%0 Journal Article
%A Ishak, M.A.I.
%A Aun, T.T.
%A Sidek, N.
%A Mohamad, S.
%A Jumbri, K.
%A Abdul Manan, N.S.
%D 2024
%F scholars:19617
%J Journal of Computational Chemistry
%K Binding energy; Complexation; Cyclodextrins; Enantiomers; Enantioselectivity; Hydrogen bonds; Ionic liquids, Docking; Docking studies; Dynamics simulation; Enantioselective; Liquid chain; Molecular docking; Molecular dynamic simulation; Propranolol; S(β); �-cyclodextrin, Molecular dynamics, beta cyclodextrin; hydrogen; ionic liquid; oxygen; propranolol, article; controlled study; enantiomer; enantioselectivity; hydrogen bond; molecular docking; molecular dynamics; simulation
%N 16
%P 1329-1351
%R 10.1002/jcc.27321
%T An enantioselective study of β-cyclodextrin and ionic liquid-β-cyclodextrin towards propranolol enantiomers by molecular dynamic simulations
%U https://khub.utp.edu.my/scholars/19617/
%V 45
%X In this study, the enantioselectivity of β-cyclodextrin and its derivatives towards propranolol enantiomers are investigated by molecular dynamic (MD) simulations. β-cyclodextrin (β-CD) have previously been shown to be able to recognize propranolol (PRP) enantiomers. To improve upon the enantioselectivity of β-cyclodextrin, we propose the use of an ionic-liquid-modified-β-cyclodextrin (β-CD-IL). β-CD-IL was found to be able to complex R and S propranolol enantiomers with differing binding energies. The molecular docking study reveals that the ionic liquid chain attached to the β-CD molecule has significant interaction with propranolol. The formation of the most stable complex occurred between (S)-β-CD-IL and (S)-propranolol with an energy of �5.80 kcal/mol. This is attributed to the formation of a hydrogen bond between the oxygen of the propranolol and the hydrogen on the primary rim of the (S)-β-CD-IL cavity. This interaction is not detected in other complexes. The root mean-squared fluctuation (RMSF) value indicates that the NH group is the most flexible molecular fragment, followed by the aromatic group. Also of note, the formation of a complex between pristine β-CD and (S)-propranolol is the least favorable. © 2024 Wiley Periodicals LLC.
%Z cited By 0