3D Models of MBP, a Biologically Active Metabolite of Bisphenol A, in Human Estrogen Receptor α and Estrogen Receptor β

PLoS ONE

Volumn 7, Issue 10, 2012, Pages

  Baker, Michael E ^a   Chandsawangbhuwana, Charlie ^b  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYL 2,4 BIS(4 HYDROXYPHENYL)PENT 1 ENE; 4,4' ISOPROPYLIDENEDIPHENOL; AMINO ACID; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HORMONE RECEPTOR INTERACTION; METABOLISM; MOLECULAR MODEL; MUTAGENESIS; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; BENZHYDRYL COMPOUNDS; BINDING SITES; BINDING, COMPETITIVE; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHENOLS; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; THERMODYNAMICS;

EID: 84867137699     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0046078     Document Type: Article

References (55)

1. Colborn T, vom Saal FS, Soto AM, (1993) Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect 101: 378-384.
2. Diamanti-Kandarakis E, Bourguignon JP, Giudice LC, Hauser R, Prins GS, et al. (2009) Endocrine-disrupting chemicals: an Endocrine Society scientific statement. Endocr Rev 30: 293-342.
3. Baker ME, (2005) Xenobiotics and the evolution of multicellular animals: emergence and diversification of ligand-activated transcription factors. Integrative and Comparative Biology 45: 172-178.
4. Markov GV, Tavares R, Dauphin-Villemant C, Demeneix BA, Baker ME, et al. (2009) Independent elaboration of steroid hormone signaling pathways in metazoans. Proc Natl Acad Sci U S A 106: 11913-11918.
5. le Maire A, Bourguet W, Balaguer P, (2010) A structural view of nuclear hormone receptor: endocrine disruptor interactions. Cell Mol Life Sci 67: 1219-1237.
6. Sladek FM, (2011) What are nuclear receptor ligands? Mol Cell Endocrinol 334: 3-13.
7. Baker ME, (2011) Insights from the structure of estrogen receptor into the evolution of estrogens: Implications for endocrine disruption. Biochem Pharmacol 82: 1-8.
8. Welshons WV, Nagel SC, vom Saal FS, (2006) Large effects from small exposures. III. Endocrine mechanisms mediating effects of bisphenol A at levels of human exposure. Endocrinology 147: S56-69.
9. Melzer D, Rice NE, Lewis C, Henley WE, Galloway TS, (2010) Association of urinary bisphenol a concentration with heart disease: evidence from NHANES 2003/06. PLoS One 5: e8673.
10. Vandenberg LN, Chahoud I, Heindel JJ, Padmanabhan V, Paumgartten FJ, et al. (2010) Urinary, circulating, and tissue biomonitoring studies indicate widespread exposure to bisphenol A. Environ Health Perspect. 118: 1055-1070.
11. Schonfelder G, Wittfoht W, Hopp H, Talsness CE, Paul M, et al. (2002) Parent bisphenol A accumulation in the human maternal-fetal-placental unit. Environ Health Perspect 110: A703-707.
12. Vandenberg LN, Hauser R, Marcus M, Olea N, Welshons WV, (2007) Human exposure to bisphenol A (BPA). Reprod Toxicol 24: 139-177.
13. Calafat AM, Ye X, Wong LY, Reidy JA, Needham LL, (2008) Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004. Environ Health Perspect 116: 39-44.
14. Oehlmann J, Schulte-Oehlmann U, Kloas W, Jagnytsch O, Lutz I, et al. (2009) A critical analysis of the biological impacts of plasticizers on wildlife. Philos Trans R Soc Lond B Biol Sci 364: 2047-2062.
15. Vandenberg LN, Maffini MV, Sonnenschein C, Rubin BS, Soto AM, (2009) Bisphenol-A and the great divide: a review of controversies in the field of endocrine disruption. Endocr Rev 30: 75-95.
16. Fernandez MF, Arrebola JP, Taoufiki J, Navalon A, Ballesteros O, et al. (2007) Bisphenol-A and chlorinated derivatives in adipose tissue of women. Reprod Toxicol 24: 259-264.
17. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D, (1993) Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132: 2279-2286.
18. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, et al. (1997) Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138: 863-870.
19. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, et al. (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139: 4252-4263.
20. Gould JC, Leonard LS, Maness SC, Wagner BL, Conner K, et al. (1998) Bisphenol A interacts with the estrogen receptor alpha in a distinct manner from estradiol. Mol Cell Endocrinol 142: 203-214.
21. Richter CA, Taylor JA, Ruhlen RL, Welshons WV, Vom Saal FS, (2007) Estradiol and Bisphenol A stimulate androgen receptor and estrogen receptor gene expression in fetal mouse prostate mesenchyme cells. Environ Health Perspect 115: 902-908.
22. Okuda K, Takiguchi M, Yoshihara S, (2010) In vivo estrogenic potential of 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene, an active metabolite of bisphenol A, in uterus of ovariectomized rat. Toxicol Lett 197: 7-11.
23. Yoshihara S, Mizutare T, Makishima M, Suzuki N, Fujimoto N, et al. (2004) Potent estrogenic metabolites of bisphenol A and bisphenol B formed by rat liver S9 fraction: their structures and estrogenic potency. Toxicol Sci 78: 50-59.
24. Eiler S, Gangloff M, Duclaud S, Moras D, Ruff M, (2001) Overexpression, purification, and crystal structure of native ER alpha LBD. Protein Expr Purif 22: 165-173.
25. Huey R, Morris GM, Olson AJ, Goodsell DS, (2007) A semiempirical free energy force field with charge-based desolvation. J Comput Chem 28: 1145-1152.
26. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, et al. (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem.
27. Trott O, Olson AJ, (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31: 455-461.
28. Mocklinghoff S, Rose R, Carraz M, Visser A, Ottmann C, et al. (2010) Synthesis and crystal structure of a phosphorylated estrogen receptor ligand binding domain. Chembiochem 11: 2251-2254.
29. Cheng T, Li X, Li Y, Liu Z, Wang R, (2009) Comparative assessment of scoring functions on a diverse test set. J Chem Inf Model 49: 1079-1093.
30. Wang R, Lai L, Wang S, (2002) Further development and validation of empirical scoring functions for structure-based binding affinity prediction. J Comput Aided Mol Des 16: 11-26.
31. Neudert G, Klebe G, (2011) DSX: a knowledge-based scoring function for the assessment of protein-ligand complexes. J Chem Inf Model 51: 2731-2745.
32. Velec HF, Gohlke H, Klebe G, (2005) DrugScore(CSD)-knowledge-based scoring function derived from small molecule crystal data with superior recognition rate of near-native ligand poses and better affinity prediction. J Med Chem 48: 6296-6303.
33. Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, et al. (1997) Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389: 753-758.
34. Warnmark A, Treuter E, Gustafsson JA, Hubbard RE, Brzozowski AM, et al. (2002) Interaction of transcriptional intermediary factor 2 nuclear receptor box peptides with the coactivator binding site of estrogen receptor alpha. J Biol Chem 277: 21862-21868.
35. Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, et al. (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95: 927-937.
36. Tanenbaum DM, Wang Y, Williams SP, Sigler PB, (1998) Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc Natl Acad Sci U S A 95: 5998-6003.
37. Baker ME, Chang DJ, (2009) 3D model of amphioxus steroid receptor complexed with estradiol. Biochem Biophys Res Commun 386: 516-520.
38. Baker ME, Chang DJ, Chandsawangbhuwana C, (2009) 3D model of lamprey estrogen receptor with estradiol and 15alpha-hydroxy-estradiol. PLoS One 4: e6038.
39. Katzenellenbogen JA, (2011) The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: addressing the "core issue" in the design of estrogen receptor ligands. J Med Chem 54: 5271-5282.
40. Seo JW, Comninos JS, Chi DY, Kim DW, Carlson KE, et al. (2006) Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer. J Med Chem 49: 2496-2511.
41. Celik L, Lund JD, Schiott B, (2007) Conformational dynamics of the estrogen receptor alpha: molecular dynamics simulations of the influence of binding site structure on protein dynamics. Biochemistry 46: 1743-1758.
42. Manas ES, Unwalla RJ, Xu ZB, Malamas MS, Miller CP, et al. (2004) Structure-based design of estrogen receptor-beta selective ligands. J Am Chem Soc 126: 15106-15119.
43. Nettles KW, Bruning JB, Gil G, O'Neill EE, Nowak J, et al. (2007) Structural plasticity in the oestrogen receptor ligand-binding domain. EMBO Rep 8: 563-568.
44. DuSell CD, Umetani M, Shaul PW, Mangelsdorf DJ, McDonnell DP, (2008) 27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol Endocrinol 22: 65-77.
45. Minutolo F, Macchia M, Katzenellenbogen BS, Katzenellenbogen JA, (2011) Estrogen receptor beta ligands: recent advances and biomedical applications. Med Res Rev 31: 364-442.
46. Lappano R, Recchia AG, De Francesco EM, Angelone T, Cerra MC, et al. (2011) The cholesterol metabolite 25-hydroxycholesterol activates estrogen receptor alpha-mediated signaling in cancer cells and in cardiomyocytes. PLoS One 6: e16631.
47. Heery DM, Kalkhoven E, Hoare S, Parker MG, (1997) A signature motif in transcriptional co-activators mediates binding to nuclear receptors. Nature 387: 733-736.
48. McKenna NJ, O'Malley BW, (2002) Combinatorial control of gene expression by nuclear receptors and coregulators. Cell 108: 465-474.
49. Smith CL, O'Malley BW, (2004) Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocr Rev 25: 45-71.
50. Jeyakumar M, Carlson KE, Gunther JR, Katzenellenbogen JA, (2011) Exploration of dimensions of estrogen potency: parsing ligand binding and coactivator binding affinities. J Biol Chem 286: 12971-12982.
51. Billon-Gales A, Krust A, Fontaine C, Abot A, Flouriot G, et al. (2011) 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 U S A 108: 13311-13316.
52. McInerney EM, Rose DW, Flynn SE, Westin S, Mullen TM, et al. (1998) Determinants of coactivator LXXLL motif specificity in nuclear receptor transcriptional activation. Genes Dev 12: 3357-3368.
53. Voegel JJ, Heine MJ, Tini M, Vivat V, Chambon P, et al. (1998) The coactivator TIF2 contains three nuclear receptor-binding motifs and mediates transactivation through CBP binding-dependent and-independent pathways. EMBO J 17: 507-519.
54. Hall JM, McDonnell DP, Korach KS, (2002) Allosteric regulation of estrogen receptor structure, function, and coactivator recruitment by different estrogen response elements. Mol Endocrinol 16: 469-486.
55. Hall JM, Korach KS, (2002) Analysis of the molecular mechanisms of human estrogen receptors alpha and beta reveals differential specificity in target promoter regulation by xenoestrogens. J Biol Chem 277: 44455-44461.