Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.
This paper reports a QSAR study for predicting the complexation of a large and heterogeneous variety of substances (233 organic compounds) with beta-cyclodextrins (beta-CDs). Several different theoretical molecular descriptors, calculated solely from the molecular structure of the compounds under investigation, and an efficient variable selection procedure, like the Genetic Algorithm, led to models with satisfactory global accuracy and predictivity. But the best-final QSAR model is based on Topological descriptors meanwhile offering a reasonable interpretation. This QSAR model was able to explain ca. 84% of the variance in the experimental activity, and displayed very good internal cross-validation statistics and predictivity on external data. It shows that the driving forces for CD complexation are mainly hydrophobic and steric (van der Waals) interactions. Thus, the results of our study provide a valuable tool for future screening and priority testing of beta-CDs guest molecules.
Pérez-Garrido
Alfonso
A
Enviromental Engineering and Toxicology Dpt., Catholic University of San Antonio, Murcia, C.P., Guadalupe 30107, Spain. Aperez@pdi.ucam.edu
Morales Helguera
Aliuska
A
Abellán Guillén
Adela
A
Cordeiro
M Natália D S
MN
Garrido Escudero
Amalio
A
D057927:Hydrophobic and Hydrophilic Interactions; D009930:Organic Chemicals / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship; D047392:beta-Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology
D009930:Organic Chemicals; D047392:beta-Cyclodextrins