Molecular mechanism of action of bisphenol and bisphenol A mediated by oestrogen receptor alpha in growth and apoptosis of breast cancer cells

British Journal of Pharmacology

Volumn 169, Issue 1, 2013, Pages 167-178

  Sengupta, S ^a   Obiorah, I ^a   Maximov, P Y ^a   Curpan, R ^b   Jordan, V C ^a  

^a GEORGETOWN UNIVERSITY   (United States)

^b ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

Author keywords

antioestrogens; apoptosis; bisphenol and bisphenol A; breast cancer; oestrogen; oestrogen receptor; triphenylethylenes

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; BIPHENYLDIOL; ENDOCRINE DISRUPTOR; ESTROGEN RECEPTOR ALPHA; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BINDING AFFINITY; BREAST CANCER; CANCER CELL; CELL GROWTH; CELL PROLIFERATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; GENE; GROWTH INHIBITION; HUMAN; HUMAN CELL; LIGAND BINDING; MOLECULAR DOCKING; PRIORITY JOURNAL; PS2 GENE; TFF1 GENE; TRANSCRIPTION INITIATION; TRANSCRIPTION REGULATION; UPREGULATION;

APOPTOSIS; BENZHYDRYL COMPOUNDS; BREAST NEOPLASMS; CELL PROLIFERATION; CHROMATIN IMMUNOPRECIPITATION; DNA; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; FEMALE; HUMANS; MCF-7 CELLS; MOLECULAR DOCKING SIMULATION; PHENOLS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; TAMOXIFEN;

EID: 84876260390     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/bph.12122     Document Type: Article

References (34)

1. Ariazi EA, Cunliffe HE, Lewis-Wambi JS, Slifker MJ, Willis AL, Ramos P, et al. (2011). Estrogen induces apoptosis in estrogen deprivation-resistant breast cancer through stress responses as identified by global gene expression across time. Proc Natl Acad Sci U S A 108: 18879-18886.
2. Bentrem D, Fox JE, Pearce ST, Liu H, Pappas S, Kupfer D, et al. (2003). Distinct molecular conformations of the estrogen receptor alpha complex exploited by environmental estrogens. Cancer Res 63: 7490-7496.
3. Bourgoin-Voillard S, Gallo D, Laios I, Cleeren A, Bali LE, Jacquot Y, et al. (2010). Capacity of type I and II ligands to confer to estrogen receptor alpha an appropriate conformation for the recruitment of coactivators containing a LxxLL motif-Relationship with the regulation of receptor level and ERE-dependent transcription in MCF-7 cells. Biochem Pharmacol 79: 746-757.
4. Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, Engstrom O, et al. (1997). Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389: 753-758.
5. Gao L, Tu Y, Agren H, Eriksson LA, (2012). Characterization of agonist binding to His524 in the estrogen receptor alpha ligand binding domain. J Phys Chem B 116: 4823-4830.
6. Gould JC, Leonard LS, Maness SC, Wagner BL, Conner K, Zacharewski T, et al. (1998). Bisphenol A interacts with the estrogen receptor alpha in a distinct manner from estradiol. Mol Cell Endocrinol 142: 203-214.
7. Hu ZZ, Kagan BL, Ariazi EA, Rosenthal DS, Zhang L, Li JV, et al. (2011). Proteomic analysis of pathways involved in estrogen-induced growth and apoptosis of breast cancer cells. PLoS ONE 6: e20410.
8. Jiang SY, Wolf DM, Yingling JM, Chang C, Jordan VC, (1992). An estrogen receptor positive MCF-7 clone that is resistant to antiestrogens and estradiol. Mol Cell Endocrinol 90: 77-86.
9. Jordan VC, (1993). Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol 110: 507-517.
10. Jordan VC, Lieberman ME, (1984). Estrogen-stimulated prolactin synthesis in vitro. Classification of agonist, partial agonist, and antagonist actions based on structure. Mol Pharmacol 26: 279-285.
11. Jordan VC, O'Malley BW, (2007). Selective estrogen-receptor modulators and antihormonal resistance in breast cancer. J Clin Oncol 25: 5815-5824.
12. Jordan VC, Lieberman ME, Cormier E, Koch R, Bagley JR, Ruenitz PC, (1984). Structural requirements for the pharmacological activity of nonsteroidal antiestrogens in vitro. Mol Pharmacol 26: 272-278.
13. Jordan VC, Koch R, Mittal S, Schneider MR, (1986). Oestrogenic and antioestrogenic actions in a series of triphenylbut-1-enes: modulation of prolactin synthesis in vitro. Br J Pharmacol 87: 217-223.
14. Jordan VC, Schafer JM, Levenson AS, Liu H, Pease KM, Simons LA, et al. (2001). Molecular classification of estrogens. Cancer Res 61: 6619-6623.
15. Kitamura S, Suzuki T, Sanoh S, Kohta R, Jinno N, Sugihara K, et al. (2005). Comparative study of the endocrine-disrupting activity of bisphenol A and 19 related compounds. Toxicol Sci 84: 249-259.
16. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der, Saag PT, et al. (1998). Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139: 4252-4263.
17. Labhart P, Karmakar S, Salicru EM, Egan BS, Alexiadis V, O'Malley BW, et al. (2005). Identification of target genes in breast cancer cells directly regulated by the SRC-3/AIB1 coactivator. Proc Natl Acad Sci U S A 102: 1339-1344.
18. Levenson AS, Catherino WH, Jordan VC, (1997). Estrogenic activity is increased for an antiestrogen by a natural mutation of the estrogen receptor. J Steroid Biochem Mol Biol 60: 261-268.
19. Levenson AS, Tonetti DA, Jordan VC, (1998). The oestrogen-like effect of 4-hydroxytamoxifen on induction of transforming growth factor alpha mRNA in MDA-MB-231 breast cancer cells stably expressing the oestrogen receptor. Br J Cancer 77: 1812-1819.
20. Lewis JS, Meeke K, Osipo C, Ross EA, Kidawi N, Li T, et al. (2005). Intrinsic mechanism of estradiol-induced apoptosis in breast cancer cells resistant to estrogen deprivation. J Natl Cancer Inst 97: 1746-1759.
21. List HJ, Lauritsen KJ, Reiter R, Powers C, Wellstein A, Riegel AT, (2001). Ribozyme targeting demonstrates that the nuclear receptor coactivator AIB1 is a rate-limiting factor for estrogen-dependent growth of human MCF-7 breast cancer cells. J Biol Chem 276: 23763-23768.
22. Liu XF, Bagchi MK, (2004). Recruitment of distinct chromatin-modifying complexes by tamoxifen-complexed estrogen receptor at natural target gene promoters in vivo. J Biol Chem 279: 15050-15058.
23. MacGregor Schafer J, Liu H, Bentrem DJ, Zapf JW, Jordan VC, (2000). Allosteric silencing of activating function 1 in the 4-hydroxytamoxifen estrogen receptor complex is induced by substituting glycine for aspartate at amino acid 351. Cancer Res 60: 5097-5105.
24. Maximov P, Sengupta S, Lewis-Wambi JS, Kim HR, Curpan RF, Jordan VC, (2011). The conformation of the estrogen receptor directs estrogen-induced apoptosis in breast cancer: a hypothesis. Horm Mol Biol Clin Investig 5: 27-34.
25. Maximov PY, Myers CB, Curpan RF, Lewis-Wambi JS, Jordan VC, (2010). Structure-function relationships of estrogenic triphenylethylenes related to endoxifen and 4-hydroxytamoxifen. J Med Chem 53: 3273-3283.
26. Metivier R, Stark A, Flouriot G, Hubner MR, Brand H, Penot G, et al. (2002). A dynamic structural model for estrogen receptor-alpha activation by ligands, emphasizing the role of interactions between distant A and E domains. Mol Cell 10: 1019-1032.
27. Metivier R, Penot G, Hubner MR, Reid G, Brand H, Kos M, et al. (2003). Estrogen receptor-alpha directs ordered, cyclical, and combinatorial recruitment of cofactors on a natural target promoter. Cell 115: 751-763.
28. Routledge EJ, White R, Parker MG, Sumpter JP, (2000). Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta. J Biol Chem 275: 35986-35993.
29. Sengupta S, Jordan VC, (2008). Selective estrogen modulators as an anticancer tool: mechanisms of efficiency and resistance. Adv Exp Med Biol 630: 206-219.
30. Sengupta S, Sharma CG, Jordan VC, (2010). Estrogen regulation of X-box binding protein-1 and its role in estrogen induced growth of breast and endometrial cancer cells. Horm Mol Biol Clin Investig 2: 235-243.
31. Shang Y, Brown M, (2002). Molecular determinants for the tissue specificity of SERMs. Science 295: 2465-2468.
32. Shao W, Keeton EK, McDonnell DP, Brown M, (2004). Coactivator AIB1 links estrogen receptor transcriptional activity and stability. Proc Natl Acad Sci U S A 101: 11599-11604.
33. Shiau AK, Barstad D, Loria PM, Cheng L, Kushner PJ, Agard DA, et al. (1998). The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95: 927-937.
34. Wolf DM, Jordan VC, (1994). The estrogen receptor from a tamoxifen stimulated MCF-7 tumor variant contains a point mutation in the ligand binding domain. Breast Cancer Res Treat 31: 129-138.