Chiral separation of lansoprazole and rabeprazole by capillary electrophoresis using dual cyclodextrin systems

Papp, Lajos Attila and Hancu, Gabriel and Gyéresi, Árpád and Kelemen, Hajnal and Szabó, Zoltán‐István and Noszál, Béla and Dubský, Pavel and Tóth, Gergő (2019) Chiral separation of lansoprazole and rabeprazole by capillary electrophoresis using dual cyclodextrin systems. ELECTROPHORESIS, 40 (21). pp. 2799-2805. ISSN 0173-0835, ESSN: 1522-2683

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Abstract

Novel capillary electrophoresis methods using CDs as chiral selectors were developed andvalidated for the chiral separation of lansoprazole and rabeprazole, two proton pump in-hibitors. Fourteen different neutral and anionic CDs were screened at pH 4 and 7 in thepreliminary analysis. Sulfobutyl-ether-␤-CD with a degree of substitution of 6.5 and 10 atneutral pH proved to be the most suitable chiral selector for both compounds. Various dualCD systems were also compared, and the possible mechanisms of enantiomer separationwere investigated. A dual selector system containing sulfobutyl-ether-␤-CD degree of sub-stitution 6.5 and native ␥ -CD proved to be the most adequate system for the separations.Method optimization was carried out using an experimental design approach, performingan initial fractional factorial screening design, followed by a central composite design toestablish the optimal analytical conditions. The optimized methods (25 m M phosphatebuffer, pH 7, 10 mM sulfobutyl-ether-␤-CD/20 mM ␥ -CD, +20 kV voltage; 17°C tempera-ture; 50 mbar/3 s injection, detection at 210 nm for lansoprazole; 25 mM phosphate buffer,pH 7, 15 mM sulfobutyl-ether-␤-CD/30 mM ␥ -CD, +20 kV voltage; 18°C temperature;50 mbar/3 s injection, detection at 210 nm for rabeprazole) provided baseline separationfor lansoprazole (Rs= 2.91) and rabeprazole (Rs= 2.53) enantiomers with favorable migra-tion order (in both cases the S-enantiomers migrates first). The optimized methods werevalidated according to current guidelines and proved to be reliable, linear, precise, andaccurate for the determination of 0.15% distomer as chiral impurity in dexlansoprazoleand dexrabeprazole samples.

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