An androgenic endocrine disruptor alters male mating behavior in the guppy (Poecilia reticulata)

Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids

“…Costs limited evaluation of other analogues with this approach. Instead, further analyses of all analogues (1)(2)(3)(4) were conducted with androgen receptor (AR), PR, and ERα reporter assays (Indigo Biosciences, State College, PA). 17 As shown in Table 2, analysis of 3 revealed that it retained substantial PR and AR activity (expressed as EC50 values, see SI Figures S21-S24 for dose response curves), with ~ 280fold reduction in PR and ~ 50-fold reduction in AR activation compared to that of parent 1.…”

“…5 Here, we report the isolation and structure elucidation of one of these products, an unusual and unexpected phenolic rearrangement product with a novel 6,5,8,5-ring system for which we propose the name dienogestenol (3). We also explore the generality of this unique rearrangement process through extension to the photolysis of other dienone pharmaceutical steroids [e.g., the androgens methyldienolone (2) and dienedione (5, see below)]. In laboratory experiments, a solar simulator was used to generate photoproduct mixtures expected in sunlit surface waters.…”