Discovering Small-Molecule Estrogen Receptor α/Coactivator Binding Inhibitors: High-Throughput Screening, Ligand Development, and Models for Enhanced Potency

ChemMedChem

Volumn 6, Issue 4, 2011, Pages 654-666

  Sun, Aiming ^a   Moore, Terry W ^b   Gunther, Jillian R ^b   Kim, Mi Sun ^a   Rhoden, Eric ^c   Du, Yuhong ^c   Fu, Haian ^c   Snyder, James P ^a   Katzenellenbogen, John A ^b  

^a EMORY UNIVERSITY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Coactivator binding inhibitors; Estrogen antagonists; Estrogen receptors; Molecular modeling; Structure activity relationships

Indexed keywords

BENZOTHIAZOLE; COACTIVATOR BINDING INHIBITOR; ESTRADIOL; ESTROGEN RECEPTOR; HORMONE RECEPTOR BLOCKING AGENT; PHENYL PIPERAZINE; PHENYL QUINAZOLINONE; PIPERAZINE; QUINAZOLINONE DERIVATIVE; STEROID RECEPTOR COACTIVATOR 1; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; MOLECULAR DOCKING; MOLECULAR INTERACTION; PRIORITY JOURNAL; REPORTER GENE; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CACO-2 CELLS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTROGEN ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; GENES, REPORTER; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGANDS; LUCIFERASES; MODELS, MOLECULAR; NUCLEAR RECEPTOR COACTIVATORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79953036084     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000507     Document Type: Article

References (53)

1. B. S. Katzenellenbogen, J. A. Katzenellenbogen, Breast Cancer Res. 2000, 2, 335-344;
2. J. A. Katzenellenbogen, B. S. Katzenellenbogen, Chem. Biol. 1996, 3, 529-536.
3. E. V. Jensen, V. C. Jordan, Clin. Cancer Res. 2003, 9, 1980-1989;
4. V. C. Jordan, J. Med. Chem. 2003, 46, 1081-1111;
5. V. C. Jordan, J. Med. Chem. 2003, 46, 883-908.
6. A. K. Shiau, D. Barstad, P. M. Loria, L. Cheng, P. J. Kushner, D. A. Agard, G. L. Greene, Cell 1998, 95, 927-937.
7. B. R. Henke, D. Heyer, Curr. Opin. Drug Discovery Dev. 2005, 8, 437-448.
8. T. W. Moore, J. A. Katzenellenbogen, Annu. Rep. Med. Chem. 2009, 44, 443-457;
9. D. Shao, T. J. Berrodin, E. Manas, D. Hauze, R. Powers, A. Bapat, D. Gonder, R. C. Winneker, D. E. Frail, J. Steroid Biochem. Mol. Biol. 2004, 88, 351-360;
10. T. W. Moore, J. R. Gunther, J. A. Katzenellenbogen, Bioconjugate Chem. 2010, 21, 1880-1889;
11. T. W. Moore, C. G. Mayne, J. A. Katzenellenbogen, Mol. Endocrinol. 2010, 24, 683-695;
12. A. A. Parent, J. R. Gunther, J. A. Katzenellenbogen, J. Med. Chem. 2008, 51, 6512-6530.
13. A. K. Shiau, D. Barstad, J. T. Radek, M. J. Meyers, K. W. Nettles, B. S. Katzenellenbogen, J. A. Katzenellenbogen, D. A. Agard, G. L. Greene, Nat. Struct. Biol. 2002, 9, 359-364;
14. J. Becerril, A. D. Hamilton, Angew. Chem. 2007, 119, 4555-4557; Angew. Chem. Int. Ed. 2007, 46, 4471-4473;
15. A. Warnmark, E. Treuter, J.-A. Gustafsson, R. E. Hubbard, A. M. Brzozowski, A. C. W. Pike, J. Biol. Chem. 2002, 277, 21862-21868.
16. D. M. Huryn, N. D. P. Cosford, Annu. Rep. Med. Chem. 2007, 42, 401-416.
17. J. R. Gunther, Y. Du, E. Rhoden, I. Lewis, B. Revennaugh, T. W. Moore, S. H. Kim, R. Dingledine, H. Fu, J. A. Katzenellenbogen, J. Biomol. Screening 2009, 14, 181-193.
18. T. R. Geistlinger, R. K. Guy, J. Am. Chem. Soc. 2003, 125, 6852-6853;
19. A. K. Galande, K. S. Bramlett, J. O. Trent, T. P. Burris, J. L. Wittliff, A. F. Spatola, ChemBioChem 2005, 6, 1991-1998;
20. A. L. Rodriguez, A. Tamrazi, M. L. Collins, J. A. Katzenellenbogen, J. Med. Chem. 2004, 47, 600-611.
21. H. Sigmund, W. Pfleiderer, Helv. Chim. Acta 2003, 86, 2299-2334;
22. J. Teppema, L. B. Sebbrell, J. Am. Chem. Soc. 1927, 49, 1779-1785.
23. A. Naya, K. Kobayashi, M. Ishikawa, K. Ohwaki, T. Saeki, K. Noguchi, N. Ohtake, Bioorg. Med. Chem. Lett. 2001, 11, 1219-1223.
24. J. Sun, M. J. Meyers, B. E. Fink, R. Rajendran, J. A. Katzenellenbogen, B. S. Katzenellenbogen, Endocrinology 1999, 140, 800-804.
25. A. L. LaFrate, J. R. Gunther, K. E. Carlson, J. A. Katzenellenbogen, Bioorg. Med. Chem. 2008, 16, 10075-10084.
26. C. R. Guimarães, M. Cardozo, J. Chem. Inf. Model. 2008, 48, 958-970;
27. N. Huang, C. Kalyanaraman, J. J. Irwin, M. P. Jacobson, J. Chem. Inf. Model. 2006, 46, 243-253.
28. W. Sherman, T. Day, M. P. Jacobson, R. A. Friesner, R. Farid, J. Med. Chem. 2006, 49, 534-553.
29. W. L. Jorgensen, Science 2004, 303, 1813-1818.
30. A. Sun, J.-J. Yoon, Y. Yin, A. Prussia, Y. Yang, J. Min, R. K. Plemper, J. P. Snyder, J. Med. Chem. 2008, 51, 3731-3741.
31. P. A. Borea, A. Dalpiaz, K. Varani, P. Gilli, G. Gilli, Biochem. Pharmacol. 2000, 60, 1549-1556;
32. P. Gilli, G. Gilli, P. A. Borea, K. Varani, A. Scatturin, A. Dalpiaz, J. Med. Chem. 2005, 48, 2026-2035.
33. R. Abel, T. Young, R. Farid, B. J. Berne, R. A. Friesner, J. Am. Chem. Soc. 2008, 130, 2817-2831;
34. E. Freire, Drug Discovery Today 2008, 13, 869-874;
35. T. Young, R. Abel, B. Kim, B. J. Berne, R. A. Friesner, Proc. Natl. Acad. Sci. USA 2007, 104, 808-813;
36. R. A. Friesner, R. B. Murphy, M. P. Repasky, L. L. Frye, J. R. Greenwood, T. A. Halgren, P. C. Sanschagrin, D. T. Mainz, J. Med. Chem. 2006, 49, 6177-6196.
37. J. D. Dunitz, Science 1994, 264, 670;
38. L. Zhang, J. Hermans, Proteins: Struct., Funct., Genet. 1996, 24, 433-438.
39. K.J. Bowers, E. Chow, H. Xu, R.O. Dror, M.P. Eastwood, B.A. Gregersen, J.L. Klepeis, I. Kolossvary, M.A. Moraes, F.D. Sacerdoti, J.K. Salmon, Y. Shan, D.E. Shaw in Proc. ACM/IEEE Conference on Supercomputing (SC06), Tampa, Florida (USA), 2006.
40. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
41. C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 23, 3-25.
42. J. A. Wells, C. L. McClendon, Nature 2007, 450, 1001-1009.
43. M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2494;
44. M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2494;
45. P. L. Toogood, J. Med. Chem. 2002, 45, 1543-1558.
46. D. M. Rosenbaum, V. Cherezov, M. A. Hanson, S. G. Rasmussen, F. S. Thian, T. S. Kobilka, H. J. Choi, X. J. Yao, W. I. Weis, R. C. Stevens, B. K. Kobilka, Science 2007, 318, 1266-1273.
47. L. A. Arnold, E. Estebanez-Perpina, M. Togashi, N. Jouravel, A. Shelat, A. C. McReynolds, E. Mar, P. Nguyen, J. D. Baxter, R. J. Fletterick, P. Webb, R. K. Guy, J. Biol. Chem. 2005, 280, 43048-43055.
48. L. A. Arnold, A. Kosinski, E. Estebanez-Perpina, R. J. Fletterick, R. K. Guy, J. Med. Chem. 2007, 50, 5269-5280;
49. J. Y. Hwang, L. A. Arnold, F. Zhu, A. Kosinski, T. J. Mangano, V. Setola, B. L. Roth, R. K. Guy, J. Med. Chem. 2009, 52, 3892-3901.
50. K. Zhu, M. R. Shirts, R. A. Friesner, J. Chem. Theory Comput. 2007, 3, 2108-2119.
51. P. D. Lyne, M. L. Lamb, J. C. Saeh, J. Med. Chem. 2006, 49, 4805-4808.
52. M. O. Jensen, R. O. Dror, H. Xu, D. W. Borhani, I. T. Arkin, M. P. Eastwood, D. E. Shaw, Proc. Natl. Acad. Sci. USA 2008, 105, 14430-14435;
53. P. Maragakis, K. Lindorff-Larsen, M. P. Eastwood, R. O. Dror, J. L. Klepeis, I. T. Arkin, M. O. Jensen, H. Xu, N. Trbovic, R. A. Friesner, A. G. Palmer III, D. E. Shaw, J. Phys. Chem. B 2008, 112, 6155-6158.