Skip Navigation


ToxSci Advance Access originally published online on January 5, 2005
Toxicological Sciences 2005 84(2):249-259; doi:10.1093/toxsci/kfi074
This Article
Right arrow Full Text Freely available
Right arrow FREE Full Text (PDF) Freely available
Right arrow All Versions of this Article:
84/2/249    most recent
kfi074v1
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in ISI Web of Science
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrow Search for citing articles in:
ISI Web of Science (50)
Right arrowRequest Permissions
Right arrow Disclaimer
Google Scholar
Right arrow Articles by Kitamura, S.
Right arrow Articles by Ohta, S.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Kitamura, S.
Right arrow Articles by Ohta, S.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

Toxicological Sciences vol. 84 no. 2 © The Author 2005. Published by Oxford University Press on behalf of the Society of Toxicology. All rights reserved. For Permissions, please email: journals.permissions@oupjournals.org

Comparative Study of the Endocrine-Disrupting Activity of Bisphenol A and 19 Related Compounds

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

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

Received September 16, 2004; accepted December 7, 2004

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 17ß-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.

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


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?


This article has been cited by other articles:


Home page
 International Journal of ToxicologyHome page
J. L. Flippin, J. M. Hedge, M. J. DeVito, G. A. LeBlanc, and K. M. Crofton
Predictive Modeling of a Mixture of Thyroid Hormone Disrupting Chemicals That Affect Production and Clearance of Thyroxine
International Journal of Toxicology, September 1, 2009; 28(5): 368 - 381.
[Abstract] [Full Text] [PDF]

Home page
 Phil Trans R Soc BHome page
C. E. Talsness, A. J. M. Andrade, S. N. Kuriyama, J. A. Taylor, and F. S. vom Saal
Components of plastic: experimental studies in animals and relevance for human health
Phil Trans R Soc B, July 27, 2009; 364(1526): 2079 - 2096.
[Abstract] [Full Text] [PDF]

Home page
 Endocr. Rev.Home page
L. N. Vandenberg, M. V. Maffini, C. Sonnenschein, B. S. Rubin, and A. M. Soto
Bisphenol-A and the Great Divide: A Review of Controversies in the Field of Endocrine Disruption
Endocr. Rev., February 1, 2009; 30(1): 75 - 95.
[Abstract] [Full Text] [PDF]

Home page
 J. Pharmacol. Exp. Ther.Home page
R. M. Pelis, R. C. Hartman, S. H. Wright, T. M. Wunz, and C. E. Groves
Influence of Estrogen and Xenoestrogens on Basolateral Uptake of Tetraethylammonium by Opossum Kidney Cells in Culture
J. Pharmacol. Exp. Ther., November 1, 2007; 323(2): 555 - 561.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
T. Hamers, J. H. Kamstra, E. Sonneveld, A. J. Murk, M. H. A. Kester, P. L. Andersson, J. Legler, and A. Brouwer
In Vitro Profiling of the Endocrine-Disrupting Potency of Brominated Flame Retardants
Toxicol. Sci., July 1, 2006; 92(1): 157 - 173.
[Abstract] [Full Text] [PDF]

Home page
 Eur J EndocrinolHome page
M. Boas, U. Feldt-Rasmussen, N. E Skakkebaek, and K. M Main
Environmental chemicals and thyroid function.
Eur. J. Endocrinol., May 1, 2006; 154(5): 599 - 611.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
E. Sonneveld, J. A. C. Riteco, H. J. Jansen, B. Pieterse, A. Brouwer, W. G. Schoonen, and B. van der Burg
Comparison of In Vitro and In Vivo Screening Models for Androgenic and Estrogenic Activities
Toxicol. Sci., January 1, 2006; 89(1): 173 - 187.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
R. M. Facciolo, M. Madeo, R. Alo, M. Canonaco, and F. Dessi-Fulgheri
Neurobiological Effects of Bisphenol A May Be Mediated by Somatostatin Subtype 3 Receptors in Some Regions of the Developing Rat Brain
Toxicol. Sci., December 1, 2005; 88(2): 477 - 484.
[Abstract] [Full Text] [PDF]


Disclaimer: Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.