The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups

Environmental Health Perspectives

Volumn 106, Issue 3, 1998, Pages 167-174

  Parez, Pilar ^a   Pulgar, Rosa ^a   Olea Serrano, Fátima ^a   Villalobos, Mercedes ^a   Rivas, Ana ^a   Metzler, Manfred ^b   Pedraza, Vicente ^a   Olea, Nicolás ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Bisphenol A; Bisphenol F; Endocrine disrupting chemicals; Hydroxylated diphenylalkanes; MCF7 breast cancer cells; Xenoestrogens

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; CARBON; DIPHENYLALKYLAMINE; ESTROGEN; ESTROGEN RECEPTOR; HYDROXYL GROUP;

ARTICLE; BINDING SITE; BIOASSAY; BREAST CANCER; CANCER CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENDOCRINE FUNCTION; HUMAN; HUMAN CELL; HYDROGEN BOND; PLASTIC INDUSTRY; PRIORITY JOURNAL; PROTEIN SECRETION; PROTEIN SYNTHESIS;

EID: 0031955255     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.98106167     Document Type: Article

References (42)

1. Colborn T, Vom Saal FS, Soto AM. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect 101:378-384 (1993).
2. Dermer OC. Bisphenol A. In: Encyclopedia of Chemical Processing and Design (McKelta JJ, ed). New York:Marcel Dekker, 1983;406-430.
3. Smith WF. Fundamentos de la Ciencia e Ingenieria de Materiales. 2nd ed. New York:McGraw-Hill, 1994,
4. Bauer RS, De La Mare HE, Klarquist JM, Newman SF. Epoxy resins and epoxides. In: Encyclopedia of Chemical Processing and Design (McKelta JJ, ed). NewYork:Marcel Dekker, 1983;261-297.
5. Nakamura S, Suzuki Y, Kojima T, Tago K. Thermal degradation of aromatic polyformals derived from bisphenol A and bisphenol AF. Thermochimica Acta 267:231-237(1995).
6. Dodds EC, Lawson W. Synthetic estrogenic agents without the phenanthrene nucleus. Nature 137:996 (1936).
7. Reid EE, Wilson E. The relation of estrogenic activity to structure in some 4,4′-dihydroxydephenylmethanes. J Am Chem Soc 66:967-968 (1944).
8. Morrissey RE, George JD, Price CJ, Tyl RW, Marr MC, Kimmel CA. The developmental toxicity of bisphenol-A in rats and mice. Fundam Appl Toxicol 8:571-582 (1987).
9. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132:2279-2286 (1993).
10. Brotons JA, Olea-Serrano MF, Villalobos M, Pedraza V, Olea N. Xenoestrogens released from lacquer coating in food cans. Environ Health Perspect 103:608-612 (1995).
11. Olea N, Pulgar R, Pérez P, Olea-Serrano F, Rivas A, Novillo-Fertrell A, Pedraza V, Soto AM, Sonnenschein C. Estrogenicity of resin-based composites and sealants used in dentistry. Environ Health Perspect 104:298-305 (1996).
12. Olea-Serrano MF, Pulgar R, Pérez P, Metzler M, Olea N. Bisphenol-A: In vitro effects. In: Hormonally Active Agents in Food (Eisenbrand G, ed). New York:VCH Publishers. In press.
13. Soto AM, Sonnenschein C. The role of estrogen on the proliferation of human breast tumor cells (MCF-7). J Steroid Biochem 23:87-94 (1985).
14. Villalobos M, Olea N, Brotons JA, Olea-Serrano MF, Ruiz de Almodóvar JM, Pedraza V, The E-SCREEN assay: comparison among different MCF7 cell stocks. Environ Health Perspect 103:844-850 (1995).
15. Soto AM, Lin TM, Justicia H, Silvia RM, Sonnenschein C. An "in culture" bioassay to assess the estrogenicity of xenobiotics (E-SCREEN), In: Chemically Induced Alterations in Sexual and Functional Development: The Wildlife/Human Connection (Colborn T, Clement C, eds). Princeton, NJ:Princeton Scientific Publishing, 1992;295-309.
16. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening, J Natl Cancer Inst 82:1107-1112 (1990).
17. Gilbert J, Doré J-C, Bignon E, Pons M, Ojasoo T. Study of the effects of basic di- and tri-phenyl derivatives on malignant cell proliferation: an example of the application of correspondence factor analysis to structure-activity relationships (SAR). Quant Struct Act Relat 13:262-274 (1994).
18. Soto AM, Justicia H, Wray JW, Sonnenschein C. p- Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene. Environ Health Perspect 92:167-173(1991).
19. Soto AM, Sonnenschein C, Chung KL, Fernández MF, Olea N, Olea Serrano F. The E-SREEN as a tool to identify estrogens: an update on estrogenic environmental pollutants. Environ Health Perspect 103(suppl 7):113-122(1995).
20. Leclercq G. Estrogens, antiestrogens and other estrogen compounds. In: Antitumor steroids (Blickenstaff RT, ed). New York:Academic Press, 1992;11-64.
21. Cummings AM, Metcalf JL. Methoxyclor regulates rat uterine estrogen induced protein. Toxicol Appl Pharmacol 130:154-160 (1995).
22. Mariotti A, Johnson S, Sodreholm K-JM, The estrogenic effect of bisGMA on estrogen-sensitive target tissues (abstract), J Dental Assoc 76:323 (1997).
23. Lewis DFV, Parker MG, King RJB. Molecular modelling of the human estrogen receptor and ligand interactions based on site-directed mutagenesis and amino acid sequence homology J Steroid Biochem Mol Biol 52:55-65 (1995).
24. Routledge EJ, Sumpter JP. Structural features of alkylphenolic chemicals associated with estrogenic activity. J Biol Chem 272:3280-3288 (1997).
25. Connor K, Rammamoorthy K, Moore M, Mustain M, Chen I, Safe S, Zacharewski T, Gillesby B, Joyeux A, Balaguer P. Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: structure- activity relationships. Toxicol Appl Pharmacol 145:111-123(1997).
26. Knuppen R, Ball P, Emons G. Importance of A-ring substitution of estrogens for the physiology and pharmacology of reproduction. J Steroid Biochem 24:193-198(1986).
27. Barral L, Cano J, López AJ, López J, Nogueira P, Ramírez C. Thermal degradation of a diglycidyl ether of bisphenol A/1,3-bisaminomethylcyclohexane (DGEBA/BAC) epoxy resin system. Thermochimica Acta 269:253-259 (1995).
28. Baker PJ. Polymers, polycarbonate, In: Encyclopedia of Chemical Processing and Design (McKelta JJ, ed). New York:Marcel Dekker, 1983:136-152.
29. Sharman M, Honeybone C, Jickels S, Castle L. Detection of residues of the epoxy adhesive component bisphenol A diglycidylether (BADGE) in microwave susceptors and its migration into food. Food Addit Contam 12:779-787 (1995).
30. Paseiro CP, Simal LJ, Paz AS, López MP, Simal GJ. Kinetics of the hydrolysis of bisphenol F diglycidyl ether in water-based food simulants. Comparison with bisphenol A diplycidyl ether. J Agric Food Chem 40:868-872 (1992).
31. Bourne LB, Milner FJM, Alberman KB. Health problems of epoxy resins and amine curing agents. Br J Ind Med 16:81-97 (1959).
32. Joost van T, Roesyanto ID, Satyawan I. Occupational sensitization to epichlorhydrin and Bisphenol A during the manufacture of epoxy resin. Contact Dermatitis 22:125-126 (1990).
33. Jolanki R, Kanerva L, Estlander T, Tarvainen K, Kerkinen H, Henricks-Eckerman ML. Occupational dermatoses from epoxy resin compounds. Contact Dermatitis 23:172-183 (1990).
34. Steiner S, Hönger G, Sagelsdorff P. Molecular dosimetry of DNA adducts in C3H mice treated with bisphenol-A diglycidylether, Carcinogenesis 13:969-972(1992).
35. 14C-DGEBPA in the mouse. Xenobiotica 11:391-399(1981).
36. 14C-DGEBPA. Xenobiotica 11:401-424 (1981).
37. Lobos JH, Leib TK, Su TM. Biodegradation of bisphenol A and other bisphenols by a Gram-negative aerobic bacterium. Appl Environ Microbiol 58:1823-1831 (1992).
38. Spivack J, Leib TK, Lobos JH. Novel pathway for bacterial metabolism of Bisphenol-A. J Biol Chem 269:7323-7329(1994).
39. Steinmetz R, Brown NG, Allen DL, Bigsby RM, Ben- Jonathan N, The environmental estrogen bisphenol A stimulates prolactin release in vitro and in vivo. Endocrinology 138:1780-1786 (1997).
40. Nagel SC, vom Saal FS, Thayer KA, Dhar MG, Boechler M, Welshons WV. Relative binding affinity- serum modified access (RBA-SMA) assay predicts the relative in vivo bioactivity of the xenoestrogens bisphenol A and octylphenol, Environ Health Perspect 105:70-76 (1997).
41. Feldman D. Editorial: Estrogens from plastic - Are we being exposed? Endocrinology 138:1777-1779 (1997).
42. Colerangle JB, Deodutta R, Profound effects of the weak environmental estrogen-like chemical bisphenol A on the growth of the mammary gland of Noble rats. J Steroid Biochem Mol Biol 60:153-160 (1997).