Binding characteristics of zearalenone analogs to estrogen receptors.

The estrogenic effect of zearalenone derivatives was investigated for their binding characteristics to cytosol and nuclear receptors in the uterus. Competition with 17beta-estradiol at the cytosol receptor sites was observed in four of the six derivatives tested, namely trans- and cis-zearalenone, zearalenol, and zearalanol. The other two, 8'-hydroxyzearalenone and 6'-aminozearalene, lacked the binding ability to receptors and were biologically inactive. trans-Zearalenone, like 17beta-estradiol, could elicit an immediate translocation of cytosol-receptor complexes into the uterine nuclei. However, it differs from either 17beta-estradiol or antiestrogens (tamoxifen) in three aspects: (a) a second wave of translocation occurred 6 to 12 hr following zearalenone injection; (b) there was a much longer nuclear retention (over 24 hr) than in the case of 17beta-estradiol; and (c) following a depletion of cytosol receptors, trans-zearalenone induced an overreplenishment by 24 hr, whereas tamoxifen is reported to suppress the replenishment.