Synthesis and biological evaluation of salpichrolide analogs as antiestrogenic agents

European Journal of Medicinal Chemistry

Volumn 82, Issue , 2014, Pages 233-241

  Sonego, Juan M ^a   Rivero, Ezequiel M ^b   Gargiulo, Lucía ^b   Lüthy, Isabel ^b   Alvarez, Lautaro D ^a   Veleiro, Adriana S ^a   Burton, Gerardo ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b Facultad de Ciencias Naturales e Instituto M Lillo   (Argentina)

Author keywords

Antiestrogenic activity; Antiproliferative activity; Salpichrolides; Withanolides

Indexed keywords

17(13-18)ABEO 5ALPHAH PREGNA 2,13,15,17 TETRAEN 1,20 DIONE; 1ALPHA HYDROXY 17(13-18) ABEO 5ALPHAH PREGNA 2,13,15,17 TETRAEN 20 ONE; 20 (TERT BUTYLDIMETHYLSILYLOXY) 17 (13-18) ABEO 5ALPHAH PREGNA 13,15,17 TRIEN 3BETA OL; 20 ACETOXY 17(13-18) ABEO 5ALPHAH PREGNA 2,13,15,17 TETRAEN 1ALPHA OL; 20 ACETOXY 17(13-18)ABEO 5ALPHAH PREGNA 13,15,17 TRIEN 3 ONE; 20 ACETOXY 17(13-18)ABEO5ALPHAH PREGNA 1,13,15,17 TETRAEN 3 ONE; 20 ACETOXY 1ALPHA,2ALPHA EPOXY 17(13-18)ABEO 5ALPHAH PREGNA 13,15,17 TRIEN 3 ONE; 3BETA ACETOXY 20 (TERT BUTYLDIMETHYLSILYLOXY) 17 (13-18)ABEO 5ALPHAH PREGNA 13,15,17 TRIENE; ANTIESTROGEN; ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; FULVESTRANT; SALPICHROLIDE A; SALPICHROLIDE B; SALPICHROLIDE DERIVATIVE; SALPICHROLIDE G; UNCLASSIFIED DRUG; ERGOSTEROL;

ANTIESTROGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESTROGEN ACTIVITY; GENETIC ALGORITHM; HUMAN; HUMAN CELL; MCF 7 CELL LINE; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS, HORMONAL; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ERGOSTEROL; ESTROGEN ANTAGONISTS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84902179219     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.067     Document Type: Article

References (25)

1. GLOBOCAN, International Agency for Research on Cancer, World Health Organization, http://globocan.iarc.fr/Pages/fact-sheets-population.aspx.
2. F. Vesuna, A. Lisok, B. Kimble, J. Domek, Y. Kato, P. van der Groep, D. Artemov, J. Kowalski, H. Carraway, P. van Diest, and V. Raman Twist contributes to hormone resistance in breast cancer by downregulating estrogen receptor-α Oncogene 31 2012 3223 3224
3. W.L. Yeh, K. Shioda, K.R. Coser, D. Rivizzigno, K.R. McSweeney, and T. Shioda Fulvestrant-Induced cell death and proteasomal degradation of estrogen receptor alpha protein in MCF-7 cells require the CSK c-Src tyrosine kinase PLoS One 8 2013 e60889
4. R.I. Misico, J.C. Oberti, V. Nicotra, G. Barboza, R.R. Gil, and G. Burton Withanolides and related steroids D.A. Kinghorn, H. Falk, J. Kobayashi, Progress in the Chemistry of Organic Natural Products vol. 94 2011 Springer-Verlag GmbH Vienna-New York 127 229
5. H. Wang, Y. Tsai, Y. Wu, F. Chang, M. Liu, W. Chen, and Ch Wu Withanolides-induced breast cancer cells death is correlated with their ability to inhibit heat protein 90 PLoS One 7 5 2012 e37764
6. X. Zhang, R. Mukerji, A.K. Samadi, and M.S. Cohen Down-regulation of estrogen receptor-alpha and rearranged during transfection tyrosine kinase is associated with withaferin A-induced apoptosis in MCF-breast cancer cells BMC Complement. Altern. Med. 11 2011 84
7. X. Zhang, B. Timmermann, A.K. Samadi, and M.S. Cohen Withaferin A induces proteasome-dependent degradation of breast cancer susceptibility gene 1 and heat shock factor 1 proteins in breast cancer cells ISRN Biochem. 2012 2012 ID 707586
8. E.R. Hahm, J. Lee, Y. Huang, and S.V. Singh Withaferin A suppresses estrogen receptor-α expression in human breast cancer cells Mol. Carcinog. 50 2011 614 624
9. R.P. Machin, A.S. Veleiro, V.E. Nicotra, J.C. Oberti, and J.M. Padrón Antiproliferative activity of withanolides against human breast cancer cell lines J. Nat. Prod. 73 2010 966 968
10. A.S. Veleiro, J.C. Oberti, and G. Burton A ring-D aromatic withanolide from Salpichroa origanifolia Phytochemistry 31 1992 935 937
11. J.M. Sonego, A.M. Cirigliano, G.M. Cabrera, G. Burton, and A.S. Veleiro Synthesis and antifungal activity of C-21 steroids with an aromatic D ring Steroids 78 2013 644 650
12. D.G. Morris Carbonyl group transpositions Chem. Soc. Rev. 11 1982 397 434
13. J.A.R. Salvador, A.J.L. Leitao, M.L. Sá e Melo, and J.R. Hanson Hydrazine hydrate induced reductive cleavage of α,β-epoxy ketones: an efficient procedure for the preparation of α,β-hydroxy ketones Tetrahedron Lett. 45 2005 1067 1070 (Pubitemid 40138883)
14. A.S. Veleiro, and G. Burton New withanolides from Salpichroa origanifolia J. Nat. Prod. 57 1994 1741 1745
15. J.G. Lemmen, C.E. van den Brink, J. Legler, P.T. van der Saag, and B. van der Burg Detection of oestrogenic activity of steroids present during mammalian gestation using oestrogen receptor-α and oestrogen receptor-β specific in vitro assays J. Endocrinol. 174 2002 435 446
16. M. Gangloff, M. Ruff, S. Eiler, S. Duclaud, J.M. Wurtz, and D. Moras Crystal structure of a mutant hERalpha ligand-binding domain reveals key structural features for the mechanism of partial agonism J. Biol. Chem. 276 2001 15059 15065
17. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662 (Pubitemid 128590223)
18. D.A. Case, T.A. Darden, T.E. Cheatham III, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, R.C. Walker, W. Zhang, K.M. Merz, B. Roberts, S. Hayik, A. Roitberg, G. Seabra, J. Swails, A.W. Goetz, I. Kolossváry, K.F. Wong, F. Paesani, J. Vanicek, R.M. Wolf, J. Liu, X. Wu, S.R. Brozell, T. Steinbrecher, H. Gohlke, Q. Cai, X. Ye, J. Wang, M.-J. Hsieh, G. Cui, D.R. Roe, D.H. Mathews, M.G. Seetin, R. Salomon-Ferrer, C. Sagui, V. Babin, T. Luchko, S. Gusarov, A. Kovalenko, and P.A. Kollman AMBER 12 2012 University of California San Francisco
19. M.C. Tettamanzi, A.S. Veleiro, J.C. Oberti, and G. Burton New hydroxylated withanolides from Salpichroa origanifolia J. Nat. Prod. 61 1998 338 342 (Pubitemid 28160720)
20. S. Bado, G. Mareggiani, N.S. Amiano, G. Burton, and A.S. Veleiro Lethal and sublethal effects of withanolides from Salpichroa origanifolia and analogues on Ceratitis capitata J. Agric. Food. Chem. 52 2004 2875 2878
21. C. Perez Pinero, A. Bruzzone, M.G. Sarappa, L.F. Castillo, and I.A. Luthy Involvement of alpha2- and beta2-adrenoceptors on breast cancer cell proliferation and tumour growth regulation Br. J. Pharmacol. 166 2012 721 736
22. Y. Berthois, J.A. Katzenellenbogen, and B.S. Katzenellenbogen Phenol red in tissue culture media is a weak estrogen: implications concerning the study of estrogen-responsive cells in culture Proc. Natl. Acad. Sci. U S A 83 1986 2496 2500 (Pubitemid 16026909)
23. Gaussian 03, Revision C.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople 2004 Gaussian, Inc. Wallingford, CT
24. T.E. Cheatham, P. Cieplak, and P.A. Kollman A modified version of the Cornell et al. force field with improved sugar pucker phases and helical repeat Biomol. Struct. Dyn. 16 1999 845 862 (Pubitemid 29157655)
25. H.J.C. Berendsen, J.P.M. Postma, W.F. Van Gunsteren, A. DiNola, and J.R. Haak Molecular dynamics with coupling to an external bath J. Chem. Phys. 81 1984 3684 3690 Técnicas