Nuclear Receptor Profiling of Bisphenol-A and Its Halogenated Analogues

Vitamins and Hormones

Volumn 94, Issue , 2014, Pages 229-251

  Delfosse, Vanessa ^a,b,c   Grimaldi, Marina ^a,c,d,e   le Maire, Albane ^a,b,c   Bourguet, William ^a,b,c   Balaguer, Patrick ^a,c,d,e  

^a INSERM   (France)

^b CNRS   (France)

^c UNIV MONTPELLIER   (France)

^d INSTITUT DE RECHERCHE EN CANCÉROLOGIE DE MONTPELLIER   (France)

^e CENTRE VAL D AURELLE   (France)

Author keywords

Bisphenol A; Endocrine disruptor; Halogenated bisphenol A; Nuclear hormone receptor

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ANDROGEN RECEPTOR; ANTIANDROGEN; BENZHYDRYL DERIVATIVE; ENDOCRINE DISRUPTOR; ESTROGEN; ESTROGEN RECEPTOR; NUCLEAR HORMONE RECEPTOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PHENOL DERIVATIVE; PREGNANE X RECEPTOR; STEROID RECEPTOR; THYROID HORMONE RECEPTOR;

ANIMAL; ARTICLE; BISPHENOL-A; CHEMISTRY; DRUG ANTAGONISM; DRUG POTENTIATION; HALOGENATED BISPHENOL-A; HALOGENATION; HUMAN; METABOLISM; POLLUTANT;

BISPHENOL-A; ENDOCRINE DISRUPTOR; HALOGENATED BISPHENOL-A; NUCLEAR HORMONE RECEPTOR;

ANDROGEN ANTAGONISTS; ANIMALS; BENZHYDRYL COMPOUNDS; ENDOCRINE DISRUPTORS; ENVIRONMENTAL POLLUTANTS; ESTROGENS, NON-STEROIDAL; HALOGENATION; HUMANS; PHENOLS; PPAR GAMMA; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; RECEPTORS, STEROID; RECEPTORS, THYROID HORMONE;

EID: 84891445363     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-800095-3.00009-2     Document Type: Chapter

References (89)

1. Abad M.C., Askari H., O'Neill J., Klinger A.L., Milligan C., Lewandowski F., et al. Structural determination of estrogen-related receptor gamma in the presence of phenol derivative compounds. The Journal of Steroid Biochemistry and Molecular Biology 2008, 108:44-54.
2. Alonso-Magdalena P., Ropero A.B., Soriano S., Garcia-Arevalo M., Ripoll C., Fuentes E., et al. Bisphenol-A acts as a potent estrogen via non-classical estrogen triggered pathways. Molecular and Cellular Endocrinology 2012, 355:201-207.
3. Ariazi E.A., Jordan V.C. Estrogen-related receptors as emerging targets in cancer and metabolic disorders. Current Topics in Medicinal Chemistry 2006, 6:203-215.
4. Baillie-Hamilton P.F. Chemical toxins: A hypothesis to explain the global obesity epidemic. Journal of Alternative and Complementary Medicine 2002, 8:185-192.
5. Benecke A., Chambon P., Gronemeyer H. Synergy between estrogen receptor alpha activation functions AF1 and AF2 mediated by transcription intermediary factor TIF2. EMBO Reports 2000, 1:151-157.
6. Bernal J. Thyroid hormone receptors in brain development and function. Nature Clinical Practice Endocrinology and Metabolism 2007, 3:249-259.
7. Bility M.T., Thompson J.T., McKee R.H., David R.M., Butala J.H., Vanden Heuvel J.P., et al. Activation of mouse and human peroxisome proliferator-activated receptors (PPARs) by phthalate monoesters. Toxicological Sciences 2004, 82:170-182.
8. Bommer M., Benecke A., Gronemeyer H., Rochette-Egly C. TIF2 mediates the synergy between RARalpha 1 activation functions AF-1 and AF-2. The Journal of Biological Chemistry 2002, 277:37961-37966.
9. Bourguet W., Germain P., Gronemeyer H. Nuclear receptor ligand-binding domains: Three-dimensional structures, molecular interactions and pharmacological implications. Trends in Pharmacological Sciences 2000, 21:381-388.
10. Bruning J.B., Parent A.A., Gil G., Zhao M., Nowak J., Pace M.C., et al. Coupling of receptor conformation and ligand orientation determine graded activity. Nature Chemical Biology 2010, 6:837-843.
11. Chevalier N., Bouskine A., Fenichel P. Bisphenol A promotes testicular seminoma cell proliferation through GPER/GPR30. International Journal of Cancer 2012, 130:241-242.
12. Chu S., Haffner G.D., Letcher R.J. Simultaneous determination of tetrabromobisphenol A, tetrachlorobisphenol A, bisphenol A and other halogenated analogues in sediment and sludge by high performance liquid chromatography-electrospray tandem mass spectrometry. Journal of Chromatography A 2005, 1097:25-32.
13. Couse J.F., Korach K.S. Estrogen receptor null mice: What have we learned and where will they lead us?. Endocrine Reviews 1999, 20:358-417.
14. Coward P., Lee D., Hull M.V., Lehmann J.M. 4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma. Proceedings of the National Academy of Sciences of the United States of America 2001, 98:8880-8884.
15. Curtis S.W., Washburn T., Sewall C., DiAugustine R., Lindzey J., Couse J.F., et al. Physiological coupling of growth factor and steroid receptor signaling pathways: Estrogen receptor knockout mice lack estrogen-like response to epidermal growth factor. Proceedings of the National Academy of Sciences of the United States of America 1996, 93:12626-12630.
16. Darnerud P.O. Toxic effects of brominated flame retardants in man and in wildlife. Environment International 2003, 29:841-853.
17. de Wit C.A., Herzke D., Vorkamp K. Brominated flame retardants in the Arctic environment-trends and new candidates. The Science of the Total Environment 2010, 408:2885-2918.
18. Delfosse V., Grimaldi M., Pons J.-L., Boulahtouf A., le Maire A., Cavailles V., et al. Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes. Proceedings of the National Academy of Sciences of the United States of America 2012, 109:14930-14935.
19. di Masi A., Marinis E.D., Ascenzi P., Marino M. Nuclear receptors CAR and PXR: Molecular, functional, and biomedical aspects. Molecular Aspects of Medicine 2009, 30:297-343.
20. Fini J., Le Mevel S., Turque N., Palmier K., Zalko D., Cravedi J., et al. An in vivo multiwell-based fluorescent screen for monitoring vertebrate thyroid hormone disruption. Environmental Science and Technology 2007, 41:5908-5914.
21. Fini J.B., Riu A., Debrauwer L., Hillenweck A., Le Mevel S., Chevolleau S., et al. Parallel biotransformation of tetrabromobisphenol A in Xenopus laevis and mammals: Xenopus as a model for endocrine perturbation studies. Toxicological Sciences 2012, 125:359-367.
22. Freitas J., Cano P., Craig-Veit C., Goodson M.L., Furlow J.D., Murk A.J. Detection of thyroid hormone receptor disruptors by a novel stable in vitro reporter gene assay. Toxicology In Vitro 2011, 25:257-266.
23. Fukazawa H., Hoshino K., Shiozawa T., Matsushita H., Terao Y. Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants. Chemosphere 2001, 44:973-979.
24. Gallart-Ayala H., Nunez O., Moyano E., Galceran M.T. Field-amplified sample injection-micellar electrokinetic capillary chromatography for the analysis of bisphenol A, bisphenol F, and their diglycidyl ethers and derivatives in canned soft drinks. Electrophoresis 2010, 31:1550-1559.
25. Gee A.C., Katzenellenbogen J.A. Probing conformational changes in the estrogen receptor: Evidence for a partially unfolded intermediate facilitating ligand binding and release. Molecular Endocrinology 2001, 15:421-428.
26. Germain P., Staels B., Dacquet C., Spedding M., Laudet V. Overview of nomenclature of nuclear receptors. Pharmacological Reviews 2006, 58:685-704.
27. Giguere V. To ERR in the estrogen pathway. Trends in Endocrinology and Metabolism 2002, 13:220-225.
28. Giguere V. Transcriptional control of energy homeostasis by the estrogen-related receptors. Endocrine Reviews 2008, 29:677-696.
29. Gould J.C., Leonard L.S., Maness S.C., Wagner B.L., Conner K., Zacharewski T., et al. Bisphenol A interacts with the estrogen receptor alpha in a distinct manner from estradiol. Molecular and Cellular Endocrinology 1998, 142:203-214.
30. Greschik H., Wurtz J.M., Sanglier S., Bourguet W., van Dorsselaer A., Moras D., et al. Structural and functional evidence for ligand-independent transcriptional activation by the estrogen-related receptor 3. Molecular Cell 2002, 9:303-313.
31. Gronemeyer H., Gustafsson J.A., Laudet V. Principles for modulation of the nuclear receptor superfamily. Nature Reviews Drug Discovery 2004, 3:950-964.
32. Grun F., Watanabe H., Zamanian Z., Maeda L., Arima K., Cubacha R., et al. Endocrine-disrupting organotin compounds are potent inducers of adipogenesis in vertebrates. Molecular Endocrinology 2006, 20:2141-2155.
33. He B., Kemppainen J.A., Wilson E.M. FXXLF and WXXLF sequences mediate the NH2-terminal interaction with the ligand binding domain of the androgen receptor. The Journal of Biological Chemistry 2000, 275:22986-22994.
34. Horard B., Vanacker J.M. Estrogen receptor-related receptors: Orphan receptors desperately seeking a ligand. Journal of Molecular Endocrinology 2003, 31:349-357.
35. Jacobs M.N., Nolan G.T., Hood S.R. Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). Toxicology and Applied Pharmacology 2005, 209:123-133.
36. Jagnytsch O., Opitz R., Lutz I., Kloas W. Effects of tetrabromobisphenol A on larval development and thyroid hormone-regulated biomarkers of the amphibian Xenopus laevis. Environmental Research 2006, 101:340-348.
37. Kallen J., Schlaeppi J.M., Bitsch F., Filipuzzi I., Schilb A., Riou V., et al. Evidence for ligand-independent transcriptional activation of the human estrogen-related receptor alpha (ERRalpha): Crystal structure of ERRalpha ligand binding domain in complex with peroxisome proliferator-activated receptor coactivator-1alpha. The Journal of Biological Chemistry 2004, 279:49330-49337.
38. Kelce W.R., Lambright C.R., Gray L.E., Roberts K.P. Vinclozolin and p, p'-DDE alter androgen-dependent gene expression: In vivo confirmation of an androgen receptor-mediated mechanism. Toxicology and Applied Pharmacology 1997, 142:192-200.
39. Kitamura S., Kato T., Iida M., Jinno N., Suzuki T., Ohta S., et al. Anti-thyroid hormonal activity of tetrabromobisphenol A, a flame retardant, and related compounds: Affinity to the mammalian thyroid hormone receptor, and effect on tadpole metamorphosis. Life Sciences 2005, 76:1589-1601.
40. Kuiper G.G., Carlsson B., Grandien K., Enmark E., Haggblad J., Nilsson S., et al. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 1997, 138:863-870.
41. Leloup Buscaglia La triiodothyronine, hormone de la métamorphose des amphibiens. Comptes rendus hebdomadaires des scéances de l'académie des sciences. Série D 1977, 284:2261-2263.
42. Lemaire G., Mnif W., Pascussi J.M., Pillon A., Rabenoelina F., Fenet H., et al. Identification of new human pregnane X receptor ligands among pesticides using a stable reporter cell system. Toxicological Sciences 2006, 91:501-509.
43. Li J., Ma M., Wang Z. In vitro profiling of endocrine disrupting effects of phenols. Toxicology In Vitro 2010, 24:201-207.
44. Liu H., Zhao H., Quan X., Zhang Y., Chen S. Formation of chlorinated intermediate from bisphenol A in surface saline water under simulated solar light irradiation. Environmental Science and Technology 2009, 43:7712-7717.
45. Lu D., Kiriyama Y., Lee K.Y., Giguere V. Transcriptional regulation of the estrogen-inducible pS2 breast cancer marker gene by the ERR family of orphan nuclear receptors. Cancer Research 2001, 61:6755-6761.
46. Matsumoto T., Sakari M., Okada M., Yokoyama A., Takahashi S., Kouzmenko A., et al. The androgen receptor in health and disease. Annual Review of Physiology 2012, 75:201-224.
47. Matsushima A., Kakuta Y., Teramoto T., Koshiba T., Liu X., Okada H., et al. Structural evidence for endocrine disruptor bisphenol A binding to human nuclear receptor ERR gamma. Journal of Biochemistry 2007, 142:517-524.
48. Matsushima A., Teramoto T., Okada H., Liu X., Tokunaga T., Kakuta Y., et al. ERRgamma tethers strongly bisphenol A and 4-alpha-cumylphenol in an induced-fit manner. Biochemical and Biophysical Research Communications 2008, 373:408-413.
49. McCarthy N. Prostate cancer: Studying the classics. Nature Reviews Cancer 2011, 11:386.
50. McLachlan J.A., Newbold R.R. Estrogens and development. Environmental Health Perspectives 1987, 75:25-27.
51. McPhaul M.J. Molecular defects of the androgen receptor. The Journal of Steroid Biochemistry and Molecular Biology 1999, 69:315-322.
52. Meerts I.A., van Zanden J.J., Luijks E.A., van Leeuwen-Bol I., Marsh G., Jakobsson E., et al. Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. Toxicological Sciences 2000, 56:95-104.
53. Mikamo E., Harada S., Nishikawa J., Nishihara T. Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor. Toxicology and Applied Pharmacology 2003, 193:66-72.
54. Mnif W., Pascussi J.M., Pillon A., Escande A., Bartegi A., Nicolas J.C., et al. Estrogens and antiestrogens activate hPXR. Toxicology Letters 2007, 170:19-29.
55. Moriyama K., Tagami T., Akamizu T., Usui T., Saijo M., Kanamoto N., et al. Thyroid hormone action is disrupted by bisphenol A as an antagonist. The Journal of Clinical Endocrinology and Metabolism 2002, 87:5185-5190.
56. Mutou Y., Ibuki Y., Terao Y., Kojima S., Goto R. Change of estrogenic activity and release of chloride ion in chlorinated bisphenol A after exposure to ultraviolet B. Biological and Pharmaceutical Bulletin 2006, 29:2116-2119.
57. Nagy L., Schwabe J.W. Mechanism of the nuclear receptor molecular switch. Trends in Biochemical Sciences 2004, 29:317-324.
58. Nettles K.W., Bruning J.B., Gil G., Nowak J., Sharma S.K., Hahm J.B., et al. NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses. Nature Chemical Biology 2008, 4:241-247.
59. Nolte R.T., Wisely G.B., Westin S., Cobb J.E., Lambert M.H., Kurokawa R., et al. Ligand binding and co-activator assembly of the peroxisome proliferator-activated receptor-[gamma]. Nature 1998, 395:137-143.
60. Okada H., Tokunaga T., Liu X., Takayanagi S., Matsushima A., Shimohigashi Y. Direct evidence revealing structural elements essential for the high binding ability of bisphenol A to human estrogen-related receptor-gamma. Environmental Health Perspectives 2008, 116:32-38.
61. Orans J., Teotico D.G., Redinbo M.R. The nuclear xenobiotic receptor pregnane X receptor: Recent insights and new challenges. Molecular Endocrinology 2005, 19:2891-2900.
62. Pacyniak E.K., Cheng X., Cunningham M.L., Crofton K., Klaassen C.D., Guo G.L. The flame retardants, polybrominated diphenyl ethers, are pregnane X receptor activators. Toxicological Sciences 2007, 97:94-102.
63. Paris F., Balaguer P., Terouanne B., Servant N., Lacoste C., Cravedi J.P., et al. Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. Molecular and Cellular Endocrinology 2002, 193:43-49.
64. Pike A.C. Lessons learnt from structural studies of the oestrogen receptor. Best Practice and Research Clinical Endocrinology and Metabolism 2006, 20:1-14.
65. Quigley C.A., De Bellis A., Marschke K.B., el-Awady M.K., Wilson E.M., French F.S. Androgen receptor defects: Historical, clinical, and molecular perspectives. Endocrine Reviews 1995, 16:271-321.
66. Renaud J.P., Moras D. Structural studies on nuclear receptors. Cellular and Molecular Life Sciences 2000, 57:1748-1769.
67. Riu A., Grimaldi M., le Maire A., Bey G., Phillips K., Boulahtouf A., et al. Peroxisome proliferator-activated receptor gamma is a target for halogenated analogs of bisphenol A. Environmental Health Perspectives 2011, 119:1227-1232.
68. Riu A., le Maire A., Grimaldi M., Audebert M., Hillenweck A., Bourguet W., et al. Characterization of novel ligands of ERalpha, Erbeta, and PPARgamma: The case of halogenated bisphenol A and their conjugated metabolites. Toxicological Sciences 2011, 122:372-382.
69. Rosen E.D., Spiegelman B.M. PPARgamma: A nuclear regulator of metabolism, differentiation, and cell growth. The Journal of Biological Chemistry 2001, 276:37731-37734.
70. Routledge E.J., White R., Parker M.G., Sumpter J.P. Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta. The Journal of Biological Chemistry 2000, 275:35986-35993.
71. Shi H., Qian L., Guo S., Zhang X., Liu J., Cao Q. Teratogenic effects of tetrabromobisphenol A on Xenopus tropicalis embryos. Comparative Biochemistry and Physiology. Toxicology and Pharmacology 2010, 152:62-68.
72. Stroheker T., Picard K., Lhuguenot J.C., Canivenc-Lavier M.C., Chagnon M.C. Steroid activities comparison of natural and food wrap compounds in human breast cancer cell lines. Food and Chemical Toxicology 2004, 42:887-897.
73. Sui Y., Ai N., Park S.H., Rios-Pilier J., Perkins J.T., Welsh W.J., et al. Bisphenol A and its analogues activate human pregnane X receptor. Environmental Health Perspectives 2012, 120:399-405.
74. Sun H., Shen O.-X., Wang X.-R., Zhou L., Zhen S.Q., Zhen X.D. Anti-thyroid hormone activity of bisphenol A, tetrabromobisphenol A and tetrachlorobisphenol A in an improved reporter gene assay. Toxicology In Vitro 2009, 23:950-954.
75. Tabb M.M., Kholodovych V., Grun F., Zhou C., Welsh W.J., Blumberg B. Highly chlorinated PCBs inhibit the human xenobiotic response mediated by the steroid and xenobiotic receptor (SXR). Environmental Health Perspectives 2004, 112:163-169.
76. Takacs M.L., Abbott B.D. Activation of mouse and human peroxisome proliferator-activated receptors (alpha, beta/delta, gamma) by perfluorooctanoic acid and perfluorooctane sulfonate. Toxicological Sciences 2007, 95:108-117.
77. Takemura H., Ma J., Sayama K., Terao Y., Zhu B.T., Shimoi K. In vitro and in vivo estrogenic activity of chlorinated derivatives of bisphenol A. Toxicology 2005, 207:215-221.
78. Takeshita A., Koibuchi N., Oka J., Taguchi M., Shishiba Y., Ozawa Y. Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription. European Journal of Endocrinology 2001, 145:513-517.
79. Tontonoz P., Hu E., Spiegelman B.M. Regulation of adipocyte gene expression and differentiation by peroxisome proliferator activated receptor gamma. Current Opinion in Genetics and Development 1995, 5:571-576.
80. Tremblay G.B., Kunath T., Bergeron D., Lapointe L., Champigny C., Bader J.A., et al. Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta. Genes and Development 2001, 15:833-838.
81. Vanacker J.M., Pettersson K., Gustafsson J.A., Laudet V. Transcriptional targets shared by estrogen receptor- related receptors (ERRs) and estrogen receptor (ER) alpha, but not by ERbeta. The EMBO Journal 1999, 18:4270-4279.
82. Vandenberg L.N., Maffini M.V., Sonnenschein C., Rubin B.S., Soto A.M. Bisphenol-A and the great divide: A review of controversies in the field of endocrine disruption. Endocrine Reviews 2009, 30:75-95.
83. Veldhoen N., Boggs A., Walzak K., Helbing C.C. Exposure to tetrabromobisphenol-A alters TH-associated gene expression and tadpole metamorphosis in the Pacific tree frog Pseudacris regilla. Aquatic Toxicology 2006, 78:292-302.
84. Wang L., Zuercher W.J., Consler T.G., Lambert M.H., Miller A.B., Orband-Miller L.A., et al. X-ray crystal structures of the estrogen-related receptor-gamma ligand binding domain in three functional states reveal the molecular basis of small molecule regulation. The Journal of Biological Chemistry 2006, 281:37773-37781.
85. Wetherill Y.B., Akingbemi B.T., Kanno J., McLachlan J.A., Nadal A., Sonnenschein C., et al. In vitro molecular mechanisms of bisphenol A action. Reproductive Toxicology 2007, 24:178-198.
86. Wilson E.M. Analysis of interdomain interactions of the androgen receptor. Methods in Molecular Biology 2011, 776:113-129.
87. Xue Y., Moore L.B., Orans J., Peng L., Bencharit S., Kliewer S.A., et al. Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Molecular Endocrinology 2007, 21:1028-1038.
88. Yu S., Wang X., Ng C.F., Chen S., Chan F.L. ERRgamma suppresses cell proliferation and tumor growth of androgen-sensitive and androgen-insensitive prostate cancer cells and its implication as a therapeutic target for prostate cancer. Cancer Research 2007, 67:4904-4914.
89. Zoeller T.R., Dowling A.L., Herzig C.T., Iannacone E.A., Gauger K.J., Bansal R. Thyroid hormone, brain development, and the environment. Environmental Health Perspectives 2002, 110(Suppl. 3):355-361.