Estrogenic Activity of Alkyl(thio)phenols and 4,4-thiodiphenol Formed from Degradation of Commercial Insecticides

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We investigated the estrogenic activity of commercial insecticides fenamiphos, fenthion, methiocarb, propaphos, sulprophos, and temephos as well as some phenolic compounds obtained as a result of their degradation. Using a yeast two-hybrid assay, the relative activities of 4-(methylthio)phenol, 3-methyl-4-(methylthio)phenol, 3,5-dimethyl-4-(methylthio)phenol, and 4,4-thiodiphenol (TDP) were evaluated as 11, 10, 4, and 1000% (10 times) that of bisphenol-A. To reveal the binding abilities of the abovementioned phenolic compounds with respect to human estrogen receptor α (hERα), we carried out ER-ELISA and found that all compounds had significant abilities, particularly, TDP. From the viewpoint of bioisosterism, we discussed the similarity between a vinylene-group, -CH=CH-, and a thioether-group, -S-. We suggest that an alkylthio-group substituted at the “para”-position of a phenol ring plays a key role in the binding abilities of the investigated phenolic compounds.