Steroidal bivalent ligands for the estrogen receptor: Design, synthesis, characterization and binding affinities

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 10, 2009, Pages 3528-3535

  LaFrate, Andrew L ^a   Carlson, Kathryn E ^a   Katzenellenbogen, John A ^a  

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

Author keywords

Bivalent ligand; Dimer; Estrogen receptor; Multivalent ligand

Indexed keywords

17ALPHA PHENYLETHINYLESTRADIOL; BUTANEDIOL; DIMER; ESTROGEN RECEPTOR; ETHINYLESTRADIOL; LIGAND; PROPANEDIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOMETRY;

DIMERIZATION; DRUG DESIGN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ETHINYL ESTRADIOL; LIGANDS;

EID: 65349120121     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.016     Document Type: Article

References (37)

1. Ballet S., Pietsch M., and Abell A.D. Protein Pept. Lett. 15 (2008) 668
2. Huskens J. Curr. Opin. Chem. Biol. 10 (2006) 537
3. Kiessling L.L., Gestwicki J.E., and Strong L.E. Angew. Chem., Int. Ed. 45 (2006) 2348
4. Krishnamurthy V.M., Semetey V., Bracher P.J., Shen N., and Whitesides G.M. J. Am. Chem. Soc. 129 (2007) 1312
5. Messer Jr. W.S. Curr. Pharm. Des. 10 (2004) 2015
6. Schamel W.W.A., and Reth M. Adv. Exp. Med. Biol. 640 (2008) 64
7. Zhang A., Liu Z., and Kan Y. Curr. Top. Med. Chem. 7 (2007) 343
8. Gestwicki J.E., Cairo C.W., Strong L.E., Oetjen K.A., and Kiessling L.L. J. Am. Chem. Soc. 124 (2002) 14922
9. Bergmann K.E., Wooge C.H., Carlson K.E., Katzenellenbogen B.S., and Katzenellenbogen J.A. J. Steroid Biochem. Mol. Biol. 49 (1994) 139
10. Osella D., Dutto G., Nervi C., McGlinchey M.J., Vessieres A., and Jaouen G. J. Organomet. Chem. 533 (1997) 97
11. Groleau S., Nault J., Lepage M., Couture M., Dallaire N., Berube G., and Gaudreault R.-C. Bioorg. Chem. 27 (1999) 383
12. Berube G., Rabouin D., Perron V., N'Zemba B., Gaudreault R.-C., Parent S., and Asselin E. Steroids 71 (2006) 911
13. Rabouin D., Perron V., N'Zemba B., Gaudreault R.-C., and Berube G. Bioorg. Med. Chem. Lett. 13 (2003) 557
14. Brzozowski A.M., Pike A.C.W., Dauter Z., Hubbard R.E., Bonn T., Engstrom O., Ohman L., Greene G.L., Gustafsson J.-A., and Carlquist M. Nature 389 (1997) 753
15. Anstead G.M., Carlson K.E., and Katzenellenbogen J.A. Steroids 62 (1997) 268
16. 2.
17. Pomper M.G., VanBrocklin H., Thieme A.M., Thomas R.D., Kiesewetter D.O., Carlson K.E., Mathias C.J., Welch M.J., and Katzenellenbogen J.A. J. Med. Chem. 33 (1990) 3143
18. Kim S.H., and Katzenellenbogen J.A. Angew. Chem., Int. Ed. 45 (2006) 7243
19. Salman M., Reddy B.R., Delgado P., Stotter P.L., Fulcher L.C., and Chamness G.C. Steroids 56 (1991) 375
20. El Amouri H., Vessieres A., Vichard D., Top S., Gruselle M., and Jaouen G. J. Med. Chem. 35 (1992) 3130
21. Lo K.K.-W., Zhang K.Y., Chung C.-K., and Kwok K.Y. Chem. Eur. J. 13 (2007) 7110
22. Top S., El Hafa H., Vessieres A., Quivy J., Vaissermann J., Hughes D.W., McGlinchey M.J., Mornon J.-P., Thoreau E., and Jaouen G. J. Am. Chem. Soc. 117 (1995) 8372
23. Gabano E., Cassino C., Bonetti S., Prandi C., Colangelo D., Ghiglia A., and Osella D. Org. Biomol. Chem. 3 (2005) 3531
24. Purohit A., Wyatt J., Hynd G., Wright J., El-Shafey A., Swamy N., Ray R., and Jones G.B. Tetrahedron Lett. 42 (2001) 8579
25. Nettles K.W., Bruning J.B., Gil G., O'Neill E.E., Nowak J., Hughs A., Kim Y., DeSombre E.R., Dilis R., Hanson R.N., Joachimiak A., and Greene G.L. EMBO Rep. 8 (2007) 563
26. Arterburn J.B., Rao K.V., and Perry M.C. Tetrahedron Lett. 41 (2000) 839
27. Kreuzer H.J., Wang R.L.C., and Grunze M. New J. Phys. 1 (1999) 21 1
28. Sundaralingam M. Nature 217 (1968) 35
29. Wiberg K.B., Murcko M.A., Laidig K.E., and MacDougall P.J. J. Phys. Chem. 94 (1990) 6956
30. Wolfe S. Acc. Chem. Res. 5 (1972) 102
31. Chinchilla R., and Najera C. Chem. Rev. 107 (2007) 874
32. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
33. Elangovan A., Wang Y.-H., and Ho T.-I. Org. Lett. 5 (2003) 1841
34. Knuf E.C., Jiang J.-K., and Gin M.S. J. Org. Chem. 68 (2003) 9166
35. Carlson K.E., Choi I., Gee A., Katzenellenbogen B.S., and Katzenellenbogen J.A. Biochemistry 36 (1997) 14897
36. Katzenellenbogen J.A., Johnson Jr. H.J., and Myers H.N. Biochemistry 12 (1973) 4085
37. Pike A.C.W., Brzozowski A.M., Hubbard R.E., Bonn T., Thorsell A.-G., Engstrom O., Ljunggren J., Gustafsson J.-A., and Carlquist M. Embo J. 18 (1999) 4608