, D. G., Chari, M. V., Little, J. M., Adcock, E. W., and Lester, R. (1984) J. Clin. Invest. 73, 1507-1514
23. Vore, M., Hadd, H., and Slikker, W., Jr. (1983) Life. Sci. 32, 2989-2993
24. Vore, M., and Slikker, W. (1985) Trends Pharmacol. Sci. 6, 256-259
25. Bock, K. W. (1992) Trends Pharmacol. Sci. 13, 223-226
26. Ritter, J. K., Sheen, Y. Y., and Owens, I. S. (1990) J. Biol. Chem. 265, 7900-7906
27. Chen, F., Ritter, J. K., Wang, M. G., McBride, O. W., Lubet, R. A., and Owens, I. S. (1993) Biochemistry 32, 10648-10657
28. Coffman, B. L., Rios, G. R., King, C. D., and Tephly, T. R. (1997) Drug Metab. Disp. 25, 1-4
29. Coffman, B. L., King, C. D., Rios, G. R., and Tephly, T. R. (1998) Drug Metab. Disp. 26, 73-77
30. Gall, W. E., Zawada, G., Mojarrabi, B., Tephly, T. R., Green, M. D., Coffman, B. L., Mackenzie, P. I., and Radominska-Pandya, A. (1999) J. Steroid Biochem. Mol. Biol. 70, 101-108
31. Wertz, P. W., Kensler, T. W., Mueller, G. C., Verma, A. K., and Boutwell, R. K. (1979) Nature 277, 227-229
32. Vogel, A. I. (1972) A Test-Book of Practical Organic Chemistry, 3rd Ed., p. 810, Longman Group Limited, London
33. Samokyszyn, V. M., Chen, T., Maddipati, K. R., Franz, T. J., Lehman, P. A., and Lloyd, R. V. (1995) Chem. Res. Toxicol. 8, 807-815
34. Mojarrabi, B., Butler, R., and Mackenzie, P. I. (1996) Biochem. Biophys. Res. Commun. 225, 785-790
35. Battaglia, E., Pritchard, M., Ouzzine, M., Fournel-Gigleux, S., Radominska, A., Siest, G., and Magdalou, J. (1994) Arch. Biochem. Biophys. 309, 266-272
36. Radominska-Pyrek, A., Zimniak, P., Chari, M., Golunski, E., Lester, R., and Pyrek, J. S. (1986) J. Lipid Res. 27, 89-101
37. Chambon, P. (1996) FASEB J. 10, 940-954
38. Samokyszyn, V. M., Sloane, B. G., Honn, K. V., and Marnett, L. J. (1984) Biochem. Biophys. Res. Commun. 124, 430-436
39. Samokyszyn, V. M., and Marnett, L. J. (1987) J. Biol. Chem. 262, 14119-14133
40. Fiorella, P. D., Giguere, V., and Napoli, J. L. (1993) J. Biol. Chem. 268, 21545-21552
41. McCormick, A. M., Napoli, J. L., Schnoes, H. K., and DeLuca, H. F. (1978) Biochemistry 17, 4085-4090
42. McCormick, A. M., Napoli, J. L., Yoshizawa, S., and DeLuca, H. F. (1980) Biochem. J. 186, 4085-4090
43. McCormick, A. M., and Napoli, J. L. (1982) J. Biol. Chem. 257, 1730-1735
44. John, K. V., Lakshmanan, M. R., and Cama, H. R. (1967) Biochem J. 103, 539-543
45. Verma, A., Slaga, T., Wertz, P., Mueller, G., and Boutwell, R. (1980) Cancer Res. 40, 2367-2371
46. Kensler, T. W., and Trush, M. A. (1981) Cancer Res. 41, 216-222
47. Sietsema, W. K., and DeLuca, H. F. (1982) J. Biol. Chem. 257, 4265-4270
48. Freyaldenhoven, M. A., Lloyd, R. V., and Samokyszyn, V. M. (1996) Chem. Res. Toxicol. 9, 677-681
49. Samokyszyn, V. M., Freyaldenhoven, M. A., Chang, H. C., Freeman, J. P., and Compadre, R. L. (1997) Chem. Res. Toxicol 10, 795-801
50. Freyaldenhoven, M. A., Lehman, P. A., Franz, T. J., Lloyd, R. V., and Samokyszyn, V. M. (1998) Chem. Res. Toxicol. 11, 102-110