17β-Hydroxysteroid dehydrogenase: Inhibitors and inhibitor design

Endocrine-Related Cancer

Volumn 3, Issue 1, 1996, Pages 41-56

  Penning, T M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIESTROGEN; CLOMIFENE; DIETHYLSTILBESTROL; ENZYME INHIBITOR; ESTROGEN; HEXESTROL; PYRAZOLE DERIVATIVE; TESTOSTERONE 17BETA DEHYDROGENASE;

BREAST CANCER; DRUG DESIGN; FEMALE; HUMAN; METABOLISM; REVIEW;

EID: 0029998812     PISSN: 13510088     EISSN: None     Source Type: Journal    
DOI: 10.1677/erc.0.0030041     Document Type: Review

References (64)

1. Adams EF, Coldham NG & James VH 1988 Steroidal regulation of oestradiol-17β dehydrogenase activity of the human breast cancer cell line MCF-7. Journal of Endocrinology 118 149-154.
2. Adamski J, Carstensen J, Husen B, Hall PF, Jungblut PW, Kaufmann M, de Launoit Y, Leenders F, Markus M & Seedorf U 1995 Characterization of the 17βhydroxysteroid dehydrogenases Type 4. International Symposium on DHEA Transformation into Androgens and Estrogens in Target Tissues: Intracrinology, Abstract No. 52.
3. Andersson S, Geissler WM, Patel S & Wu L 1995 The molecular biology of androgenic 17β-hydroxysteroid dehydrogenases. Journal of Steroid Biochemistry and Molecular Biology 53 37-39.
4. Arias F, Sweet F & Warren JC 1973 Affinity labeling of steroid binding sites. Study of the active site of 20βhydroxysteroid dehydrogenase with 6β- and 11αbromoacetoxy-progesterone. Journal of Biological Chemistry 248 5641-5647.
5. Auchus RJ & Covey DF 1986 Mechanism-based inactivation of 17β,20α-hydroxysteroid dehydrogenase by an acetylenic secoestradiol. Biochemistry 25 7295-7300.
6. 13C NMR. Journal of the American Chemical Society 109 280-282.
7. Auchus RJ, Covey DF, Bork V & Schaefer J 1988 Solid-state NMR observation of cysteine and lysine Michael adducts of inactivated estradiol dehydrogenase. Journal of Biological Chemistry 263 11640-11645.
8. Betz G 1971 Reaction mechanism of 17β-estradiol dehydrogenase determined by equilibrium rate exchange. Journal of Biological Chemistry 246 2063-2068.
9. 53-ketosteroid isomerase by steroidal 17β-oxiranes. Evidence for two modes of binding in steroid-enzyme complexes. Biochemical and Biophysical Research Communications 95 1131-1137.
10. Blomquist CH, Lindemann NJ & Hakanson EY 1984 Inhibition of 17β-hydroxysteroid dehydrogenase (17βHSD) activities of human placenta by steroids and nonsteroidal hormone agonists and antagonists. Steroids 43 571-586.
11. Blomquist CH, Lindemann NJ & Hakanson EY 1985 17β-Hydroxysteroid and 20α-hydroxysteroid dehydrogenase activities of human placental microsomes: kinetic evidence for two enzymes differing in substrate specificity. Archives of Biochemistry and Biophysics 239 206-215.
12. 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-hydroxy-butyrate dehydrogenase. Biochemistry 14 2235-2241.
13. 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.
14. Chin CC & Warren JC 1975 Synthesis of 16α- bromoacetoxyestradiol 3-methyl ether and study of the steroid binding site of human placental estradiol 17βdehydrogenase. Journal of Biological Chemistry 250 7682-7686.
15. Couture P, Theriault C, Simard J & Labrie F 1993 Androgen receptor-mediated stimulation of 17βhydroxysteroid dehydrogenase activity by dihydrotestosterone and medroxyprogesterone acetate in ZR-75-1 human breast cancer cells. Endocrinology 132 179-185.
16. Covey DF 1979 Synthesis of 17β-[(1S)-1-hydroxy-2-propynyl]- and 17β-[(1R)-1-hydroxy-2propynyl]androst-4-en-3-one. Potential suicide substrates of 20α- and 20β-hydroxysteroid dehydrogenases. Steroids 34 199-206.
17. +dependent 15-hydroxyprostaglandin dehydrogenase yields a catalytically inactive enzyme. Biochemical and Biophysical Research Communications 176 840-845.
18. Farkas A & Rosler A 1993 Ten years experience with masculinizing genitoplasty in male pseudohermaphroditism due to 17β-hydroxysteroid dehydrogenase deficiency. European Journal of Pediatrics 152 (Suppl) S88-S90.
19. Fisher HF, Conn EE, Vennesland B & Westheimer FH 1953 The enzymatic transfer of hydrogen. I. The reaction catalyzed by alcohol dehydrogenase. Journal of Biological Chemistry 202 687-697.
20. Geissler WM, Davis DL, Wu L, Bradshaw KD, Patel S, Mendonca BB, Elliston KO, Wilson JD, Russell DW & Andersson S 1994 Malepseudohermaphroditism caused by mutations of testicular 17β-hydroxysteroid dehydrogenase 3. Nature Genetics 7 34-39.
21. 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.
22. 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 Å resolution. Structure 3 503-513.
23. Gross DJ, Landau H, Kohn G, Farkas A, Elrayyes E, El-Shawwa R, Lasch EE & Rosler A 1986 Male pseudohermaphroditism due to 17β-hydroxysteroid dehydrogenase deficiency: gender reassignment in early infancy. Acta Endocrinologica 112 238-246.
24. Inano H & Tamaoki B 1975 Relationship between steroids and pyridine nucleotides in the oxido-reduction catalyzed by the 17&-hydroxysteroid dehydrogenase purified from the porcine testicular microsomal fraction. European Journal of Biochemistry 53 319-326.
25. Inano H & Tamaoki B 1986 Testicular 17β-hydroxysteroid dehydrogenase: molecular properties and reaction mechanism. Steroids 48 1-26.
26. Jarabak J & Talalay P 1960 Stereospecificity of hydrogen transfer by pyridine nucleotide-linked hydroxysteroid dehydrogenases. Journal of Biological Chemistry 235 2147-2154.
27. Jarabak J & Sack GH Jr 1969 Soluble 17β-hydroxysteroid dehydrogenase from human placenta. The binding of pyridine nucleotides and steroids. Biochemistry 8 2203-2212.
28. 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. Journal of Biological Chemistry 237 345-357.
29. 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.
30. 5-3-ketosteroid isomerase. Identification of the amino acid modified by steroidal 17β-oxiranes. Journal of Biological Chemistry 258 909-915.
31. Krozowski Z 1994 The short-chain alcohol dehydrogenase superfamily : variations on a common theme. Journal of Steroid Biochemistry and Molecular Biology 51 125-130.
32. Lawate SS & Covey DF 1990 Trifluoromethylacetylenic alcohols as affinity labels. Inactivation of estradiol dehydrogenase by a trifluoromethylacetylenic secostradiol. Journal of Medicinal Chemistry 33 2319-2321.
33. Levy MA, Holt DA, Brandt M & Metcalf BW 1987 Inhibition of 3(17)β-hydroxysteroid dehydrogenase from Pseudomonas testosteroni by steroidal A ring fused pyrazoles. Biochemistry 26 2270-2279.
34. Lin S-X, Zhu D-W, Azzi A, Breton R & Labrie F 1995 The 3D structure of estrogenic 17β-HSD. International Symposium on DHEA Transformation into Androgens and Estrogens in Target Tissues: Intracrinology, Abstract No. 53.
35. Loewus FA, Ofner P, Fisher HF, Westheimer FH & Vennesland B 1953 The enzymatic transfer of hydrogen. II. The reaction catalyzed by lactic dehydrogenase. Journal of Biological Chemistry 202 699-704.
36. Luu-The V, 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. Molecular Endocrinology 3 1301-1309.
37. 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-hydroxysteroid dehydrogenase genes. Molecular Endocrinology 4 268-275.
38. 3H-oestradiol by normal breast and breast tumor tissues in post-menopausal women. International Journal of Cancer 38 193-196.
39. 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.
40. Murdock GL, Pineda J, Nagorsky N, Lawrence SS, Heritage R & Warren JC 1991 Estradiol 17&dehydrogenase: full enzymatic activity in the absence of zinc. Biochimica et Biophysica Acta 1076 197-202.
41. Obeid J & White PC 1992 Tyr-179 and Lys-183 are essential for the enzymatic activity of 11βhydroxysteroid dehydrogenase. Biochemical and Biophysical Research Communications 188 222-227.
42. Pelletier JD, Labrie F & Poirier D 1994 N-butyl,N-methyl,11-[3′, 17′β-(dihydroxy)-1′,3′,5′(10′)-estratrien- 16′-alpha-yl]-9(R/S)-bromo undecanamide: synthesis and 17β-HSD inhibiting, estrogenic and antiestrogenic activities. Steroids 59 536-547.
43. Peltoketo H, Isomaa V, Maentausta O & Vihko R 1988 Complete amino acid sequence of human placental 17βhydroxysteroid dehydrogenase deduced from cDNA. FEBS Letters 239 73-77.
44. Penning TM & Ricigliano JW 1991 Mechanism based inhibition of hydroxysteroid dehydrogenases. Journal of Enzyme Inhibition 5 165-198.
45. Penning TM, Thornton R & Ricigliano JW 1991 Clues to the development of mechanism-based inactivators of 3α-hydroxysteroid dehydrogenase: comparison of steroidal and nonsteroidal Michael acceptors and epoxides. Steroids 56 420-427.
46. 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. Biochemical Journal 304 289-293.
47. Rando RR 1974a Chemistry and enzymology of kcat inhibitors. Science 185 320-324.
48. Rando RR 1974b Allyl alcohol-induced irreversible inhibition of yeast alcohol dehydrogenase. Biochemical Pharmacology 23 2328-2331.
49. Ricigliano JW & Penning TM 1989 Synthesis and evaluation of non-steroidal mechanism-based inactivators of 3α-hydroxysteroid dehydrogenase. Biochemical Journal 262 139-149.
50. Ricigliano JW & Penning TM 1990 Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3αhydroxysteroid dehydrogenase. Biochemical Journal 269 749-755.
51. Silverman RB 1988 Introduction. In Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology, vol 1, pp 3-27, Boca Raton: CRC Press.
52. Simard J, Feunteun J, Lenoir G, Tonin P, Normand T, Luu-The V, Vivier A, Lasko D, Morgan K, Rouleau G, Lynch H, Labrie F & Narod SA 1993 Genetic mapping of the breast-ovarian cancer syndrome to a small interval on chromosome 17q12-21: exclusion of candidate genes EDH17β2 and RARA. Human Molecular Genetics 2 1193-1199.
53. Strickler RC, Sweet F & Warren JC 1975 Affinity labeling of steroid binding sites. Study of the active site of 20β-hydroxysteroid dehydrogenase with 2α-bromoacetoxyprogesterone and 11α-bromoacetoxyprogesterone. Journal of Biological Chemistry 250 7656-7662.
54. Sweet F, Arias F & Warren JC 1972 Affinity labeling of steroid binding sites. Synthesis of 16-bromoacetoxyprogesterone and its use for affinity labeling 20-hydroxysteroid dehydrogenase. Journal of Biological Chemistry 247 3424-3433.
55. Theorell H & Yonetani T 1963 Liver alcohol dehydrogenase-DPN-pyrazole complex: a model of a ternary intermediate in the enzyme reaction. Biochemische Zeitschrift 338 537-553.
56. Theorell H, Yonetani T & Sjoberg B 1969 On the effects of some heterocyclic compounds on the enzymic activity of liver alcohol dehydrogenase. Acta Chemica Scandinavica 23 255-260.
57. Thomas JL, LaRochelle MC, Covey DF & Strickler RC 1983 Inactivation of human placental 17β,20αhydroxysteroid dehydrogenase by 16-methylene estrone, an affinity alkylator enzymatically generated from 16-methylene estradiol-17β. Journal of Biological Chemistry 258 11500-11504.
58. Tobias B, Covey DF & Strickler RC 1982 Inactivation of human placental 17β-estradiol dehydrogenase and 20αhydroxysteroid dehydrogenase with active site-directed 17β-propynyl-substituted progestin analogs. Journal of Biological Chemistry 257 2783-2786.
59. Tremblay MR, Auger S & Poirer D 1995 Synthesis of 16(bromoalkyl)-estradiols having inhibitory effects on human placental estradiol 17β-hydroxysteroid dehydrogenases (17β-HSD Type 1). Bioorganic and Medicinal Chemistry 3 505-523.
60. Vermeulen A, Deslypere JP, Paridaens R, Leclerq G, Roy F & Heusen JC 1986 Aromatase, 17β-hydroxysteroid dehydrogenase and intratissular sex hormone concentrations in cancerous and normal glandular breast tissue in postmenopausal women. European Journal of Cancer and Clinical Oncology 22 515-525.
61. Walsh CT 1984 Suicide substrates, mechanism-based enzyme inactivators: recent developments. Annual Review of Biochemistry 53 493-535.
62. Wilson SC, Hodgins, MB & Scott JS 1987 Incomplete masculinization due to a deficiency of 17βhydroxysteroid dehydrogenase: comparison of prepubertal and peripubertal siblings. Clinical Endocrinology 26 459-469.
63. Wilson SC, Oakey RE & Scott JS 1988 Steroid metabolism in testes of patients with incomplete masculinization due to androgen insensitivity or 17β-hydroxysteroid dehydrogenase deficiency and normally differentiated males. Journal of Steroid Biochemistry 29 649-655.
64. 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. Journal of Biological Chemistry 268 12964-12969.