Discovery of potent ligands for estrogen receptor β by structure-based virtual screening

Journal of Medicinal Chemistry

Volumn 53, Issue 14, 2010, Pages 5361-5365

  Shen, Jie ^a   Tan, Chengfang ^a   Zhang, Yanyan ^a   Li, Xi ^a   Li, Weihua ^a   Huang, Jin ^a   Shen, Xu ^a,b   Tang, Yun ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; SELECTIVE ESTROGEN RECEPTOR MODULATOR; TAMOXIFEN;

ANIMAL CELL; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHO CELLS; CRICETINAE; CRICETULUS; DATABASES, FACTUAL; DRUG SCREENING ASSAYS, ANTITUMOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; SELECTIVE ESTROGEN RECEPTOR MODULATORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77954749599     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100369g     Document Type: Article

References (24)

1. Kuiper, G. G.; Carlsson, B.; Grandien, K.; Enmark, E.; Haggblad, J.; Nilsson, S.; Gustafsson, J. A. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta Endocrinology 1997, 138, 863-870 (Pubitemid 27089735)
2. Korach, K. S.; Emmen, J. M.; Walker, V. R.; Hewitt, S. C.; Yates, M.; Hall, J. M.; Swope, D. L.; Harrell, J. C.; Couse, J. F. Update on animal models developed for analyses of estrogen receptor biological activity J. Steroid Biochem. Mol. Biol. 2003, 86, 387-391
3. Osborne, C. K. Tamoxifen in the treatment of breast cancer N. Engl. J. Med. 1998, 339, 1609-1618
4. Veeneman, G. H. Non-steroidal subtype selective estrogens Curr. Med. Chem. 2005, 12, 1077-1136
5. Peng, J.; Sengupta, S.; Jordan, V. C. Potential of selective estrogen receptor modulators as treatments and preventives of breast cancer Anti-Cancer Agents Med. Chem. 2009, 9, 481-499
6. Zhao, C.; Dahlman-Wright, K.; Gustafsson, J. A. Estrogen receptor beta: an overview and update Nucl. Recept. Signaling 2008, 6, e003
7. Cvoro, A.; Paruthiyil, S.; Jones, J. O.; Tzagarakis-Foster, C.; Clegg, N. J.; Tatomer, D.; Medina, R. T.; Tagliaferri, M.; Schaufele, F.; Scanlan, T. S.; Diamond, M. I.; Cohen, I.; Leitman, D. C. Selective activation of estrogen receptor-beta transcriptional pathways by an herbal extract Endocrinology 2007, 148, 538-547
8. Harris, H. A.; Albert, L. M.; Leathurby, Y.; Malamas, M. S.; Mewshaw, R. E.; Miller, C. P.; Kharode, Y. P.; Marzolf, J.; Komm, B. S.; Winneker, R. C.; Frail, D. E.; Henderson, R. A.; Zhu, Y.; Keith, J. C., Jr. Evaluation of an estrogen receptor-beta agonist in animal models of human disease Endocrinology 2003, 144, 4241-4249
9. Hillisch, A.; Peters, O.; Kosemund, D.; Muller, G.; Walter, A.; Schneider, B.; Reddersen, G.; Elger, W.; Fritzemeier, K. H. Dissecting physiological roles of estrogen receptor alpha and beta with potent selective ligands from structure-based design Mol. Endocrinol. 2004, 18, 1599-1609
10. Manas, E. S.; Unwalla, R. J.; Xu, Z. B.; Malamas, M. S.; Miller, C. P.; Harris, H. A.; Hsiao, C.; Akopian, T.; Hum, W. T.; Malakian, K.; Wolfrom, S.; Bapat, A.; Bhat, R. A.; Stahl, M. L.; Somers, W. S.; Alvarez, J. C. Structure-based design of estrogen receptor-β selective ligands J. Am. Chem. Soc. 2004, 126, 15106-15119
11. Compton, D. R.; Sheng, S.; Carlson, K. E.; Rebacz, N. A.; Lee, I. Y.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Pyrazolo[1,5-a]pyrimidines: estrogen receptor ligands possessing estrogen receptor β antagonist activity J. Med. Chem. 2004, 47, 5872-5893
12. De Angelis, M.; Stossi, F.; Carlson, K. A.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Indazole estrogens: highly selective ligands for the estrogen receptor β J. Med. Chem. 2005, 48, 1132-1144
13. Mewshaw, R. E.; Edsall, R. J., Jr.; Yang, C.; Manas, E. S.; Xu, Z. B.; Henderson, R. A.; Keith, J. C., Jr.; Harris, H. A. ERβ ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERβ selectivity J. Med. Chem. 2005, 48, 3953-3979
14. Norman, B. H.; Dodge, J. A.; Richardson, T. I.; Borromeo, P. S.; Lugar, C. W.; Jones, S. A.; Chen, K.; Wang, Y.; Durst, G. L.; Barr, R. J.; Montrose-Rafizadeh, C.; Osborne, H. E.; Amos, R. M.; Guo, S.; Boodhoo, A.; Krishnan, V. Benzopyrans are selective estrogenreceptor β agonists with novel activity in models of benign prostatic hyperplasia J. Med. Chem. 2006, 49, 6155-6157
15. Gungor, T.; Chen, Y.; Golla, R.; Ma, Z.; Corte, J. R.; Northrop, J. P.; Bin, B.; Dickson, J. K.; Stouch, T.; Zhou, R.; Johnson, S. E.; Seethala, R.; Feyen, J. H. Synthesis and characterization of 3-arylquinazolinone and 3-arylquinazolinethione derivatives as selective estrogen receptor beta modulators J. Med. Chem. 2006, 49, 2440-2455
16. Minutolo, F.; Bertini, S.; Granchi, C.; Marchitiello, T.; Prota, G.; Rapposelli, S.; Tuccinardi, T.; Martinelli, A.; Gunther, J. R.; Carlson, K. E.; Katzenellenbogen, J. A.; Macchia, M. Structural evolutions of salicylaldoximes as selective agonists for estrogen receptor β J. Med. Chem. 2009, 52, 858-867
17. Waibel, M.; De Angelis, M.; Stossi, F.; Kieser, K. J.; Carlson, K. E.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Bibenzyl- and stilbene-core compounds with non-polar linker atom substituents as selective ligands for estrogen receptor beta Eur. J. Med. Chem. 2009, 44, 3412-3424
18. Knox, A. J. S.; Meegan, M. J.; Sobolev, V.; Frost, D.; Zisterer, D. M.; Williams, D. C.; Lloyd, D. G. Target specific virtual screening: optimization of an estrogen receptor screening platform J. Med. Chem. 2007, 50, 5301-5310
19. Knox, A. J.; Yang, Y.; Lloyd, D. G.; Meegan, M. J. Virtual screening of the estrogen receptor Expert Opin. Drug Discovery 2008, 3, 853-866
20. Kawamura, Y.; Ogawa, Y.; Nishimura, T.; Kikuchi, Y.; Nishikawa, J.-i.; Nishihara, T.; Tanamoto, K. Estrogenic activities of UV stabilizers used in food contact plastics and benzophenone derivatives tested by the yeast two-hybrid assay J. Health Sci. 2003, 49, 205-212
21. Shen, J.; Li, W.; Liu, G.; Tang, Y.; Jiang, H. Computational insights into the mechanism of ligand unbinding and selectivity of estrogen receptors J. Phys. Chem. B 2009, 113, 10436-10444
22. Zeng, J.; Li, W.; Zhao, Y.; Liu, G.; Tang, Y.; Jiang, H. Insights into ligand selectivity in estrogen receptor isoforms: molecular dynamics simulations and binding free energy calculations J. Phys. Chem. B 2008, 112, 2719-2726
23. Schrödinger Suite; Schrödinger, LLC, New York, 2008.
24. Lin, Z.; Shen, H.; Huang, J.; Chen, S.; Chen, L.; Chen, J.; Liu, G.; Jiang, H.; Shen, X. Butyl 4-(butyryloxy)benzoate functions as a new selective estrogen receptor beta agonist and induces GLUT4 expression in CHO-K1 cells J. Steroid Biochem. Mol. Biol. 2008, 110, 150-156