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Toxicological Sciences
Article . 2014 . Peer-reviewed
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Are Structural Analogues to Bisphenol A Safe Alternatives?

Authors: Anna Kjerstine, Rosenmai; Marianne, Dybdahl; Mikael, Pedersen; Barbara Medea, Alice van Vugt-Lussenburg; Eva Bay, Wedebye; Camilla, Taxvig; Anne Marie, Vinggaard;

Are Structural Analogues to Bisphenol A Safe Alternatives?

Abstract

Bisphenol A (BPA) is a chemical with widespread human exposure suspected of causing low-dose effects. Thus, a need for developing alternatives to BPA exists. Structural analogues of BPA have already been detected in foods and humans. Due to the structural analogy of the alternatives, there is a risk of effects similar to BPA.The aim was to elucidate and compare the hazards of bisphenol B (BPB), bisphenol E (BPE), bisphenol F (BPF), bisphenol S (BPS) and 4-cumylphenol (HPP) to BPA.In vitro studies on steroidogenesis, receptor activity, and biomarkers of effect, as well as Quantitative Structure-Activity Relationship (QSAR) modeling.All test compounds caused the same qualitative effects on estrogen receptor and androgen receptor activities, and most of the alternatives exhibited potencies within the same range as BPA. Hormone profiles for the compounds indicated a specific mechanism of action on steroidogenesis which generally lead to decreased androgen, and increased estrogen and progestagen levels. Differential effects on corticosteroid synthesis were observed suggesting a compound-specific mechanism. Overall, BPS was less estrogenic and antiandrogenic than BPA, but BPS showed the largest efficacy on 17α-hydroxyprogesterone (17α-OH progesterone). Finally, there were indications of DNA damage, carcinogenicity, oxidative stress, effects on metabolism, and skin sensitization of one or more of the test compounds.Interference with the endocrine system was the predominant effect of the test compounds. A substitution of BPA with these structural analogues should be carried out with caution.

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Keywords

Molecular Structure, Quantitative Structure-Activity Relationship, Neoplasms, Experimental, Endocrine Disruptors, Oxidative Stress, Teratogens, Phenols, Tandem Mass Spectrometry, Animals, Bisphenol A Compounds, Benzhydryl Compounds, Chromatography, High Pressure Liquid, DNA Damage

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
382
Top 0.1%
Top 1%
Top 1%
bronze