β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers

Rahim, Nurul Yani; Tay, Kheng Soo; Mohamad, Sharifah

doi:10.1007/s10847-016-0629-9

Cited by 25 publications

(16 citation statements)

References 36 publications

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“…The b-CD-BIMOTs-CSP was synthesized according to the procedure reported previously (Rahim et al, 2016a(Rahim et al, , 2016b. Meanwhile, the preparation of b-CD-DIMOTs-CSP involved the following four steps.…”

Section: Synthesis Of Cspsmentioning

confidence: 99%

“…Ts 2 O was prepared according to our previous publications (Rahim et al, 2016a(Rahim et al, , 2016b, primarily by dissolving p-toluene sulfonyl chloride (2.00 g, 10.4 mmol) in dichloromethane (DCM) (12.5 mL). Then, p-toluene sulfonic acid (0.52 g, 2.63 mmol) was added gradually with vigorous stirring under nitrogen atmosphere.…”

Section: Synthesis Of Cspsmentioning

confidence: 99%

“…Hexane (50 ml) was added to the filtrate and a precipitate was obtained after drying overnight under reduced pressure. b-CDOTs was also prepared according to our previously reported method (Rahim et al, 2016a(Rahim et al, , 2016b. C 10 MIm (10 mol equivalent) was then added dropwise to a stirred solution of dry b-CDOTs (1.00 g, 0.78 mmol) in anhydrous DMF (40 ml) to prepare b-CD-DIMOTs.…”

Section: Synthesis Of Cspsmentioning

confidence: 99%

“…Spectra of Si-TDI (a) show the presence of the isocyanate (O ¼ C ¼ N-) group at 2280 cm À1 . The para position isocyanate group is expected to react with OH groups on the surface of silica to form Si-TDI (Arnold, 1957;Rahim et al, 2016aRahim et al, , 2016b. The remaining isocyanate group at ortho-position would react with secondary OH group of b-CD or b-CD functionalized IL.…”

Section: Ftir Characterizationmentioning

confidence: 99%

“…In our previous work, we introduced the preparation, characterization and chromatographic performance of b-CD-BIMOTs-CSP ( Figure 1) (Rahim et al, 2016a(Rahim et al, , 2016b. It was observed that compared with native b-CD-CSP, b-CD-BIMOTs-CSP possessed excellent chiral recognition abilities towards the selected b-blockers and flavonoids.…”

Section: Introductionmentioning

confidence: 99%

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Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

Rahim

Tay

Mohamad

2017

Adsorption Science & Technology

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Recently, we reported a new chiral stationary phase prepared using b-cyclodextrin functionalized with aromatic ionic liquid which is aimed to enhance the performance of enantioseparation of flavonoids and b-blockers. In this paper, the characteristics and performance of previously prepared chiral stationary phase denoted as b-CD-BIMOTs were compared with the newly synthesized chiral stationary phase denoted as b-CD-DIMOTs. b-CD-DIMOTs were prepared by functionalization of b-cyclodextrin with aliphatic ionic liquid. The obtained b-CD-BIMOTs and b-CD-DIMOTs stationary phases were compared with native b-CD stationary phase for the enantioseparation of non-steroidal anti-inflammatory drugs (NSAIDs) (ibuprofen, indoprofen, ketoprofen and fenoprofen). The b-CD-BIMOTs stationary phase showed greater chiral resolution capabilities rather than b-CD-DIMOTs and native b-CD stationary phases. Further, in order to understand the interaction of enantioseparation, the inclusion complex formation between NSAIDs and b-CD-BIMOTs was studied using 1 H NMR, NOESY and UV/Vis. The enantioseparated NSAIDs were found to form multiple interactions with b-CD-BIMOTs-CSP.

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Section: Synthesis Of Cspsmentioning

confidence: 99%

Section: Synthesis Of Cspsmentioning

confidence: 99%

Section: Synthesis Of Cspsmentioning

confidence: 99%

Section: Ftir Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

Rahim

Tay

Mohamad

2017

Adsorption Science & Technology

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An enantioselective study of β‐cyclodextrin and ionic liquid‐β‐cyclodextrin towards propranolol enantiomers by molecular dynamic simulations

Ishak,

Aun,

Sidek

et al. 2024

J Comput Chem

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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.

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Inclusion Complexes of β-Cyclodextrin/Pioglitazone and β-Cyclodextrin-Ionic Liquid/Pioglitazone: Spectroscopic Methods Combined with Molecular Docking Studies

Rahim

Zuki

Jumbri

et al. 2021

Proceedings of the 6th International Conference on Fundamental and Applied Sciences

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β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers

Cited by 25 publications

References 36 publications

Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

An enantioselective study of β‐cyclodextrin and ionic liquid‐β‐cyclodextrin towards propranolol enantiomers by molecular dynamic simulations

Inclusion Complexes of β-Cyclodextrin/Pioglitazone and β-Cyclodextrin-Ionic Liquid/Pioglitazone: Spectroscopic Methods Combined with Molecular Docking Studies

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