Molecular endocrinology of hydroxysteroid dehydrogenases

Endocrine Reviews

Volumn 18, Issue 3, 1997, Pages 281-305

  Penning, Trevor M ^a,b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; HYDROXYSTEROID DEHYDROGENASE;

ANDROGEN SYNTHESIS; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME CONFORMATION; ENZYME INDUCTION; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; ESTROGEN SYNTHESIS; GENE EXPRESSION REGULATION; HUMAN; MOLECULAR CLONING; PRIORITY JOURNAL; PROGESTERONE SYNTHESIS; REVIEW; STRUCTURE ACTIVITY RELATION;

3-HYDROXYSTEROID DEHYDROGENASES; AMINO ACID SEQUENCE; ANIMALS; CLONING, MOLECULAR; DNA, COMPLEMENTARY; HUMANS; HYDROXYSTEROID DEHYDROGENASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; SEQUENCE HOMOLOGY, AMINO ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030925341     PISSN: 0163769X     EISSN: None     Source Type: Journal    
DOI: 10.1210/er.18.3.281     Document Type: Review

References (193)

1. Krozowski Z 1994 The short-chain alcohol dehydrogenase superfamily: variations on a common theme. J Steroid Biochem Mol Biol 51:125-130
2. Jornvall H, Persson B, Krook M, Atrian S, Gonzalez-Duarte R, Jeffery J, Ghosh D 1995 Short-chain dehydrogenases/reductases (SDR). Biochemistry 34:6003-6013
3. Pawlowski JE, Huizinga M, Penning TM 1991 Cloning and sequencing of the cDNA for rat liver 3α-hydroxysteroid/dihydrodiol dehydrogenase. J Biol Chem 266:8820-8825
4. Deyashiki Y, Ohshima K, Nakanishi M, Sato K, Matsuura K, Hara A 1995 Molecular cloning and characterization of mouse estradiol 17β-dehydrogenase (A-specific), a member of the aldoketoreductase family. J Biol Chem 270:10461-10467
5. Lacy WR, Washenick KJ, Cook RG, Dunbar BS 1993 Molecular cloning and expression of an abundant rabbit ovarian protein with 20α-hydroxysteroid dehydrogenase activity. Mol Endocrinol 7:58-66 [published erratum appears in Mol Endocrinol 7:1239, 1993]
6. Miura R, Shiota K, Noda K, Yagi S, Ogawa T, Takahashi M 1994 Molecular cloning of cDNA for rat ovarian 20α-hydroxysteroid dehydrogenase (HSD1). Biochem J 299:561-567
7. Penning TM, Ricigliano JW 1991 Mechanism based inhibition of hydroxysteroid dehydrogenases. J Enzym Inhib 5:165-198
8. Penning TM 1996 17β-Hydroxysteroid dehydrogenase: inhibitors and inhibitor design. Endocr Relat Cancer 3:41-56
9. The VL, Lachance Y, Labrie C, Leblanc G, Thomas JL, Strickler RC, Labrie F 1989 Full length cDNA structure and deduced amino acid sequence of human 3β-hydroxy-5-ene steroid dehydrogenase. Mol Endocrinol 3:1310-1312
10. 4/isomerase from placenta: expression in nonsteroidogenic cells of a protein that catalyzes the dehydrogenation/isomerization of C21 and C19 steroids. Endocrinology 126:2493-2498
11. 4-isomerase in human adrenals and gonads. Mol Endocrinol 5:1147-1157
12. Potts GO, Batzold FM, Snyder BW 1987 Endocrinology of trilostane and epostane. In: Furr BJA, Wakeling AE (eds) Pharmacology and Clinical Uses of Inhibitors of Hormone Secretion and Action. Baillière Tindall, London, pp 326-336
13. Crooij MJ, de Nooyer CC, Rao BR, Berends GT, Gooren LJ, Janssens J 1988 Termination of early pregnancy by the 3β-hydroxysteroid dehydrogenase inhibitor epostane. N Engl J Med 319:813-817
14. Thomas JL, Berko EA, Faustino A, Myers RP, Strickler RC 1988 Human placental 3β-hydroxy-5-ene-steroid dehydrogenase and steroid 5→4-ene-isomerase: purification from microsomes, substrate kinetics, and inhibition by product steroids. J Steroid Biochem 31:785-793
15. Labrie F, Simard J, Luu-The V, Pelletier G, Belghmi K, Belanger A 1994 Structure, regulation and role of 3β-hydroxysteroid dehydrogenase, 17β-hydroxysteroid dehydrogenase and aromatase enzymes in the formation of sex steroids in classical and peripheral intracrine tissues. Baillieres Clin Endocrinol Metab 8:451-474
16. 4 isomerase by site-directed mutagenesis and expression in HeLa cells. J Biol Chem 266:14842-14845
17. de Launoit Y, Zhao H, Belanger A, Labrie F, Simard J 1992 Expression of liver-specific member of the 3β-hydroxysteroid dehydrogenase family, an isoform possessing an almost exclusive 3-ketosteroid reductase activity. J Biol Chem 267:4513-4517
18. 4 isomerase (3β-HSD) family. The exclusive 3β-HSD gene expression in the skin. J Biol Chem 268:19659-19668
19. Payne AH, Clarke TR, Bain PA 1995 The murine 3β-hydroxysteroid dehydrogenase multigene family: structure, function and tissue-specific expression. J Steroid Biochem Mol Biol 53:111-118
20. 4 isomerase. FEBS Lett 259:153-157
21. 4 isomerase: structure and expression in steroidogenic and peripheral tissues in primate. Mol Cell Endocrinol 75:101-110
22. 4-isomerase expression and activity by adrenocorticotropin and corticosterone in the rat. Endocrinology 129:2077-2084
23. 4-isomerase expression by adrenocorticotropin in bovine adrenocortical cells. Endocrinology 128:139-145
24. Chedrese PJ, The VL, Labrie F, Juorio AV, Murphy BD 1990 Evidence for the regulation of 3β-hydroxysteroid dehydrogenase messenger RNA by human chorionic gonadotrophin in luteinized porcine granulosa cells. Endocrinology 126:2228-2230
25. Chedrese PJ, Zhang D, Luu The V, Labrie F, Juorio AV, Murphy BD 1990 Regulation of mRNA expression of 3β-hydroxy-5-ene steroid dehydrogenase in porcine granulosa cells in culture: a role for the protein kinase-C pathway. Mol Endocrinol 4:1532-1538
26. 4 isomerase gene and its expression in mammalian cells. J Biol Chem 265: 20469-20475
27. 4 isomerase (3β-HSD) gene: adrenal and gonadal specificity. DNA Cell Biol 10:701-711
28. Tremblay Y, Beaudoin C 1993 Regulation of 3β-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase messenger ribonucleic acid levels by cyclic adenosine 3′,5′-monophosphate and phorbol myristate acetate in human choriocarcinoma cells. Mol Endocrinol 7:355-364
29. Bird IM, Imaishi K, Pasquarette MM, Rainey WE, Mason JI 1996 Regulation of 3β-hydroxysteroid dehydrogenase expression in human adrenocortical H295R cells. J Endocrinol 150:S165-173
30. Guerin SL, Leclerc S, Verreault H, Labrie F, Luu-The V 1995 Overlapping cis-acting elements located in the first intron of the gene for type I 3β-hydroxysteroid dehydrogenase modulate its transcriptional activity. Mol Endocrinol 9:1583-1597
31. Rheaume E, Sanchez R, Simard J, Chang YT, Wang J, Pang S, Labrie F 1994 Molecular basis of congenital adrenal hyperplasia in two siblings with classical nonsalt-losing 3β-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab 79:1012-1018
32. Zerah M, Rheaume E, Mani P, Schram P, Simard J, Labrie F, New MI 1994 No evidence of mutations in the genes for type I and type II 3β-hydroxysteroid dehydrogenase (3β HSD) in nonclassical 3β HSD deficiency. J Clin Endocrinol Metab 79:1811-1817
33. Simard J, Rheaume E, Mebarki F, Sanchez R, New MI, Morel Y, Labrie F 1995 Molecular basis of human 3β-hydroxysteroid dehydrogenase deficiency. J Steroid Biochem Mol Biol 53:127-138
34. Rheaume E, Simard J, Morel Y, Mebarki F, Zachmann M, Forest MG, New MI, Labrie F 1992 Congenital adrenal hyperplasia due to point mutations in the type II 3β-hydroxysteroid dehydrogenase gene. Nat Genet 1:239-245
35. Simard J, Rheaume E, Sanchez R, Laflamme N, de Launoit Y, Luu-The V, van Seters AP, Gordon RD, Bettendorf M, Heinrich U, Moshang T, New MI, Labrie F 1993 Molecular basis of congenital adrenal hyperplasia due to 3β-hydroxysteroid dehydrogenase deficiency. Mol Endocrinol 7:716-728
36. Simard J, Rheaume E, Leblanc JF, Wallis SC, Joplin GF, Gilbey S, Allanson J, Mettler G, Bettendorf M, Heinrich U, Labrie F 1994 Congenital adrenal hyperplasia caused by a novel homozygous frameshift mutation 273ΔAA in type II 3β-hydroxysteroid dehydrogenase gene (HSD3B2) in three male patients of Afghan/Pakistani origin. Hum Mol Genet 3:327-330
37. Sanchez R, Rheaume E, Laflamme N, Rosenfield RL, Labrie F, Simard J 1994 Detection and functional characterization of the novel missense mutation Y254D in type II 3β-hydroxysteroid dehydrogenase (3β HSD) gene of a female patient with nonsalt-losing 3β HSD deficiency. J Clin Endocrinol Metab 78:561-567
38. Mebarki F, Sanchez R, Rheaume E, Laflamme N, Simard J, Forest MG, Bey-Omar F, David M, Labrie F, Morel Y 1995 Nonsalt-losing male pseudohermaphroditism due to the novel homozygous N100S mutation in the type II 3β-hydroxysteroid dehydrogenase gene. J Clin Endocrinol Metab 80:2127-2134
39. Rheaume E, Sanchez R, Mebarki F, Gagnon E, Carel JC, Chaussain JL, Morel Y, Labrie F, Simard J 1995 Identification and characterization of the G15D mutation found in a male patient with 3β-hydroxysteroid dehydrogenase (3β-HSD) deficiency: alteration of the putative NAD-binding domain of type II 3β-HSD. Biochemistry 34:2893-2900
40. Andersson S, Geissler WM, Patel S, Wu L 1995 The molecular biology of androgenic 17β-hydroxysteroid dehydrogenases. J Steroid Biochem Mol Biol 53:37-39
41. Jarabak J, Adams JA, Williams-Ashman HG, Talalay P 1962 Purification of a 17β-hydroxysteroid dehydrogenase of human placenta and studies on its transhydrogenase function. J Biol Chem 237:345-357
42. Jarabak J, Sack Jr GH 1969 A souble 17β-hydroxysteroid dehydrogenase from human placenta. The binding of pyridine nucleotides and steroids. Biochemistry 8:2203-2212
43. Adams EF, Coldham NG, James VH 1988 Steroidal regulation of oestradiol-17β dehydrogenase activity of the human breast cancer cell line MCF-7. J Endocrinol 118:149-154
44. Reed MJ, Singh A, Ghilchik MW, Coldham NG, Purohit A 1991 Regulation of oestradiol 17β-hydroxysteroid dehydrogenase in breast tissues: the role of growth factors. J Steroid Biochem Mol Biol 39:791-798
45. Peltoketo H, Isomaa V, Maentausta O, Vihko R 1988 Complete amino acid sequence of human placental 17β-hydroxysteroid dehydrogenase deduced from cDNA. FEBS Lett 239:73-77
46. The VL, Labrie C, Zhao HF, Couet J, Lachance Y, Simard J, Leblanc G, Cote J, Berube D, Gagne R, Labrie F 1989 Characterization of cDNAs for human estradiol 17β-dehydrogenase and assignment of the gene to chromosome 17: evidence of two mRNA species with distinct 5′-termini in human placenta. Mol Endocrinol 3:1301-1309
47. Gast MJ, Sims HF, Murdock GL, Gast PM, Strauss AW 1989 Isolation and sequencing of a complementary deoxyribonucleic acid clone encoding human placental 17β-estradiol dehydrogenase: identification of the putative cofactor binding site. Am J Obstet Gynecol 161:1726-1731
48. Poutanen M, Miettinen M, Vihko R 1993 Differential estrogen substrate specificities for transiently expressed human placental 17β-hydroxysteroid dehydrogenase and an endogenous enzyme expressed in cultured COS-m6 cells. Endocrinology 133:2639-2644
49. Puranen TJ, Poutanen MH, Peltoketo HE, Vihko PT, Vihko RK 1994 Site-directed mutagenesis of the putative active site of human 17β-hydroxysteroid dehydrogenase type 1. Biochem J 304:289-293
50. Breton R, Yang F, Jin JZ, Li B, Labrie F, Lin SX 1994 Human 17β-hydroxysteroid dehydrogenase: overproduction using a baculovirus expression system and characterization. J Steroid Biochem Mol Biol 50:275-282
51. Wu L, Einstein M, Geissler WM, Chan HK, Elliston KO, Andersson S 1993 Expression cloning and characterization of human 17β-hydroxysteroid dehydrogenase type 2, a microsomal enzyme possessing 20α-hydroxysteroid dehydrogenase activity. J Biol Chem 268:12964-12969
52. Geissler WM, Davis DL, Wu L, Bradshaw KD, Patel S, Mendonca BB, Elliston KO, Wilson JD, Russell DW, Andersson S 1994 Male pseudohermaphroditism caused by mutations of testicular 17β-hydroxysteroid dehydrogenase 3. Nat Genet 7:34-39
53. Andersson S 1995 17β-Hydroxysteroid dehydrogenase: isozymes and mutations. J Endocrinol 146:197-200
54. Adamski J, Normand T, Leenders F, Monte D, Begue A, Stehelin D, Jungblut PW, de Launoit Y 1995 Molecular cloning of a novel widely expressed human 80 kDa 17β-hydroxysteroid dehydrogenase IV. Biochem J 311:437-443
55. Leenders F, Tesdorpf J, Markus M, Engel T, Seedorf U, Adamski J 1996 Porcine 80-kDa protein reveals intrinsic 17β-hydroxysteroid dehydrogenase, fatty acyl-CoA-hydratase/dehydrogenase and sterol transfer activities. J Biol Chem 271:5438-5442
56. Carstensen JF, Tesdorpf JG, Kaufmann M, Markus MM, Husen B, Leenders F, Jakob F, de Launoit Y, Adamski J 1996 Characterization of 17β-hydroxysteroid dehydrogenase IV. J Endocrinol 150: S3-S12
57. Markus M, Husen B, Leenders F, Jungblut P, Hall P, Adamski J 1995 The organelles containing porcine 17β-estradiol dehydrogenase are peroxisomes. Eur J Cell Biol 68:263-267
58. Luu-The V, Labrie C, Simard J, Lachance Y, Zhao HF, Couet J, Leblanc G, Labrie F 1990 Structure of two in tandem human 17β-hydroxy steroid dehydrogenase genes. Mol Endocrinol 4:268-275
59. Fournet-Dulguerov N, MacLusky NJ, Leranth CZ, Todd R, Mendelson CR, Simpson ER, Naftolin F 1987 Immunohistochemical localization of aromatase cytochrome P-450 and estradiol dehydrogenase in the syncytiotrophoblast of the human placenta. J Clin Endocrinol Metab 65:757-764
60. Sawetawan C, Milewich L, Word RA, Carr BR, Rainey WE 1994 Compartmentalization of type I 17β-hydroxysteroid oxidoreductase in the human ovary. Mol Cell Endocrinol 99:161-168
61. Mäentausta O, Sormunen R, Isomaa V, Lehto VP, Jouppila P, Vihko R 1991 Immunohistochemical localization of 17β-hydroxysteroid dehydrogenase in the human endometrium during the menstrual cycle. Lab Invest 65:582-587
62. Pasqualini JR, Gelly C, Nguyen BL, Vella C 1989 Importance of estrogen sulfates in breast cancer. J Steroid Biochem 34:155-163
63. Tremblay Y, Ringler GE, Morel Y, Mohandas TK, Labrie F, Strauss III JF, Miller WL 1989 Regulation of the gene for estrogenic 17-ketosteroid reductase lying on chromosome 17cen - q25. J Biol Chem 264:20458-20462
64. Casey ML, MacDonald PC, Andersson S 1994 17β-Hydroxysteroid dehydrogenase type 2: chromosomal assignment and progestin regulation of gene expression in human endometrium. J Clin Invest 94:2135-2141
65. Labrie Y, Durocher F, Lachance Y, Turgeon C, Simard J, Labrie C, Labrie F 1995 The human type II 17β-hydroxysteroid dehydrogenase gene encodes two alternatively spliced mRNA species. DNA Cell Biol 14:849-861
66. Winqvist R, Peltoketo H, Isomaa V, Grzeschik KH, Mannermaa A, Vihko R 1990 The gene for 17β-hydroxysteroid dehydrogenase maps to human chromosome 17, bands q12-q21, and shows an RFLP with Sca I. Hum Genet 85:473-476
67. Peltoketo H, Isomaa V, Vihko R 1992 Genomic organization and DNA sequences of human 17β-hydroxysteroid dehydrogenase genes and flanking regions. Localization of multiple Alu sequences and putative cis-acting elements. Eur J Biochem 209:459-466
68. Saez JM, De Peretti E, Morera AM, David M, Bertrand J 1971 Familial male pseudohermaphroditism with gynecomastia due to a testicular 17-ketosteroid reductase defect. I. Studies in vivo. J Clin Endocrinol Metab 32:604-610
69. Forest M 1981 Inborn errors of testosterone biosynthesis. In: The Intersex Child: Pediatric Adolescent Endocrinology. Karger, Basel, vol 8:133-135
70. Peterson R, Imperato-McGinley J 1984 Male Pseudo-hermaphroditism due to Inherited Deficiencies of Testosterone Biosynthesis. Raven Press, New York, pp 301-319
71. Virdis R, Saenger P 1984 17β-Hydroxysteroid dehydrogenase deficiency. In: Adrenal Diseases in Childhood: Pediatric Adolescent Endocrinology. Karger, Basel, vol 13:110-124
72. Andersson S, Geissler WM, Wu L, Davis DL, Grumbach MM, New MI, Schwarz HP, Blethen SL, Mendonca BB, Bloise W, Witchel SF, Cutler Jr GB, Griffin JE, Wilson JD, Russel DW 1996 Molecular genetics and pathophysiology of 17β-hydroxysteroid dehydrogenase 3 deficiency. J Clin Endocrinol Metab 81:130-136
73. Funder JW, Pearce PT, Smith R, Smith AI 1988 Mineralocorticoid action: target tissue specificity is enzyme, not receptor, mediated. Science 242:583-585
74. Stewart PM, Whorwood CB 1994 11β-Hydroxysteroid dehydrogenase activity and corticosteroid hormone action. Steroids 59: 90-95
75. Krozowski ZS, Provencher PH, Smith RE, Obeyesekere VR, Mercer WR, Albiston AL 1994 Isozymes of 11β-hydroxysteroid dehydrogenase: which enzyme endows mineralocorticoid specificity? Steroids 59:116-120
76. Mune T, Rogerson FM, Nikkila H, Agarwal AK, White PC 1995 Human hypertension caused by mutations in the kidney isozyme of 11β-hydroxysteroid dehydrogenase. Nat Genet 10:394-399
77. Stewart PM, Wallace AM, Valentino R, Burt D, Shackleton CH, Edwards CR 1987 Mineralocorticoid activity of liquorice: 11β-hydroxysteroid dehydrogenase deficiency comes of age. Lancet 2:821-824
78. Monder C, Stewart PM, Lakshmi V, Valentino R, Burt D, Edwards CR 1989 Licorice inhibits corticosteroid 11β-dehydrogenase of rat kidney and liver: in vivo and in vitro studies. Endocrinology 125:1046-1053
79. Agarwal AK, Monder C, Eckstein B, White PC 1989 Cloning and expression of rat cDNA encoding corticosteroid 11β-dehydrogenase. J Biol Chem 264:18939-18943
80. Agarwal AK, Tusie-Luna MT, Monder C, White PC 1990 Expression of 11β-hydroxysteroid dehydrogenase using recombinant vaccinia virus. Mol Endocrinol 4:1827-1832
81. Rundle SE, Funder JW, Lakshmi V, Monder C 1989 The intrarenal localization of mineralocorticoid receptors and 11β-dehydrogenase: immunocytochemical studies. Endocrinology 125:1700-1704
82. Moore CD, Mellon SH, Murai J, Siiteri PT, Miller WL 1993 Structure and function of the hepatic form of 11β-hydroxysteroid dehydrogenase in the squirrel monkey, an animal model of glucocorticoid resistance. Endocrinology 133:368-375
83. Albiston A, Obeyesekere V, Smith R, Krozowski Z 1994 Cloning and tissue distribution of the human 11-HSD type 2 enzyme. Mol Cell Endocrinol 105:R11-R17
84. +-dependent isoform of 11β-hydroxysteroid dehydrogenase: cloning and characterization of cDNA from sheep kidney. J Biol Chem 269:25959-25962
85. Mercer WR, Krozowski ZS 1992 Localization of an 11β-hydroxysteroid dehydrogenase activity to the distal nephron. Evidence for the existence of two species of dehydrogenase in the rat kidney. Endocrinology 130:540-543
86. Krozowski TL, Stuchbery S, White P, Monder C, Funder JW 1990 Characterization of 11β-hydroxysteroid dehydrogenase gene expression: identification of multiple unique forms of messenger ribonucleic acid in the rat kidney. Endocrinology 127:3009-3013
87. Krozowski Z, Obeyesekere V, Smith R, Mercer W 1992 Tissue-specific expression of an 11β-hydroxysteroid dehydrogenase with a truncated N-terminal domain. A potential mechanism for differential intracellular localization within mineralocorticoid target cells. J Biol Chem 267:2569-2574
88. Monder C 1991 Corticosteroids, receptors, and the organ-specific functions of 11β-hydroxysteroid dehydrogenase. FASEB J 5:3047-3054
89. Castello R, Schwarting R, Muller C, Hierholzer K 1989 Immunohistochemical localization of 11β-hydroxysteroid dehydrogenase in rat kidney with monoclonal antibody. Ren Physiol Biochem 12:320-327
90. Tannin GM, Agarwal AK, Monder C, New MI, White PC 1991 The human gene for 11β-hydroxysteroid dehydrogenase. Structure, tissue distribution, and chromosomal localization. J Biol Chem 266: 16653-16658
91. Agarwal AK, Rogerson FM, Mune T, White PC 1995 Gene structure and chromosomal localization of human HSD11K gene encoding the kidney (type 2) isozyme of 11β-hydroxysteroid dehydrogenase. Genomics 195-199
92. White PC, Obeid J, Agarwal AK, Tannin GM, Nikkila H 1994 Genetic analysis of 11β-hydroxysteroid dehydrogenase. Steroids 59:111-115
93. Wilson RC, Harbison MD, Krozowski ZS, Funder JW, Shackleton CH, Hanauske-Abel HM, Wei JQ, Hertecant J, Moran A, Neiberger RE, Balfe J, Fattah A, Daneman D, Licholai T, New MI 1995 Several homozygous mutations in the gene for 11β-hydroxysteroid dehydrogenase type 2 in patients with apparent mineralocorticoid excess. J Clin Endocrinol Metab 80:3145-3150
94. Wilson RC, Krozowski ZS, Li K, Obeyesekere VR, Razzaghy-Azar M, Harbison MD, Wei JQ, Shackleton CH, Funder JW, New MI 1995 A mutation in the HSD11B2 gene in a family with apparent mineralocorticoid excess. J Clin Endocrinol Metab 80:2263-2266
95. Obeyesekere V, Ferrari P, Andrews R, Wilson R, New M, Funder J, Krozowski Z 1995 The R337C mutation generates a high Km 11β-hydroxysteroid dehydrogenase type II enzyme in a family with apparent mineralocorticoid excess. J Clin Endocrinol Metab 80:3381-3383
96. +oxidoreductase of rat ventral prostate. Biochemistry 14:810-817
97. Jacobi GH, Moore RJ, Wilson JD 1977 Characterization of the 3α-hydroxysteroid dehydrogenase of dog prostate. J Steroid Biochem 8:719-723
98. Jacobi GH, Wilson JD 1976 The formation of 5α-androstane-3α,17β-diol by dog prostate. Endocrinology 99:602-610
99. Liao S, Liang T, Fang S, Castaneda E, Shao TC 1973 Steroid structure and androgenic activity. Specificities involved in the receptor binding and nuclear retention of various androgens. J Biol Chem 248:6154-6162
100. Jacobi GH, Moore RJ, Wilson JD 1978 Studies on the mechanism of 3α-androstanediol-induced growth of the dog prostate. Endocrinology 102:1748-1758
101. Isaacs JT 1983 Changes in dihydrotestosterone metabolism and the development of benign prostatic hyperplasia in the aging beagle. J Steroid Biochem 18:749-757
102. Majewska MD, Harrison NL, Schwartz RD, Barker JL, Paul SM 1986 Steroid hormone metabolites are barbiturate-like modulators of the GABA receptor. Science 232:1004-1007
103. A receptor. Mechanism of action and physiological significance. Prog Neurobiol 38:379-395
104. A receptor function. Trends Pharmacol Sci 16:295-303
105. Lambert J, Peters J, Sturgess N, Hales T 1990 Steroid Modulation of the GABAA Receptor Complex: Electrophysiological Studies. Ciba Foundation Symposium. Wiley, Chichester, U.K., vol 153: 56-82
106. Penning TM, Mukharji I, Barrows S, Talalay P 1984 Purification and properties of a 3α-hydroxysteroid dehydrogenase of rat liver cytosol and its inhibition by anti-inflammatory drugs. Biochem J 222:601-611
107. Smithgall TE, Penning TM 1988 Electrophoretic and immunochemical characterization of 3α-hydroxysteroid/dihydrodiol dehydrogenases of rat tissues. Biochem J 254:715-721
108. Pawlowski JE, Penning TM 1994 Overexpression and mutagenesis of the cDNA for rat liver 3α-hydroxysteroid/dihydrodiol dehydrogenase. Role of cysteines and tyrosines in catalysis. J Biol Chem 269:13502-13510
109. Cheng KC, White PC, Qin KN 1991 Molecular cloning and expression of rat liver 3α-hydroxysteroid dehydrogenase. Mol Endocrinol 5:823-828
110. Stolz A, Rahimi-Kiani M, Ameis D, Chan E, Ronk M, Shively JE 1991 Molecular structure of rat hepatic 3α-hydroxysteroid dehydrogenase. A member of the oxidoreductase gene family. J Biol Chem 266:15253-15257
111. Usui E, Okuda K, Kato Y, Noshiro M 1994 Rat hepatic 3α-hydroxysteroid dehydrogenase: expression of cDNA and physiological function in bile acid biosynthetic pathway. J Biochem (Tokyo) 115:230-237
112. Carper D, Nishimura C, Shinohara T, Dietzchold B, Wistow G, Craft C, Kador P, Kinoshita JH 1987 Aldose reductase and p-crystallin belong to the same protein superfamily as aldehyde reductase. FEBS Lett 220:209-213
113. Petrash JM, Favello AD 1989 Isolation and characterization of cDNA clones encoding aldose reductase. Curr Eye Res 8:1021-1027
114. Bohren KM, Bullock B, Wermuth B, Gabbay KH 1989 The aldo-keto reductase superfamily. cDNAs and deduced amino acid sequences of human aldehyde and aldose reductases. J Biol Chem 264:9547-9551
115. Chung S, LaMendola J 1989 Cloning and sequence determination of human placental aldose reductase gene. J Biol Chem 264:14775-14777
116. Watanabe K, Fujii Y, Nakayama K, Ohkubo H, Kuramitsu S, Kagamiyama H, Nakanishi S, Hayaishi O 1988 Structural similarity of bovine lung prostaglandin F synthase to lens e-crystallin of the European common frog. Proc Natl Acad Sci USA 85:11-15
117. Tomarev SI, Zinovieva RD, Dolgilevich SM, Luchin SV, Krayev AS, Skryabin KG, Gause Jr GG 1984 A novel type of crystallin in the frog eye lens. 35-kDa polypeptide is not homologous to any of the major classes of lens crystallins. FEBS Lett 171:297-302
118. Hara A, Taniguchi H, Nakayama T, Sawada H 1990 Purification and properties of multiple forms of dihydrodiol dehydrogenase from human liver. J Biochem (Tokyo) 108:250-254
119. Deyashiki Y, Ogasawara A, Nakayama T, Nakanishi M, Miyabe Y, Sato K, Hara A 1994 Molecular cloning of two human liver 3α-hydroxysteroid/dihydrodiol dehydrogenase isoenzymes that are identical with chiordecone reductase and bile-acid binder. Biochem J 299:545-552
120. Stolz A, Hammond L, Lou H, Takikawa H, Ronk M, Shively JE 1993 cDNA cloning and expression of the human hepatic bile acid-binding protein. A member of the monomeric reductase gene family. J Biol Chem 268:10448-10457
121. Khanna M, Qin KN, Wang RW, Cheng KC 1995 Substrate specificity, gene structure, and tissue-specific distribution of multiple human 3α-hydroxysteroid dehydrogenases. J Biol Chem 270:20162-20168
122. Lin H-K, Jez JM, Penning TM, Cloning of a human prostate cDNA with high sequence identity to rat liver 3α-hydroxy steroid/dihydrodiol dehydrogenase. Program of the International Symposium on DHEA Transformation into Androgens and Estrogens in Target Tissues: Intracrinology. Quebec City, Canada, 1995, Abstract 37
123. Dufort I, Soucy P, Labrie F, Luu-The V 1996 Molecular cloning of human type 3 3α-hydroxysteroid dehydrogenase that differs from 20α-hydroxysteroid dehydrogenase by seven amino acids. Biochem Biophys Res Commun 228:474-479
124. Hou YT, Xia W, Pawlowski JE, Penning TM 1994 Rat dihydrodiol dehydrogenase: complexity of gene structure and tissue-specific and sexually dimorphic gene expression. Cancer Res 54:247-255
125. Penning TM, Isaacson K, Lyttle CR 1992 Hormonal regulation of 3α-hydroxysteroid/dihydrodiol dehydrogenase in rat liver cytosol. Biochem Pharmacol 43:1148-1151
126. Mode A, Norstedt G, Simic B, Eneroth P, Gustafsson JA 1981 Continuous infusion of growth hormone feminizes hepatic steroid metabolism in the rat. Endocrinology 108:2103-2108
127. Mode A, Gustafsson JA, Jansson JO, Eden S, Isaksson O 1982 Association between plasma level of growth hormone and sex differentiation of hepatic steroid metabolism in the rat. Endocrinology 111:1692-1697
128. Zaphiropoulos PG, Mode A, Norstedt G, Gustafsson JA 1989 Regulation of sexual differentiation in drug and steroid metabolism. Trends Pharmacol Sci 10:149-153
129. Norstedt G, Wrange O, Gustafsson JA 1981 Multihormonal regulation of the estrogen receptor in rat liver. Endocrinology 108: 1190-1196
130. Lin HK, Penning TM 1995 Cloning, sequencing, and functional analysis of the 5′-flanking region of the rat 3α-hydroxysteroid/ dihydrodiol dehydrogenase gene. Cancer Res 55:4105-4113
131. Graham A, Brown L, Hedge PJ, Gammack AJ, Markham AF 1991 Structure of the human aldose reductase gene. J Biol Chem 266: 6872-6877
132. Lou H, Hammond L, Sharma V, Sparkes RS, Lusis AJ, Stolz A 1994 Genomic organization and chromosomal localization of a novel human hepatic dihydrodiol dehydrogenase with high affinity bile acid binding. J Biol Chem 269:8416-8422
133. Khanna M, Qin KN, Klisak I, Belkin S, Sparkes RS, Cheng KC 1995 Localization of multiple human dihydrodiol dehydrogenase (DDH1 and DDH2) and chlordecone reductase (CHDR) genes in chromosome 10 by the polymerase chain reaction and fluorescence in situ hybridization. Genomics 25:588-590
134. Atwater JA, Wisdom R, Verma IM 1990 Regulated mRNA stability. Annu Rev Genet 24:519-541
135. Peltz SW, Jacobson A 1992 mRNA stability: in trans-it. Curr Opin Cell Biol 4:979-983
136. Hou YT, Lin HK, Penning TM 1996 Dexamethasone regulation of the rat 3α-hydroxysteroid/dihydrodiol dihydrogenase (3α-HSD/ DD) gene. Proc Am Assoc Cancer Res 37:3596 (Abstract)
137. Tomkins G 1956 Enzymatic mechanisms of hormone metabolism 1. Oxidation and reduction of the steroid nucleus. Recent Prog Horm Res 12:125-133
138. Tomkins G 1956 A mammalian 3α-hydroxysteroid dehydrogenase. J Biol Chem 218:437-447
139. Weinstein BI, Gordon GG, Southren AL 1983 Potentiation of glucocorticoid activity by 5β-dihydrocortisol: its role in glaucoma. Science 222:172-173
140. Southren AL, l'Hommedieu D, Gordon GG, Weinstein BI 1987 Intraocular hypotensive effect of a topically applied cortisol metabolite: 3α, 5β-tetrahydrocortisol. Invest Ophthalmol Vis Sci 28: 901-903
141. Wiest WG, Wilcox RB 1961 Purification and properties of rat ovarian 20α-hydroxysteroid dehydrogenase. J Biol Chem 236:2425-2428
142. Wilcox RB, Wiest WG 1966 Further studies of rat ovarian 20α-hydroxysteroid dehydrogenase. Steroids 7:395-413
143. Mori M, Wiest WG 1979 Purification of rat ovary 20α-hydroxysteroid dehydrogenase by affinity chromatography. J Steroid Biochem 11:1443-1449
144. Strauss III JF, Stambaugh Jr RL 1974 Induction of 20α-hydroxysteroid dehydrogenase in rat corpora lutea of pregnancy by prostaglandin F-2α. Prostaglandins 5:73-85
145. Warren JC, Murdock GL, Ma Y, Goodman SR, Zimmer WE 1993 Molecular cloning of testicular 20α-hydroxysteroid dehydrogenase: identity with aldose reductase. Biochemistry 32:1401-1406
146. Tobias B, Covey DF, Strickler R 1982 Inactivation of human placental 17β-estradiol dehydrogenase and 20α-hydroxysteroid dehydrogenase with active site-directed 17β-propynyl-substituted progestin analogs. J Biol Chem 257:2783-2786
147. Jones PB, Hsueh AJ 1981 Direct stimulation of ovarian progesterone-metabolizing enzyme by gonadotropin-releasing hormone in cultured granulosa cells. J Biol Chem 256:1248-1254
148. Mao J, Duan WR, Albarracin CT, Parmer TG, Gibori G 1994 Isolation and characterization of a rat luteal cDNA encoding 20α-hydroxysteroid dehydrogenase. Biochem Biophys Res Commun 201:1289-1295
149. Baker ME, Fanestil DD 1991 Licorice, computer-based analyses of dehydrogenase sequences, and the regulation of steroid and prostaglandin action. Mol Cell Endocrinol 78:C99-102
150. Baker ME 1991 Genealogy of regulation of human sex and adrenal function, prostaglandin action, snapdragon and petunia flower colors, antibiotics, and nitrogen fixation: functional diversity from two ancestral dehydrogenases. Steroids 56:354-360
151. Baker M 1995 Enoyl-acyl-carrier-protein reductase and Mycobacterinin tuberculosis InhA do not conserve the Tyr-Xaa-Xaa-Xaa-Lys motif in mammalian 11β- and 17β-hydroxysteroid dehydrogenases and Drosophila alcohol dehydrogenase. Biochem J 309:1029-1030
152. Baker ME 1996 Unusual evolution of 11β-hydroxysteroid and retinol dehydrogenases. Bioessays 18:63-70
153. Ensor CM, Tai HH 1991 Site-directed mutagenesis of the conserved tyrosine 151 of human placental NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase yields a catalytically inactive enzyme. Biochem Biophys Res Commun 176:840-845
154. Chen Z, Jiang JC, Lin ZG, Lee WR, Baker ME, Chang SH 1993 Site-specific mutagenesis of Drosophila alcohol dehydrogenase: evidence for involvement of tyrosine-152 and lysine-156 in catalysis. Biochemistry 32:3342-3346
155. Obeid J, White PC 1992 Tyr-179 and Lys-183 are essential for enzymatic activity of 11β-hydroxysteroid dehydrogenase. Biochem Biophys Res Commun
156. Tanaka M, Ohno S, Adachi S, Nakajin S, Shinoda M, Nagahama Y 1992 Pig testicular 20β-hydroxysteroid dehydrogenase exhibits carbonyl reductase-like structure and activity. cDN A cloning of pig testicular 20β-hydroxysteroid dehydrogenase. J Biol Chem 267: 13451-13455
157. Marekov L, Krook M, Jornvall H 1990 Prokaryotic 20β-hydroxysteroid dehydrogenase is an enzyme of the 'short-chain, non-metalloenzyme' alcohol dehydrogenase type. FEBS Lett 266:51-54
158. Krook M, Marekov L, Jornvall H 1990 Purification and structural characterization of placental NAD(+)-linked 15-hydroxyprostaglandin dehydrogenase. The primary structure reveals the enzyme to belong to the short-chain alcohol dehydrogenase family. Biochemistry 29:738-743
159. Dothie JM, Giglio JR, Moore CB, Taylor SS, Hartley BS 1985 Ribitol dehydrogenase of Klebsiella aerogenes. Sequence and properties of wild-type and mutant strains. Biochem J 230:569-578
160. Wermuth B, Bohren KM, Heinemann G, von Wartburg JP, Gabbay KH 1988 Human carbonyl reductase. Nucleotide sequence analysis of a cDNA and amino acid sequence of the encoded protein. J Biol Chem 263:16185-16188
161. Hallam SE, Malpartida F, Hopwood DA 1988 Nucleotide sequence, transcription and deduced function of a gene involved in polyketide antibiotic synthesis in Streptomyces coelicolor. Gene 74: 305-320
162. Navre M, Ringold GM 1988 A growth factor-repressible gene associated with protein kinase C-mediated inhibition of adipocyte differentiation. J Cell Biol 107:279-286
163. Ghosh D, Weeks CM, Grochulski P, Duax WL, Erman M, Rimsay RL, Orr JC 1991 Three-dimensional structure of holo 3α,20β-hydroxysteroid dehydrogenase: a member of a short-chain dehydrogenase family. Proc Natl Acad Sci USA 88:10064-10068
164. Ghosh D, Erman M, Wawrzak Z, Duax WL, Pangborn W 1994 Mechanism of inhibition of 3α,20β-hydroxysteroid dehydrogenase by a licorice-derived steroidal inhibitor. Structure 2:973-980
165. Ghosh D, Wawrzak Z, Weeks CM, Duax WL, Erman M 1994 The refined three-dimensional structure of 3α,20β-hydroxysteroid dehydrogenase and possible roles of the residues conserved in short-chain dehydrogenases. Structure 2:629-640
166. Ghosh D, Pletnev VZ, Zhu DW, Wawrzak Z, Duax WL, Pangborn W, Labrie F, Lin SX 1995 Structure of human estrogenic 17β-hydroxysteroid dehydrogenase at 2.20 A resolution. Structure 3:503-513
167. 4-3-oxosteroid-5β-reductase and substrate specificity of the expressed enzyme. Eur J Biochem 219:357-363
168. 4-ketosteroid-5β-reductase of rat liver. FEBS Lett 238:215-218
169. Betz G, Warren JC 1968 Reaction mechanism and stereospecificity of 20β-hydroxysteroid dehydrogenase. Arch Biochem Biophys 128: 745-752
170. Betz G, Taylor P 1970 Reaction mechanism of 20β-hydroxysteroid dehydrogenase determined by equilibrium rate exchange. Arch Biochem Biophys 137:109-114
171. Betz G 1971 Reaction mechanism of 17β-estradiol dehydrogenase determined by equilibrium rate exchange. J Biol Chem 246:2063-2068
172. Askonas LJ, Ricigliano JW, Penning TM 1991 The kinetic mechanism catalysed by homogeneous rat liver 3α-hydroxysteroid dehydrogenase. Evidence for binary and ternary dead-end complexes containing non-steroidal anti-inflammatory drugs. Biochem J 278: 835-841
173. Grimshaw CE, Shahbaz M, Putney CG 1990 Mechanistic basis for nonlinear kinetics of aldehyde reduction catalyzed by aldose reductase. Biochemistry 29:9947-9955
174. Kubiseski TJ, Hyndman DJ, Morjana NA, Flynn TG 1992 Studies on pig muscle aldose reductase. Kinetic mechanism and evidence for a slow conformational change upon coenzyme binding. J Biol Chem 267:6510-6517
175. Grimshaw CE, Bohren KM, Lai CJ, Gabbay KH 1995 Human aldose reductase: rate constants for a mechanism including interconversion of ternary complexes by recombinant wild-type enzyme. Biochemistry 34:14356-14365
176. Grimshaw CE, Bohren KM, Lai CJ, Gabbay KH 1995 Human aldose reductase: subtle effects revealed by rapid kinetic studies of the C298A mutant enzyme. Biochemistry 34:14366-14373
177. Grimshaw CE, Bohren KM, Lai CJ, Gabbay KH 1995 Human aldose reductase: pK of tyrosine 48 reveals the preferred ionization state for catalysis and inhibition. Biochemistry 34:14374-14384
178. Fisher HF, Conn EE, Vennesland B, Westheimer FH 1953 The enzymatic transfer of hydrogen. 1. The reaction catalyzed by alcohol dehydrogenase. J Biol Chem 202:687-697
179. Loewus FA, Ofner P, Fisher HF, Westheimer FH, Vennesland B 1953 The enzymatic transfer of hydrogen. II. The reaction catalyzed by lactic dehydrogenase. J Biol Chem 202:699-704
180. Bloxham DP, Giles IG, Wilton DC, Akhtar M 1975 The mechanism of the bond forming events in pyridine nucleotide linked oxidoreductases. Studies with epoxide inhibitors of lactic dehydrogenase and β-hydroxybutyrate dehydrogenase. Biochemistry 14:2235-2241
181. Talalay P 1963 Hydroxysteroid dehydrogenases. In: Boyer PD, Lardy M, Myrback K (eds) Enzymes. Academic Press, New York, vol 7:177-202
182. Inano H, Tamaoki B 1974 Purification and properties of NADP-dependent 17β-hydroxysteroid dehydrogenase solubilized from porcine-testicular microsomal fraction. Eur J Biochem 44:13-23
183. Jarabak J, Talalay P 1960 Stereospecificity of hydrogen transfer by pyridine nucleotide-linked hydroxysteroid dehydrogenases. J Biol Chem 235:2147-2154
184. Kersey WH, Wilcox RB 1970 Stereochemistry of hydrogen transfer by rat ovary 20α-hydroxysteroid dehydrogenase. Biochemistry 9:1284-1286
185. Chin CC, Warren JC 1975 Synthesis of 16α-bromoacetoxy estradiol 3-methyl ether and study of the steroid binding site of human placental estradiol 17β-dehydrogenase. J Biol Chem 250:7682-7686
186. Murdock GL, Chin CC, Warren JC 1986 Human placental estradiol 17β-dehydrogenase: sequence of a histidine-bearing peptide in the catalytic region. Biochemistry 25:641-646
187. Azzi A, Rehse PH, Zhu D-W, Campbell R, Labrie F, Lin S-X 1996 Crytsal structure of human estrogenic 17β-hydroxysteroid dehydrogenase complexed with 17β-estradiol. Nat Struct Biol 3:665-668
188. + identifies two principal targets for the design of inhibitors. Structure 4:905-915
189. Hoog SS, Pawlowski JE, Alzari PM, Penning TM, Lewis M 1994 Three-dimensional structure of rat liver 3α-hydroxysteroid/dihydrodiol dehydrogenase: a member of the aldo-keto reductase superfamily. Proc Natl Acad Sci USA 91:2517-2521
190. +. Biochemistry 35:10702-10711
191. Wilson DK, Bohren KM, Gabbay KH, Quiocho FA 1992 An unlikely sugar substrate site in the 1.65 A structure of the human aldose reductase holoenzyme implicated in diabetic complications. Science 257:81-84
192. Ricigliano JW, Penning TM 1990 Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3α-hydroxysteroid dehydrogenase. Biochem J 269:749-755
193. Schlegel B, Penning T, Site-directed mutagenesis of the catalytic triad of rat liver 3α-hydroxysteroid dehydrogenase. Program of the International Symposium on DHEA Transformation into Androgens and Estrogens in Target Tissues: Intracrinology. Quebec City, Canada, 1995, Abstract 10