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  • Screening of bisphenol A, triclosan and paraben analogues as modulators of the glucocorticoid and androgen receptor activities.

Screening of bisphenol A, triclosan and paraben analogues as modulators of the glucocorticoid and androgen receptor activities.

Toxicology in vitro : an international journal published in association with BIBRA (2014-09-07)
Katra Kolšek, Martina Gobec, Irena Mlinarič Raščan, Marija Sollner Dolenc
ABSTRACT

A homeostasis of the glucocorticoid and androgen endocrine system is essential to human health. Their disturbance can lead to various diseases, for example cardiovascular, inflammatory and autoimmune diseases, infertility, cancer. Fifteen widely used industrial chemicals that disrupt endocrine activity were selected for evaluation of potential (anti)glucocorticoid and (anti)androgenic activities. The human breast carcinoma MDA-kb2 cell line was utilized for reporter gene assays, since it expresses both the androgen and the glucocorticoid-responsive reporter. Two new antiandrogens, 4,4'-sulfonylbis(2-methylphenol) (dBPS) and 4,4'-thiodiphenol (THIO), and two new antiglucocorticoids, bisphenol Z and its analog bis[4-(2-hydroxyethoxy)phenyl] sulfone (BHEPS) were identified. Moreover, four new glucocorticoid agonists (methyl paraben, ethyl paraben, propyl paraben and bisphenol F) were found. To elucidate the structure-activity relationship of bisphenols, we performed molecular docking experiments with androgen and glucocorticoid receptor. These docking experiments had shown that bulky structures such as BHEPS and bisphenol Z act as antiglucocorticoid, because they are positioned toward helix H12 in the antagonist conformation and could therefore be responsible for H12 conformational change and the switch between agonistic and antagonistic conformation of receptor. On the other hand smaller structures cannot interact with H12. The results of in vitro screening of fifteen industrial chemicals as modulators of the glucocorticoid and androgen receptor activities demand additional in vivo testing of these chemicals for formulating any relevant hazard identification to human health.

MATERIALS
Product Number
Brand
Product Description

Supelco
Butylparaben, Pharmaceutical Secondary Standard; Certified Reference Material
Pricing and availability is not currently available.
Supelco
Triclosan, Pharmaceutical Secondary Standard; Certified Reference Material
Pricing and availability is not currently available.
Hydrocortisone for peak identification, European Pharmacopoeia (EP) Reference Standard
Pricing and availability is not currently available.
USP
Triclosan, United States Pharmacopeia (USP) Reference Standard
Pricing and availability is not currently available.
Supelco
Bisphenol A, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Pricing and availability is not currently available.
USP
Butylparaben, United States Pharmacopeia (USP) Reference Standard
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, tested according to Ph. Eur.
Pricing and availability is not currently available.
Sigma-Aldrich
Propyl 4-hydroxybenzoate, tested according to Ph. Eur.
Pricing and availability is not currently available.
Sigma-Aldrich
4,4′-Cyclohexylidenebisphenol, 98%
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, ≥99%, FCC
Pricing and availability is not currently available.
Sigma-Aldrich
3,4,4′-Trichlorocarbanilide, 99%
Pricing and availability is not currently available.
Sigma-Aldrich
Triclosan, 97.0-103.0% (active substance, GC)
Pricing and availability is not currently available.
Sigma-Aldrich
Butyl 4-hydroxybenzoate, ≥99%
Pricing and availability is not currently available.
Sigma-Aldrich
Bisphenol A, 97%
Pricing and availability is not currently available.
Supelco
Bisphenol A, ≥99%
Pricing and availability is not currently available.
Sigma-Aldrich
Butyl 4-hydroxybenzoate, ≥99.0% (GC)
Pricing and availability is not currently available.
Sigma-Aldrich
Mifepristone, ≥98%
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, BioReagent, suitable for insect cell culture
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, ReagentPlus®, ≥99.0%, crystalline
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, analytical standard
Pricing and availability is not currently available.
Sigma-Aldrich
Methyl 4-hydroxybenzoate, BioXtra, ≥99.0% (titration)
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Sigma-Aldrich
Propyl 4-hydroxybenzoate, BioXtra
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Sigma-Aldrich
Propyl 4-hydroxybenzoate, ≥99%
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Methyl parahydroxybenzoate, European Pharmacopoeia (EP) Reference Standard
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Butyl parahydroxybenzoate, European Pharmacopoeia (EP) Reference Standard
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Supelco
Propylparaben, Pharmaceutical Secondary Standard; Certified Reference Material
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Supelco
Hydrocortisone, Pharmaceutical Secondary Standard; Certified Reference Material
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Supelco
Methylparaben, Pharmaceutical Secondary Standard; Certified Reference Material
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Propyl parahydroxybenzoate, European Pharmacopoeia (EP) Reference Standard
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USP
Propylparaben, United States Pharmacopeia (USP) Reference Standard
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