Enantioselective separation of zopiclone on immobilized polysaccharide chiral stationary phase by HPLC: Method development and validation

Kozlov, Oleksandr; Záhoráková, Daniela; Gondová, Taťána

doi:10.1016/j.jpba.2020.113549

Cited by 9 publications

(5 citation statements)

References 24 publications

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“…None of them showed sufficient enantioresolution. Finally, the Lux i-Amylose-1 column (immobilized amylose tris(3,5-dimethylphenylcarbamate)) provided satisfactory results enabling validation of the method and its further use for the analysis of zopiclone in tablets [ 37 ]. The ( R )- and ( S )-zopiclone were also determined in human hair on a Chiral Art Cellulose-SC column based on immobilized cellulose tris(3,5-dichlorophenylcarbamate) using previous optimized extraction to prevent decomposition of the analytes [ 38 ].…”

Section: Polysaccharide-based Stationary Phasesmentioning

confidence: 99%

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Grybinik

Bosáková

2021

Monatsh Chem

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Graphic abstract This review provides a brief survey of chiral separation of pharmaceutically active substances published over the last 3 years (2018–2020). Chiral separation of drugs is an important area of research. The control of enantiomeric purity and determination of individual enantiomeric drug molecules is a necessity especially for clinical, analytical, and regulatory purposes. Among chromatographic resolution methods, high-performance liquid chromatography based on chiral stationary phases remains the most popular and effective method used for chiral separation of various drugs. In this review, attention is paid to several classes of chiral stationary phases that have been the most frequently used for drug enantioseparation during this period.

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Section: Polysaccharide-based Stationary Phasesmentioning

confidence: 99%

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Grybinik

Bosáková

2021

Monatsh Chem

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“…It has been acknowledged that the preparative separation of enantiomers by chromatography on CSPs is a suitable alternative to more traditional methods, such as enantioselective synthesis and enzymatically catalyzed transformations to acquire enantiopure drugs 22–25 . The screening of the chiral column and mobile phase takes place in the initial step of the chiral method development process, followed by the optimization of the remaining chromatographic conditions 26,27 . Upon screenings on various polysaccharide‐based stationary phases, namely, Chiralpak IA (amylose‐based) [tris(3,5‐dimethylphenylcarbamate)], Chiralpak IG (amylose‐based) [tris(3‐chloro‐5 methylphenylcarbamate)], and Chiralpak IC (Cellulose‐based) [tris(3,5‐dichlorophenylcarbamate)], an expected analytical chiral resolution was observed on Chiralpak IC.…”

Section: Resultsmentioning

confidence: 99%

“…[22][23][24][25] The screening of the chiral column and mobile phase takes place in the initial step of the chiral method development process, followed by the optimization of the remaining chromatographic conditions. 26,27 [tris(3,-5-dichlorophenylcarbamate)], an expected analytical chiral resolution was observed on Chiralpak IC. For analytical separations, Chiralpak IC was employed, and the retention factor (k) for the first eluted enantiomer, separation factor (α), and the resolution (R s ) were found as 0.17, 1.29, and 2.45, respectively.…”

Section: Enantioselective Hplc Methods Optimizationmentioning

confidence: 94%

Enantioselective polar‐organic mode high‐performance liquid chromatographic separation of lifitegrast on immobilized polysaccharide stationary phase and its application to pH‐dependent chiral interconversion studies

Kandula,

Rayala,

Parmar

et al. 2024

Chirality

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Abstract(S)‐Lifitegrast (LFT) is the novel integrin antagonist, approved by the Food and drug administration, to treat signs and symptoms of dry eye disease. Synthesis of racemic LFT, preparative and analytical enantiomer separation, and chiral interconversion studies are lacking in the literature. Hence, in our study, synthesis of LFT racemate, chiral preparative purification procedure of enantiomer, and comprehensive analytical advancements are focused on rapid enantioselective separation and pH‐dependent chiral interconversion studies. The synthesis of LFT racemate employed 2‐amino‐3‐(3‐(methylsulfonyl)phenyl)propanoic acid hydrochloride and 2‐(benzofuran‐6‐carbonyl)‐5,7‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐6‐carbonyl chloride as starting materials. (R)‐LFT was isolated from the racemate by preparative chiral HPLC and characterized using Q‐TOF, FT‐IR, NMR spectroscopy, and chiral HPLC. The purity of (R)‐LFT was determined to have an enantiomeric excess of 99.12%. A precise, accurate, rapid HPLC‐DAD enantioselective analytical method has been developed on Chiralpak IC [tris(3,5‐dichloro phenyl carbamate) immobilized on cellulose] using water and methanol as mobile phase. The chiral interconversion study reveals 0.22% and 0.21% of interconversion of (S)‐LFT into (R)‐LFT at 80°C in pH 7.4 and 9.5 buffers, respectively, on the 24th day. An alternative route to enantioselective synthesis of LFT enantiomers by chromatographic separation is proposed. The validated enantioselective HPLC method will help to test the regular quality control samples.

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“…It is known that chiral separation is influenced by both enantioselective (chiral) and nonselective (achiral) interactions, which can significantly vary with temperature [21]. Partition behavior of enantiomers in HPLC mainly involves the transfer of analytes from mobile phase to stationary phase, and its retention mechanism could be studied by thermodynamic analysis.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation of five racemic N‐alkyl drugs by reverse phase HPLC using sulfobutylether‐β‐cyclodextrin as a chiral mobile phase additive

Chen

You

Fang

et al. 2022

J of Separation Science

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Analytical enantioseparations of five N-alkyl drugs, fluoxetine hydrochloride, labetalol, venlafaxine hydrochloride, trans-paroxol, and atropine sulfate, were investigated by reverse phase high-performance liquid chromatography with sulfobutylether-β-cyclodextrin as chiral mobile phase additive. Effects of various factors such as composition of mobile phase, concentration of cyclodextrins, and column temperature on retention and enantioselectivity were studied. Apparent formation constant between methanol, acetonitrile, and sulfobutylether-βcyclodextrin were determined to be 2.90 × 10 −3 and 1.00 × 10 −4 L mmol −1 under 25 • C using UV-spectrophotometry. Van't Hoff plots were used to investigate thermodynamic parameters for enantiomers-stationary phase interaction and formation of inclusion complex. Two retention models were employed individually for evaluation of inclusion complexation between five racemates and sulfobutylether-β-cyclodextrin. The second model with complex adsorption was more accord with the retention behavior of fluoxetine hydrochloride, labetalol, and venlafaxine hydrochloride enantiomers, while the first model was more consistent with the retention behaviors of trans-paroxol and atropine sulfate.In the selected mobile phase, stoichiometric ratio for both of inclusion complex was found to be 1:1.

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Enantioselective separation of zopiclone on immobilized polysaccharide chiral stationary phase by HPLC: Method development and validation

Cited by 9 publications

References 24 publications

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

An overview of chiral separations of pharmaceutically active substances by HPLC (2018–2020)

Enantioselective polar‐organic mode high‐performance liquid chromatographic separation of lifitegrast on immobilized polysaccharide stationary phase and its application to pH‐dependent chiral interconversion studies

Enantioseparation of five racemic N‐alkyl drugs by reverse phase HPLC using sulfobutylether‐β‐cyclodextrin as a chiral mobile phase additive

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