A plurality of molecular targets: The receptor ecosystem for bisphenol-A (BPA)

Hormones and Behavior

Volumn 101, Issue , 2018, Pages 59-67

  MacKay, Harry ^a   Abizaid, Alfonso ^b  

^a U S DEPARTMENT OF AGRICULTURE   (United States)

^b CARLETON UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ANDROGEN RECEPTOR; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR GAMMA; G PROTEIN COUPLED RECEPTOR 30; GLUCOCORTICOID RECEPTOR; NUCLEAR ESTROGEN RECEPTOR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; THYROID HORMONE RECEPTOR; UNCLASSIFIED DRUG; BENZHYDRYL DERIVATIVE; CELL RECEPTOR; ENDOCRINE DISRUPTOR; ESTROGEN; PHENOL DERIVATIVE;

BINDING AFFINITY; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN INTERACTION; PROTEIN TARGETING; RECEPTOR BINDING; REVIEW; SIGNAL TRANSDUCTION; ANIMAL; CELL NUCLEUS; DRUG EFFECT; GENETICS; METABOLISM;

ANIMALS; BENZHYDRYL COMPOUNDS; CELL NUCLEUS; ENDOCRINE DISRUPTORS; ESTROGENS; HUMANS; PHENOLS; RECEPTORS, ANDROGEN; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, ESTROGEN; RECEPTORS, THYROID HORMONE; SIGNAL TRANSDUCTION;

EID: 85035123383     PISSN: 0018506X     EISSN: 10956867     Source Type: Journal    
DOI: 10.1016/j.yhbeh.2017.11.001     Document Type: Review

References (111)

1. Adlanmerini, M., Solinhac, R., Abot, A., Fabre, A., Raymond-Letron, I., Guihot, A.-L., Boudou, F., Sautier, L., Vessieres, E., Kim, S.H., Liere, P., Fontaine, C., Krust, A., Chambon, P., Katzenellenbogen, J.a., Gourdy, P., Shaul, P.W., Henrion, D., Arnal, J.-F., Lenfant, F., Mutation of the palmitoylation site of estrogen receptor α in vivo reveals tissue-specific roles for membrane versus nuclear actions. Proc. Natl. Acad. Sci. 111:2 (2014), E283–E290.
2. Ahmadian, M., Suh, J., Hah, N., Liddle, C., PPARgamma signaling and metabolism: the good, the bad and the future. Nat. Med., 19(5), 2013.
3. Arase, S., Ishii, K., Igarashi, K., Aisaki, K., Yoshio, Y., Matsushima, A., Shimohigashi, Y., Arima, K., Kanno, J., Sugimura, Y., Endocrine disrupter bisphenol A increases in situ estrogen production in the mouse urogenital sinus. Biol. Reprod. 84:4 (2011), 734–742.
4. Askew, E.B., Minges, J.T., Hnat, A.T., Wilson, E.M., Structural features discriminate androgen receptor N/C terminal and coactivator interactions. Mol. Cell. Endocrinol. 348:2 (2012), 403–410.
5. Atlas, E., Pope, L., Wade, M.G., Kawata, A., Boudreau, A., Boucher, J.G., Bisphenol A increases aP2 expression in 3T3L1 by enhancing the transcriptional activity of nuclear receptors at the promoter. Adipocytes 3:3 (2014), 170–179.
6. Barak, Y., Nelson, M.C., Ong, E.S., Jones, Y.Z., Ruiz-Lozano, P., Chien, K.R., Koder, a., Evans, R.M., PPAR gamma is required for placental, cardiac, and adipose tissue development. Mol. Cell 4:4 (1999), 585–595.
7. Blair, R.M., Fang, H., Branham, W.S., Hass, B.S., Dial, S.L., Moland, C.L., Tong, W., Shi, L., Perkins, R., Sheehan, D.M., The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol. Sci. 54:1 (2000), 138–153.
8. Bolli, A., Galluzzo, P., Ascenzi, P., Del Pozzo, G., Manco, I., Vietri, M.T., Mita, L., Altucci, L., Mita, D.G., Marino, M., Laccase treatment impairs bisphenol A-induced cancer cell proliferation affecting estrogen receptor alpha-dependent rapid signals. IUBMB Life 60:12 (2008), 843–852.
9. Boucher, J.G., Boudreau, A., Ahmed, S., Atlas, E., In Vitro Effects of Bisphenol A β-D-Glucuronide (BPA-G) on Adipogenesis in Human and Murine Preadipocytes. Environ. Health Perspect. 123:12 (2015), 1287–1293.
10. Chambliss, K., Wu, Q., Non-nuclear estrogen receptor α signaling promotes cardiovascular protection but not uterine or breast cancer growth in mice. J. Clin. Invest., 120(7), 2010.
11. Chandra, V., Huang, P., Hamuro, Y., Raghuram, S., Wang, Y., Burris, T.P., Rastinejad, F., Structure of the intact PPAR-gamma-RXR- nuclear receptor complex on DNA. Nature 456:7220 (2008), 350–356.
12. Chen, S., Zhou, D., Hsin, L.-Y., Kanaya, N., Wong, C., Yip, R., Sakamuru, S., Xia, M., Yuan, Y.-C., Witt, K., Teng, C., AroER tri-screen is a biologically relevant assay for endocrine disrupting chemicals modulating the activity of aromatase and/or the estrogen receptor. Toxicol. Sci. 139 (2014), 198–209.
13. Christensen, K.L.Y., Lorber, M., Koch, H.M., Kolossa-Gehring, M., Morgan, M.K., Population variability of phthalate metabolites and bisphenol A concentrations in spot urine samples versus 24- or 48-h collections. J. Expo. Sci. Environ. Epidemiol. 22:6 (2012), 632–640.
14. Chung, E., Genco, M.C., Megrelis, L., Ruderman, J.V., Effects of bisphenol A and triclocarban on brain-specific expression of aromatase in early zebrafish embryos. Proc. Natl. Acad. Sci. U. S. A. 108:43 (2011), 17732–17737.
15. Corrales, J., Kristofco, L.A., Baylor Steele, W., Yates, B.S., Breed, C.S., Spencer Williams, E., Brooks, B.W., Global assessment of bisphenol a in the environment: review and analysis of its occurrence and bioaccumulation. Dose-Response 13:3 (2015), 1–29.
16. Covaci, A., Hond, E.D., Geens, T., Govarts, E., Koppen, G., Frederiksen, H., Knudsen, L.E., Mørck, T.A., Gutleb, A.C., Guignard, C., Cocco, E., Horvat, M., Heath, E., Kosjek, T., Mazej, D., Tratnik, J.S., Castaño, A., Esteban, M., Cutanda, F., Ramos, J.J., Berglund, M., Larsson, K., Jönsson, B.A., Biot, P., Casteleyn, L., Joas, R., Joas, A., Bloemen, L., Sepai, O., Exley, K., Schoeters, G., Angerer, J., Kolossa-Gehring, M., Fiddicke, U., Aerts, D., Koch, H.M., Urinary BPA measurements in children and mothers from six European member states: overall results and determinants of exposure. Environ. Res. 141 (2015), 77–85.
17. Delfosse, V., Grimaldi, M., Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes. Proc. Natl. Acad. Sci. 109 (2012), 14930–14935.
18. Dodds, E., Lawson, W., Synthetic oestrogenic agents without the phenanthrene nucleus. Nature, 137, 1936, 996.
19. Dong, S., Terasaka, S., Kiyama, R., Bisphenol A induces a rapid activation of Erk1/2 through GPR30 in human breast cancer cells. Environ. Pollut. 159:1 (2011), 212–218.
20. Eladak, S., Grisin, T., Moison, D., Guerquin, M.-J., N'Tumba-Byn, T., Pozzi-Gaudin, S., Benachi, A., Livera, G., Rouiller-Fabre, V., Habert, R., A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound. Fertil. Steril. 2 (2014), 11–21.
21. Fang, H., Tong, W., Branham, W.S., Moland, C.L., Dial, S.L., Hong, H., Xie, Q., Perkins, R., Owens, W., Sheehan, D.M., Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. Chem. Res. Toxicol. 16:10 (2003), 1338–1358.
22. Filardo, E.J., Quinn, J.a., Bland, K.I., Frackelton, a.R., Estrogen-induced activation of Erk-1 and Erk-2 requires the G protein-coupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HB-EGF. Mol. Endocrinol. 14:10 (2000), 1649–1660.
23. Filardo, E.J., Quinn, J.a., Frackelton, a.R., Bland, K.I., Estrogen action via the G protein-coupled receptor, GPR30: stimulation of adenylyl cyclase and cAMP-mediated attenuation of the epidermal growth factor receptor-to-MAPK signaling axis. Mol. Endocrinol. 16:1 (2002), 70–84.
24. Fiocchetti, M., Ascenzi, P., Marino, M., Neuroprotective effects of 17β-estradiol rely on estrogen receptor membrane initiated signals. Front. Physiol., 3, 2012, 73.
25. Geens, T., Roosens, L., Neels, H., Covaci, A., Assessment of human exposure to Bisphenol-A, Triclosan and Tetrabromobisphenol-A through indoor dust intake in Belgium. Chemosphere 76:6 (2009), 755–760.
26. Gore, A.C., Chappell, V.A., Fenton, S.E., Flaws, J.A., Nadal, A., Prins, G.S., Toppari, J., Zoeller, R.T., Executive summary to EDC-2: the endocrine society's second scientific statement on endocrine-disrupting chemicals. Endocr. Rev. 36:6 (2015), 593–602.
27. Gould, J.C., Leonard, L.S., Maness, S.C., Wagner, B.L., Conner, K., Zacharewski, T., Safe, S., McDonnell, D.P., Gaido, K.W., Bisphenol A interacts with the estrogen receptor alpha in a distinct manner from estradiol. Mol. Cell. Endocrinol. 142:1–2 (1998), 203–214.
28. Green, H., Kehinde, O., An established preadipose cell line and its differentiation in culture. II. Factors affecting the adipose conversion. Cell 5:1 (1975), 19–27.
29. Gronemeyer, H., Gustafsson, J.-A., Laudet, V., Principles for modulation of the nuclear receptor superfamily. Nat. Rev. Drug Discov. 3:11 (2004), 950–964.
30. Grygiel-Górniak, B., Peroxisome proliferator-activated receptors and their ligands: nutritional and clinical implications–a review. Nutr. J., 13, 2014, 17.
31. Heimeier, R.a., Das, B., Buchholz, D.R., Shi, Y.B., The xenoestrogen bisphenol A inhibits postembryonic vertebrate development by antagonizing gene regulation by thyroid hormone. Endocrinology 150:6 (2009), 2964–2973.
32. Heldring, N., Pike, A., Andersson, S., Matthews, J., Cheng, G., Hartman, J., Tujague, M., Ström, A., Treuter, E., Warner, M., Gustafsson, J.-A., Estrogen receptors: how do they signal and what are their targets. Physiol. Rev. 87:3 (2007), 905–931.
33. Hessel, E.V., Ezendam, J., van Broekhuizen, F.A., Hakkert, B., DeWitt, J., Granum, B., Guzylack, L., Lawrence, B.P., Penninks, A., Rooney, A.A., Piersma, A.H., van Loveren, H., Assessment of recent developmental immunotoxicity studies with bisphenol A in the context of the 2015 EFSA t-TDI. Reprod. Toxicol. 65 (2016), 448–456.
34. Hiroi, H., Tsutsumi, O., Momoeda, M., Takai, Y., Osuga, Y., Taketani, Y., Differential interactions of bisphenol A and 17beta-estradiol with estrogen receptor alpha (ERalpha) and ERbeta. Endocr. J. 46:6 (1999), 773–778.
35. Hoekstra, E.J., Simoneau, C., Release of bisphenol A from polycarbonate: a review. Crit. Rev. Food Sci. Nutr. 53:4 (2013), 386–402.
36. Hoffmann, M., Fiedor, E., Ptak, A., Bisphenol A and its derivatives tetrabromobisphenol A and tetrachlorobisphenol A induce apelin expression and secretion in ovarian cancer cells through a peroxisome proliferator-activated receptor gamma-dependent mechanism. Toxicol. Lett. 269 (2017), 15–22.
37. Hong, H., Yang, L., Stallcup, M.R., Hormone-independent transcriptional activation and coactivator binding by novel orphan nuclear receptor ERR3. J. Biol. Chem. 274:32 (1999), 22618–22626.
38. Hong, S.-H., Ahmadian, M., Yu, R.T., Atkins, A.R., Downes, M., Evans, R.M., Nuclear receptors and metabolism: from feast to famine. Diabetologia 57:5 (2014), 860–867.
39. Imai, T., Takakuwa, R., Marchand, S., Dentz, E., Bornert, J.-M., Messaddeq, N., Wendling, O., Mark, M., Desvergne, B., Wahli, W., Chambon, P., Metzger, D., Peroxisome proliferator-activated receptor gamma is required in mature white and brown adipocytes for their survival in the mouse. Proc. Natl. Acad. Sci. U. S. A. 101:13 (2004), 4543–4547.
40. Issemann, I., Green, S., Activation of a Member of the Steroid Hormone Receptor Superfamily by Peroxisome Proliferators. Nature 347 (1990), 645–650.
41. Juge-Aubry, C., Pernin, A., Favez, T., Burger, a.G., Wahli, W., Meier, C.a., Desvergne, B., DNA binding properties of peroxisome proliferator-activated receptor subtypes on various natural peroxisome proliferator response elements: importance of the 5′-flanking region. J. Biol. Chem. 272:40 (1997), 25252–25259.
42. Kelly, M.J., Rønnekleiv, O.K., Membrane-initiated actions of estradiol that regulate reproduction, energy balance and body temperature. Front. Neuroendocrinol. 33:4 (2012), 376–387.
43. Kershaw, E.E., Schupp, M., Guan, H.-P., Gardner, N.P., Lazar, M.a., Flier, J.S., PPARgamma regulates adipose triglyceride lipase in adipocytes in vitro and in vivo. Am. J. Physiol. Endocrinol. Metab. 293:6 (2007), E1736–45.
44. Kinch, C.D., Ibhazehiebo, K., Jeong, J.-H., Habibi, H.R., Kurrasch, D.M., Low-dose exposure to bisphenol A and replacement bisphenol S induces precocious hypothalamic neurogenesis in embryonic zebrafish. Proc. Natl. Acad. Sci. U. S. A. 112:5 (2015), 1475–1480.
45. Kolšek, K., Gobec, M., Mlinarič Raščan, I., Sollner Dolenc, M., Screening of bisphenol A, triclosan and paraben analogues as modulators of the glucocorticoid and androgen receptor activities. Toxicol. in Vitro 29:1 (2015), 8–15.
46. Krishnan, A., Stathis, P., Bisphenol-A: an Estrogenic Substance is Released from Polycarbonate Flasks during Autoclaving. Endocrinology 132 (1993), 2279–2286.
47. Kuiper, G.G., Carlsson, B., Grandien, K., Enmark, E., Häggblad, J., Nilsson, S., Gustafsson, J.A., Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138:3 (1997), 863–870.
48. Kurosawa, T., Hiroi, H., Tsutsumi, O., Ishikawa, T., Osuga, Y., Fujiwara, T., Inoue, S., Muramatsu, M., Momoeda, M., Taketani, Y., The activity of bisphenol A depends on both the estrogen receptor subtype and the cell type. Endocr. J. 49:4 (2002), 465–471.
49. Kwon, S., Stedman, D.B., Elswick, B.a., Cattley, R.C., Welsch, F., Pubertal development and reproductive functions of Crl:CD BR Sprague-Dawley rats exposed to bisphenol A during prenatal and postnatal development. Toxicol. Sci. 55 (2000), 399–406.
50. Lagarde, F., Beausoleil, C., Belcher, S.M., Belzunces, L.P., Emond, C., Guerbet, M., Rousselle, C., Non-monotonic dose-response relationships and endocrine disruptors: a qualitative method of assessment. Environ. Health 14:13 (2015), 1–15.
51. Lakind, J.S., Levesque, J., Dumas, P., Bryan, S., Clarke, J., Naiman, D.Q., Comparing United States and Canadian population exposures from National Biomonitoring Surveys: bisphenol A intake as a case study. J. Expo. Sci. Environ. Epidemiol. 22:3 (2012), 219–226.
52. Lalwani, N., Fahl, W., Reddy, J., Detection of a nafenopin-binding protein in rat liver cytosol associated with the induction of peroxisome proliferation by hypolipidemic compounds. Biochem. Biophys. Res. Commun., 116(2), 1983.
53. Lee, H.J., Chattopadhyay, S., Gong, E.-Y., Ahn, R.S., Lee, K., Antiandrogenic effects of bisphenol A and nonylphenol on the function of androgen receptor. Toxicol. Sci. 75:1 (2003), 40–46.
54. Li, J., Ma, M., Wang, Z., A two-hybrid yeast assay to quantify the effects of xenobiotics on retinoid X receptor-mediated gene expression. Toxicol. Lett. 176:3 (2008), 198–206.
55. Li, J., Ma, M., Wang, Z., In vitro profiling of endocrine disrupting effects of phenols. Toxicol. in Vitro 24:1 (2010), 201–207.
56. Liu, X., Matsushima, A., Shimohigashi, M., Shimohigashi, Y., A characteristic back support structure in the bisphenol A-binding pocket in the human nuclear receptor ERRγ. PLoS One, 9(6), 2014, e101252.
57. Marino, M., Ascenzi, P., Steroid hormone rapid signaling: the pivotal role of S-palmitoylation. IUBMB Life 58:12 (2006), 716–719.
58. Marino, M., Pellegrini, M., La Rosa, P., Acconcia, F., Susceptibility of estrogen receptor rapid responses to xenoestrogens: physiological outcomes. Steroids 77:10 (2012), 910–917.
59. Masuno, H., Kidani, T., Sekiya, K., Sakayama, K., Shiosaka, T., Yamamoto, H., Honda, K., Bisphenol A in combination with insulin can accelerate the conversion of 3T3-L1 fibroblasts to adipocytes. J. Lipid Res. 43:5 (2002), 676–684.
60. Masuno, H., Iwanami, J., Kidani, T., Sakayama, K., Honda, K., Bisphenol a accelerates terminal differentiation of 3T3-L1 cells into adipocytes through the phosphatidylinositol 3-kinase pathway. Toxicol. Sci. 84:2 (2005), 319–327.
61. Meitzen, J., Luoma, J.I., Boulware, M.I., Hedges, V.L., Peterson, B.M., Tuomela, K., Britson, K.a., Mermelstein, P.G., Palmitoylation of estrogen receptors is essential for neuronal membrane signaling. Endocrinology 154:11 (2013), 4293–4304.
62. Micevych, P., Dominguez, R., Membrane estradiol signaling in the brain. Front. Neuroendocrinol. 30:3 (2009), 315–327.
63. Michałowicz, J., Bisphenol A - sources, toxicity and biotransformation. Environ. Toxicol. Pharmacol. 37:2 (2014), 738–758.
64. Montes-Grajales, D., Olivero-Verbel, J., Computer-aided identification of novel protein targets of bisphenol A. Toxicol. Lett. 222:3 (2013), 312–320.
65. Moriyama, K., Tagami, T., Akamizu, T., Usui, T., Saijo, M., Kanamoto, N., Hataya, Y., Shimatsu, A., Kuzuya, H., Nakao, K., Thyroid hormone action is disrupted by bisphenol A as an antagonist. J. Clin. Endocrinol. Metab. 87:11 (2002), 5185–5190.
66. National Toxicology Program, NTP-CERHR monograph on the potential human reproductive and developmental effects of bisphenol A. Nat. Inst. Health, 2008, 08–5994.
67. Nohynek, G.J., Borgert, C.J., Dietrich, D., Rozman, K.K., Endocrine disruption: fact or urban legend?. Toxicol. Lett. 223:3 (2013), 295–305.
68. 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. Environ. Health Perspect. 116:1 (2008), 32–38.
69. Paris, F., Balaguer, P., Térouanne, B., Servant, N., Lacoste, C., Cravedi, J.-P., Nicolas, J.-c., Sultan, C., Phenylphenols, biphenols, bisphenol-A and 4-tert- octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. Mol. Cell. Endocrinol. 193:1–2 (2002), 43–49.
70. Pedram, A., Razandi, M., Kim, J.K., O'Mahony, F., Lee, E.Y., Luderer, U., Levin, E.R., Developmental phenotype of a membrane only estrogen receptor (MOER) mouse. J. Biol. Chem. 284:6 (2009), 3488–3495.
71. Pedram, A., Razandi, M., Blumberg, B., Levin, E.R., Membrane and nuclear estrogen receptor collaborate to suppress adipogenesis but not triglyceride content. FASEB J., 2015, 1–11.
72. Pereira-Fernandes, A., Demaegdt, H., Vandermeiren, K., Hectors, T.L.M., Jorens, P.G., Blust, R., Vanparys, C., Evaluation of a screening system for obesogenic compounds: screening of endocrine disrupting compounds and evaluation of the PPAR dependency of the effect. PLoS One, 8(10), 2013, e77481.
73. Perera, L., Li, Y., Coons, L.A., Houtman, R., van Beuningen, R., Goodwin, B., Auerbach, S.S., Teng, C.T., Binding of bisphenol A, bisphenol AF, and bisphenol S on the androgen receptor: coregulator recruitment and stimulation of potential interaction sites. Toxicol. in Vitro 44 (2017), 287–302.
74. Phrakonkham, P., Viengchareun, S., Belloir, C., Lombès, M., Artur, Y., Canivenc-Lavier, M.-C., Dietary xenoestrogens differentially impair 3T3-L1 preadipocyte differentiation and persistently affect leptin synthesis. J. Steroid Biochem. Mol. Biol. 110:1–2 (2008), 95–103.
75. Pottenger, L.H., Domoradzki, J.Y., Markham, D.a., Hansen, S.C., Cagen, S.Z., Waechter, J.M., The relative bioavailability and metabolism of bisphenol A in rats is dependent upon the route of administration. Toxicol. Sci. 54:1 (2000), 3–18.
76. Prasanth, G.K., Divya, L.M., Sadasivan, C., Bisphenol-A can bind to human glucocorticoid receptor as an agonist: an in silico study. J. Appl. Toxicol. 30:July (2010), 769–774.
77. Prossnitz, E.R., Arterburn, J.B., Smith, H.O., Oprea, T.I., Sklar, L.a., Hathaway, H.J., Estrogen signaling through the transmembrane G protein-coupled receptor GPR30. Annu. Rev. Physiol. 70 (2008), 165–190.
78. Rehan, M., Ahmad, E., Sheikh, I.A., Abuzenadah, A.M., Damanhouri, G.A., Bajouh, O.S., Al Basri, S.F., Assiri, M.M., Beg, M.A., Androgen and progesterone receptors are targets for bisphenol a (BPA), 4-methyl-2,4-bis-(p-hydroxyphenyl)pent-1-ene-A potent metabolite of BPA, and 4-tert-octylphenol: a computational insight. PLoS One 10:9 (2015), 1–18.
79. Reif, D.M., Martin, M.T., Tan, S.W., Houck, K.a., Judson, R.S., Richard, A.M., Knudsen, T.B., Dix, D.J., Kavlock, R.J., Endocrine profiling and prioritization of environmental chemicals using ToxCast data. Environ. Health Perspect. 118:12 (2010), 1714–1720.
80. Revankar, C.M., Cimino, D.F., Sklar, L.a., Arterburn, J.B., Prossnitz, E.R., A transmembrane intracellular estrogen receptor mediates rapid cell signaling. Science 307:5715 (2005), 1625–1630.
81. Revankar, C.M., Mitchell, H.D., Field, A.S., Burai, R., Corona, C., Ramesh, C., Sklar, L.A., Arterburn, J.B., Prossnitz, E.R., Synthetic estrogen derivatives demonstrate the functionality of intracellular GPR30. ACS Chem. Biol. 2:8 (2007), 536–544.
82. Reynolds, R.M., Glucocorticoid excess and the developmental origins of disease: two decades of testing the hypothesis - 2012 Curt Richter award winner. Psychoneuroendocrinology 38:1 (2013), 1–11.
83. Richter, C.A., Taylor, J.A., Ruhlen, R.L., Welshons, W.V., vom Saal, F.S., Estradiol and bisphenol A stimulate androgen receptor and estrogen receptor gene expression in fetal mouse prostate mesenchyme cells. Environ. Health Perspect. 115:6 (2007), 902–908.
84. Riu, A., Grimaldi, M., le Maire, A., Bey, G., Phillips, K., Boulahtouf, A., Perdu, E., Zalko, D., Bourguet, W., Balaguer, P., Peroxisome proliferator-activated receptor γ is a target for halogenated analogs of bisphenol A. Environ. Health Perspect. 119:9 (2011), 1227–1232.
85. Rubin, B.S., Bisphenol A: an endocrine disruptor with widespread exposure and multiple effects. J. Steroid Biochem. Mol. Biol. 127:1–2 (2011), 27–34.
86. vom Saal, F.S., Welshons, W.V., Large effects from small exposures. II. The importance of positive controls in low-dose research on bisphenol A. Environ. Res. 100:1 (2006), 50–76.
87. Sargis, R.M., Johnson, D.N., Choudhury, R.a., Brady, M.J., Environmental endocrine disruptors promote adipogenesis in the 3T3-L1 cell line through glucocorticoid receptor activation. Obesity 18:7 (2010), 1283–1288.
88. Smith, A., Bosch, M., Wagner, E.J., Rønnekleiv, O., Kelly, M., The membrane estrogen receptor ligand STX rapidly enhances GABAergic signaling in NPY/AgRP neurons: role in mediating the anorexigenic effects of 17β-estradiol. Am. J. Physiol. Endocrinol. Metab. 305:5 (2013), E632–40.
89. Somm, E., Schwitzgebel, V.M., Toulotte, A., Cederroth, C.R., Combescure, C., Nef, S., Aubert, M.L., Hüppi, P.S., Perinatal exposure to bisphenol a alters early adipogenesis in the rat. Environ. Health Perspect. 117:10 (2009), 1549–1555.
90. Srivastava, D.P., Waters, E.M., Mermelstein, P.G., Kramár, E.a., Shors, T.J., Liu, F., Rapid estrogen signaling in the brain: implications for the fine-tuning of neuronal circuitry. J. Neurosci. 31:45 (2011), 16056–16063.
91. Stavreva, D.A., Varticovski, L., Levkova, L., George, A.A., Davis, L., Pegoraro, G., Blazer, V., Iwanowicz, L., Hager, G.L., Novel cell-based assay for detection of thyroid receptor beta-interacting environmental contaminants. Toxicology 368-369:2016 (2016), 69–79.
92. Sun, H., Xu, L.-C., Chen, J.-F., Song, L., Wang, X.-R., Effect of bisphenol A, tetrachlorobisphenol A and pentachlorophenol on the transcriptional activities of androgen receptor-mediated reporter gene. Food Chem. Toxicol. 44:11 (2006), 1916–1921.
93. Sun, H., Shen, O.X., Wang, X.R., Zhou, L., Zhen, S.Q., Chen, X.D., Anti-thyroid hormone activity of bisphenol A, tetrabromobisphenol A and tetrachlorobisphenol A in an improved reporter gene assay. Toxicol. in Vitro 23:5 (2009), 950–954.
94. Takayanagi, S., Tokunaga, T., Liu, X., Okada, H., Matsushima, A., Shimohigashi, Y., Endocrine disruptor bisphenol A strongly binds to human estrogen-related receptor gamma (ERRγ) with high constitutive activity. Toxicol. Lett. 167:2 (2006), 95–105.
95. Tan, M.E., Li, J., Xu, H.E., Melcher, K., Yong, E.-L., Androgen receptor: structure, role in prostate cancer and drug discovery. Acta Pharmacol. Sin., 2014, 1–21.
96. Teeguarden, J.G., Calafat, A.M., Ye, X., Doerge, D.R., Churchwell, M.I., Gunawan, R., Graham, M.K., Twenty-four hour human urine and serum profiles of bisphenol a during high-dietary exposure. Toxicol. Sci. 123:1 (2011), 48–57.
97. Teng, C., Goodwin, B., Shockley, K., Xia, M., Huang, R., Norris, J., Merrick, B.A., Jetten, A.M., Austin, C.P., Tice, R.R., Bisphenol A affects androgen receptor function via multiple mechanisms. Chem. Biol. Interact. 203:3 (2013), 556–564.
98. Thomas, P., Dong, J., Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J. Steroid Biochem. Mol. Biol. 102:1–5 (2006), 175–179.
99. Thomas, P., Pang, Y., Filardo, E.J., Dong, J., Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells. Endocrinology 146:2 (2005), 624–632.
100. Tohmé M., Prud'homme, S.M., Boulahtouf, A., Samarut, E., Brunet, F., Bernard, L., Bourguet, W., Gibert, Y., Balaguer, P., Laudet, V., Estrogen-related receptor γ is an in vivo receptor of bisphenol A. FASEB J. 28:7 (2014), 3124–3133.
101. Tyl, R.W., Myers, C.B., Marr, M.C., Sloan, C.S., Castillo, N.P., Veselica, M.M., Seely, J.C., Dimond, S.S., Van Miller, J.P., Shiotsuka, R.N., Beyer, D., Hentges, S.G., Waechter, J.M., Two-generation reproductive toxicity study of dietary bisphenol A in CD-1 (Swiss) mice. Toxicol. Sci. 104:2 (2008), 362–384.
102. Upmeier, A., Degen, G.H., Diel, P., Michna, H., Bolt, H.M., Toxicokinetics of bisphenol A in female DA/Han rats after a single i.v. and oral administration. Arch. Toxicol. 74:8 (2000), 431–436.
103. Vandenberg, L.N., Hauser, R., Marcus, M., Olea, N., Welshons, W.V., Human exposure to bisphenol A (BPA). Reprod. Toxicol. 24:2 (2007), 139–177.
104. Vandenberg, L.N., Colborn, T., Hayes, T.B., Heindel, J.J., Jacobs, D.R., Lee, D.H., Shioda, T., Soto, A.M., vom Saal, F.S., Welshons, W.V., Zoeller, R.T., Myers, J.P., Hormones and endocrine-disrupting chemicals: low-dose effects and nonmonotonic dose responses. Endocr. Rev. 33:3 (2012), 378–455.
105. Vom Saal, F.S., Nagel, S.C., Coe, B.L., Angle, B.M., Taylor, J.a., The estrogenic endocrine disrupting chemical bisphenol A (BPA) and obesity. Mol. Cell. Endocrinol. 354:1–2 (2012), 74–84.
106. Vom Saal, F.S., Prins, G.S., Welshons, W.V., Report of very low real-world exposure to bisphenol A is unwarranted based on a lack of data and flawed assumptions. Toxicol. Sci. 125:1 (2012), 318–320.
107. Wang, J., Sun, B., Hou, M., Pan, X., Li, X., The environmental obesogen bisphenol A promotes adipogenesis by increasing the amount of 11β-hydroxysteroid dehydrogenase type 1 in the adipose tissue of children. Int. J. Obes. 37:7 (2013), 999–1005.
108. Wang, H., Ding, Z., Shi, Q.M., Ge, X., Wang, H.X., Li, M.X., Chen, G., Wang, Q., Ju, Q., Zhang, J.P., Zhang, M.R., Xu, L.C., Anti-androgenic mechanisms of Bisphenol A involve androgen receptor signaling pathway. Toxicology 387:May (2017), 10–16.
109. Yang, X., Liu, H., Yang, Q., Liu, J., Chen, J., Shi, L., Predicting anti-androgenic activity of bisphenols using molecular docking and quantitative structure-activity relationships. Chemosphere 163 (2016), 373–381.
110. Youssef, J., Badr, M.Z., PPARs: history and advances. Badr, M.Z., Youssef, J.A., (eds.) Peroxisome Proliferator-Activated Receptors (PPARs), volume 952 of Methods in Molecular Biology, 2013, Humana Press, Totowa, NJ.
111. Zoeller, R.T., Bansal, R., Parris, C., Bisphenol-A, an environmental contaminant that acts as a thyroid hormone receptor antagonist in vitro, increases serum thyroxine, and alters RC3/neurogranin expression in the developing rat brain. Endocrinology 146:2 (2005), 607–612.