Structural basis for agonism and antagonism for a set of chemically related progesterone receptor modulators

Journal of Biological Chemistry

Volumn 286, Issue 40, 2011, Pages 35079-35086

  Lusher, Scott J ^a   Raaijmakers, Hans C A ^a   Vu Pham, Diep ^a   Dechering, Koen ^a   Lam, Tsang Wai ^a   Brown, Angus R ^b   Hamilton, Niall M ^b   Nimz, Olaf ^b   Bosch, Rolien ^a   McGuire, Ross ^a   Oubrie, Arthur ^a   De Vlieg, Jacob ^a,c  

^a DMPK   (Netherlands)

^b MSD   (United Kingdom)

^c RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING MODES; DIVERGENT SERIES; PROGESTERONE RECEPTOR; STRUCTURAL BASIS; TRANSCRIPTIONAL RESPONSE; X-RAY STRUCTURE;

BINDING ENERGY; DIMERS; MONOMERS;

LIGANDS;

ARGININE; GLYCINE; METHIONINE; MIFEPRISTONE; NORETHISTERONE; ORG A; ORG B; ORG C; PROGESTERONE RECEPTOR; PROGESTERONE RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

ALPHA HELIX; ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DOSE RESPONSE; DRUG ANTAGONISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HYDROGEN BOND; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN EXPRESSION; X RAY ANALYSIS;

ANIMALS; BINDING SITES; CHO CELLS; CRICETINAE; CRICETULUS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; LIGANDS; MIFEPRISTONE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NORETHINDRONE; PROGESTERONE; PROTEIN BINDING; PROTEIN CONFORMATION; RECEPTORS, PROGESTERONE;

EID: 80053427683     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M111.273029     Document Type: Article

References (39)

1. Lu, N. Z., Wardell, S. E., Burnstein, K. L., Defranco, D., Fuller, P. J., Giguere, V., Hochberg, R. B., McKay, L., Renoir, J. M., Weigel, N. L., Wilson, E. M., McDonnell, D. P., and Cidlowski, J. A. (2006) Pharmacol. Rev. 58, 782-797
2. Madauss, K. P., Stewart, E. L., and Williams, S. P. (2007) Med. Res. Rev. 27, 374-400
3. Spitz, I. M., and Chwalisz, K. (2000) Steroids 65, 807-815
4. Benagiano, G., Bastianelli, C., and Farris, M. (2008) Expert Opin. Pharmacother. 9, 2459-2472
5. Benagiano, G., Bastianelli, C., and Farris, M. (2008) Expert Opin. Pharmacother. 9, 2473-2485
6. Benagiano, G., Bastianelli, C., and Farris, M. (2008) Expert Opin. Pharmacother. 9, 2487-2496
7. Spitz, I. M. (2003) Steroids 68, 981-993
8. Winneker, R. C., Fensome, A., Zhang, P., Yudt, M. R., McComas, C. C., and Unwalla, R. J. (2008) Steroids 73, 689-701
9. Chabbert-Buffet, N., Meduri, G., Bouchard, P., and Spitz, I. M. (2005) Hum. Reprod. Update 11, 293-307
10. DeManno, D., Elger, W., Garg, R., Lee, R., Schneider, B., Hess-Stumpp, H., Schubert, G., and Chwalisz, K. (2003) Steroids 68, 1019-1032
11. Thompson, S. K., Washburn, D. G., Frazee, J. S., Madauss, K. P., Hoang, T. H., Lapinski, L., Grygielko, E. T., Glace, L. E., Trizna, W., Williams, S. P., Duraiswami, C., Bray, J. D., and Laping, N. J. (2009) Bioorg. Med. Chem. Lett. 19, 4777-4780
12. Kallander, L. S., Washburn, D. G., Hoang, T. H., Frazee, J. S., Stoy, P., Johnson, L., Lu, Q., Hammond, M., Barton, L. S., Patterson, J. R., Azzarano, L. M., Nagilla, R., Madauss, K. P., Williams, S. P., Stewart, E. L., Duraiswami, C., Grygielko, E. T., Xu, X., Laping, N. J., Bray, J. D., and Thompson, S. K. (2010) Bioorg. Med. Chem. Lett. 20, 371-374
13. Williams, S. P., and Sigler, P. B. (1998) Nature 393, 392-396
14. Bain, D. L., Heneghan, A. F., Connaghan-Jones, K. D., and Miura, M. T. (2007) Annu. Rev. Physiol. 69, 201-220
15. Kumar, R., and Thompson, E. B. (2003) Mol. Endocrinol. 17, 1-10
16. Egea, P. F., Klaholz, B. P., and Moras, D. (2000) FEBS Lett. 476, 62-67
17. Moras, D., and Gronemeyer, H. (1998) Curr. Opin. Cell Biol. 10, 384-391
18. Bourguet, W., Germain, P., and Gronemeyer, H. (2000) Trends Pharmacol. Sci. 21, 381-388
19. Weatherman, R. V., Fletterick, R. J., and Scanlan, T. S. (1999) Annu. Rev. Biochem. 68, 559-581
20. Madauss, K. P., Grygielko, E. T., Deng, S. J., Sulpizio, A. C., Stanley, T. B., Wu, C., Short, S. A., Thompson, S. K., Stewart, E. L., Laping, N. J., Williams, S. P., and Bray, J. D. (2007) Mol. Endocrinol. 21, 1066-1081
21. Raaijmakers, H. C., Versteegh, J. E., and Uitdehaag, J. C. (2009) J. Biol. Chem. 284, 19572-19579
22. Petit-Topin, I., Turque, N., Fagart, J., Fay, M., Ulmann, A., Gainer, E., and Rafestin-Oblin, M. E. (2009) Mol. Pharmacol. 75, 1317-1324
23. Brown, A. R., Bosies, M., Cameron, H., Clark, J., Cowley, A., Craighead, M., Elmore, M. A., Firth, A., Goodwin, R., Goutcher, S., Grant, E., Grassie, M., Grove, S. J., Hamilton, N. M., Hampson, H., Hillier, A., Ho, K. K., Kiczun, M., Kingsbury, C., Kultgen, S. G., Littlewood, P. T., Lusher, S. J., Macdonald, S., McIntosh, L., McIntyre, T., Mistry, A., Morphy, J. R., Nimz, O., Ohlmeyer, M., Pick, J., Rankovic, Z., Sherborne, B., Smith, A., Speake, M., Spinks, G., Thomson, F., Watson, L., and Weston, M. (2011) Bioorg. Med. Chem. Lett. 21, 137-140
24. Jones, D. G., Liang, X., Stewart, E. L., Noe, R. A., Kallander, L. S., Madauss, K. P., Williams, S. P., Thompson, S. K., Gray, D. W., and Hoekstra, W. J. (2005) Bioorg. Med. Chem. Lett. 15, 3203-3206
25. Potterton, E., Briggs, P., Turkenburg, M., and Dodson, E. (2003) Acta Crystallogr. D Biol. Crystallogr. 59, 1131-1137
26. Dijkema, R., Schoonen, W. G., Teuwen, R., van der Struik, E., De Ries, R. J., van der Kar, B. A., and Olijve, W. (1998) J. Steroid Biochem. Mol. Biol. 64, 147-156
27. Schoonen, W. G., Dijkema, R., De Ries, R. J., Wagenaars, J. L., Joosten, J. W., De Gooyer, M. E., Deckers, G. H., and Kloosterboer, H. J. (1998) J. Steroid Biochem. Mol. Biol. 64, 157-170
28. Schoonen, W. G., Deckers, G., De Gooijer, M. E., De Ries, R., Mathijssen- Mommers, G., Hamersma, H., and Kloosterboer, H. J. (2000) J. Steroid Biochem. Mol. Biol. 74, 109-123
29. Keightley, D. D. (1979) Eur. J. Cancer 15, 785-790
30. Washburn, D. G., Hoang, T. H., Frazee, J. S., Johnson, L., Hammond, M., Manns, S., Madauss, K. P., Williams, S. P., Duraiswami, C., Tran, T. B., Stewart, E. L., Grygielko, E. T., Glace, L. E., Trizna, W., Nagilla, R., Bray, J. D., and Thompson, S. K. (2009) Bioorg. Med. Chem. Lett. 19, 4664-4668
31. Zhang, Z., Olland, A. M., Zhu, Y., Cohen, J., Berrodin, T., Chippari, S., Appavu, C., Li, S., Wilhem, J., Chopra, R., Fensome, A., Zhang, P., Wrobel, J., Unwalla, R. J., Lyttle, C. R., and Winneker, R. C. (2005) J. Biol. Chem. 280, 28468-28475
32. Madauss, K. P., Deng, S. J., Austin, R. J., Lambert, M. H., McLay, I., Pritchard, J., Short, S. A., Stewart, E. L., Uings, I. J., and Williams, S. P. (2004) J. Med. Chem. 47, 3381-3387
33. Krieger, E., Darden, T., Nabuurs, S. B., Finkelstein, A., and Vriend, G. (2004) Proteins 57, 678-683
34. Bledsoe, R. K., Stewart, E. L., and Pearce, K. H. (2004) Vitam. Horm. 68, 49-91
35. Bledsoe, R. K., Madauss, K. P., Holt, J. A., Apolito, C. J., Lambert, M. H., Pearce, K. H., Stanley, T. B., Stewart, E. L., Trump, R. P., Willson, T. M., and Williams, S. P. (2005) J. Biol. Chem. 280, 31283-31293
36. Fagart, J., Huyet, J., Pinon, G. M., Rochel, M., Mayer, C., and Rafestin- Oblin, M. E. (2005) Nat. Struct. Mol. Biol. 12, 554-555
37. Geller, D. S., Farhi, A., Pinkerton, N., Fradley, M., Moritz, M., Spitzer, A., Meinke, G., Tsai, F. T., Sigler, P. B., and Lifton, R. P. (2000) Science 289, 119-123
38. Huyet, J., Pinon, G. M., Fay, M. R., Fagart, J., and Rafestin-Oblin, M. E. (2007) Mol. Pharmacol. 72, 563-571
39. Li, Y., Suino, K., Daugherty, J., and Xu, H. E. (2005) Mol. Cell 19, 367-380