Structure of estradiol metal chelate and estrogen receptor complex: The basis for designing a new class of selective estrogen receptor modulators

Journal of Medicinal Chemistry

Volumn 54, Issue 10, 2011, Pages 3575-3580

  Li, Min Jun ^a   Greenblatt, Harry M ^a   Dym, Orly ^a   Albeck, Shira ^a   Pais, Adi ^a   Gunanathan, Chidambaram ^a   Milstein, David ^a   Degani, Hadassa ^a   Sussman, Joel L ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AFIMOXIFENE; EPTAPIRONE; ESTRADIOL; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR ALPHA; EUROPIUM; FULVESTRANT; METAL CHELATE; METAL COMPLEX; N BUTYL 11 (3,17BETA DIHYDROXYESTRA 1,3,5(10) TRIEN 7ALPHA YL) N METHYLUNDECANAMIDE; RALOXIFENE; SELECTIVE ESTROGEN RECEPTOR MODULATOR;

ARTICLE; BREAST CANCER; COMPLEX FORMATION; CRYSTAL STRUCTURE; DIMERIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; LIGAND BINDING; NONHUMAN; PROTEIN DOMAIN; THREE DIMENSIONAL IMAGING;

CHELATING AGENTS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; EUROPIUM; HUMANS; LIGANDS; METALS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SELECTIVE ESTROGEN RECEPTOR MODULATORS;

EID: 79957708369     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200192y     Document Type: Article

References (36)

1. Deroo, B. J.; Korach, K. S. Estrogen receptors and human disease J. Clin. Invest. 2006, 116, 561-570 (Pubitemid 43326860)
2. Heldring, N.; Pike, A.; Andersson, S.; Matthews, J.; Cheng, G.; Hartman, J.; Tujague, M.; Strom, A.; Treuter, E.; Warner, M.; Gustafsson, J. A. Estrogen receptors: How do they signal and what are their targets Physiol. Rev. 2007, 87, 905-931 (Pubitemid 47084672)
3. McDonnell, D. P.; Ching-Yi, C.; John, D. N. Capitalizing on the Complexities of Estrogen Receptor Pharmacology in the Quest for the Perfect SERM Ann. N. Y. Acad. Sci. 2001, 949, 16-35 (Pubitemid 34059958)
4. Ott, I.; Gust, R. Preclinical and clinical studies on the use of platinum complexes for breast cancer treatment Anticancer Agents Med. Chem. 2007, 7, 95-110 (Pubitemid 46062407)
5. Gunanathan, C.; Pais, A.; Furman-Haran, E.; Seger, D.; Eyal, E.; Mukhopadhyay, S.; Ben-David, Y.; Leitus, G.; Cohen, H.; Vilan, A.; Degani, H.; Milstein, D. Water-soluble contrast agents targeted at the estrogen receptor for molecular magnetic resonance imaging Bioconjugate Chem. 2007, 18, 1361-1365 (Pubitemid 47464039)
6. Pike, A. C.; Brzozowski, A. M.; Walton, J.; Hubbard, R. E.; Thorsell, A. G.; Li, Y. L.; Gustafsson, J. A.; Carlquist, M. Structural insights into the mode of action of a pure antiestrogen Structure 2001, 9, 145-153 (Pubitemid 32215278)
7. el Amouri, H.; Vessieres, A.; Vichard, D.; Top, S.; Gruselle, M.; Jaouen, G. Syntheses and affinities of novel organometallic-labeled estradiol derivatives: a structure-affinity relationship J. Med. Chem. 1992, 35, 3130-3135
8. Gabano, E.; Cassino, C.; Bonetti, S.; Prandi, C.; Colangelo, D.; Ghiglia, A.; Osella, D. Synthesis and characterisation of estrogenic carriers for cytotoxic Pt(II) fragments: biological activity of the resulting complexes Org. Biomol. Chem. 2005, 3, 3531-3539 (Pubitemid 41508916)
9. Lee, J.; Burdette, J. E.; MacRenaris, K. W.; Mustafi, D.; Woodruff, T. K.; Meade, T. J. Rational Design, Synthesis, and Biological Evaluation of Progesterone-Modified MRI Contrast Agents Chem. Biol. 2007, 14, 824-834 (Pubitemid 47086379)
10. Brzozowski, A. M.; Pike, A. C.; Dauter, Z.; Hubbard, R. E.; Bonn, T.; Engstrom, O.; Ohman, L. G. G. L.; Gustafsson, J. A.; Carlquist, M. Molecular basis of agonism and antagonism in the oestrogen receptor Nature 1997, 389, 753-758 (Pubitemid 27458965)
11. Gee, A. C.; Katzenellenbogen, J. A. Probing conformational changes in the estrogen receptor: evidence for a partially unfolded intermediate facilitating ligand binding and release Mol. Endocrinol. 2001, 15, 421-428 (Pubitemid 32221919)
12. Tamrazi, A.; Carlson, K. E.; Katzenellenbogen, J. A. Molecular sensors of estrogen receptor conformations and dynamics Mol. Endocrinol. 2003, 17, 2593-2602 (Pubitemid 37542220)
13. Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 1998, 95, 927-937 (Pubitemid 29019045)
14. Heldring, N.; Pawson, T.; McDonnell, D.; Treuter, E.; Gustafsson, J. A.; Pike, A. C. Structural insights into corepressor recognition by antagonist-bound estrogen receptors J. Biol. Chem. 2007, 282, 10449-10455 (Pubitemid 47096592)
15. Egner, U.; Heinrich, N.; Ruff, M.; Gangloff, M.; Mueller-Fahrnow, A.; Wurtz, J. M. Different ligands-different receptor conformations: Modeling of the hER alpha LBD in complex with agonists and antagonists Med. Res. Rev. 2001, 21, 523-539 (Pubitemid 32959241)
16. Nettles, K. W.; Bruning, J. B.; Gil, G.; O?Neill, E. E.; Nowak, J.; Guo, Y.; Kim, Y.; DeSombre, E. R.; Dilis, R.; Hanson, R. N.; Joachimiak, A.; Greene, G. L. Structural plasticity in the oestrogen receptor ligand-binding domain EMBO Rep. 2007, 8, 563-568 (Pubitemid 47214710)
17. Suino-Powell, K.; Xu, Y.; Zhang, C.; Tao, Y. G.; Tolbert, W. D.; Simons, S. S., Jr.; Xu, H. E. Doubling the size of the glucocorticoid receptor ligand binding pocket by deacylcortivazol Mol. Cell. Biol. 2008, 28, 1915-1923 (Pubitemid 351342623)
18. Chrencik, J. E.; Orans, J.; Moore, L. B.; Xue, Y.; Peng, L.; Collins, J. L.; Wisely, G. B.; Lambert, M. H.; Kliewer, S. A.; Redinbo, M. R. Structural disorder in the complex of human pregnane X receptor and the macrolide antibiotic rifampicin Mol. Endocrinol. 2005, 19, 1125-1134 (Pubitemid 40594113)
19. Celik, L.; Lund, J. D.; Schiott, B. Conformational dynamics of the estrogen receptor alpha: molecular dynamics simulations of the influence of binding site structure on protein dynamics Biochemistry 2007, 46, 1743-1758 (Pubitemid 46290551)
20. Sonoda, M. T.; Martinez, L.; Webb, P.; Skaf, M. S.; Polikarpov, I. Ligand dissociation from estrogen receptor is mediated by receptor dimerization: Evidence from molecular dynamics simulations Mol. Endocrinol. 2008, 22, 1565-1578 (Pubitemid 351920391)
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. Burendahl, S.; Danciulescu, C.; Nilsson, L. Ligand unbinding from the estrogen receptor: A computational study of pathways and ligand specificity Proteins 2009, 77, 842-856
23. Hegy, G. B.; Shackleton, C. H.; Carlquist, M.; Bonn, T.; Engstrom, O.; Sjoholm, P.; Witkowska, H. E. Carboxymethylation of the human estrogen receptor ligand-binding domain-estradiol complex: HPLC/ESMS peptide mapping shows that cysteine 447 does not react with iodoacetic acid Steroids 1996, 61, 367-373
24. Leduc, A. M.; Trent, J. O.; Wittliff, J. L.; Bramlett, K. S.; Briggs, S. L.; Chirgadze, N. Y.; Wang, Y.; Burris, T. P.; Spatola, A. F. Helix-stabilized cyclic peptides as selective inhibitors of steroid receptor-coactivator interactions Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11273-11278 (Pubitemid 37205925)
25. Goldstein, S. W.; Bordner, J.; Hoth, L. R.; Geoghegan, K. F. Chemical and biochemical issues related to X-ray crystallography of the ligand-binding domain of estrogen receptor alpha Bioconjugate Chem. 2001, 12, 406-413 (Pubitemid 32464187)
26. McPherson, A.; Cudney, B. Searching for silver bullets: An alternative strategy for crystallizing macromolecules J. Struct. Biol. 2006, 156, 387-406 (Pubitemid 44751480)
27. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode Methods Enzymol. 1997, 276, 307-326 (Pubitemid 27085611)
28. McCoy, A. J. Solving structures of protein complexes by molecular replacement with Phaser Acta Crystallogr., Sect. D: Biol. Crystallogr. 2007, 63, 32-41
29. The CCP4 suite: Programs for protein crystallography. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1994, 50, 760-763.
30. Moriarty, N. W.; Grosse-Kunstleve, R. W.; Adams, P. D. electronic Ligand Builder and Optimization Workbench (eLBOW): A tool for ligand coordinate and restraint generation Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, 65, 1074-1080
31. Adams, P. D.; Afonine, P. V.; Bunkoczi, G.; Chen, V. B.; Davis, I. W.; Echols, N.; Headd, J. J.; Hung, L.-W.; Kapral, G. J.; Grosse-Kunstleve, R. W.; McCoy, A. J.; Moriarty, N. W.; Oeffner, R.; Read, R. J.; Richardson, D. C.; Richardson, J. S.; Terwilliger, T. C.; Zwart, P. H. PHENIX: A comprehensive Python-based system for macromolecular structure solution Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 213-221
32. Emsley, P.; Cowtan, K. Coot: Model-building tools for molecular graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132 (Pubitemid 41742764)
33. Painter, J.; Merritt, E. A. Optimal description of a protein structure in terms of multiple groups undergoing TLS motion Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 439-450
34. Chen, V. B.; Arendall, W. B., III; Headd, J. J.; Keedy, D. A.; Immormino, R. M.; Kapral, G. J.; Murray, L. W.; Richardson, J. S.; Richardson, D. C. MolProbity: All-atom structure validation for macromolecular crystallography Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 12-21
35. Anstead, G. M.; Carlson, K. E.; Katzenellenbogen, J. A. The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site Steroids 1997, 62, 268-303 (Pubitemid 27114399)
36. Gangloff, M.; Ruff, M.; Eiler, S.; Duclaud, S.; Wurtz, J. M.; Moras, D. Crystal structure of a mutant hERalpha ligand-binding domain reveals key structural features for the mechanism of partial agonism J. Biol. Chem. 2001, 276, 15059-15065