Identification of covalent attachment site of antiestrogenic estradiol 11β-derivatives on human estrogen receptor α ligand-binding domain

Journal of Steroid Biochemistry and Molecular Biology

Volumn 98, Issue 2-3, 2006, Pages 111-121

  Aliau, Sigrid ^a   Mattras, Hélène ^a   Borgna, Jean Louis ^a  

^a INSERM   (France)

Author keywords

Affinity labeling; Estradiol 11 derivatives; Estrogen receptor; Ligand binding domain; Mass spectrometry

Indexed keywords

11 BETA BROMOACETAMIDOETHOXYPHENYLESTRADIOL; 11 BETA BROMOACETAMIDOPENTOXYPHENYLESTRADIOL; 4 HYDROXYTAMOXIFEN; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR ALPHA; GLUTATHIONE TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HORMONE DETERMINATION; LIGAND BINDING; MASS SPECTROMETRY; MOLECULAR MODEL; PROTEIN DOMAIN; SCATCHARD PLOT;

AFFINITY LABELS; AMINO ACID SEQUENCE; BINDING SITES; CRYSTALLIZATION; CYSTEINE; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; GLUTATHIONE TRANSFERASE; HUMANS; LIGANDS; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; RECOMBINANT FUSION PROTEINS;

EID: 31444435269     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2005.09.006     Document Type: Article

References (23)

1. D.J. Mangelsdorf, C. Thummel, M. Beato, P. Herrlich, G. Schultz, K. Umesono, B. Blumberg, P. Kastner, M. Mark, P. Chambon, and R.M. Evans The nuclear receptor superfamily: the second decade Cell 83 1995 835 839
2. S.M. Aronica, and B.S. Katzenellenbogen Progesterone receptor regulation in uterine cells: stimulation by estrogens, cyclic adenosine 3′,5′-monophosphate and insulin-like growth factor I and suppression by antiestrogens and protein kinase inhibitors Endocrinology 128 1991 2045 2052
3. J.M. Beekman, G.F. Allan, S.Y. Tsai, M.J. Tsai, and B.W. O'Malley Transcriptional activation by the estrogen receptor requires a conformational change in the ligand-binding domain Mol. Endocrinol. 7 1993 1266 1274
4. J.G. Moggs, and G. Orphanides Estrogen receptors: orchestrators of pleiotropic cellular responses EMBO Rep. 2 2001 775 781
5. A.M. Brzozowski, A.C.W. Pike, Z. Dauter, R.E. Hubbard, T. Bonn, O. Engström, L. Öhman, G.L. Greene, J.Å. Gustafsson, and M. Carlquist Molecular basis of agonism and antagonism in the oestrogen receptor Nature 389 1997 753 758
6. D.M. Tanenbaum, Y. Wang, S.P. Williams, and P.B. Sigler Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains Proc. Natl. Acad. Sci. U.S.A. 95 1998 5998 6003
7. A.K. Shiau, D. Barstad, P.M. Loria, L. Cheng, P.J. Kushner, D.A. Agard, and G.L. Greene The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 95 1998 927 937
8. S. Eiler, M. Gangloff, S. Duclaud, D. Moras, and M. Ruff Overexpression, purification, and crystal structure of native ERα LBD Protein Expr. Purif. 22 2001 165 173
9. A.K. Shiau, D. Barstad, J.T. Radek, M.J. Meyers, K.W. Nettles, B.S. Katzenellenbogen, J.A. Katzenellenbogen, D.A. Agard, and G.L. Greene Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism Nat. Struct. Biol. 9 2002 359 364
10. A.C.W. Pike, A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.G. Thorsell, O. Engström, J. Ljunggren, J.Å. Gustafsson, and M. Carlquist Structure of the ligand-binding domain of oestrogen receptor beta in the presence of partial agonist and a full antagonist EMBO J. 18 1999 4608 4618
11. A.C.W. Pike, A.M. Brzozowski, J. Walton, R.E. Hubbard, A.G. Thorsell, Y.L. Li, J.Å. Gustafsson, and M. Carlquist Structural insights into the mode of action of a pure antiestrogen Structure 9 2001 145 153
12. H. Mattras, S. Aliau, E. Richard, J.C. Bonnafous, P. Jouin, and J.L. Borgna Identification by MALDI-TOF mass spectrometry of 17α- bromoacetamidopropylestradiol covalent attachment sites on estrogen receptor α Biochemistry 41 2002 15713 15727
13. H. Mattras, S. Aliau, E. Demey, J. Poncet, J.L. Borgna, Mass spectrometry identification of covalent attachment sites of two related estrogenic ligands on human estrogen receptor α, J. Steroid Biochem. Mol. Biol. 48 (4-5), in press.
14. D. El Garrouj, S. Aliau, A. Aumelas, and J.L. Borgna Steroidal affinity labels of the estrogen receptor. 2. 17α-(haloacetamidoalkyl)estradiols J. Med. Chem. 38 1995 2339 2348
15. R. White, J.A. Lees, M. Needham, J. Ham, and M. Parker Structural organization and expression of the mouse estrogen receptor Mol. Endocrinol. 1 1987 735 744
16. S. Aliau, G. Delettre, H. Mattras, D. El Garrouj, F. Nique, G. Teutsch, and J.L. Borgna Steroidal affinity labels of the estrogen receptor α. Electrophilic 11β-aryl derivatives of estradiol J. Med. Chem. 43 2000 613 628
17. S. Aliau, D. El Garrouj, A. Yasri, B.S. Katzenellenbogen, and J.L. Borgna 17α-(Haloacetamidoalkyl)estradiols alkylate the human estrogen receptor at cysteine residues 417 and 530 Biochemistry 36 1997 5861 5867
18. S. Aliau, H. Mattras, E. Richard, and J.L. Borgna Cysteine 530 of the human estrogen receptor α is the main covalent attachment site of 11β-(aziridinylalkoxyphenyl)estradiols Biochemistry 38 1999 14752 14762
19. G. Teutsch, R. Deraedt, D. Philibert, in: D. Lednicer (Ed.), Chronicles of Drug Discovery, vol. 3, American Chemical Society, Washington, DC, 1993, pp. 1-43.
20. J.P. Blondeau, and P. Robel Determination of protein-ligand binding constants at equilibrium in biological samples Eur. J. Biochem. 55 1975 375 384
21. M. Karas, and F. Hillenkamp Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons Anal. Biochem. 60 1988 2299 2301
22. K.W. Harlow, D.N. Smith, J.A. Katzenellenbogen, and B.S. Katzenellenbogen Identification of cysteine-530 as the covalent attachment site of an affinity labeling estrogen (ketononestrol aziridine) and antiestrogen (tamoxifen aziridine) in the human estrogen receptor J. Biol. Chem. 264 1989 17476 17485
23. K.M. Hurth, M.J. Nilges, K.E. Carlson, A. Tamrazi, R.L. Belford, and J.A. Katzenellenbogen Ligand-induced changes in estrogen receptor conformation as measured by site-directed spin labeling Biochemistry 43 2004 1891 1907