Biochemical and biological evaluation of novel potent coumarin inhibitor of 17β-HSD type 1

Chemico-Biological Interactions

Volumn 191, Issue 1-3, 2011, Pages 60-65

  Starcevic S ^a   Kocbek, P ^a   Hribar, G ^b   Lanisnik Rizner T ^a   Gobec, S ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

17 HSD type 1; Coumarin inhibitor; Hormone dependent breast cancer; Soluble recombinant enzyme

Indexed keywords

17BETA HYDROXYSTEROID DEHYDROGENASE TYPE 1; 17BETA HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITOR; COUMARIN DERIVATIVE; ESTRONE; OXIDOREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CELL FREE SYSTEM; CELL PROLIFERATION; CONFERENCE PAPER; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PURIFICATION; ESCHERICHIA COLI; GROWTH INHIBITION; HUMAN; HUMAN CELL; PH; PROTEIN EXPRESSION;

17-HYDROXYSTEROID DEHYDROGENASES; CELL LINE, TUMOR; CELL PROLIFERATION; COUMARINS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; ESCHERICHIA COLI; ESTROGENS; HUMANS; SOLUBILITY;

ESCHERICHIA COLI;

EID: 79956133533     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2011.01.002     Document Type: Conference Paper

References (44)

1. Y. Laplante, C. Rancourt, D. Poirier, Relative involvement of three 17β-hydroxysteroid dehydrogenases (types 1, 7 and 12) in the formation of estradiol in various breast cancer cell lines using selective inhibitors, Mol. Cell. Endocrinol. 301 (2009) 146-153.
2. M.Meier, G. Möller, J. Adamski, Perspectives in understanding the role ofhuman 17β hydroxysteroid dehydrogenases in health and disease, Ann. N. Y. Acad. Sci. 1155 (2009) 15-24.
3. J.M. Day, H.J. Tutill, A. Purohit, M.J. Reed, Design and validation of specific inhibitors of 17β-hydroxysteroid dehydrogenases for therapeutic application in breast and prostate cancer, and in endometriosis, Endocr. Relat. Cancer 15 (2008) 665-692.
4. G. Moeller, J. Adamski, Multifunctionality of human 17β- hydroxysteroid dehydrogenases, Mol. Cell. Endocrinol. 248 (2006) 47-55.
5. J. Su, M. Lin, J.L. Napoli, Complementary deoxyribonucleic acid cloning and enzymatic characterization of a novel 17{beta}/3{alpha}-hydroxysteroid/ retinoid short-chain dehydrogenase/reductase, Endocrinology 140 (1999) 5275-5284.
6. Y.A. Moon, J.D. Horton, Identification of two mammalian reductases involved in the two-carbon fatty acyl elongation cascade, J. Biol. Chem. 278 (2003) 7335-7343.
7. N. Shafqat, H.U. Marschall, C. Filling, E. Nordling, X.Q. Wu, L. Björk, J. Thyberg, E. Martensson, S. Salim, H. Jörnwall, U. Oppermann, Expanded substrate screenings of human and Drosophila type 10b 17.-hydroxysteroid dehydrogenases (HSDs) reveal multiple specificities in bile acid and steroid hormone metabolism: characterization of multifunctional 3α/7α/7β/17β/20β/21-HSD, Biochem. J. 376 (2003) 49-60. (Pubitemid 37492899)
8. V. Luu-The, Y. Zhang, D. Poirier, F. Labrie, Characteristics of human types 1, 2 and 3 17β-hydroxysteroid dehydrogenase activities: oxidation/reduction and inhibition, J. Steroid Biochem. Mol. Biol. 55 (1995) 581-587. (Pubitemid 26019342)
9. G. Shayamala, Y.C. Chou, R.D. Cardiff, E. Vargis, Effect of c-neu/ErbB2 expression levels on estrogen receptor α-dependent proliferation in mammary epithelial cells: implications for breast cancer biology, Cancer Res. 66 (2006) 10391-10398. (Pubitemid 44799759)
10. Y.R. Lee, J. Park, H.N. Yu, J.S. Kim, H.J. Youn, S.H. Jung, Up-regulation of PI3K/Akt signaling by 17β-estradiol through activation of estrogen receptor-α, but not estrogen receptor-β, and stimulates cell growth in breast cancer cells, Biochem. Biophys. Res. Commun. 336 (2005) 1221-1226.
11. S.X. Lin, F. Yang, J.Z. Jin, R. Breton, D.W. Zhu, V. Luu-The, F. Labrie, Subunit identity of the dimeric 17β-hydroxysteroid dehydrogenase from human placenta, J. Biol. Chem. 267 (1992) 16182-16187.
12. H. Peltoketo, V. Luu-The, J. Simard, 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.
13. C. Sawetawan, L. Milewicha, R.A. Worda, B.R. Carra, W.E. Rainey, Compartmentalization of type 1 17β-hydroxysteroid oxidoreductase in the human ovary, Mol. Cell. Endocrinol. 94 (1994) 161-168.
14. N. Fournet-Dulguerov, N.J. MacLusky, C.Z. Leranth, R. Todd, C.R. Mendelson, E.R. Simpson, F. Naftolin, Immunohistochemical localization of aromatase cytochrome P-450 and estradiol dehydrogenase in the syncytiotrophoblast of the human placenta, J. Clin. Endocrinol. Metab. 65 (1987) 757-764. (Pubitemid 17157398)
15. H. Sasano, A.R. Frost, R. Saitoh, N. Harada, M. Poutanen, R. Vihko, S.E. Bulun, S.G. Silverberg, H. Nagura, Aromatase and 17 beta-hydroxysteroid dehydrogenase type 1 in human breast carcinoma, J. Clin. Endocrinol. Metab. 81 (1996) 4042-4046. (Pubitemid 26380415)
16. P. Vihko, A. Herrala, P. Härkönen, V. Isomaa, H. Kaija, R. Kurkela, Y. Li, A. Pulkka, Control of cell proliferation by steroids: the role of 17β-HSDs, Mol. Cell. Endocrinol. 248 (2006) 141-148.
17. H. Dassen, C. Punyadeera, R. Kamps, B. Delvoux, A. Van Langendonckt, J. Donnez, B. Husen, H. Thole, G. Dunselman, P. Groothuis, Estrogen-metabolizing enzymes in endometrium and endometriosis, Hum. Reprod. 22 (2007) 3148-3158.
18. T. Šmuc, N. Hevir, M. Ribič-Pucelj, B. Hussen, H. Thole, T. Lanišnik Rižner, Disturbed estrogen and progesterone action in ovarian endometriosis, Moll. Cell. Endocrinol. 301 (2009) 59-64.
19. P. Vihko, V. Isomaa, D. Ghosh, Structure and function of 17β-hydroxysteroid dehydrogenase type 1 and type 2, Mol. Cell. Endocrinol. 171 (2001) 71-76. (Pubitemid 32098199)
20. O.O. Oduwole, V.V. Isomaa, P. Nokelainen, F. Stenbäck, P.T. Vihko, Downregulation of estrogen metabolizing 17β-hydroxysteroid dehydrogenase type 2 expression correlates inversely with Ki67 proliferation marker in colon-cancer development, Int. J. Cancer 97 (2002) 1-6.
21. J. Day, H.J. Tutill, S.P. Newman, A. Purohit, H.R. Lawrence, N. Vicker, B.V.L. Potter, M.J. Reed, 17β-Hydroxysteroid dehydrogenase type 1 and type 2: association between mRNA expression and activity in cell lines, Mol. Cell. Endocrinol. 248 (2006) 246-249.
22. A.O. Mueck, H. Seeger, D. Wallwiener, Comparison of the proliferative effects of estradiol and conjugated equine estrogens on human breast cancer cells and impact of continuous combined progestogen addition, Climacteric 6 (2003) 221-227. (Pubitemid 37188282)
23. Y. Miyoshi, A. Ando, E. Shiba, T. Taguchi, Y. Tamaki, S. Noguchi, Involvement of up-regulation of 17β-hydroxysteroid dehydrogenase type 1 in maintenance of intratumoral high estradiol levels in postmenopausal breast cancers, Int. J. Cancer 94 (2001) 685-689. (Pubitemid 33035688)
24. C. Gunnarsson, E. Hellqvist, O. Stal, 17β-Hydroxysteroid dehydrogenases involved in local oestrogen synthesis have prognostic significance in breast cancer, Br. J. Cancer 92 (2005) 547-552. (Pubitemid 40395536)
25. P. Kruchten, R. Werth, S. Marchais-Oberwinkler, M. Frotscher, R.W. Hartmann, Development of a biological screening system for the evaluation of highly active and selective 17β-HSD1 inhibitors as potential therapeutic targets, Mol. Cell. Endocrinol. 301 (2009) 154-157.
26. D. Ghosh, V.Z. Pletnev, D.W. Zhu, Z. Wawrzak, W.L. Duax, W. Pangborn, F. Labrie, S.X. Lin, Structure of human estrogenic 17β-hydroxysteroid dehydrogenase at 2.20 Å resolution, Structure 3 (1995) 503-513.
27. A. Azzi, P.H. Rehse, D.W. Zhu, R.L. Campbell, F. Labrie, S.X. Lin, Crystal structure of human estrogenic 17β-hydroxysteroid dehydrogenase complexed with 17β-estradiol, Nat. Struct. Biol. 3 (1996) 665-668. (Pubitemid 26260054)
28. + identifies two principal targets for the design of inhibitors, Structure 3 (1996) 905-915.
29. +, Proc. Natl. Acad. Sci. 96 (1999) 840-845.
30. M. Mazumdar, D. Fournier, D.W. Zhu, C. Cadot, D. Poirier, S.X. Lin, Binary and ternary crystal structure analyses of a novel inhibitor with 17β-HSD type 1: a lead compound for breast cancer therapy, Biochem. J. 424 (2009) 357-366.
31. D. Poirier, R.P. Boivin, M.B. Tremblay, M. Bérubé, W. Qiu, S.X. Lin, Estradiol - adenosine hybrid compounds designed to inhibit type 1 17β-hydroxysteroid dehydrogenase, J. Med. Chem. 48 (2005) 8143-8147.
32. + breast cancer cell proliferation induced by estrone, Bioorg. Med. Chem. 16 (2008) 1849-1860.
33. T. Lamminen, T. Saloniemi, K. Huhtinen, P. Koskimies, J. Messinger, B. Husen, H. Thole, M. Poutanen, In-vivo mouse model for analysis of hydroxysteroid (17β) dehydrogenase 1 inhibitors, Mol. Cell. Endocrinol. 301 (2009) 158-162.
34. J. Messinger, L. Hirvelä, B. Husen, L. Kangas, P. Koskimies, O. Pentikäinen, P. Saaraenketo, H. Thole, New inhibitors of 17β-hydroxysteroid dehydrogenase type 1, Mol. Cell. Endocrinol. 248 (2006) 192-198.
35. E. Bey, S. Marchais-Oberwinkler, M. Negri, P. Kruchten, A. Oster, T. Klein, A. Spadaro, R. Werth, M. Frotscher, B. Birk, R.W. Hartmann, New insights into the SAR and binding mode of bis(hydroxyphenyl)thiophenes and -bezenes: influence of additional substituents on 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) inhibitory activity and selectivity, J. Med. Chem. 51 (2009) 6724-6743.
36. F. Yang, D.W. Zhu, J.Y. Wang, S.X. Lin, Rapid purification yielding highly active 17β-hydroxysteroid dehydrogenase: application of hydrophobic interaction and affinity fast protein liquid chromatography, J. Chromatogr. 582 (1992) 71-76.
37. R. Breton, F. Yang, J.Z. Jin, B. Li, F. Labrie, S.X. Lin, Human 17beta-hydroxysteroid dehydrogenase: overproduction using a baculovirus expression system and characterization, J. Steroid Biochem. Mol. Biol. 50 (1994) 275-282.
38. Y.H. Chang, Y.L. Wang, J.Y. Lin, L.Y. Chuang, C.C. Hwang, Expression, purification, and characterization of a human recombinant 17β- hydroxysteroid dehydrogenase type 1 in Escherichia coli, Mol. Biotechnol. 44 (2010) 133-139.
39. D.P. Sherbet, O.L. Guryev, M. Papari-Zareei, D. Mizrachi, S. Rambally, S. Akbar, R.J. Auchus, Biochemical factors governing the steady-state estrone/estradiol ratios catalyzed by human 17β-hydroxysteroid dehydrogenases types 1 and 2 in HEK-293 cells, Endocrinology 150 (2009) 4154-4162.
40. Š. Starčević, P. Brožič, S. Turk, J. Cesar, T. Lanišnik-Rižner, S. Gobec, Synthesis and biological evaluation of (6- and 7-Phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), J. Med. Chem 54 (2011) 248-261.
41. J.Z. Jin, S.X. Lin, Human estrogenic 17β-hydroxysteroid dehydrogenase: predominance of estrone reduction and its induction by NADPH, Biochem. Biophys. Res. Commun. 259 (1999) 489-493.
42. J.M. Day, P.A. Foster, H.J. Tutill, M.F.C. Parsons, S.P. Newman, S.K. Chander, G.M. Allan, H.R. Lawrence, N. Vicker, B.V.L. Potter, M.J. Reed, A. Purohit, 17β-Hydroxysteroid dehydrogenase type 1, and not type 12, is a target for endocrine therapy of hormone-dependent breast cancer, Int. J. Cancer 122 (2008) 1931-1940. (Pubitemid 351441181)
43. L.J. Duncan, M.J. Reed, The role and proposed mechanism by which oestradiol 17β-hydroxysteroid dehydrogenase regulates breast tumour oestrogen concentrations, J. Steroid Biochem. Mol. Biol. 55 (1995) 565-572. (Pubitemid 26019341)
44. P. Kruchten, R. Werth, E. Bey, A. Oster, S. Marchais-Oberwinkler, M. Frotscher, R.W. Hartmann, Selective inhibition of 17β-hydroxysteroid dehydrogenase type 1 (17BHSD1) reduces estrogen responsive cell growth of T-47D breast cancer cells, J. Steroid Biochem. Mol. Biol. 114 (2009) 200-206.