Chiral separation and a molecular modeling study of eight azole antifungals on the cellulose tris(3,5-dichlorophenylcarbamate) chiral stationary phase

Zhu, Bolin; Zhao, Fan; Yu, Jia; Wang, Zhaokun; Song, Yongbo; Li, Qing

doi:10.1039/c8nj01845f

Cited by 32 publications

(16 citation statements)

References 34 publications

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“…This year, the first modelling by docking of chloro‐substituted polysaccharide selectors have been reported. Indeed, enantioselection of eight azole antifungals (Table ) on the chlorinated cellulose tris (3,5‐dichlorophenylcarbamate) (CDCPC) has been modelled by Li and co‐workers by using molecular docking . The variation of the binding energies (average energy of the best cluster with the lowest docking energy) of the complexes formed by R ‐ and S ‐enantiomers was in agreement with the observed enantioselectivity under NP elution conditions (Table ).…”

Section: Polysaccharide Derivativesmentioning

confidence: 59%

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Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

et al. 2019

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Liquid‐phase enantioseparations have been fruitfully applied in several fields of science. Various applications along with technical and theoretical advancements contributed to increase significantly the knowledge in this area. Nowadays, chromatographic techniques, in particular HPLC on chiral stationary phase, are considered as mature technologies. In the last thirty years, CE has been also recognized as one of the most versatile technique for analytical scale separation of enantiomers. Despite the huge number of papers published in these fields, understanding mechanistic details of the stereoselective interaction between selector and selectand is still an open issue, in particular for high‐molecular weight chiral selectors like polysaccharide derivatives. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a basic tool in enantioseparation science. In this field, molecular docking and dynamics simulations proved to be extremely adaptable to model and visualize at molecular level the spatial proximity of interacting molecules in order to predict retention, selectivity, enantiomer elution order, and profile noncovalent interaction patterns underlying the recognition process. On this basis, topics and trends in using docking and molecular dynamics as theoretical complement of experimental LC and CE chiral separations are described herein. The basic concepts of these computational strategies and seminal studies performed over time are presented, with a specific focus on literature published between 2015 and November 2018. A systematic compilation of all published literature has not been attempted.

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Section: Polysaccharide Derivativesmentioning

confidence: 59%

“…In Table , a summary of some representative docking and MD studies published in the period 2015‐2018 is reported . Firstly, in polysaccharides modelling, an important issue concerns the preparation of a built polymer which is representative of the ‘real’ polysaccharide derivative.…”

Section: Polysaccharide Derivativesmentioning

confidence: 99%

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

et al. 2019

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“…HPLC analysis is known to have a limitation in providing direct evidence of the specific binding sites of analytes with the chiral selector. On the other hand, computational docking offers further insights into the detailed geometry information and binding energy of the chiral selector-analyte complex [ 40 ]. Thus, computational docking has been proposed as simple approaches for understanding the chiral recognition mechanism on CSPs [ 41 , 42 , 43 , 44 ].…”

Section: Discussionmentioning

confidence: 99%

Immobilization of Chondroitin Sulfate A onto Monolithic Epoxy Silica Column as a New Chiral Stationary Phase for High-Performance Liquid Chromatographic Enantioseparation

et al. 2021

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Chondroitin sulfate A was covalently immobilized onto a monolithic silica epoxy column involving a Schiff base formation in the presence of ethylenediamine as a spacer and evaluated in terms of its selectivity in enantioseparation. The obtained column was utilized as a chiral stationary phase in enantioseparation of amlodipine and verapamil using a mobile phase consisting of 50 mM phosphate buffer pH 3.5 and UV detection. Sample dilution by organic solvents (preferably 25% v/v acetonitrile-aqueous solution) was applied to achieve baseline enantioresolution (Rs > 3.0) of the individual drug models within 7 min, an excellent linearity (R2 = 0.999) and an interday repeatability of 1.1% to 1.8% RSD. The performance of the immobilized column for quantification of racemate in commercial tablets showed a recovery of 86–98% from tablet matrices. Computational modeling by molecular docking was employed to investigate the feasible complexes between enantiomers and the chiral selector.

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“…Retention factors k = (t R − t 0 )/t 0 were based on void times t 0 estimated from the earliest baseline perturbation as described by Zhu et al [49]. Resolution R s = (1.18 × (t R1 − t R2 ))/(w h1 + w h2 ) was calculated according to the European Pharmacopoeia from the difference of retention and the sum of peak width at half-height (w h ) [50].…”

Section: Methodsmentioning

confidence: 99%

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

et al. 2019

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Chiral metabolites of ketamine exerting rapid-onset yet sustained antidepressant effects may be marketed directly in the future, but require chemo- and enantio-selective chromatographic methods for quality assurance and control. The chromatographic behavior of S-/R-ketamine, S-/R-norketamine, S-/R-dehydronorketamine, and (2R,6R)-/(2S,6S)-hydroxynorketamine in supercritical fluid chromatography (SFC) was investigated computationally and experimentally with the aim of identifying problematic pairs of enantiomers and parameters for chiral resolution. Retention on three different polysaccharide-based chiral stationary phases (Lux Amylose-2, i-Amylose-3, and i-Cellulose-5) provided new information on the significance of halogen atoms as halogen bond donors and hydrogen bond acceptors for enantioselectivity, which could be corroborated in silico by molecular docking studies. Modifiers inversely affected enantioselectivity and retention. Methanol yielded lower run times but superior chiral resolution compared to 2-propanol. Lower temperatures than those conventionally screened did not impair phase homogeneity but improved enantioresolution, at no cost to reproducibility. Thus, sub-ambient temperature subcritical fluid chromatography (SubFC), essentially low-temperature HPLC with subcritical CO2, was applied. The optimization of the SubFC method facilitated the chiral separation of ketamine and its metabolites, which was applied in combination with direct injection and online supercritical fluid extraction to determine the purity of pharmaceutical ketamine formulations for proof of concept.

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Chiral separation and a molecular modeling study of eight azole antifungals on the cellulose tris(3,5-dichlorophenylcarbamate) chiral stationary phase

Abstract: Four immobilized polysaccharide-based chiral stationary phases have been examined for their enantioselectivity on azole analytes using normal phase liquid chromatography.

Cited by 32 publications

References 34 publications

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

Immobilization of Chondroitin Sulfate A onto Monolithic Epoxy Silica Column as a New Chiral Stationary Phase for High-Performance Liquid Chromatographic Enantioseparation

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

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