Ishak, Mohamad Adil Iman and Aun, Tan Tiek and Sidek, Nadiah and Mohamad, Sharifah and Jumbri, Khairulazhar and Manan, Ninie Suhana Abdul (2024) An enantioselective study of β-cyclodextrin and ionic liquid-β-cyclodextrin towards propranolol enantiomers by molecular dynamic simulations. JOURNAL OF COMPUTATIONAL CHEMISTRY, 45 (16). pp. 1329-1351. ISSN 0192-8651, DOI https://doi.org/10.1002/jcc.27321.
Full text not available from this repository.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.
| Item Type: | Article |
|---|---|
| Funders: | Ministry of Education, Malaysia (FRGS/1/2020/STG04/UM/02/3) |
| Uncontrolled Keywords: | docking; enantiomers; molecular dynamics simulation; propranolol; beta-cyclodextrin |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 05 Nov 2024 08:54 |
| Last Modified: | 05 Nov 2024 08:54 |
| URI: | http://eprints.um.edu.my/id/eprint/45596 |
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