title: Theoretical and Molecular Docking Study of Ketoconazole on Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as Chiral Selector.
abstract: A molecular docking study, using molecular mechanics calculations with AutoDock and semi-empirical PM3 calculations, was used to predict the enantiodiscrimination of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and ketoconazole (KTZ) enantiomers. A Density Functional Theory (DFT) single-point calculation at the level of B3LYP/6-311G (d,p) was performed for the PM3-optimized complexes to obtain more accurate binding energy and the electronic structures of the complexes. The difference in energies of the inclusion complexes between the KTZ enantiomers and TMβCD is probably a measure of chiral discrimination, which results in the separation of the enantiomers as observed in the experimental studies.
authors.affiliation: Separation Science & Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310, UTM, Johor Bahru, Johor, Malaysia.
authors.forename: Siti Rosilah
authors.initials: SR
authors.lastname: Arsad
authors.affiliation: Separation Science & Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310, UTM, Johor Bahru, Johor, Malaysia.|Frontier Materials Research Alliance, Universiti Teknologi Malaysia, 81310, UTM, Johor Bahru, Johor, Malaysia.
authors.forename: Hasmerya
authors.initials: H
authors.lastname: Maarof
authors.affiliation: Separation Science & Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310, UTM, Johor Bahru, Johor, Malaysia.|Frontier Materials Research Alliance, Universiti Teknologi Malaysia, 81310, UTM, Johor Bahru, Johor, Malaysia.
authors.forename: Wan Aini
authors.initials: WA
authors.lastname: Wan Ibrahim
authors.affiliation: Department of Pharmaceutical and Medicinal Chemistry, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Giza, Egypt.
authors.forename: Hassan Y
authors.initials: HY
authors.lastname: Aboul-Enein
mesh_terms: D001393:Azoles / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D062105:Molecular Docking Simulation; D011789:Quantum Theory; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D001393:Azoles; D047392:beta-Cyclodextrins; C000609658:heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin
keywords: DFT; PM3; autodock; cyclodextrin; molecular modeling