title: Anabolic and androgenic activities of 19-nor-testosterone steroids: QSAR study using quantum and physicochemical molecular descriptors.
abstract: Quantitative structure-activity relationship (QSAR) study of 19-nor-testosterone steroids family was performed using quantum and physicochemical molecular descriptors. The quantum-chemical descriptors were calculated using semiempirical calculations. The descriptor values were statistically correlated using multi-linear regression analysis. The QSAR study indicated that the electronic properties of these derivatives have significant relationship with observed biological activities. The found QSAR equations explain that the energy difference between the LUMO and HOMO, the total dipole moment, the chemical potential and the value of the net charge of different carbon atoms in the steroid nucleus showed key interaction of these steroids with their anabolic-androgenic receptor binding site. The calculated values predict that the 17α-cyclopropyl-17β, 3β-hydroxy-4-estrene compound presents the highest anabolic-androgenic ratio (AAR) and the 7α-methyl-17β-acetoxy-estr-4-en-3-one compound the lowest AAR. This study might be helpful in the future successful identification of "real" or "virtual" anabolic-androgenic steroids.
authors.affiliation: Laboratory of Theoretical and Computational Chemistry, University of Havana, La Habana, Cuba.
authors.forename: Yoanna María
authors.initials: YM
authors.lastname: Alvarez-Ginarte
authors.forename: Luis Alberto
authors.initials: LA
authors.lastname: Montero-Cabrera
authors.forename: José Manuel García
authors.initials: JM
authors.lastname: de la Vega
authors.forename: Pedro
authors.initials: P
authors.lastname: Noheda-Marín
authors.forename: Yovani
authors.initials: Y
authors.lastname: Marrero-Ponce
authors.forename: José Alberto
authors.initials: JA
authors.lastname: Ruíz-García
mesh_terms: D045930:Anabolic Agents / Q000737:chemistry* / Q000494:pharmacology*; D000728:Androgens / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D015195:Drug Design; D008297:Male; D008956:Models, Chemical; D015394:Molecular Structure; D018482:Muscle, Skeletal / Q000187:drug effects; D009277:Nandrolone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D011467:Prostate / Q000187:drug effects; D021281:Quantitative Structure-Activity Relationship; D051381:Rats; D017208:Rats, Wistar; D012669:Seminal Vesicles / Q000187:drug effects
chemical_list: D045930:Anabolic Agents; D000728:Androgens; D009277:Nandrolone