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Examination of the in Vitro (Anti)estrogenic, (Anti)androgenic and (Anti)dioxin-Like Activities of Tetralin, Indane and Isochroman Derivatives Using Receptor-Specific Bioassays

Examination of the in Vitro (Anti)estrogenic, (Anti)androgenic and (Anti)dioxin-Like Activities of Tetralin, Indane and Isochroman Derivatives Using Receptor-Specific Bioassays

Richard H M M Schreurs, Edwin Sonneveld, Paul T van der Saag, Bart van der Burg, Willem Seinen

Toxicol Lett. 2005 Apr 10;156(2):261-75.

PMID: 15737489

Abstract:

Molecules derived from tetralin, indane and isochroman are often used in the synthesis of fragrance materials. The two polycyclic musk fragrances AHTN (6-acetyl-1,1,2,4,4,7-hexamethyltetralin), HHCB (1,2,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran) and ADBI (4-acetyl-1,1-dimethyl-6-tert-butylindane) are derived from tetralin, isochroman and indane, respectively. In previous studies, AHTN and HHCB have been shown to antagonize estrogen receptors (ERs), both in vitro and in vivo. Here, we used two newly developed reporter gene assays, to examine the agonistic and antagonistic properties of several indane, tetralin and isochroman derivatives towards the human androgen receptor (AR) and aryl hydrocarbon receptor (AhR). Additionally, we also assessed (anti)estrogenicity of these compounds. A number of compounds showed weak estrogenic activity towards the human ER alpha. Several compounds showed (anti)estrogenic effects, starting at a concentration of 0.1 microM. Surprisingly, almost all compounds were found to be AR antagonists, starting at 0.1 microM. None of the compounds tested, showed either agonism or antagonism towards the AhR. Non-specific effects via crosstalk of the AhR and the ER or AR can therefore be ruled out. As far as we are aware, molecules derived from indane, tetralin and isochroman showing direct interaction with the ER and AR have not been reported previously.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP21145777	6-Acetyl-1,1,2,4,4,7-hexamethyltetralin		21145-77-7	Price

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