Enantioseparation and modelling study of six proton pump inhibitors on a novel 3, 5-dichloro-phenylcarbamated β-cyclodextrin chemically bonded chiral stationary phase by high performance liquid chromatography

Abstract

A fully substituted β-cyclodextrin derivative chemically bonded chiral stationary phase for high performance liquid chromatography, named MDCPC was prepared by linking 3, 5-dichloro-phenylcarbamated mono-6-ethylenediamine-β-cyclodextrin to the surface of silica support. The as-prepared MDCPC was successfully characterized by scanning electron microscopy, fourier transform infrared spectra, solid state nuclear magnetic resonance spectra, elemental analysis and thermogravimetric analysis. The enantioselectivity of MDCPC was systematically evaluated by using proton pump inhibitors including omeprazole, lansoprazole, pantoprazole sodium, ilaprazole, rabeprazole sodium and tenatoprazole under the normal phase, polar organic phase, and reversed phase conditions. Effects of the mobile phase compositions and buffers on enantioseparation were investigated in different modes. As a result, MDCPC showed a better chromatographic performance in enantioselectivity, and all tested compounds were successfully enantioseparated. Findings of the molecular docking showed that hydrogen bonding, hydrophobic interaction and inclusion complexation played an important role in improving enantioselectivity. Additionally, good repeatability, column-to-column reproducibility and stability of MDCPC were observed by the study of chiral or achiral separation. As a novel chiral stationary phase, MDCPC was supposed to be a promising prospect in the further analysis of chiral drugs.