Nonsteroidal bivalent estrogen ligands: An application of the bivalent concept to the estrogen receptor

ACS Chemical Biology

Volumn 8, Issue 4, 2013, Pages 707-715

  Shan, Min ^a   Carlson, Kathryn E ^b   Bujotzek, Alexander ^c   Wellner, Anja ^d   Gust, Ronald ^d   Weber, Marcus ^c   Katzenellenbogen, John A ^b   Haag, Rainer ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

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

^c ZUSE INSTITUTE BERLIN   (Germany)

^d UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

DIETHYLSTILBESTROL; DIMER; ESTROGEN RECEPTOR; HYDROXYTAMOXIFEN; LIGAND; NONSTEROIDAL BIVALENT ESTROGEN LIGAND; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; COMPARATIVE STUDY; CONFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG DESIGN; HORMONAL THERAPY; HYDROGEN BOND; LIGAND BINDING; PRIORITY JOURNAL; RECEPTOR AFFINITY; THERMODYNAMICS;

CELL LINE; COMPUTER SIMULATION; ESTROGENS; HUMANS; LIGANDS; MODELS, MOLECULAR; RECEPTORS, ESTROGEN; THERMODYNAMICS;

EID: 84876571899     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb3006243     Document Type: Article

References (50)

1. Avendaño, C. and Menéndez, J. C. (2008) Anticancer Drugs That Inhibit Hormone Action. In Medicinal Chemistry of Anticancer Drugs, pp 53-92, Elsevier, Amsterdam.
2. Weatherman, R. V. (2008) Untangling the Estrogen Receptor Web: Tools to Selectively Study Estrogen-binding Receptors. In Nuclear Receptors as Drug Targets (Ottow, E. and Weinmann, H., Eds.), pp 47-64, Wiley-VCH, Weinheim.
3. Jordan, V. C. and Furr, B. J. A. (2002) An Introduction to the Regulation of Sex Steroids for the Treatment of Cancer. In Hormone Therapy in Breast and Prostate Cancer, pp 1-14, Humana Press, Totowa.
4. Mangelsdorf, D. J., Thummel, C., Beato, M., Herrlich, P., Schutz, G., Umesono, K., Blumberg, B., Kastner, P., Mark, M., Chambon, P., and Evans, R. M. (1995) The nuclear receptor superfamily: The second decade Cell 83, 835-839
5. Olefsky, J. M. (2001) Nuclear receptor minireview series J. Biol. Chem. 276, 36863-36864
6. Couse, J. F., Lindzey, J., Grandien, K., Gustafsson, J. A., and Korach, K. S. (1997) Tissue distribution and quantitative analysis of estrogen receptor-α (ERα) and estrogen receptor-β (ERβ) messenger ribonucleic acid in the wild-type and ER alpha-knockout mouse Endocrinology 138, 4613-4621
7. Grese, T. A., Sluka, J. P., Bryant, H. U., Cullinan, G. J., Glasebrook, A. L., Jones, C. D., Matsumoto, K., Palkowitz, A. D., Sato, M., Termine, J. D., Winter, M. A., Yang, N. N., and Dodge, J. A. (1997) Molecular determinants of tissue selectivity in estrogen receptor modulators Proc. Natl. Acad. Sci. U.S.A. 94, 14105-14110
8. Jordan, V. C. (2003) Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions J. Med. Chem. 46, 883-908
9. Jordan, V. C. (2003) Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 2. Clinical considerations and new agents J. Med. Chem. 46, 1081-1111
10. Minutolo, F., Macchia, M., Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (2011) Estrogen receptor β ligands: Recent advances and biomedical applications Med. Res. Rev. 31, 364-442
11. Bertini, S., De Cupertinis, A., Granchi, C., Bargagli, B., Tuccinardi, T., Martinelli, A., Macchia, M., Gunther, J. R., Carlson, K. E., Katzenellenbogen, J. A., and Minutolo, F. (2011) Selective and potent agonists for estrogen receptor beta derived from molecular refinements of salicylaldoximes Eur. J. Med. Chem. 46, 2453-2462
12. Katzenellenbogen, J. A. (2011) The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: Addressing the "Core Issue" in the Design of Estrogen Receptor Ligands J. Med. Chem. 54, 5271-5282
13. Fisher, B., Costantino, J. P., Wickerham, D. L., Redmond, C. K., Kavanah, M., Cronin, W. M., Vogel, V., Robidoux, A., Dimitrov, N., Atkins, J., Daly, M., Wieand, S., Tan-Chiu, E., Ford, L., and Wolmark, N. (1998) Tamoxifen for prevention of breast cancer: Report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study J. Natl. Cancer Inst. 90, 1371-1388
14. Parent, A. A., Gunther, J. R., and Katzenellenbogen, J. A. (2008) Blocking estrogen signaling after the hormone: Pyrimidine-core inhibitors of estrogen receptor-coactivator binding J. Med. Chem. 51, 6512-6530
15. Gunther, J. R., Moore, T. W., Cottins, M. L., and Katzenellenbogen, J. A. (2008) Amphipathic benzenes are designed inhibitors of the estrogen receptor α/steroid receptor coactivator interaction ACS Chem. Biol. 3, 282-286
16. Phillips, C., Roberts, L. R., Schade, M., Bazin, R., Bent, A., Davies, N. L., Moore, R., Pannifer, A. D., Pickford, A. R., Prior, S. H., Read, C. M., Scott, A., Brown, D. G., Xu, B., and Irving, S. L. (2011) Design and structure of stapled peptides binding to estrogen receptors J. Am. Chem. Soc. 133, 9696-9699
17. Brandt, M. E. and Vickery, L. E. (1997) Cooperativity and dimerization of recombinant human estrogen receptor hormone-binding domain J. Biol. Chem. 272, 4843-4849
18. Tamrazi, A., Carlson, K. E., Daniels, J. R., Hurth, K. M., and Katzenellenbogen, J. A. (2002) Estrogen receptor dimerization: Ligand binding regulates dimer affinity and dimer dissociation rate Mol. Endocrinol. 16, 2706-2719
19. Bergmann, K. E., Wooge, C. H., Carlson, K. E., Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (1994) Bivalent ligands as probes of estrogen-receptor action J. Steroid Biochem. Mol. Biol. 49, 139-152
20. Groleau, S., Nault, J., Lepage, M., Couture, M., Dallaire, N., Bérubé, G., and Gaudreault, R. C. (1999) Synthesis and preliminary in vitro cytotoxic activity of new triphenylethylene dimers Bioorg. Chem. 27, 383-394
21. 2-symmetric 17β-estradiol dimers Bioorg. Med. Chem. Lett. 13, 557-560
22. Bérubé, G., Rabouina, D., Perron, V., N'Zemba, B., Gaudreault, R. C., Parenta, S., and Asselin, E. E. (2006) Synthesis of unique 17β-estradiol homo-dimers, estrogen receptors binding affinity evaluation and cytocidal activity on breast, intestinal and skin cancer cell lines Steroids 71, 911-921
23. LaFrate, A. L., Carlson, K. E., and Katzenellenbogen, J. A. (2009) Steroidal bivalent ligands for the estrogen receptor: Design, synthesis, characterization and binding affinities Bioorg. Med. Chem. 17, 3528-3535
24. Wendlandt, A. E., Yelton, S. M., Lou, D. Y., Watt, D. S., and Noonan, D. J. (2010) Synthesis and functional analysis of novel bivalent estrogens Steroids 75, 825-833
25. Abendroth, F., Bujotzek, A., Shan, M., Haag, R., Weber, M., and Seitz, O. (2011) DNA-controlled bivalent presentation of ligands for the estrogen receptor Angew. Chem., Int. Ed. 50, 8592-8596
26. Shan, M., Bujotzek, A., Abendroth, F., Wellner, A., Gust, R., Seitz, O., Weber, M., and Haag, R. (2011) Conformational analysis of bivalent estrogen receptor ligands: From intramolecular to intermolecular binding ChemBioChem 12, 2587-2598
27. Bertozzi, C. R. and Kiessling, L. L. (2001) Chemical glycobiology Science 291, 2357-2364
28. Gestwicki, J. E., Cairo, C. W., Strong, L. E., Oetjen, K. A., and Kiessling, L. L. (2002) Influencing receptor-ligand binding mechanisms with multivalent ligand architecture J. Am. Chem. Soc. 124, 14922-14933
29. Mammen, M., Choi, S. K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 37, 2754-2794
30. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2006) Synthetic multivalent ligands as probes of signal transduction Angew. Chem., Int. Ed. 45, 2348-2368
31. Schwefel, D., Maierhofer, C., Beck, J. G., Seeberger, S., Diederichs, K., Möller, H. M., Welte, W., and Wittmann, V. (2010) Structural basis of multivalent binding to wheat germ agglutinin J. Am. Chem. Soc. 132, 8704-8719
32. Testa, B., Jenner, P., Kilpatrick, G. J., Eltayar, N., Vandewaterbeemd, H., and Marsden, C. D. (1987) Do Thermodynamic studies provide information on both the binding to and the activation of dopaminergic and other receptors Biochem. Pharmacol. 36, 4041-4046
33. 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., and Greene, G. L. (2007) Structural plasticity in the oestrogen receptor ligand-binding domain EMBO Rep. 8, 563-568
34. Shiau, A. K., Barstad, D., Loria, P. M., Cheng, L., Kushner, P. J., Agard, D. A., and Greene, G. L. (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 95, 927-937
35. Pike, A. C. W., Brzozowski, A. M., Hubbard, R. E., Bonn, T., Thorsell, A. G., Engstrom, O., Ljunggren, J., Gustafsson, J. K., and Carlquist, M. (1999) Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist EMBO J. 18, 4608-4618
36. Winkler, V. W., Nyman, M. A., and Egan, R. S. (1971) Diethylstilbestrol cis-trans isomerization and estrogen activity of diethylstilbestrol isomers Steroids 17, 197-207
37. Katzenellenbogen, J. A., Johnson, H. J., and Myers, H. N. (1973) Photoaffinity labels for estrogen binding proteins of rat uterus Biochemistry 12, 4085-4092
38. Carlson, K. E., Choi, I., Gee, A., Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (1997) Altered ligand binding properties and enhanced stability of a constitutively active estrogen receptor: Evidence that an open pocket conformation is required for ligand interaction Biochemistry 36, 14897-14905
39. Waibel, M., De Angelis, M., Stossi, F., Kieser, K. J., Carlson, K. E., Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (2009) Bibenzyl- and stilbene-core compounds with non-polar linker atom substituents as selective ligands for estrogen receptor beta Eur. J. Med. Chem. 44, 3412-3424
40. Williams, A. B., Weiser, P. T., Hanson, R. N., Gunther, J, R., and Katzenellenbogen, J. A. (2009) Synthesis of biphenyl proteomimetics as estrogen receptor-α coactivator binding inhibitors Org. Lett. 11, 5370-5373
41. Wang, Y., Chirgadze, N. Y., Briggs, S. L., Khan, S., Jensen, E. V., and Burris, T. P. (2006) A second binding site for hydroxytamoxifen within the coactivator-binding groove of estrogen receptor β Proc. Natl. Acad. Sci. U.S.A. 103, 9908-9911
42. Robertson, D. W., Katzenellenbogen, J. A., Long, D. J., Rorke, E. A., and Katzenellenbogen, B. S. (1982) Tamoxifen anti-estrogens-A comparison of the activity, pharmacokinetics, and metabolic-Activation of the cis-isomer and trans-isomer of tamoxifen J. Steroid Biochem. Mol. Biol. 16, 1-13
43. Katzenellenbogen, J. A., Carlson, K. E., and Katzenellenbogen, B. S. (1985) Facile geometric isomerization of phenolic non-steroidal estrogens and antiestrogens: limitations to the interpretation of experiments characterizing the activity of individual isomers J. Steroid Biochem. 22, 589-596
44. Kim, S. and Katzenellenbogen, J. A. (2000) Triarylethylene bisphenols with a novel cycle are ligands for the estrogen receptor Bioorg. Med. Chem. 8, 785-793
45. Li, M. J., Greenblatt, H. M., Dym, O., Albeck, S., Pais, A., Gunanathan, C., Milstein, D., Degani, H., and Sussman, J. L. (2011) Structure of estradiol metal chelate and estrogen receptor complex: The basis for designing a new class of selective estrogen receptor modulators J. Med. Chem. 54, 3575-3580
46. Krishnamurthy, V. M., Estroff, L. A., and Whitesides, G. M. (2006) Multivalency in Ligand Design. In Fragment-based Approaches in Drug Discovery (Jahnke, W. and Erlanson, D. A., Eds.), pp 11-54, Wiley-VCH, Weinheim.
47. Bujotzek, A., Shan, M., Haag, R., and Weber, M. (2011) Towards a rational spacer design for bivalent inhibition of estrogen receptor J. Comput. Aided Mol. Des. 25, 253-262
48. Kjellander, R. and Florin, E. (1981) Water structure and changes in thermal stability of the system poly(ethylene oxide)-water J. Chem. Soc., Faraday Trans. 1 77, 2053-2077
49. LaFrate, A. L. (2008) Bivalent Ligands for the Estrogen Receptor. In Synthesis and Biological Evaluation of Coactivator Binding Inhibitors and Bivalent Ligands for the Estrogen Receptor, pp 60-116, University of Illinois at Urbana-Champaign, Urbana.
50. Sun, A., Moore, T. W., Gunther, J. R., Kim, M., Rhoden, E., Du, Y., Fu, H., Snyder, J. P., and Katzenellenbogen, J. A. (2011) Discovering small-molecule estrogen receptor α/coactivator binding inhibitors: high-throughput screening, ligand development, and models for enhanced potency ChemMedChem 6, 654-666