Characterization of UDP-glucuronosyltransferases active on steroid hormones

Journal of Steroid Biochemistry and Molecular Biology

Volumn 69, Issue 1-6, 1999, Pages 413-423

  Hum, Dean W ^a   Bélanger, Alain ^a   Lévesque, Éric ^a   Barbier, Olivier ^a   Beaulieu, Martin ^a   Albert, Caroline ^a   Vallée, Michel ^a   Guillemette, Chantal ^a   Tchernof, André ^a   Turgeon, David ^a   Dubois, Stéphanie ^a  

^a LAVAL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BOLDENONE; GLUCURONOSYLTRANSFERASE;

AMINO ACID SEQUENCE; ANIMAL MODEL; CONFERENCE PAPER; ENZYME ACTIVITY; ENZYME BLOOD LEVEL; GENE EXPRESSION; GLUCURONIDATION; HORMONE METABOLISM; HORMONE RESPONSE; MONKEY; NONHUMAN; PROMOTER REGION; PROSTATE; PROTEIN LOCALIZATION; STEROID METABOLISM; TISSUE DISTRIBUTION; TISSUE SPECIFICITY;

ANIMALS; DIHYDROTESTOSTERONE; GLUCURONOSYLTRANSFERASE; HUMANS;

EID: 0345643392     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(99)00061-8     Document Type: Conference Paper

References (73)

1. Dutton G.J. Glucuronidation of Drugs and Other Compounds. 1980;CRC Press, Boca Raton, Fla.
2. Tephly T.R., Burchell B. UDP-glucuronosyltransferases: a family of detoxifying enzymes. Trends Pharmac. Sci. 11:(7):1990;276-279.
3. Burchell B., Coughtrie M.W. UDP-glucuronosyltransferases. Pharmac. Ther. 43:(2):1989;261-289.
4. Mulder G.J. Glucuronidation and its role in regulation of biological activity of drugs. Annu. Rev. Pharmac. Tox. 32:1992;25-49.
5. Burchell B., Coughtrie M.W.H., Jansen P.L.M. Function and regulation of UDP-glucuronosyltransferase genes in health and liver disease: report of the Seventh International Workshop on Glucuronidation, September 1993, Pitlochry, Scotland. Hepatology. 20:(6):1994;1622-1630.
6. Clarke D.J., Burchell B. The uridine diphosphate glucuronosyltransferase multigene family: function and regulation. Frederic C.K.F.C. Handbook of Experimental Pharmacology. vol. 112:1994;3-43.
7. Mackenzie P.I., Owens I.S., Burchell B., Bock K.W., Bock K.W., Bairoch A., Bélanger A., Gigleux S.F., Green M., Hum D.W., Chowdhury J.R., Ritter J.K., Schachter H., Tephly T.R., Tipton K.F., Nebert D.W. The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics. 7:1997;255-269.
8. Owens I.S., Ritter J.K. Gene structure at the human UGT1 locus creates diversity in isozymes structure, substrate specificity, and regulation. Prog. Nucleic Acids Res. 51:1995;306-338.
9. Emi Y., Ikushiro S., Iyanagi T. Drug-responsive and tissue-specific alternative expression of multiple first exons in rat UDP-glucuronosyltransferase family 1 (UGT1) gene complex. J. Biochem. Tokyo. 117:(2):1995;392-399.
10. Owens I.S., Ritter J.K. The novel bilirubin/phenol UDP-glucuronosyltransferase UGT1 gene locus: implications for multiple nonhemolytic familial hyperbilirubinemia phenotypes. Pharmacogenetics. 2:(3):1992;93-108.
11. Ritter J.K., Chen F., Sheen Y.Y., Tran H.M., Kimura S., Yeatman M.T., Owens I.S. A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini. J. Biol. Chem. 267:(5):1992;3257-3261.
12. Ritter J.K., Yeatman R.T., Femera P., Owens I.S. Identification of a genetic alteration in the code for bilirubin UDP-glucuronosyltransferase in the UGT1 gene complex of a Crigler-Najjar type 1 patients. J. Clin. Invest. 9:1992;150-155.
13. Ritter J.K., Yeatman M.T., Kaiser C., Gridelli B., Owens I.S. A phenylalanine codon deletion at the UGT1 gene complex locus of a Crigler-Najjar type I patient generates a pH-sensitive bilirubin UDP-glucuronosyltransferase. J. Biol. Chem. 268:(31):1993;23573-23579.
14. J.K. Ritter, Y.Y. Sheen, F. Chen, H.M. Tran, I.S. Owens, Two human liver bilirubin UDP-glucuronosyltransferases with identical C-termini result from 5′ alternative splicing, FASEB J (1991) A1173 (Abstr.).
15. Ebner T., Burchell B. Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family. Drug. Metab. Dispos. 21:(1):1993;50-55.
16. Senafi S.B., Clarke D.J., Burchell B. 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. 303:1994;233-240.
17. King C.D., Green M.D., Rios G.R., Coffman B.L., Owens I.S., Bishop W.P., Tephly T.R. The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1. Arch. Biochem. Biophys. 332:1996;92-100.
18. Green M.D., Tephly T.R. Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug. Metab. Disp. 24:1996;356-363.
19. Mojarrabi B., Butler R., Mackenzie P.I. cDNA cloning and characterization of the human UDP-glucuronosyltransferase, UGT1A3. Biochem. Biophys. Res. Commun. 225:1996;785-790.
20. Strassburg C., Manns M.P., Tukey R.H. Expression of the UDP-glucuronosyltransferase 1A locus in human colon. J. Biol. Chem. 273:1998;8719-8726.
21. Lazard D., Zupko K., Poria Y., Nef P., Lazarovits J., Horn S., Khen M., Lancet D. Odorant signal termination by olfactory UDP glucuronosyl transferase. Nature. 349:1991;790-793.
22. Chung L.W., Coffey D.S. Androgen glucuronide: Difference in its formation by human normal and benign hyperplastic prostates. Invest. Urol. 15:1978;385-388.
23. Adams J., Phillips N., Young C. Formation of glucuronides of estradiol-17 beta by human mammary cancer cells. J. Steroid Biochem. 33:1989;1023-1025.
24. Bélanger A., Couture J., Caron S., Roy R. Determination of non-conjugated and conjugated steroid levels in plasma and prostate after separation on C-18 columns. Ann. N.Y. Acad. Sci. 595:1990;251-259.
25. Bélanger A., Caron S., Labrie F., Naldoni C., Dogliotti L., Angeli A. Levels of eighteen non-conjugated and conjugated steroids in human breast cyst fluid: relationships with cyst type. Eur. J. Cancer. 26:1990;277-281.
26. Prevost J., Brochu M., Belanger A., Lambert R. Conjugated and unconjugated C-21, C-19 and C-18 steroid concentrations in human follicular fluid from hyperstimulated follicles. Gynecol. Endocr. 1:1987;331-338.
27. Bélanger G., Beaulieu M., Lévesque E., Hum D.W., Bélanger A. Expression and characterization of a novel UDP-Glucuronosyltransferase, UGT2B9, from cynomulgus monkey. DNA Cell Biol. 16:1997;1195-1205.
28. Bélanger G., Beaulieu M., Marcotte B., Lévesque É, Guillemette C., Hum D.W., Bélanger A. Expression of transcripts encoding steroid UDP-glucuronosyltransferases in human prostate hyperplastic tissue and the LNCaP cell line. Molec. Cell. Endocr. 113:1995;165-173.
29. Beaulieu M., Lévesque É, Hum D.W., Bélanger A. Isolation and characterization of a novel cDNA encoding a human UDP-glucuronosyltransferase active on C19 steroids. J. Biol. Chem. 271:1996;22855-22862.
30. Beaulieu M., Lévesque É, Barbier O., Turgeon D., Bélanger G., Hum D.W., Bélanger A. Isolation and characterization of a simian UDP-glucuronosyltransferase UGT2B18 active on 3-hydroxyandrogens. J. Molec. Biol. 275:1998;785-794.
31. Lévesque É, Beaulieu M., Green M.D., Tephly T.R., Bélanger A., Hum D.W. Isolation and characterization of UGT2B15(Y85): A UDP-glucuronosyltransferase encoded by a polymorphic gene. Pharmacogenetics. 7:1997;317-325.
32. Guillemette C., Lévesque É, Beaulieu M., Turgeon D., Hum W.D., Bélanger A. Differential regulation of two UDP-glucuronosyltransferases, UGT2B15 and UGT2B17, in human prostate LNCaP cells. Endocrinology. 138:1997;2998-3005.
33. Guillemette C., Hum D.W., Bélanger A. Regulation of steroid glucuronosyltransferase activities and transcripts by androgen in the human prostatic cancer LNCaP cell line. Endocrinology. 137:1995;2872-2879.
34. Bélanger A., Hum D.W., Beaulieu M., Lévesque É, Guillemette C., Tchernof A., Bélanger G., Turgeon D., Dubois S. Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues. J. Steroid Biochem. Molec. Biol. 65:1998;301-310.
35. Bélanger A., Brochu M., Lacoste D., Noel C., Labrie F., Dupont A., Cusan L., Caron S., Couture J. Steroid glucuronides: human circulatory levels and formation by LNCaP cells. J. Steroid Biochem. Molec. Biol. 40:1991;593-598.
36. Labrie F., Bélanger A., Cusan L., Gomez J., Candas B. Marked decline in serum concentrations of adrenal C19 sex steroid precursors and conjugated androgen metabolites during aging. J. Clin. Endocr. Metab. 82:1997;2396-2402.
37. Ritter J.K., Crawford J.M., Owens I.S. Cloning of two human liver bilirubin UDP-glucuronosyltransferases cDNAs with expression in COS-1 cells. J. Biol. Chem. 266:1991;1043-1047.
38. Harding D., Fournel-Gigleux S., Jackson M.R., Burchell B. Cloning and substrate specificity of a human phenol UDP- glucuronosyltransferase expressed in COS-7 cells. Proc. Natl. Acad. Sci. USA. 85:1988;8381-8385.
39. Strassburg C.P., Oldhafer K., Manns M.P., Tukey R.H. Differential expression of the UGT1A locus in human liver, biliary, and gastric tissue: identification of UGT1A7 and UGT1A10 transcripts in extrahepatic tissue. Molec. Pharmacol. 52:1997;212-220.
40. Wooster R., Sutherland L., Ebner T., Clarke D., Da Cruz e Silva O., Burchell B. Cloning and stable expression of a new member of the human liver phenol/bilirubin: UDP-glucuronosyltransferase cDNA family. Biochem. J. 278:1991;465-469.
41. Mojarrabi B., Mackenzie P.I. The human UDP glucuronosyltransferase, UGT1A10, glucuronidates mycophenolic acid. Biochem. Biophys. Res. Commun. 238:1997;775-778.
42. Chen F., Ritter J.K., Wang mG, Mcbride O.W., Lubet R.A., Owens I.S. Characterization of cloned human dihydrotestosterone/androstanediol UDP-glucuronosyltransferase and its comparison to other steroid isoforms. Biochemistry. 32:1993;10648-10657.
43. Guillemette C., Hum D.W., Belanger A. Evidence for a role of glucuronosyltransferase in the regulation of androgen action in the human prostatic cancer cell line LNCaP. J. Steroid Biochem. Molec. Biol. 57:1996;225-231.
44. Guillemette C., Bélanger A. Glucuronosyltransferase activity in human cancer cell line LNCaP. Molec. Cell. Endocr. 107:1995;131-139.
45. Guillemette C., Hum D.W., Bélanger A. Specificity of glucuronosyltransferase activity in the human cancer cell line LNCaP, evidence for the presence of at least two UGT enzymes. J. Steroid Biochem. Molec. Biol. 55:1995;355-362.
46. Guillemette C., Bélanger A. Regulation of dihydrotestosterone levels by UDP-Glucuronosyltransferase activites in the LNCaP cell line. 12th International Symposium of the Journal of Steroid Biochemistry and Molecular Biology, Berlin, Germany. 1995.
47. Coffman B.L., King C.D., Rios G.R., Tephly T.R. The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab. Disp. 26:1998;73-77.
48. Jin C.J., Mackenzie P.I., Miners J.O. The regio and stereo-selectivity of C19 and C21 hydroxysteroid glucuronidation by UGT2B7 and UGT2B11. Archs Biochem. Biophys. 341:1997;207-211.
49. A. Techernof, É Lévesque, M. Beaulieu, P. Couture, J.P. Després, D.W. Hum, A. Bélanger, Expression of the androgen metabolizing enzyme UGT2B15 in adipose tissue and relative expression measurement using a competitive RT-PCR method, Clin. Endocr (in press).
50. Wilson J.D., Gloyna R.E., Siiteri P.K. Androgen metabolism in the hypertrophic prostate. J. Steroid Biochem. 6:1975;443-445.
51. Wilding G. The importance of steroid hormones in prostate cancer. Cancer Surg. 14:1992;113-130.
52. M. El-Alfy, V. Luu-The, X-F. Huang, L. Brger, F. Labrie, G. Pelletier, Localization of type 5 17β-hydroxysteroid dehydrogenase, 3β-hydroxsteoid dehydrogenase and androgen receptor in the human prostate by in situ hybridization and immunocytochemistry, Endocrinology (in press).
53. Lyall R., Zilberstein A., Gazit A., Gilon C., Levitzki A., Schlessinger J. Tyrphostins inhibit epidermal growth factor(EGF)-receptor tyrosine kinase activity in living cells and EGF-stimulated cell proliferation. J. Biol. Chem. 264:1989;14503-14509.
54. Gill G., Kawamoto T., Cochet C., Ad L., Sato G., Masui H., McLeod C., Mendelsohn J. Monoclonal anti-epidermal growth factor receptor antibodies which are inhibitors of epidermal growth factor binding and antagonists of epidermal growth factor-stimulated tyrosine protein kinase activity. J. Biol. Chem. 259:1984;7755-7760.
55. Henttu P., Vihko P. Growth factor regulation of gene expression in the human prostatic carcinoma cell line LNCaP. Cancer Res. 53:1993;1051-1058.
56. Culig Z., Hobisch A., Cronauer M., Radmayr C., Trapman J., Hittmair A., Bartsch G., Klocker H. Androgen receptor activation in prostatic tumor cell lines by insulin-like growth factor-I, keratinocyte growth factor, and epidermal growth factor. Cancer. Res. 54:1994;5474-5478.
57. Schuurmans A.L.G., Bolt J., Mulder E. Androgens stimulate both growth rate and epidermal growth factor receptor activity of the human prostate tumor cell LNCaP. Prostate. 12:1988;55-63.
58. Wilding G., Valverius E., Knabbe C., Gelmann E.P. Role of transforming growth factor a in human prostate cell growth. Prostate. 15:1989;1-12.
59. Connolly J.M., Rose D.P. Production of epidermal growth factor and transforming growth factor-alpha by the androgen-responsive LNCaP human prostate cancer cell line. Prostate. 16:1990;209-218.
60. Carruba G., Leake R.E., Rinaldi F., Chalmers D., Comito L., Sorci C., Pavone Macaluso M., Castagnetta L.A. Steroid-growth factor interaction in human prostate cancer. Steroids. 59:1994;412-420.
61. Gleave M., Hsieh J.T., Gao C., von Eschenbach A.C., Chung W.K. Acceleration of human prostate cancer growth in vivo by factors produced by prostate and bone fibroblasts. Cancer Res. 51:1991;3753-3761.
62. Nakamoto T., Chang C., Li A., Chodak G.W. Basic fibroblast growth factor in human prostate cancer cells. Cancer Res. 52:1992;571-577.
63. Zuck B., Goepfert C., Nedlin-Chittka A., Sohrt K., Voigt K.D., Knabbe C. Regulation of fibroblast growth factor-like protein(s) in the androgen-responsive human prostate carcinoma cell line LNCaP. J. Steroid Biochem. Molec. Biol. 41:1992;659-663.
64. Henttu P., Liao S.S., Vihko P. Androgens up-regulate the human prostate-specific antigen messenger ribonucleic acid (messenger RNA), but down-regulate the prostatic acid phosphatase messenger RNA in the LNCaP cell line. Endocrinology. 130:1992;766-772.
65. Lévesque É, Beaulieu M., Guillemette C., Hum D.W., Bélanger A. Effect of interleukins on UGT2B15 and UGT2B17 steroid uridine diphosphate-glucuronosyltransferase expression and activity in the LNCAP cell line. Endocrinology. 139:1998;2375-2381.
66. Beaulieu M., Lévesque É, Tchernof A., Beatty B., Bélanger A., Hum D.W. Chromosomal localization, structure and regulation of the UGT2B17 gene, encoding a steroid metabolizing enzyme. DNA Cell Biol. 16:1997;1143-1155.
67. Guillemette C., Hum D.W., Bélanger A. Levels of plasma C19 steroids and 5a-reduced C19 steroid glucuronides in primates, rodents, and domestic animals. Am. J. Physiol. 271:1996;E348-E353.
68. Labrie F. Intracrinology. Molec. Cell. Endocr. 78:1991;C113-C118.
69. Bélanger G., Barbier O., Hum D.W., Bélanger A. Molecular cloning, expression and characterization of a monkey steroid uridine-diphospho-glucuronosyltransferase, UGT2B19, that conjugates testosterone. Eur. J. Biochem. 260:1999;704-708.
70. Barbier O., Bélanger A., Hum D.W. Cloning and characterization of a simian UDP- glucoronosyltransferase enzyme UGT2B20, a novel C19 steroid conjugating protein. Biochem. J. 337:1999;567-574.
71. Green M., Oturu E.M., Tephly T.R. Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug Metab. Disp. 22:1994;799-805.
72. 458): A UDP-glucuronosyltransferase rncoded by a polymorphic gene with differential substrate specificity. 1998;. submitted.
73. Beaulieu M., Lévesque É, Hum D.W., Bélanger A. Isolation and characterization of a human orphan UDP-glucuronosyltransferase, UGT2B11. Biochem. Biophys. Res. Comm. 248:1998;44-50.