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Aiming the search of novel regulators of lipid metabolism and their potential targets, in this study we performed molecular modeling of eight isomeric 17(20) Z - and 17(20) Е -pregna-5,17(20)-dien-21-oyl amides differing in structure of the amide moiety. Analysis of the low energy сonformers revealed that all 17(20) E -isomers had three main energy minima (corresponding to values of the dihedral angle q (С17=C20-C21=O) ~ 0°, ~ 120° and ~ 240°), the most occupied minimum was found to correspond to q ~ 0°; while 17(20) Z -isomers had either one or two pools of low energy conformations. Molecular docking of these compounds to the ligand-binding site of the nuclear receptor LXRb (a potential target) indicates high probability of binding for Е -isomers and the absence of that for Z -isomers. Results of the molecular modeling were confirmed by an experiment in which stimulation of triglyceride biosynthesis in Hep G2 cells in the presence of 17(20) Е -3b-hydroxypregna-5,17(20)-dien-21-оyl (hydroxyethyl)amide was demonstrated.

Molecular modeling of interaction of 17(20) and 17(20) E-pregna-5,17(20)-dien-21-oyl amides with the nuclear receptor LXRb