Radical-scavenging Activity of Estrogen and Estrogen-like Compounds Using the Induction Period Method

Abstract: The radical-scavenging activity of estrogens (estrone, 2-hydroxyestradiol),estrogen-like compounds (diethylstilbestrol, DES; bisphenol A, BPA) and the mono-phenolic compound 2,6-di-t-butyl-4-methoxyphenol (BMP) was investigated using themethod of measuring the induction period for polymerization of methyl methacrylate(MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) andbenzoyl peroxide (BPO) at 70°C using differential scanning calorimetry (DSC). Thestoichiometric factor (n, number of free radicals trapped by one mole of antioxidantmoiety) for the AIBN system declined in the order BMP (2.0), 2-hydroxyestradiol (2.0)>DES (1.3) > BPA (1.2) > estrone (0.9), whereas that for the BPO system declined in theorder BMP (2.0) >DES (1.9), BPA (1.9) > estrone (1.3) > 2-hydroxyestradiol (0.7). Theinhibition rate constant (kinh x 10^-3 M^-1s^-1) for the AIBN system declined in the orderestrone (2.2) > BPA (2.0) > DES (1.9) > 2-hydroxyestradiol (1.2) > BMP (1.1), whereasthat for the BPO system declined in the order 2-hydroxyestradiol (3.2) > estrone (1.4) >DES (1.2) > BPA (1.0) > BMP (0.9). The radical-scavenging activity for bioactivecompounds such as estrogens should be evaluated using these two methods (the n and kinh)to elucidate the mechanism of a particular reaction. The great difference of the n and kinhfor estrogens between the AIBN and BPO system suggested that their oxidation process iscomplex.