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ToxSci Advance Access published online on January 5, 2005
Toxicological Sciences, doi:10.1093/toxsci/kfi074
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Toxicological Sciences © Society of Toxicology 2004; all rights reserved.
Received September 16, 2004
Accepted December 7, 2004

Endocrine Toxicology

Comparative study of the endocrine-disrupting activity of bisphenol A and 19 related compounds

Shigeyuki Kitamura 1*, Tomoharu Suzuki 1, Seigo Sanoh 1, Ryuki Kohta 2, Norimasa Jinno 1, Kazumi Sugihara 1, Shin'ichi Yoshihara 1, Nariaki Fujimoto 3, Hiromitsu Watanabe 3, and Shigeru Ohta 1

1 Graduate School of Biomedical Sciences, Hiroshima University, Kasumi 1-2-3, Minami-ku, Hiroshima 734-8551, Japan
2 Graduate School of Biomedical Sciences, Hiroshima University, Kasumi 1-2-3, Minami-ku, Hiroshima 734-8551, Japan
3 Research Institute for Radiation Biology and Medicine, Hiroshima University, Kasumi 1-2-3, Minami-ku, Hiroshima 734-8551, Japan

* To whom correspondence should be addressed.
Shigeyuki Kitamura, E-mail: skitamu{at}hiroshima-u.ac.jp


  Abstract

The endocrine-disrupting activities of bisphenol A (BPA) and 19 related compounds were comparatively examined by means of different in vitro and in vivo reporter assays. BPA and some related compounds exhibited estrogenic activity in human breast cancer cell line MCF-7, but there were remarkable differences in activity. Tetrachlorobisphenol A (TCBPA) showed the highest activity, followed by bisphenol B, BPA and tetramethylbisphenol A (TMBPA); 2,2-bis(4-hydroxyphenyl)-1-propanol, 1,1-bis(4-hydroxyphenyl)propionic acid and 2,2-diphenylpropane showed little or no activity. Anti-estrogenic activity against 17{beta}-estradiol was observed with TMBPA and tetrabromobisphenol A (TBBPA). TCBPA, TBBPA and BPA gave positive responses in the in vivo uterotrophic assay using ovariectomized mice. In contrast, BPA and some related compounds showed significant inhibitory effects on the androgenic activity of 5{alpha}-dihydrotestosterone in mouse fibroblast cell line NIH3T3. TMBPA showed the highest antagonistic activity, followed by bisphenol AF, bisphenol AD, bisphenol B and BPA. However, TBBPA, TCBPA and 2,2-diphenylpropane were inactive. TBBPA, TCBPA, TMBPA and 3,3'-dimethylbisphenol A exhibited significant thyroid hormonal activity towards rat pituitary cell line GH3, which releases growth hormone in a thyroid hormone-dependent manner. However, BPA and other derivatives did not show such activity. The results suggest that the 4-hydroxyl group of the A-phenyl ring and the B-phenyl ring of BPA derivatives are required for these hormonal activities, and substituents at the 3,5-positions of the phenyl rings and the bridging alkyl moiety markedly influence the activities.

Keywords: estrogenic activity; anti-androgenic activity; thyroid hormonal activity; bisphenol A; bisphenol derivative; human breast cancer cell line MCF-7; rat pituitary cell line GH3.
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