Identification of novel functional inhibitors of 17β-hydroxysteroid dehydrogenase type III (17β-HSD3)

Prostate

Volumn 65, Issue 2, 2005, Pages 159-170

  Spires, Thomas E ^a   Fink, Brian E ^a   Kick, Ellen K ^a   You, Dan ^a   Rizzo, Cheryl A ^a   Takenaka, Ivone ^a   Lawrence, R Michael ^a   Ruan, Zheming ^a   Salvati, Mark E ^a   Vite, Gregory D ^a   Weinmann, Roberto ^a   Attar, Ricardo M ^a   Gottardis, Marco M ^a   Lorenzi, Matthew V ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Androgen receptor; Androstenedione; Endocrine therapy; Prostate cancer

Indexed keywords

2 AMINOBENZAMIDE; 3 O BENZYLANDROSTERONE; ANDROGEN RECEPTOR; ANDROSTENEDIONE; BMS 856; CHLOROPHENOL; ENZYME INHIBITOR; GLYCYRRHETINIC ACID; HORMONE RECEPTOR; HYDROXYFLUTAMIDE; NATURAL PRODUCT; TESTOSTERONE; TESTOSTERONE 17BETA DEHYDROGENASE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; GENETIC TRANSCRIPTION; HORMONAL THERAPY; HORMONE ACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROSTATE CANCER; TESTOSTERONE SYNTHESIS;

17-HYDROXYSTEROID DEHYDROGENASES; ANDROSTENEDIONE; ANTHRANILIC ACIDS; ANTI-INFLAMMATORY AGENTS; DRUG EVALUATION, PRECLINICAL; GLYCYRRHETINIC ACID; HUMANS; MALE; PROSTATIC NEOPLASMS; TESTOSTERONE;

EID: 25444469173     PISSN: 02704137     EISSN: None     Source Type: Journal    
DOI: 10.1002/pros.20279     Document Type: Article

References (36)

1. Scher HI, Buchanan G, Gerald W, Butler LM, Tilley WD. Targeting the androgen receptor: Improving outcomes for castration-resistant prostate cancer. Endocr Relat Cancer 2004;11:459-476.
2. Roach M. Hormonal therapy and radiotherapy for localized prostate cancer: Who, where and how long? J Urol 2003;170:S35-S40.
3. Labrie F, Luu-The V, Lin SX, Simard J, Labrie C. Role of 17 beta-hydroxysteroid dehydrogenases in sex steroid formation in peripheral intracrine tissues. Trends Endocrinol Metab 2000;11: 421-427.
4. Labrie F, Luu-The V, Labrie C, Simard J. DHEA and its transformation into androgens and estrogens in peripheral target tissues: Intracrinology. Front Neuroendocrinol 2001;22:185-212.
5. Ebeling P, Koivisto VA. Physiological importance of dehydroepiandrosterone. Lancet 1994;343:1479-1481.
6. Adams JB. Control of secretion and the function of C19-delta 5-steroids of the human adrenal gland. Mol Cell Endocrinol 1985;41:1-17.
7. Adamski J, Jakob FJ. A guide to 17beta-hydroxysteroid dehydrogenases. Mol Cell Endocrinol 2001;171:1-4.
8. Mindnich R, Moller G, Adamski J. The role of 17 beta-hydroxysteroid dehydrogenases. Mol Cell Endocrinol 2004; 218:7-20.
9. Labrie F, Dupont A, Belanger A. Important Advances in Oncology, de Vita VT, Hellman S, Rosenberg SA, eds. Lippencott Publishing, Philadelphia. 1985; 193-200.
10. Nishiyama T, Hashimoto Y, Takahashi K. The influence of androgen deprivation therapy on dihydrotestosterone levels in the prostatic tissue of patients with prostate cancer. Clin Cancer Res 2004;10:7121-7126.
11. Geissler WM, Davis DL, Wu L, Bradshaw KD, Patel S, Mendonca BB, Elliston KO, Wilson JD, Russell DW, Andersson S. Male pseudohermaphroditism caused by mutations of testicular 17 beta-hydroxysteroid dehydrogenase 3. Nat Genet 1994; 7:34-39.
12. Luu-The V, Zhang Y, Poirier D, Labrie F. Characteristics of human types 1, 2 and 3 17beta-hydroxysteroid dehydrogenase activities: Oxidation/reduction and inhibition. J Steroid Biochem Mol Biol 1995;55:581-587.
13. Sha JA, Dudley K, Rajapaksha WR, O'Shaughnessy PJ. Sequence of mouse 17beta-hydroxysteroid dehydrogenase type 3 cDNA and tissue distribution of the type 1 and type 3 isoform mRNAs. J Steroid Biochem Mol Biol 1997;60:19-24.
14. Koh E, Noda T, Kanaya J, Namiki M. Differential expression of 17beta-hydroxysteroid dehydrogenase isozyme genes in prostate cancer and noncancer tissues. Prostate 2002;53:154-159.
15. Moghrabi N, Hughes IA, Dunaif A, Andersson S. Deleterious missense mutations and silent polymorphism in the human 17beta-hydroxysteroid dehydrogenase 3 gene (HSD17B3). J Clin Endocrinol Metab 1998;83:2855-2860.
16. Rosler A, Silverstein S, Abeliovich D. A (R80Q) mutation in 17 beta-hydroxysteroid dehydrogenase type 3 gene among Arabs of Israel is associated with pseudohermaphroditism in males and normal asymptomatic females. J Clin Endocrinol Metab 1996;81:1827-1831.
17. Andersson S, Geissler WM, Wu L, Davis DL, Grumbach MM, New MI, Schwarz HP, Blethen SL, Mendonca BB, Bloise W, Witchel SF, Cutler GB Jr, Griffin JE, Wilson JD, Russel DW. Molecular genetics and pathophysiology of 17beta-hydroxysteroid dehydrogenase 3 deficiency. J Clin Endocrinol Metab 1996; 81:130-136.
18. Wang C, Yeung F, Liu PC, Attar RM, Geng J, Chung LW, Gottardis M, Kao C. Identification of a novel transcription factor, GAGATA-binding protein, involved in androgen-mediated expression of prostate-specific antigen. J Biol Chem 2003;278: 32423-32430.
19. Yamaguchi T, Kawamoto K, Uchida N, Uchida K, Watanabe S. Three cell lines showing androgen-dependent, -independent, and -suppressed phenotypes, established from a single tumor of androgen-dependent Shionogi carcinoma 115. In Vitro Cell Dev Biol 1992;28A:245-254.
20. Maltais R, Luu-The V, Poirier D. Parallel solid-phase synthesis of 3beta-peptido-3alpha-hydroxy-5alpha-androstan-17-one derivatives for inhibition of type 3 17beta-hydroxysteroid dehydrogenase. Bioorg Med Chem 2001;9:3101-3111.
21. Marini-Bettolo R, Tasai CSJ, Thomas YR, Wiesner K. A one-step synthesis of 17a-hydroxy cardenolides and iso-cardenolides from C17 steroidal ketones. Heterocycles 1981;15:305-308.
22. McKeever BM, Hawkins BK, Geissler WM, Wu L, Sheridan RP, Mosley RT, Andersson S. Amino acid substitution of arginine 80 in 17beta-hydroxysteroid dehydrogenase type 3 and its effect on NADPH cofactor binding and oxidation/reduction kinetics. Biochim Biophys Acta 2002;1601:29-37.
23. Dufort I, Labrie F, Luu-The V. Human types 1 and 3 3alpha-hydroxysteroid dehydrogenases: Differential lability and tissue distribution. J Clin Endocrinol Metab 2001;86:841-846.
24. Dufort I, Rheault P, Huang XF, Soucy P, Luu-The V. Characteristics of a highly labile human type 5 17beta-hydroxysteroid dehydrogenase. Endocrinology 1999;140:568-574.
25. Krazeisen A, Breitling R, Moller G, Adamski J. Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. Mol Cell Endocrinol 2001;171:151-162.
26. Michael AE, Evagelatou M, Norgate DP, Clarke RJ, Antoniw JW, Stedman BA, Brennan A, Welsby R, Bujalska I, Stewart PM, Cooke BA. Isoforms of 11beta-hydroxysteroid dehydrogenase in human granulosa-lutein cells. Mol Cell Endocrinol 1997;132: 43-52.
27. Sakamoto K, Wakabayashi K. Inhibitory effect of glycyrrhetinic acid on testosterone production in rat gonads. Endocrinol Jpn 1988;35:333-342.
28. Fenton MA, Shuster TD, Fertig AM, Taplin ME, Kolvenbag G, Bubley GJ, Balk SP. Functional characterization of mutant androgen receptors from androgen-independent prostate cancer. Clin Cancer Res 1997;3:1383-1388.
29. Poirier D. Inhibitors of 17 beta-hydroxysteroid dehydrogenases. Curr Med Chem 2003;10:453-477.
30. Maltais R, Luu-The V, Poirier D. Synthesis and optimization of a new family of type 3 17beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry. J Med Chem 2002; 45:640-653.
31. Levy MA, Holt DA, Brandt M, Metcalf BW. Inhibition of 3(17)beta-hydroxysteroid dehydrogenase from Pseudomonas testosteroni by steroidal A ring fused pyrazoles. Biochemistry 1987;26:2270-2279.
32. Zhang P, Bao L, Zuckett JF, Jia ZJ, Woolfrey J, Arfsten A, Edwards S, Sinha U, Hutchaleelaha A, Lambing JL, Hollenbach SJ, Scarborough RM, Zhu BY. Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors with improved functional activity. Bioorg Med Chem Lett 2004;14: 989-993.
33. Clader JW, Billard W, Binch H III, Chen LY, Crosby G Jr, Duffy RA, Ford J, Kozlowski JA, Lachowicz JE, Li S, Liu C, McCombie SW, Vice S, Zhou G, Greenlee WJ. Muscarinic M2 antagonists: Anthranilamide derivatives with exceptional selectivity and in vivo activity. Bioorg Med Chem 2004;12:319-326.
34. Mohler JL, Gregory CW, Ford OH III, Kim D, Weaver CM, Petrusz P, Wilson EM, French FS. The androgen axis in recurrent prostate cancer. Clin Cancer Res 2004;10:440-448.
35. Feldman BJ, Feldman D. The development of androgen-independent prostate cancer. Nat Rev Cancer 2001;1:34-45.
36. Campos SM. Aromatase inhibitors for breast cancer in postmenopausal women. Oncologist 2004;9:126-136.