Inclusion complexes of N-sulfamoyloxazolidinones with β-cyclodextrin: A molecular modeling approach

Dinar, Karim; Sahra, Khalil; Seridi, Achour; Kadri, Mekki

doi:10.1016/j.cplett.2014.02.004

Cited by 19 publications

(9 citation statements)

References 50 publications

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“…The complexes of CD CSP and enantiomers in reversed-phase HPLC conditions are selected for the simulation of optimized interaction structures. The energy-minimized structures were firstly obtained with the chiral carbon pointing towards the narrow rim of CD during the docking process using PM3 method 35 . During docking, the enantiomer was rotated ~30 o every time in CD cavity.…”

Section: Methodsmentioning

confidence: 99%

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Tang

Zhang

Lin

et al. 2015

Sci Rep

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The separation of racemic molecules is of crucial significance not only for fundamental research but also for technical application. Enantiomers remain challenging to be separated owing to their identical physical and chemical properties in achiral environments. Chromatographic techniques employing chiral stationary phases (CSPs) have been developed as powerful tools for the chiral analysis and preparation of pure enantiomers, most of which are of biological and pharmaceutical interests. Here we report our efforts in developing high-performance phenylcarbamated cyclodextrin (CD) clicked CSPs. Insights on the impact of CD functionalities in structure design are provided. High-efficiency enantioseparation of a range of aryl alcohols and flavanoids with resolution values (Rs) over 10 were demonstrated by per(3-chloro-4-methyl)phenylcarbamated CD clicked CSP. Comparison study and molecular simulations suggest the improved enantioselectivity was attributed to higher interactions energy difference between the complexes of enantiomers and CSPs with phenylcarbamated CD bearing 3-chloro and 4-methyl functionalities.

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Section: Methodsmentioning

confidence: 99%

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Tang

Zhang

Lin

et al. 2015

Sci Rep

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“…Molecular dynamics (MD) simulations can give important insights into the energetics of structural interactions. The hydrated structure of β-CD in aqueous solution [ 18 ] and those showing host–guest interactions between the β-CD structure and guest molecules in its inclusion compounds have been reported [ 19 – 21 ]. Moreover, MD simulations of β-CD in water and ethanol mixtures have been performed to investigate the orientation of the co-solvent in the hydrophobic cavity of the β-CD [ 22 ].…”

Section: Introductionmentioning

confidence: 99%

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

Rungnim¹,

Phunpee²,

Kunaseth³

et al. 2015

Beilstein J. Org. Chem.

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SummaryCyclodextrins (CDs) have been extensively utilized as host molecules to enhance the solubility, stability and bioavailability of hydrophobic drug molecules through the formation of inclusion complexes. It was previously reported that the use of co-solvents in such studies may result in ternary (host:guest:co-solvent) complex formation. The objective of this work was to investigate the effect of ethanol as a co-solvent on the inclusion complex formation between α-mangostin (α-MGS) and β-CD, using both experimental and theoretical studies. Experimental phase-solubility studies were carried out in order to assess complex formation, with the mechanism of association being probed using a mathematical model. It was found that α-MGS was poorly soluble at low ethanol concentrations (0–10% v/v), but higher concentrations (10–40% v/v) resulted in better α-MGS solubility at all β-CD concentrations studied (0–10 mM). From the equilibrium constant calculation, the inclusion complex is still a binary complex (1:1), even in the presence of ethanol. The results from our theoretical study confirm that the binding mode is binary complex and the presence of ethanol as co-solvent enhances the solubility of α-MGS with some effects on the binding affinity with β-CD, depending on the concentration employed.

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“…The energy gaps reflect chemical activities of molecules and describe the final stabilization of NDCF-(H2O)5 molecules [27]. According to Table 2, the greatest energy gaps (∆E) is in the addition of five water molecules.…”

Section: Molecular Orbitalsmentioning

confidence: 99%

Density Functional Theory (DFT) and Natural Bond Orbital (NBO) Analysis of Intermolecular Hydrogen Bond Interaction in "Phosphorylated Nata De Coco - Water"

2018

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Inclusion complexes of N-sulfamoyloxazolidinones with β-cyclodextrin: A molecular modeling approach

Cited by 19 publications

References 50 publications

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

Density Functional Theory (DFT) and Natural Bond Orbital (NBO) Analysis of Intermolecular Hydrogen Bond Interaction in "Phosphorylated Nata De Coco - Water"

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