Y. M. Alvarez-Ginarte, L. A. Montero-Cabrera, J. M. García-de la Vega, A. Bencomo-Martínez, A. Pupo Meriño, A. Agramonte-Delgado, Y. Marrero-Ponce, J. Ruiz-García, H. Mikosch:
"Integration of Ligand and Structure-Based Virtual Screening for Identification of Leading Anabolic Steroids.";
Journal of Steroid Biochemistry and Molecular Biology, 138 (2013), S. 348 - 358.

Kurzfassung englisch:
Parallel ligand- and structure-based virtual screenings of 269 steroids with anabolic ac-tivity evaluated in vivo were performed. The quantitative structure-activity relationship (QSAR) model expressed by selected descriptors as the octanol-water partition coeffi-cient, the molar volume and the quantum mechanical calculated charge values on atoms C1, C2, C5, C9, C10, C14 and C17 of the steroid skeleton, express structural features of anabolic steroids (AS) contributing to the transport and steroid-receptor interaction. On the other hand, computational simulations of a candidate ligand binding to a receptor study (a "docking" procedure) predict the association of these AS with the human an-drogen receptor (AR). Fourteen compounds were identified as lead; the most potent was the 7α-Methylestr-4-en-3, 17-dione. It was concluded that a good anabolic activity re-quires hydrogen bonding interactions between either Arg752 and Gln711 residues (in the vicinity of cycles A) with the O3 atom of the steroid and either Asn705 and Thr877 residues (in the vicinity of cycles D of steroid) with O17 atom.

Anabolic steroids; Virtual screening; Quantum and physicochemical molecular descriptor; Cluster analysis; QSAR and docking studies

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