Structural basis of the multispecificity demonstrated by 17β-hydroxysteroid dehydrogenase types 1 and 5

Molecular and Cellular Endocrinology

Volumn 248, Issue 1-2, 2006, Pages 38-46

  Lin, S X ^a   Shi, R ^a   Qiu, W ^a   Azzi, A ^a   Zhu, D W ^a   Dabbagh, H Al ^a   Zhou, M ^a  

^a LAVAL UNIVERSITY   (Canada)

Author keywords

17 hydroxysteroid dehydrogenase types 1 and 5; AKR1C3; Aldo keto reductase; Alternative binding; Flexibility of binding site; Multi specificity of enzymes; Pseudo symmetry of C 19 steroids; Short chain dehydrogenase reductase

Indexed keywords

ESTRADIOL; TESTOSTERONE 17BETA DEHYDROGENASE; TESTOSTERONE 17BETA DEHYDROGENASE TYPE 1; TESTOSTERONE 17BETA DEHYDROGENASE TYPE 5; UNCLASSIFIED DRUG;

BINDING SITE; BIOSYNTHESIS; BREAST; CONFERENCE PAPER; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME STRUCTURE; HORMONE STRUCTURE; HORMONE SYNTHESIS; HUMAN; NONHUMAN; ORGAN DISTRIBUTION; OVARY; OXIDATION REDUCTION REACTION; PLACENTA; PRIORITY JOURNAL; PROTEIN EXPRESSION; STEROID METABOLISM; STEROIDOGENESIS;

17-HYDROXYSTEROID DEHYDROGENASES; 3-HYDROXYSTEROID DEHYDROGENASES; ESTRADIOL DEHYDROGENASES; HUMANS; HYDROXYPROSTAGLANDIN DEHYDROGENASES; PROTEIN CONFORMATION; STEROIDS; SUBSTRATE SPECIFICITY; TISSUE DISTRIBUTION;

EID: 33644973274     PISSN: 03037207     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mce.2005.11.035     Document Type: Conference Paper

References (45)

1. J.B. Adams Control of secretion and the function of C19-delta 5-steroids of the human adrenal gland Mol. Cell. Endocrinol. 41 1985 1 17
2. A. Azzi, P.H. Rehse, D.-W. Zhu, R.L. Campbell, F. Labrie, and S.-X. Lin Crystal structure of human estrogenic 17β-hydroxysteroid dehydrogenase complexed with 17β-estradiol Nat. Struct. Biol. 3 1996 665 668
3. R. Breton, D. Housset, C. Mazza, and J.C. Fontecilla-Camps The structure of a complex of human 17β-hydroxysteroid dehydrogenase with estradiol and NADP identifies two principal targets for the design of inhibitors Structure 4 1996 905 915
4. Chang, H.-J., Shi, R., Rehse, P., Lin, S.-X., 2003. Identifying Androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis. JBC Papers in Press. Published on October 21, 2003 as Manuscript M3 10446200. J. Biol. Chem. Paper version 2004 27 9 (4), 2689-2696.
5. C.C. Chin, J.B. Denser, and J.C. Warren Crystallization of human placental estradiol 17β-dehydrogenase J. Biol. Chem. 254 1976 3700 3705
6. Y. Deyashiki, K. Ohshima, M. Nakanishi, K. Sato, K. Matsuura, and A. Hara Molecular cloning and characterization of mouse estradiol 17beta-dehydrogenase (A-specific), a member of the aldoketoreductase family J. Biol. Chem. 270 1995 10461 10467
7. I. Dufort, P. Rheault, X.-F. Huang, P. Soucy, and V. Luu-The Characteristics of a highly labile human type 5 17β-hydroxysteroid dehydrogenase Endocrinology 140 1999 1 7
8. L.L. Engel, and E.V. Groman Human placental 17β-estradiol dehydrogenase: characterization and structural studies Recent Prog. Horm. Res. 30 1974 130 169
9. Gangloff, A., Shi, R., Nahoum, V., Lin, S.-X., 2002. Pseudo-symmetry of C19-steroids, alternative binding orientations, and multispecificity in human estrogenic 17β-hydroxysteroid dehydrogenase. FASEB J. express article 10. 1096/fj. 02-0397 fje. Published on line December 17, 2002. Paper version 2003: 17, 274-276.
10. D. Ghosh, V.Z. Pletnev, D.-W. Zhu, W.L. Duax, Z. Wawrzak, W. Pangborn, F. Labrie, and S.-X. Lin Structure of human estrogenic 17β-hydroxysteroid dehydrogenase at 2.20 Å resolution Structure 3 1995 503 513
11. Q. Han, L.C. Robert, A. Gangloff, Y.-W. Huang, and S.-X. Lin Dehydroepiandrosterone and Dihydrotestosterone recognition by human estrogenic 17β-hydroxysteroid dehydrogenase J. Biol. Chem. 275 2000 1105 1111
12. S.S. Hoog, J.E. Pawlowski, P.M. Alzari, T.M. Penning, and M. Lewis Three-dimensional structure of rat liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase: a member of the aldo-keto reductase superfamily Proc. Natl. Acad. Sci. U.S.A. 91 1994 2517 2521
13. L.Y. Hsu, and C.E. Nordman Phase transition and crystal structure of the 37 degrees C form of cholesterol Science 220 4597 1983 604 606
14. L.Y. Hsu, J.W. Kampf, and C.E. Nordman Structure and pseudosymmetry of cholesterol at 310 K Acta Crystallogr. B 58 Pt 2 2002 260 264
15. J.-Z. Jin, and S.-X. Lin Human estrogenic 17β-hydroxysteroid dehydrogenase: predominance of estrogen reduction and its induction by NADPH Biochem. Biophys. Res. Commun. 259 1999 489 493
16. H.J. Karavolas, M.L. Baedecker, and L.L. Engel Human placental 17β-dehydrogenase: V: purification and partial characterization of the diphosphopyridine nucleotide (triphosphopyridine nucleotide)-linked enzyme J. Biol. Chem. 245 1970 4948 4952
17. M. Khanna, K.-N. Qin, R.W. Wan, and K.-C. Cheng Substrate specificity, gene structure, and tissue specific distribution of multiple human 3α-hydroxysteroid dehydrogenase J. Biol. Chem. 270 1995 20162 20168
18. Labrie, F., Dupont, A., Belanger, A, 1985. Complete androgen blockade for the treatment of the prostate cancer. In: Lippincott, J.B. (Ed.), Important Advances in Oncology, pp. 193-217.
19. F. Labrie, V. Luu-The, C. Labrie, A. Bélanger, J. Simard, S.-X. Lin, and G. Pelletier Endocrine and intracrine sources of androgens in women: inhibition of breast cancer and other roles of androgens and their precursor dehydroepiandrosterone Endocr. Rev. 24 2 2003 152 182
20. F. Labrie, V. Luu-The, S.-X. Lin, J. Simard, and C. Labrie Role of 17β-hydroxysteroid dehydrogenases in sex steroid formation in peripheral intracrine tissues Trends Endocrinol. Metab. 11 10 2000 421 427
21. H.-K. Lin, J.M. Jez, B.B. Schlegel, D.M. Peehl, J.A. Pachter, and T.M. Penning Expression and characterization of recombinant type 2 3α-hydroxysteroid dehydrogenases (HSD) from human prostate: demonstration of bifunctional 3α/17β-HSD activity and cellular distribution Mol. Endocrinol. 11 1997 1971 1984
22. Lin, S.-X., Shi, R., Qiu, W., Chang, H.-J., Nahoum, V., Rehse, P., Zhu, D.-W., Zhou, M., 2003. Structural variety of steroid-metabolizing enzymes. In: Proceeding of the 85th Annual Meeting of the Endocrine Society. June 19-22, Philadelphia, p. 518.
23. A.L. Lovering, J.P. Ride, C.M. Bunce, J.C. Desmond, S.M. Cummings, and S.A. White Crystal structures of prostaglandin D2 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin Cancer Res. 64 2004 1802 1810
24. V. Luu-The, C. Labrie, H.F. Zhao, J. Couet, Y. Lachance, J. Simard, G. Leblanc, J. Côté, D. Bérubé, R. Gagné, and F. Labrie Characterization of cDNAs for human estradiol 17β-dehydrogenase and assignment of the gene to chromosome 17: evidence for the two mRNA species with distinct 5′ termini in human placenta Mol. Endocrinol. 3 1989 1301 1309
25. G. Mendoza-Hernandez, M. Calcagno, H.R. Sanchez-Nuncio, and J.C. Diaz-zagoya Dehydroepiandrosterone is a substrate for estradiol 17β-dehydrogenase from human placenta Biochem. Biophys. Res. Commun. 119 1984 83 87
26. R. Mindnich, G. Möller, and J. Adamski The role of 17β-hydroxysteroid dehydrogenases Mol. Cell. Endocrinol. 218 2004 7 20
27. G.L. Murdock, C.C. Chin, and J.C. Warren Human placental estradiol 17β-hydroxysteroid dehydrogenases: sequence of a histidine-bearing peptide in the catalytic region Biochemistry 25 1986 567 572
28. Nahoum, V., Gangloff, A., Shi, R., Lin, S.-X. 2003. How estrogen-specific proteins discriminate estrogens from androgens: a common steroid-binding site architecture. FASEB J. express article 10. 1096/fj.02-0524fje. Published online May 20, Paper version 1003: 17, 1334-1336.
29. U. Oppermann, C. Filling, M. Hult, N. Shafqat, X. Wu, M. Lindh, J. Shafqat, E. Nordling, Y. Kallberg, B. Persson, and H. Jorvall Short-chain dehydrogenase/reductase (SDR): the 2002 update Chem. Biol. Interact. 143-144 2003 247 253
30. H. Peltoketo, V. Luu-The, J. Simard, and J. Adamski 17β- Hydroxysteroid dehydrogenase (HSD)/17-ketosteroid reductase (KSR) family; nomenclature and main characteristics of the 17HSD/KSR enzymes J. Mol. Endocrinol. 23 1999 1 11
31. T.M. Penning, M.E. Burezynski, J.M. Jez, C.F. Hung, H.-K. Lin, H. Ma, M. Moore, N. Palackal, and K. Ratnam Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones Biochem. J. 351 2000 67 77
32. T.M. Penning, M.E. Burczynski, J.M. Jez, H.-K. Lin, H. Ma, M. Moore, K. Ratnam, and N. Palackal Structure-function and inhibitor design of type 5 17-b-hydroxysteroid dehydrogenase (AKR1C3) Mol. Cell. Endocrinol. 171 2001 137 149
33. R. Poulin, D. Baker, and F. Labrie Androgens inhibit basal and estrogen-induced cell proliferation in the ZR-75-1 human breast cancer cell line Breast Cancer Res. Treat. 12 1988 213 225
34. R. Poulin, D. Poirier, Y. Merand, C. Thériault, A. Bélanger, and F. Labrie Extensive esterification of adrenal C-19-delta5-sex ateroids to long-chain fatty acids in the ZR-75-1 human breast cancer cell line J. Biol. Chem. 264 1989 9335 9343
35. T. Puranen, M. Poutanen, H. Ghosh, R. Vihko, and P. Vihko Origin of substrate specificity of human and rat 17 beta-hydroxysteroid dehydrogenase type 1, using chimeric enzymes and site-directed substitutions Endocronology 138 1997 3532 3539
36. W. Qiu, R.L. Campbell, A. Gangloff, P. Dupuis, P. Boivin, M.R. Tremblay, D. Poirier, and S.-X. Lin A concerted, rational design of 17β- hydroxysteroid dehydrogenase inhibitors: complex structure with estradiol-adenosine hybrids with high affinity FASEB J. 16 2002 1829 1831
37. W. Qiu, M. Zhou, F. Labrie, and S.-X. Lin Crystal structures of the multispecific 17beta-hydroxysteroid dehydrogenase type 5: critical androgen regulation in human peripheral tissues Mol. Endocrinol. 18 2004 1798 1807
38. + Proc. Natl. Acad. Sci. U.S.A. 96 1999 840 845
39. R. Shi, and S.-X. Lin Cofactor hydrogen bonding onto the protein main chain is conserved in the short-chain dehydrogenase/reductase family and contributes to nicotinamide orientation J. Biol. Chem. 271 2004 16778 16785
40. Steckelbroeck, S., Jin, Y., Gopishetty, S., Oyesanmi, B., Penning, T.M., 2003. Human cytosolic 3α-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3β-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action. J. Biol. Chem., doi:10.1074/jbc.M313308200 paper version 2004: 279, 10784-10795.
41. R.C. Strickler, B. Tobias, and D.F. Covey Human placental 17 beta-estradiol dehydrogenase and 20 alpha-hydroxysteroid dehydrogenase. Two activities at a single enzyme active site J. Biol. Chem. 256 1 1981 316 321
42. Zhang, Y. Dufort, I., Soucy, P., Labrie, F., Luu-The, V., 1995. Cloning and expression of human type 5 17beta-hydroxysteroid dehydrogenase. In: Proceedings of the Abstracts of papers presented at the 77th Annual Meeting of the Endocrine Society, June 14-17, Washington, DC, p. 62.
43. B.S. Zhorov, and S.-X. Lin Monte Carlo-minimized energy profile of estradiol in the ligand-binding tunnel of 17β-hydroxysteroid dehydrogenase: atomic mechanisms of steroid recognition Proteins 38 4 2000 414 427
44. M. Zhou, W. Qiu, H.J. Chang, A. Gangloff, and S.-X. Lin Purification, crystallization and preliminary X-ray diffraction results of human 17beta-hydroxysteroid dehydrogenase type 5 Acta Crystallogr. D58 2002 1048 1050
45. + J. Mol. Biol. 234 1993 242 244