Supramolecular interaction of 2,4-dichlorophenol and β-cyclodextrin functionalized ionic liquid and its preliminary study in sensor application

Mohamad, Sharifah; Chandrasekaram, Kumuthini; Rasdi, Fairuz Liyana Mohd; Manan, Ninie Suhana Abdul; Raoov, Muggundha; Sidek, Nadiah; Fathullah, Syed Fariq

doi:10.1016/j.molliq.2015.10.044

Cited by 11 publications

(9 citation statements)

References 30 publications

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“…In this study, the effect of inclusion complexes on the solubility of ketoconazole and miconazole was examined. 34 An excess amount of ketoconazole or miconazole (5 mg) was added in separate vials containing 5 ml of water at various pH values (3.0-7.0). In the same way, ketoconazole or miconazole was added, respectively, into a solution that contained β-CD or HP-β-CD, respectively.…”

Section: Dissolubility Studymentioning

confidence: 99%

“…However, the solubility improved when the compounds were added to the solution containing CDs, which had a higher effect in the presence of HPβ-CD compared with β-CD. 34…”

Section: Dissolubility Studymentioning

confidence: 99%

“…A decrease in solubility for both ketoconazole and miconazole was detected within pH 3.0 to 7.0 (Figure 5). However, the solubility improved when the compounds were added to the solution containing CDs, which had a higher effect in the presence of HP‐β‐CD compared with β‐CD 34 …”

Section: Formation Of Inclusion Complexes Between Host and Guestmentioning

confidence: 99%

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Enantioseparation of ketoconazole and miconazole by capillary electrophoresis and a study on their inclusion interactions with β‐cyclodextrin and derivatives

et al. 2020

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A chiral separation method coupled with capillary electrophoresis (CE) analysis for ketoconazole and miconazole enantiomers using chiral selectors such as β-cyclodextrin (β-CD) and hydroxypropyl-β-CD (HP-β-CD) was developed in this study, which included the optimisation, validation and application of the method on the antifungal cream samples. The formation of inclusion complex between the hosts (β-CD and HP-β-CD) and guests (ketoconazole and miconazole) were compared and analysed using ultraviolet-visible spectrophotometry, nuclear magnetic resonance (NMR) spectroscopy and molecular docking methods. Results from the study showed that in a concentration that ranged between 0.25 and 50 mg L −1 , the linear calibration curves of each enantiomer had a high coefficient of regression (R 2 > 0.999), low limit of detection (0.075 mg L −1) and low limit of quantification (0.25 mg L −1). The relative standard deviation (RSD) of the intraday and interday analyses ranged from 0.79% to 8.01% and 3.30% to 11.43%, respectively, while the recoveries ranged from 82.0% to 105.7% (RSD < 7%, n = 3). The most probable structure of the inclusion complexes was proposed based on the findings from the molecular docking studies conducted using the PatchDock server.

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Section: Dissolubility Studymentioning

confidence: 99%

“…However, the solubility improved when the compounds were added to the solution containing CDs, which had a higher effect in the presence of HPβ-CD compared with β-CD. 34…”

Section: Dissolubility Studymentioning

confidence: 99%

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Enantioseparation of ketoconazole and miconazole by capillary electrophoresis and a study on their inclusion interactions with β‐cyclodextrin and derivatives

et al. 2020

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“…The presence of the ionic species improved the enantioseparation of β-blockers and avonoids thanks to the formation of intermolecular inclusion complex but also owing to an original π-π interaction between the aromatic guest and the imidazolium cycle (Rahim et al 2016a;Rahim et al 2016b). The original electrochemical properties of ionic liquids and the high supramolecular recognition properties of cyclodextrins were also tested on metallic supports such as Pt-Co (Zhao et al 2010), graphite (Mohamad et al 2015;Rasdi et al 2016), Fe 3 O 4 (Sinniah et al 2015, Bahadorikhalili et al 2019, Au-graphene oxide (Li et al 2016) producing new nanoparticles and hybrid nanomaterials (Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

“…1b). The ionic liquid playing the role of supported stabilizer electrolyte provides higher sensitive carbon paste electrodes leading to environmentally-friendly electrochemical sensors for non-enzymatic glucose reaction (Zhao et al 2010) or to detect 2,4-dichlorophenol (Mohamad et al 2015;Rasdi et al 2016). In the same way, magnetite nanoparticles coated with β-CD-IL produced new electrode material able to recognize bisphenol A (Sinniah et al 2015) and sunset yellow (Li et al 2016).…”

Section: Introductionmentioning

confidence: 99%

New ternary water-soluble support from self-assembly of β-cyclodextrin-ionic liquid and an anionic polymer for a dialysis device

Bouyahya

Sembo-Backonly

Favrelle-Huret

et al. 2021

Environ Sci Pollut Res

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We developed a new hybrid material resulting from an innovative supramolecular tripartite association between an ionic liquid covalently immobilized on primary β-cyclodextrins rim and an anionic watersoluble polymer. Two hydrophilic ternary complexes based on native and permethylated β-cyclodextrins substituted with an ionic liquid and immobilized on poly(styrene sulfonate) (CD-IL + PSS − and CD(OMe)IL + PSS − ) were obtained by simple dialysis with a cyclodextrin maximal grafting rate of 25% and 20% on the polymer, respectively. These polyelectrolytes are based on electrostatic interactions between the opposite charges of the imidazolium cation of the ionic liquid and the poly(styrene sulfonate) anion.The inclusion properties of the free cavities of the cyclodextrins and the synergic effect of the polymeric matrix were studied with three reference guests such as phenolphthalein, p-nitrophenol, and 2anilinonaphthalene-6-sulfonic acid using UV-visible, uorescent, and NMR spectroscopies. The support has been applied successfully in dialysis device to extract and concentrated aromatic model molecule. This simple and exible synthetic strategy opens the way to new hybrid materials useful for fast and lowcost ecofriendly extraction techniques relevant for green analytical chemistry.

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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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Supramolecular interaction of 2,4-dichlorophenol and β-cyclodextrin functionalized ionic liquid and its preliminary study in sensor application

Cited by 11 publications

References 30 publications

Enantioseparation of ketoconazole and miconazole by capillary electrophoresis and a study on their inclusion interactions with β‐cyclodextrin and derivatives

Enantioseparation of ketoconazole and miconazole by capillary electrophoresis and a study on their inclusion interactions with β‐cyclodextrin and derivatives

New ternary water-soluble support from self-assembly of β-cyclodextrin-ionic liquid and an anionic polymer for a dialysis device

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

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