QSAR modeling of peripheral versus central benzodiazepine receptor binding affinity of 2-phenylimidazo[1,2-a]pyridineacetamides using optimal descriptors calculated with SMILES

Kunal Roy, Andrey Toropov, Ivan Raska

Research output: Contribution to journalArticle

Abstract

The optimization of correlation weights scheme has been applied to model Peripheral Benzodiazepine Receptor (PBR) binding affinity (ovary and cortex) and PBR binding selectivity (peripheral versus central benzodiazepine receptor) of 2-phenylimidazo[1,2-a]pyridineacetamides. In the present study, optimal descriptors based on Simplified Molecular Input Line Entry System (SMILES) notation have been used for the modeling purpose. The optimized descriptor formulated based on the data of training set generated statistically acceptable relations (for PBR cortex, q2 = 0.717, r2 = 0.756; for PBR ovary, q2 = 0.836, r2 = 0.852; for PBR cortex selectivity, q2 = 0.732, r2 = 0.784; for PBR ovary selectivity, q2 = 0.828, r2 = 0.845). When the relations of PBR binding affinity or selectivity with the optimized molecular descriptor formulated based on the data of the training set was used for the calculation of the corresponding response parameters of the test set, rPred 2 values were found to be satisfactory (for PBR cortex, 0.692; for PBR ovary, 0.682; for PBR ovary selectivity, 0.772) except in the case of PBR cortex selectivity (rPred 2 being 0.321). The results indicate promising potential of the optimization of correlation weights based on SMILES notation in modeling studies.

Original languageEnglish
Pages (from-to)460-468
Number of pages9
JournalQSAR and Combinatorial Science
Volume26
Issue number4
DOIs
Publication statusPublished - Apr 2007

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Benzodiazepines
Quantitative Structure-activity Relationship
Quantitative Structure-Activity Relationship
GABA-A Receptors
Receptor
Descriptors
Affine transformation
Line
Ovary
Selectivity
Modeling
Cortex
Notation
Molecular Descriptors
Weights and Measures
Optimization
Test Set

Keywords

  • Optimal descriptor
  • Peripheral benzodiazepine receptor
  • QSAR
  • SMILES

ASJC Scopus subject areas

  • Discrete Mathematics and Combinatorics
  • Pharmacology

Cite this

QSAR modeling of peripheral versus central benzodiazepine receptor binding affinity of 2-phenylimidazo[1,2-a]pyridineacetamides using optimal descriptors calculated with SMILES. / Roy, Kunal; Toropov, Andrey; Raska, Ivan.

In: QSAR and Combinatorial Science, Vol. 26, No. 4, 04.2007, p. 460-468.

Research output: Contribution to journalArticle

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