3D models of human ERα and ERβ complexed with 5-androsten-3β,17β-diol

Steroids

Volumn 77, Issue 12, 2012, Pages 1192-1197

  Baker, Michael E ^a   Uh, Kayla Y ^b   Chandsawangbhuwana, Charlie ^c  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

5 Androstenediol; Brain microglia; Estrogen receptor ; Multiple sclerosis

Indexed keywords

25 HYDROXYCHOLESTEROL; 26 HYDROXYCHOLESTEROL; ANDROSTENEDIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; STEROID DELTA ISOMERASE;

ARTICLE; COMPUTER MODEL; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; MULTIPLE SCLEROSIS; PROTEIN FUNCTION; PROTEIN INTERACTION; PROTEIN STRUCTURE; STEROID BINDING;

AMINO ACID SEQUENCE; ANDROSTENEDIOL; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN STABILITY;

EID: 84865443555     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.07.014     Document Type: Article

References (51)

1. H. Escriva, F. Delaunay, and V. Laudet Ligand binding and nuclear receptor evolution BioEssays 22 2000 717 727
2. S. Bertrand, F.G. Brunet, H. Escriva, G. Parmentier, V. Laudet, and M. Robinson-Rechavi Evolutionary genomics of nuclear receptors: from twenty-five ancestral genes to derived endocrine systems Mol Biol Evol 21 2004 1923 1937
3. M.E. Baker Xenobiotics and the evolution of multicellular animals: emergence and diversification of ligand-activated transcription factors Integr Comp Biol 45 2005 172 178
4. G.V. Markov, R. Tavares, C. Dauphin-Villemant, B.A. Demeneix, M.E. Baker, and V. Laudet Independent elaboration of steroid hormone signaling pathways in metazoans Proc Natl Acad Sci USA 106 2009 11913 11918
5. P. Huang, V. Chandra, and F. Rastinejad Structural overview of the nuclear receptor superfamily: insights into physiology and therapeutics Annu Rev Physiol 72 2010 247 272
6. J.T. Bridgham, G.N. Eick, C. Larroux, K. Deshpande, M.J. Harms, and M.E. Gauthier Protein evolution by molecular tinkering: diversification of the nuclear receptor superfamily from a ligand-dependent ancestor PLoS Biol 8 2010
7. M.E. Baker Origin and diversification of steroids: co-evolution of enzymes and nuclear receptors Mol Cell Endocrinol 334 2011 14 20
8. G.G. Kuiper, B. Carlsson, K. Grandien, E. Enmark, J. Haggblad, and S. Nilsson Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta Endocrinology 138 1997 863 870
9. G.G. Kuiper, J.G. Lemmen, B. Carlsson, J.C. Corton, S.H. Safe, and P.T. van der Saag Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta Endocrinology 139 1998 4252 4263
10. A.M. Brzozowski, A.C. Pike, Z. Dauter, R.E. Hubbard, T. Bonn, and O. Engstrom Molecular basis of agonism and antagonism in the oestrogen receptor Nature 389 1997 753 758
11. A.K. Shiau, D. Barstad, P.M. Loria, L. Cheng, P.J. Kushner, and D.A. Agard The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen Cell 95 1998 927 937
12. A.C. Pike Lessons learnt from structural studies of the oestrogen receptor Best Pract Res Clin Endocrinol Metab 20 2006 1 14
13. Z. Weihua, R. Lathe, M. Warner, and J.A. Gustafsson An endocrine pathway in the prostate, ERbeta, AR, 5alpha-androstane-3beta,17beta-diol, and CYP7B1, regulates prostate growth Proc Natl Acad Sci USA 99 2002 13589 13594
14. N. Sugiyama, R.P. Barros, M. Warner, and J.A. Gustafsson ERbeta: recent understanding of estrogen signaling Trends Endocrinol Metab 21 2010 545 552
15. K. Saijo, J.G. Collier, A.C. Li, J.A. Katzenellenbogen, and C.K. Glass An ADIOL-ERbeta-CtBP transrepression pathway negatively regulates microglia-mediated inflammation Cell 145 2011 584 595
16. P.H. Jellinck, M. Kaufmann, A. Gottfried-Blackmore, B.S. McEwen, G. Jones, and K. Bulloch Selective conversion by microglia of dehydroepiandrosterone to 5-androstenediol-A steroid with inherent estrogenic properties J Steroid Biochem Mol Biol 107 2007 156 162
17. A. Gottfried-Blackmore, A. Sierra, P.H. Jellinck, B.S. McEwen, and K. Bulloch Brain microglia express steroid-converting enzymes in the mouse J Steroid Biochem Mol Biol 109 2008 96 107
18. W.S. Griffin Inflammation and neurodegenerative diseases Am J Clin Nutr 83 2006 470S 474S
19. Y.S. Kim, and T.H. Joh Microglia, major player in the brain inflammation: their roles in the pathogenesis of Parkinson's disease Exp Mol Med 38 2006 333 347
20. C.K. Glass, K. Saijo, B. Winner, M.C. Marchetto, and F.H. Gage Mechanisms underlying inflammation in neurodegeneration Cell 140 2010 918 934
21. V.W. Yong, and S. Rivest Taking advantage of the systemic immune system to cure brain diseases Neuron 64 2009 55 60
22. G. Raivich, and R. Banati Brain microglia and blood-derived macrophages: molecular profiles and functional roles in multiple sclerosis and animal models of autoimmune demyelinating disease Brain Res Brain Res Rev 46 2004 261 281
23. M.E. Baker Insights from the structure of estrogen receptor into the evolution of estrogens: implications for endocrine disruption Biochem Pharmacol 82 2011 1 8
24. S. Mocklinghoff, R. Rose, M. Carraz, A. Visser, C. Ottmann, and L. Brunsveld Synthesis and crystal structure of a phosphorylated estrogen receptor ligand binding domain ChemBioChem 11 2010 2251 2254
25. S. Eiler, M. Gangloff, S. Duclaud, D. Moras, and M. Ruff Overexpression, purification, and crystal structure of native ER alpha LBD Protein Expr Purif 22 2001 165 173
26. A. Warnmark, E. Treuter, J.A. Gustafsson, R.E. Hubbard, A.M. Brzozowski, and A.C. Pike Interaction of transcriptional intermediary factor 2 nuclear receptor box peptides with the coactivator binding site of estrogen receptor alpha J Biol Chem 277 2002 21862 21868
27. R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell A semiempirical free energy force field with charge-based desolvation J Comput Chem 28 2007 1145 1152
28. G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, and D.S. Goodsell AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility J Comput Chem 30 2009 2785 2791
29. R.S. Muthyala, S. Sheng, K.E. Carlson, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Bridged bicyclic cores containing a 1,1-diarylethylene motif are high-affinity subtype-selective ligands for the estrogen receptor J Med Chem 46 2003 1589 1602
30. P. Wolohan, and D.E. Reichert Use of binding energy in comparative molecular field analysis of isoform selective estrogen receptor ligands J Mol Graph Model 23 2004 23 38
31. M.E. Baker, D.J. Chang, and C. Chandsawangbhuwana 3D model of lamprey estrogen receptor with estradiol and 15alpha-hydroxy-estradiol PLoS ONE 4 2009 e6038
32. J.A. Katzenellenbogen The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: addressing the "core issue" in the design of estrogen receptor ligands J Med Chem 54 2011 5271 5282
33. C. Huggins, E.V. Jensen, and A.S. Cleveland Chemical structure of steroids in relation to promotion of growth of the vagina and uterus of the hypophysectomized rat J Exp Med 100 1954 225 240
34. J. Adams, M. Garcia, and H. Rochefort Estrogenic effects of physiological concentrations of 5-androstene-3 beta,17 beta-diol and its metabolism in MCF7 human breast cancer cells Cancer Res 41 1981 4720 4726
35. L.G. Van Doorn, J. Berenschot-Roozendaal, J. Poortman, J.H. Thijssen, and F. Schwarz Binding characteristics of 5-androstene-3 beta, 17 beta-diol and estradiol-17 beta to the cytoplasmic estrogen receptor of the immature rat uterus J Steroid Biochem 16 1982 661 671
36. M.K. Lindberg, S. Moverare, S. Skrtic, H. Gao, K. Dahlman-Wright, and J.A. Gustafsson Estrogen receptor (ER)-beta reduces ERalpha-regulated gene transcription, supporting a "ying yang" relationship between ERalpha and ERbeta in mice Mol Endocrinol 17 2003 203 208
37. Z. Weihua, S. Andersson, G. Cheng, E.R. Simpson, M. Warner, and J.A. Gustafsson Update on estrogen signaling FEBS Lett 546 2003 17 24
38. J.M. Hall, and D.P. McDonnell The estrogen receptor beta-isoform (ERbeta) of the human estrogen receptor modulates ERalpha transcriptional activity and is a key regulator of the cellular response to estrogens and antiestrogens Endocrinology 140 1999 5566 5578
39. S. Tiwari-Woodruff, L.B. Morales, R. Lee, and R.R. Voskuhl Differential neuroprotective and antiinflammatory effects of estrogen receptor (ER)alpha and ERbeta ligand treatment Proc Natl Acad Sci USA 104 2007 14813 14818
40. 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 USA 95 1998 5998 6003
41. A. le Maire, W. Bourguet, and P. Balaguer A structural view of nuclear hormone receptor: endocrine disruptor interactions Cell Mol Life Sci 67 2010 1219 1237
42. A.C. Pike, A.M. Brzozowski, R.E. Hubbard, T. Bonn, A.G. Thorsell, and O. Engstrom Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist EMBO J 18 1999 4608 4618
43. E.E. Baulieu Neurosteroids: of the nervous system, by the nervous system, for the nervous system Recent Prog Horm Res 52 1997 1 32
44. M. Schumacher, S. Weill-Engerer, P. Liere, F. Robert, R.J. Franklin, and L.M. Garcia-Segura Steroid hormones and neurosteroids in normal and pathological aging of the nervous system Prog Neurobiol 71 2003 3 29
45. N. Sugiyama, S. Andersson, R. Lathe, X. Fan, P. Alonso-Magdalena, and T. Schwend Spatiotemporal dynamics of the expression of estrogen receptors in the postnatal mouse brain Mol Psychiatry 14 223-32 2009 117
46. C. Dalla, K. Antoniou, Z. Papadopoulou-Daifoti, J. Balthazart, and J. Bakker Male aromatase-knockout mice exhibit normal levels of activity, anxiety and "depressive-like" symptomatology Behav Brain Res 163 2005 186 193
47. C.D. DuSell, M. Umetani, P.W. Shaul, D.J. Mangelsdorf, and D.P. McDonnell 27-Hydroxycholesterol is an endogenous selective estrogen receptor modulator Mol Endocrinol 22 2008 65 77
48. M. Umetani, H. Domoto, A.K. Gormley, I.S. Yuhanna, C.L. Cummins, and N.B. Javitt 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen Nat Med 13 2007 1185 1192
49. R. Lappano, A.G. Recchia, E.M. De Francesco, T. Angelone, M.C. Cerra, and D. Picard The cholesterol metabolite 25-hydroxycholesterol activates estrogen receptor alpha-mediated signaling in cancer cells and in cardiomyocytes PLoS ONE 6 2011 e16631
50. M. Jeyakumar, K.E. Carlson, J.R. Gunther, and J.A. Katzenellenbogen Exploration of dimensions of estrogen potency: parsing ligand binding and coactivator binding affinities J Biol Chem 286 2011 12971 12982
51. A. Billon-Gales, A. Krust, C. Fontaine, A. Abot, G. Flouriot, and C. Toutain Activation function 2 (AF2) of estrogen receptor-alpha is required for the atheroprotective action of estradiol but not to accelerate endothelial healing Proc Natl Acad Sci USA 108 2011 13311 13316