An enantioselective study of β-cyclodextrin and ionic liquid-β-cyclodextrin towards propranolol enantiomers by molecular dynamic simulations
Document Type
Article
Publication Date
6-1-2024
Abstract
In this study, the enantioselectivity of beta-cyclodextrin and its derivatives towards propranolol enantiomers are investigated by molecular dynamic (MD) simulations. beta-cyclodextrin (beta-CD) have previously been shown to be able to recognize propranolol (PRP) enantiomers. To improve upon the enantioselectivity of beta-cyclodextrin, we propose the use of an ionic-liquid-modified-beta-cyclodextrin (beta-CD-IL). beta-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 beta-CD molecule has significant interaction with propranolol. The formation of the most stable complex occurred between (S)-beta-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)-beta-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 beta-CD and (S)-propranolol is the least favorable.
Keywords
docking, enantiomers, molecular dynamics simulation, propranolol, beta-cyclodextrin
Divisions
CHEMISTRY
Funders
Ministry of Education, Malaysia (FRGS/1/2020/STG04/UM/02/3)
Publication Title
JOURNAL OF COMPUTATIONAL CHEMISTRY
Volume
45
Issue
16
Publisher
Wiley
Publisher Location
111 RIVER ST, HOBOKEN 07030-5774, NJ USA