Density functional theory based quantitative structure-property relationship studies on coumarin-based prodrugs

Xinying Yang
2012 BioScience Trends  
A coumarin-based prodrug system plays a significant role in preparing esterase-sensitive prodrugs of amines and peptides. The electronic structures of 27 coumarin-based prodrugs developed in our lab were calculated at a B3LYP/6-31+G (d,p) level with a Gaussian 03 program. The calculated structural parameters were taken as theoretical descriptors to establish five novel QSPR models. The SMLR linear model (q 2 = 0.427, r 2 = 0.516) and the PLS linear model (q 2 = 0.584, r 2 = 0.663) were
more » ... with descriptors selected by an Unsupervised Forward Selection method. Another three nonlinear QSPR models were established by a Polynomial Neural Network (PNN) Simulation method (q 2 = 0.692, 0.675, 0.663; r 2 = 0.700, 0.688, 0.672). We suggest that the QSPR models derived here, especially the PNN models, can be used to predict the release kinetics of coumarin-based prodrugs as well as design new derivatives of coumarin-based prodrug candidates.
doi:10.5582/bst.2012.v6.5.234 fatcat:hwylbsmlyfc4losh4yzgih4nae