Bisphenol AF is a full agonist for the estrogen receptor ERalpha but a highly specific antagonist for ERbeta

Environ Health Perspect. 2010 Sep;118(9):1267-72. doi: 10.1289/ehp.0901819. Epub 2010 Apr 28.

Abstract

Background: Bisphenol AF has been acknowledged to be useful for the production of CF3-containing polymers with improved chemical, thermal, and mechanical properties. Because of the lack of adequate toxicity data, bisphenol AF has been nominated for comprehensive toxicological characterization.

Objectives: We aimed to determine the relative preference of bisphenol AF for the human nuclear estrogenic receptors ERalpha and ERbeta and the bisphenol A-specific estrogen-related receptor ERRgamma, and to clarify structural characteristics of receptors that influence bisphenol AF binding.

Methods: We examined receptor-binding activities of bisphenol AF relative to [3H]17beta-estradiol (for ERalpha and ERbeta) and [3H]bisphenol A (for ERRgamma). Functional luciferase reporter gene assays were performed to assess receptor activation in HeLa cells.

Results: We found that bisphenol AF strongly and selectively binds to ERs over ERRgamma. Furthermore, bisphenol AF receptor-binding activity was three times stronger for ERbeta [IC50 (median inhibitory concentration) = 18.9 nM] than for ERalpha. When examined using a reporter gene assay, bisphenol AF was a full agonist for ERalpha. In contrast, it was almost completely inactive in stimulating the basal constitutive activity of ERbeta. Surprisingly, bisphenol AF acted as a distinct and strong antagonist against the activity of the endogenous ERbeta agonist 17beta-estradiol.

Conclusion: Our results suggest that bisphenol AF could function as an endocrine-disrupting chemical by acting as an agonist or antagonist to perturb physiological processes mediated through ERalpha and/or ERbeta.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzhydryl Compounds
  • Estradiol / pharmacology
  • Estrogen Receptor alpha / antagonists & inhibitors*
  • Estrogen Receptor alpha / metabolism*
  • Estrogen Receptor beta / agonists*
  • Estrogen Receptor beta / metabolism*
  • HeLa Cells
  • Humans
  • Phenols / chemistry
  • Phenols / metabolism*
  • Phenols / pharmacology*
  • Protein Binding
  • Receptors, Estrogen / metabolism

Substances

  • Benzhydryl Compounds
  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Phenols
  • Receptors, Estrogen
  • Estradiol
  • bisphenol A