An enantioselective study of ß-cyclodextrin and ionic liquid-ß-cyclodextrin towards propranolol enantiomers by molecular dynamic simulations.
J Comput Chem
; 45(16): 1329-1351, 2024 Jun 15.
Article
em En
| MEDLINE
| ID: mdl-38372509
ABSTRACT
In this study, the enantioselectivity of ß-cyclodextrin and its derivatives towards propranolol enantiomers are investigated by molecular dynamic (MD) simulations. ß-cyclodextrin (ß-CD) have previously been shown to be able to recognize propranolol (PRP) enantiomers. To improve upon the enantioselectivity of ß-cyclodextrin, we propose the use of an ionic-liquid-modified-ß-cyclodextrin (ß-CD-IL). ß-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 ß-CD molecule has significant interaction with propranolol. The formation of the most stable complex occurred between (S)-ß-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)-ß-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 ß-CD and (S)-propranolol is the least favorable.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Comput Chem
Assunto da revista:
QUIMICA
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Malásia