3D-chiral quadratic indices of the 'molecular pseudograph's atom adjacency matrix' and their application to central chirality codification: classification of ACE inhibitors and prediction of sigma-receptor antagonist activities

Bioorganic & Medicinal Chemistry
Yovani Marrero PonceEduardo A Castro

Abstract

Quadratic indices of the 'molecular pseudograph's atom adjacency matrix' have been generalized to codify chemical structure information for chiral drugs. These 3D-chiral quadratic indices make use of a trigonometric 3D-chirality correction factor. These indices are nonsymmetric and reduced to classical (2D) descriptors when symmetry is not codified. By this reason, it is expected that they will be useful to predict symmetry-dependent properties. 3D-Chirality quadratic indices are real numbers and thus, can be easily calculated in TOMOCOMD-CARDD software. These descriptors circumvent the inability of conventional 2D quadratic indices (Molecules 2003, 8, 687-726. http://www.mdpi.org) and other (chirality insensitive) topological indices to distinguish sigma-stereoisomers. In this paper, we extend our earlier work by applying 3D-chirality quadratic indices to two data sets containing chiral compounds. Consequently, in order to test the potential of this novel approach in drug design we have modelled the angiotesin-converting enzyme inhibitory activity of perindoprilate's sigma-stereoisomers combinatorial library. Two linear discriminant analysis (LDA) models were obtained. The first one model was performed considering all data set...Continue Reading

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Citations

Oct 19, 2005·Journal of Computer-aided Molecular Design·Yovani Marrero-Ponce, Juan A Castillo-Garit
Oct 18, 2011·SAR and QSAR in Environmental Research·M Jalali-HeraviD Taherinia
Nov 3, 2011·PloS One·Guillermin Agüero-ChapinAgostinho Antunes
Jan 27, 2005·Bioorganic & Medicinal Chemistry·Humberto González-DíazEugenio Uriarte
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yovani Marrero PonceEduardo A Castro
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yovani Marrero PonceFrancisco Torrens
Aug 12, 2008·Journal of Theoretical Biology·Cristian Robert MunteanuAlexandre Lopes de Magalhães
Jul 15, 2017·SAR and QSAR in Environmental Research·C R García-JacasA R Rodríguez-León
Aug 18, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Isela GarcíaGenerosa Gómez
Mar 17, 2007·ChemMedChem·Yovani Marrero-PonceRichard Rotondo
May 13, 2008·Journal of Computational Chemistry·Juan A Castillo-GaritVicente Romero-Zaldivar
Oct 23, 2010·Chemical Biology & Drug Design·Gerardo M Casañola-MartinConcepción Abad
May 17, 2008·Journal of Computer-aided Molecular Design·Yovani Marrero-PonceVicente J Arán
Nov 9, 2005·Bioorganic & Medicinal Chemistry Letters·Humberto González-DíazYenny González-Díaz
Nov 11, 2008·Journal of Theoretical Biology·Alcides Perez-BelloHumberto González-Díaz
Dec 30, 2008·Journal of Theoretical Biology·Cristian Robert MunteanuHumberto González-Díaz

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