Chemical and biochemical issues related to x-ray crystallography of the ligand-binding domain of estrogen receptor α

Bioconjugate Chemistry

Volumn 12, Issue 3, 2001, Pages 406-413

  Goldstein, Steven W ^a   Bordner, Jon ^a   Hoth, Lise R ^a   Geoghegan, Kieran F ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 VINYLPYRIDINE; AMINO ACID; ANION EXCHANGE CHROMATOGRAPHY; BACTERIAL PROTEIN; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG MANUFACTURE; ESCHERICHIA COLI; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; IODOACETIC ACID; LIGAND BINDING; MASS SPECTROMETRY; PROTEIN DOMAIN; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; ESCHERICHIA COLI; LIGANDS; MASS SPECTROMETRY; PROTEINS;

AFFINITY COLUMN; AFFINITY MATRIX; CARBOXYMETHYLATED; DIASTEREOMERS; ESTROGEN RECEPTOR Α; LIGAND BINDING DOMAIN; OESTROGENS; PHENOLICS; SUPERNATANTS; WET GELS;

X RAY CRYSTALLOGRAPHY;

EID: 0035008357     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc000127d     Document Type: Article

References (26)

1. McKenna, N. J., Xu, J., Nawaz, Z., Tsai, S. Y., Tsai, M. J., and O'Malley, B. W. (1999) Nuclear receptor coactivators: multiple enzymes, multiple complexes, multiple functions. J. Steroid Biochem. Mol. Biol. 69, 3-12.
2. Weatherman, R. V., Fletterick, R. J., and Scanlan, T. S. (1999) Nuclear-receptor ligands and ligand-binding domains. Annu. Rev. Biochem. 68, 559-581.
3. Kraichely, D. M., Sun, J., Katzenellenbogen, J. A., and Katzenellenbogen, B. S. (2000) Conformational changes and coactivator recruitment by novel ligands for estrogen receptor-α and estrogen receptor-β: Correlations with biological character and distinct differences among SRC coactivator family members. Endocrinology 141, 3534-3545.
4. Brzozowski, A. M., Pike, A. C. W., Dauter, Z., Hubbard, R. E., Bonn, T., Engström, O., Öhman, L., Greene, G. L., Gustafsson, J. A., and Carlquist, M. (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389, 753-758.
5. Tanenbaum, D. M., Wang, Y., Williams, S. P., and Sigler, P. B. (1998) Crystallographic comparison of the estrogen and progesterone receptors ligand binding domains. Proc. Natl. Acad. Sci. U.S.A. 95, 5998-6003.
6. 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.
7. Pike, A. C. W., Brzozowski, A. M., Hubbard, R. E., Bonn, T., Thorsell, A. G., Engström, 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.
8. Grese, T. A., and Dodge, J. A. (1998) Selective estrogen receptor modulators (SERMs). Curr. Pharm. Des. 4, 71-92.
9. Bryant, H. U., and Dere, W. H. (1998) Selective estrogen receptor modulators: an alternative to hormone replacement therapy. Proc. Soc. Exp. Biol. Med. 217, 45-52.
10. Dhingra, K. (1999) Antiestrogens - tamoxifen, SERMs and beyond. Investigat. New Drugs 17, 285-311.
11. Egea, P. F., Klaholz, B. P., and Moras, D. (2000) Ligand-protein interactions in nuclear receptors of hormones. FEBS Lett. 476, 62-67.
12. Seielstad, D. A., Carlson, K. E., Katzenellenbogen, J. A., Kushner, P. J., and Greene, G. L. (1995) Molecular characterization by mass spectrometry of the human estrogen receptor ligand-binding domain expressed in Escherichia coli. Mol. Endocrinol. 9, 647-658.
13. Greene, G. L., Nolan, C., Engler, J. P., and Jensen, E. V. (1980) Monoclonal antibodies to human estrogen receptor. Proc. Natl. Acad. Sci. U.S.A. 77, 5115-5119.
14. Rosati, R. L., Da Silva Jardine, P., Cameron, K. O., Thompson, D. D., Ke, H. Z., Toler, S. M., Brown, T. A., Pan, L. C., Ebbinghaus, C. F., Reinhold, A. R., Elliott, N. C., Newhouse, B. N., Tjoa, C. M., Sweetnam, P. M., Cole, M. J., Arriola, M. W., Gauthier, J. W., Crawford, D. T., Nickerson, D. F., Pirie, C. M., Qi, H., Simmons, H. A., and Tkalcevic, G. T. (1998) Discovery and preclinical pharmacology of a novel, potent, nonsteroidal estrogen receptor agonist/antagonist, CP-336156, a diaryltetrahydronaphthalene. J. Med. Chem. 41, 2928-2931.
15. Ke, H. Z., Paralkar, V. M., Grasser, W. A., Crawford, D. T., Qi, H., Simmons, H. A., Pirie, C. M., Chidsey-Frink, K. L., Owen, T. A., Smock, S. L., Chen, H. K., Jee, W. S., Cameron, K. O., Rosati, R. L., Brown, T. A., DaSilva-Jardine, P., and Thompson, D. D. (1998) Effects of CP-336, 156, a new, nonsteroidal estrogen agonist/antagonist, on bone, serum cholesterol, uterus and body composition in rat models. Endocrinology 139, 2068-2076.
16. Salman, M., Ruiz, A. A., Stotter, P. L., and Chamness, G. C. (1987) A progesterone receptor affinity chromatography reagent: 17 α-hexynyl nortestosterone Sepharose. J. Steroid Biochem. 26, 383-391.
17. Hegy, G. B., Shackleton, C. H., Carlquist, M., Bonn, T., Engström, O., Sjöholm, P., and Witkowska, H. E. (1996) 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 61, 367-373.
18. Geoghegan, K. F. (1996) Modification of amino groups, in Current Protocols in Protein Science. (J. E. Coligan, B. M. Dunn, H. L. Ploegh, D. W. Speicher, and P. T. Wingfield, Eds.) pp 15.2.1-15.2.18, John Wiley, New York.
19. el Garrouj, D., Aumelas, A., and Borgna, J. L. (1993) Steroidal affinity labels of the estrogen receptor. 1. 17 α-(Bromoacetoxy)alkyl/alkynylestradiols. J. Med. Chem. 36, 2973-2983.
20. Jonscher, K. R., and Yates, J. R. (1997) The quadrupole ion trap mass spectrometer - a small solution to a big challenge. Anal. Biochem. 244, 1-15.
21. Eng, J. K., McCormack, A., L., and Yates, J. R., III. (1994) An approach to correlate tandem mass spectral data of peptides with amino acid sequences in a protein database. J. Am. Soc. Mass Spectrom. 5, 976-989.
22. Vonderhaar, B., and Mueller, G. C. (1969) Binding of estrogen receptor to estradiol immobilized on insoluble resins. Biochim. Biophys. Acta 176, 626-631.
23. Sica, V., Parikh, I., Nola, E., Puca, G. A., and Cuatrecasas, P. (1973) Affinity chromatography and the purification of estrogen receptors. J. Biol. Chem. 248, 6543-6458.
24. Feng, W., Graumann, K., Hahn, R., and Jungbauer, A. (1999) Affinity chromatography of human estrogen receptor-alpha expressed in Saccharomyces cerevisiae. Combination of heparin- and 17β-estradiol-affinity chromatography. J. Chromatog. A 852, 161-173.
25. Greene, G. L., and Jensen, E. V. (1982) Monoclonal antibodies as probes for estrogen receptor detection and characterization. J. Steroid Biochem. 16, 353-359.
26. Poirier, D., Labrie, C., Merand, Y., and Labrie, F. (1990) Derivatives of ethynylestradiol with oxygenated 17 alpha-alkyl side chain: synthesis and biological activity. J. Steroid Biochem. 36, 133-142.