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

Volumn 10, Issue 9, 2015, Pages

  Rehan, Mohd ^a   Ahmad, Ejaz ^a   Sheikh, Ishfaq A ^a   Abuzenadah, Adel M ^a   Damanhouri, Ghazi A ^a   Bajouh, Osama S ^b   Al Basri, Samera F ^b   Assiri, Mansour M ^b   Beg, Mohd A ^a  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b King Abdulaziz University   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYL 2,4 BIS(4 HYDROXYPHENYL)PENT 1 ENE; 4 TERT OCTYLPHENOL; 4,4' ISOPROPYLIDENEDIPHENOL; ANDROGEN RECEPTOR; ASPARAGINE; LEUCINE; METHIONINE; NORETHISTERONE; PHENOL DERIVATIVE; PHENYLALANINE; PROGESTERONE RECEPTOR; TESTOSTERONE; UNCLASSIFIED DRUG; XENOBIOTIC AGENT; 4-METHYL-2,4-BIS(4-HYDROXYPHENYL)PENT-1-ENE; 4-TERT-OCTYLPHENOL; BENZHYDRYL DERIVATIVE; ENDOCRINE DISRUPTOR; LIGAND;

ARTICLE; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; LIGAND BINDING; MOLECULAR DOCKING; PREDICTION; PROTEIN PROTEIN INTERACTION; RECEPTOR BINDING; CHEMISTRY;

BENZHYDRYL COMPOUNDS; ENDOCRINE DISRUPTORS; LIGANDS; MOLECULAR DOCKING SIMULATION; PHENOLS; RECEPTORS, ANDROGEN; RECEPTORS, PROGESTERONE;

EID: 84945960712     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0138438     Document Type: Article

References (67)

1. Gurunath S, Pandian Z, Anderson RA, Bhattacharya S (2011) Defining infertility-A systematic review of prevalence studies. Hum Reprod Update 17: 575-588. doi: 10.1093/humupd/dmr015 PMID: 21493634
2. Kamel RM (2010) Management of infertile couple: An evidence-based protocol. Reprod Biol Endocrinol 8: 21. doi: 10.1186/1477-7827-8-21 PMID: 20205744
3. Oberpenning R, Muthny FA, Oberpenning F (2010) Psychology of fertility disorders. Chapt. 25. In: Nieschlag E, Behre H, Nieschlag S, editors. Andrology: Male reproductive health and dysfunction. 3rd edition, Springer-Verlag, Heidelberg, pp 521-537.
4. Forti G, Krausz C (1998) Clinical review 100: Evaluation and treatment of the infertile couple. J Clin Endocrinol Metab 83: 4177-4188. PMID: 9851748
5. WHO-UNEP (2013) State of the science of endocrine disrupting chemicals 2012. Bergman A, Heindel JJ, Jobling S, Kidd KA, Zoeller RT, editors. WHO Press, Geneva, Switzerland.
6. Patel S, Zhou C, Rattan S, Flaws JA (2015) Effects of endocrine-disrupting chemicals on the ovary. Biol Reprod 93: 20, 1-9.
7. Luccio-Camelo DC, Prins GS (2011) Disruption of androgen receptor signaling in males by environmental chemicals. J Steroid Biochem Mol Biol 127: 74-82. doi: 10.1016/j.jsbmb.2011.04.004 PMID: 21515368
8. Marques-Pinto A, Carvalho D (2013) Human infertility: Are endocrine disruptors to blame? Endocr Connect 2: R15-29. doi: 10.1530/EC-13-0036 PMID: 23985363
9. 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. doi: 10.1016/j.toxlet.2010.04.017 PMID: 20435109
10. Baker ME, Chandsawangbhuwana C (2012) 3D Models of MBP, a biologically active metabolite of bisphenol A, in human estrogen receptor a and estrogen receptor ß. PLoS ONE 7: E46078.
11. 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. doi: 10.1289/ehp. 10753 PMID: 18197297
12. Vandenberg LN, Chauhoud I, Heindel JJ, Padmanabhan V, Paumgartten FJ, Schoenfelder G (2010) Urinary, circulating and tissue biomonitoring studies indicate widespread exposure to bisphenol A. Environ Health Perspect 118: 1055-1070. doi: 10.1289/ehp.0901716 PMID: 20338858
13. Asimakopoulos AG, Thomaidis NS, Koupparis MA (2012) Recent trends in biomonitoring of bisphenol A, 4-t-octylephenol, and 4-nonylphenol. Toxicol Lett 210: 141-154. doi: 10.1016/j.toxlet.2011.07.032 PMID: 21888958
14. Yi B, Kim C, Park M, Han Y, Park JY, Yang M (2013) Association between endocrine disrupting phenols in colostrums and maternal and infant health. Int J Endocrinol 2013: 282381. doi: 10.1155/2013/282381 PMID: 23737772
15. Diamanti-Kandarakis E, Bourguignon JP, Giudice LC, Hauser R, Prins GS, Soto AM, et al. (2009) Endocrine-disrupting chemicals: An Endocrine Society scientific statement. Endocr Rev 30: 293-342. doi: 10.1210/er.2009-0002 PMID: 19502515
16. Rubin BS (2011) Bisphenol A: An endocrine disruptor with widespread exposure and multiple effects. J Steroid Biochem Mol Biol 127: 27-34. doi: 10.1016/j.jsbmb.2011.05.002 PMID: 21605673
17. Rochester JR (2013) Bisphenol A and human health: A review of literature. Reprod Toxicol 42: 132-155. doi: 10.1016/j.reprotox.2013.08.008 PMID: 23994667
18. Bloom MS, Kim D, Vom Saal FS, Taylor JA, Cheng G, Lamb JD, et al. (2011) Bisphenol A exposure reduces the estradiol response to gonadotropin stimulation during in vitro fertilization. Fertil Steril 96: 672-677. doi: 10.1016/j.fertnstert.2011.06.063 PMID: 21813122
19. Mok-Lin E, Ehrlich S, Williams PL, Petrozza J, Wright DL, Calafat AM, et al. (2010) Urinary bisphenol A concentrations and ovarian response among women undergoing IVF. Int J Androl 33: 385-393. doi: 10.1111/j.1365-2605.2009.01014.x PMID: 20002217
20. Ehrlich S, Williams PL, Missmer SA, Flaws JA, Berry KF, Calafat AM, et al. (2012) Urinary bisphenol A concentrations and implantation failure among women undergoing in vitro fertilization. Environ Health Perspect 120: 978-983. doi: 10.1289/ehp.1104307 PMID: 22484414
21. Caserta D, Bordi G, Ciardo F, Marci R, La Rocca C, Tait S, et al. (2013) The influence of endocrine disruptors in a selected population of infertile women. Gynecol Endocrinol 29: 444-447. doi: 10.3109/09513590.2012.758702 PMID: 23347089
22. Kandaraki E, Chatzigeorgiou A, Livadas S, Palioura E, Economou F, Koutsilieris M, et al. (2011) Endocrine disruptors and polycystic ovary syndrome (PCOS): Elevated serum levels of bisphenol A in women with PCOS. J Clin Endocrinol Metab 96: E480-484. doi: 10.1210/jc.2010-1658 PMID: 21193545
23. Takeuchi T, Tsutsumi O, Ikezuki Y, Takai Y, Taketani Y (2004) Positive relationship between androgen and the endocrine disruptor, bisphenol A, in normal women and women with ovarian dysfunction. Endocr J 51: 165-169. PMID: 15118266
24. Hao J, Wang J, Zhao W, Ding L, Gao E, YuanW(2011) [Effect of bisphenol A exposure on sex hormone level in occupational women]. Wei Sheng Yan Jiu 40: 312-314, 319. PMID: 21695901
25. Cobellis L, Colacurci N, Trabucco E, Carpentiero C, Grumetto L (2009) Measurement of bisphenol A and bisphenol B levels in human blood sera from healthy and endometriotic women. Biomed Chromatogr 23: 1186-1190. doi: 10.1002/bmc.1241 PMID: 19444800
26. Zheng YM, Wang Y, Zhao J, Dai YH, Luo XM, Shen ZJ, et al. (2012) [Association between serum bisphenol-A and recurrent spontaneous abortion: A 1: 2 case-control study China]. Zhonghua Liu Xing Bing Xue Za Zhi 33: 841-845. PMID: 22967341
27. Cantonwine D, Meeker JD, Hu H, Sanchez BN, Lamadrid-Figueroa H, Mercado-Garcia A, et al. (2010) Bisphenol A exposure in Mexico City and risk of prematurity: A pilot nested case control study. Environ Health 9: 62. doi: 10.1186/1476-069X-9-62 PMID: 20955576
28. Li DK, Zhou Z, Miao M, He Y, Wang J, Ferber J, et al. (2011) Urine bisphenol-A (BPA) level in relation to semen quality. Fertil Steril 95: 625-630. doi: 10.1016/j.fertnstert.2010.09.026 PMID: 21035116
29. Li DK, Zhou Z, Miao M, He Y, Qing D, Wu T, et al. (2010) Relationship between urine bisphenol-A level and declining male sexual function. J Androl 31: 500-506. doi: 10.2164/jandrol.110.010413 PMID: 20467048
30. Meeker JD, Ehrlich S, Toth TL, Wright DL, Calafat AM, Trisini AT, et al. (2010) Semen quality and sperm DNA damage in relation to urinary bisphenol A among men from an infertility clinic. Reprod Toxicol 30: 532-539. doi: 10.1016/j.reprotox.2010.07.005 PMID: 20656017
31. Meeker JD, Calafat AM, Hauser R (2010) Urinary bisphenol A concentrations in relation to serum thyroid and reproductive hormone levels in men from an infertility clinic. Environ Sci Technol 44: 1458-1463. doi: 10.1021/es9028292 PMID: 20030380
32. Mendiola J, Jorgensen N, Andersson AM, Calafat AM, Ye X, Redmon JB, et al. (2010) Are environmental levels of bisphenol A associated with reproductive function in fertile men? Environ Health Perspect 118: 1286-1291. doi: 10.1289/ehp.1002037 PMID: 20494855
33. Manfo FPT, Jubendradass R, Nantia EA, Moundipa PF, Mathur PP (2014) Adverse effects of bisphenol A on male reproductive function. Rev Environ Contam Toxicol 228: 57-82. doi: 10.1007/978-3-319-01619-1-3 PMID: 24162092
34. Zhuang W, Wu K, Wang Y, Zhu H, Deng Z, Peng L, et al. (2015) Association of serum bisphenol-A concentration and male reproductive function among exposed workers. Arch Environ Contam Toxicol 68: 38-45. doi: 10.1007/s00244-014-0078-7 PMID: 25213476
35. Miao M, Yuan W, He Y, Zhou Z, Wang J, Gao E, et al. (2011) In utero exposure to bisphenol-A and anogenital distance of male offspring. Birth Defects Res A Clin Mol Teratol 91: 867-872. doi: 10.1002/bdra.22845 PMID: 21987463
36. Chou WC, Chen JL, Lin CF, Chen YC, Shih FC, Chuang CY (2011) Biomonitoring of bisphenol A concentrations in maternal and umbilical cord blood in regard to birth outcomes and adipokine expression: A birth cohort study in Taiwan. Environ Health 10: 94. doi: 10.1186/1476-069X-10-94 PMID: 22050967
37. Qiao L, Zheng L, Cai D (2010) [Study on the levels of the bisphenol A, octylphenol, 4-nonylphenol in serum of precocious girls]. Wei Sheng Yan Jiu 39: 9-12. PMID: 20364578
38. Tang CY, Li AQ, Guan YB, Li Y, Cheng XM, Li P, et al. (2012) Influence of polluted SY River on child growth and sex hormones. Biomed Environ Sci 25: 291-296. doi: 10.3967/0895-3988.2012.03.006 PMID: 22840579
39. Ben Maamar M, Lesne L, Desdoits-Lethimonier C, Coiffec I, Lassurguere J, Lavoue V, et al. (2015) An investigation of the endocrine-disruptive effects of bisphenol a in human and rat fetal testes. PLoS One 10: E0117226. doi: 10.1371/journal.pone.0117226 PMID: 25706302
40. Blake CA, Boockfor FR (1997) Chronic administration of the environmental pollutant 4-tert-octylphenol to adult male rats interferes with the secretion of luteinizing hormone, follicle-stimulating hormone, prolactin, and testosterone. Biol Reprod 57: 255-266. PMID: 9241038
41. Laws SC, Carey SA, Ferrell JM, Bodman GJ, Cooper RL (2000) Estrogenic activity of octylphenol, nonylphenol, bisphenol A and methoxychlor in rats. Toxicol Sci 54: 154-167. PMID: 10746942
42. Myllymaki SA, Karjalainen M, Haavisto TE, Toppari J, Paranko J (2005) Infantile 4-tert-octylphenol exposure transiently inhibits rat ovarian steroidogenesis and steroidogenic acute regulatory protein (StAR) expression. Toxicol Appl Pharmacol 207: 59-68. PMID: 16054900
43. Bian Q, Qian J, Xu L, Chen J, Song L, Wang X (2006) The toxic effects of 4-tert-octylphenol on the reproductive system of male rats. Food Chem Toxicol 44: 1355-1361. PMID: 16631297
44. Jung YW, Hong EJ, Choi KC, Jeung EB (2005) Novel progestogenic activity of environmental endocrine disruptors in the upregulation of calbindin-D9k in an immature mouse model. Toxicol Sci 83: 78-88. PMID: 15509668
45. Mueller SO, Korach KS (2001) Mechanisms of estrogen receptor-mediated agonistic and antagonistic effects. In: Metzler M, editor. The handbook of environmental chemistry. Springer-Verlag, Berlin Heidelberg, pp. 3-11.
46. Pihlajamaa P, Sahu B, Janne OA (2015) Determinants of receptor-and tissue-specific actions in androgen signaling. Endocr Rev 2015: Er20151034.
47. Ellmann S, Sticht H, Thiel F, Beckmann MW, Strick R, Strissel PL (2009) Estrogen and progesterone receptors: From molecular structures to clinical targets. Cell Mol Life Sci 66: 2405-2426. doi: 10.1007/s00018-009-0017-3 PMID: 19333551
48. Fang H, Tong W, Branham WS, Moland CL, Dial SL, Hong H, et al. (2003) Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. Chem Res Toxicol 6: 1338-1358.
49. Lee HJ, Chattopadhyay S, Gong EY, Ahn RS, Lee K (2003) Antiandrogenic effects of bisphenol A and nonylphenol on the function of androgen receptor. Toxicol Sci 75: 40-46. PMID: 12805653
50. 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. PMID: 15635150
51. Kolsek K, Gobec M, Mlinaric Rascan I, Sollner Dolenc M (2015) Screening of bisphenol A, triclosan and paraben analogues as modulators of the glucocorticoid and androgen receptor activities. Toxicol In Vitro 29: 8-15. doi: 10.1016/j.tiv.2014.08.009 PMID: 25192815
52. Wang H, Li J, Gao Y, Xu Y, Pan Y, Tsuji I, et al. (2010) Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor. Asian J Androl 12: 535-547. doi: 10.1038/aja.2010.14 PMID: 20436506
53. Delfosse V, Grimaldi M, Pons JL, Boulahtouf A, le Maire A, Cavailles V, et al. (2012) Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes. Proc Natl Acad Sci U S A 109: 14930-14935. doi: 10.1073/pnas.1203574109 PMID: 22927406
54. Wang X, Li X, Shi W, Wei S, Giesy JP, Yu H, et al. (2013) Docking and CoMSIA studies on steroids and non-steroidal chemicals as androgen receptor ligands. Ecotoxicol Environ Saf 89: 143-149. doi: 10. 1016/j.ecoenv.2012.11.020 PMID: 23260236
55. Ewing TJ, Makino S, Skillman AG, Kuntz ID (2001) DOCK 4.0: Search strategies for automated molecular docking of flexible molecule databases. J Comput Aided Mol Des 15: 411-428. PMID: 11394736
56. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, et al. (2004) Chimera-A visualization system for exploratory research and analysis. J Comput Chem 25: 1605-1612. PMID: 15264254
57. DeLano WL (2002) The PyMOL Molecular Graphics System. San Carlos, CA. DeLano Scientific.
58. Wallace AC, Laskowski RA, Thornton JM (1995) LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Protein Eng 8: 127-134. PMID: 7630882
59. Laskowski RA, Swindells MB (2011) LigPlot-: Multiple ligand-protein interaction diagrams for drug discovery. J Chem Inf Model 51: 2778-2786. doi: 10.1021/ci200227u PMID: 21919503
60. Ghosh KS, Sen S, Sahoo BK, Dasgupta S (2009) A spectroscopic investigation into the interactions of 3'-O-carboxy esters of thymidine with bovine serum albumin. Biopolymers 91: 737-744. doi: 10.1002/bip.21220 PMID: 19402143
61. Hubbard SJ, Thornton JM (1993) 'Naccess', computer program. Technical Report. Department of Biochemistry and Molecular Biology, University College London.
62. 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. PMID: 12197663
63. Wang R, Lu Y, Wang S (2003) Comparative evaluation of 11 scoring functions for molecular docking. J Med Chem 46: 2287-2303. PMID: 12773034
64. Robert CE (2004) MUSCLE: Multiple sequence alignment with high accuracy and high throughput. Nucleic Acids Res 32: 1792-1797. PMID: 15034147
65. Clamp M, Cuff J, Searle SM, Barton GJ (2004) The Jalview Java alignment editor. Bioinformatics 20: 426-427. PMID: 14960472
66. Waterhouse AM, Procter JB, Martin DMA, Clamp M, Barton GJ (2009) Jalview Version 2-A multiple sequence alignment editor and analysis workbench. Bioinformatics 25: 1189-1191. doi: 10.1093/bioinformatics/btp033 PMID: 19151095
67. Yoshihara S, Mizutare T, Makishima M, Suzuki N, Fujimoto N, Igarashi K, 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. PMID: 14691209