A novel β-cyclodextrin derivative chemically bonded chiral stationary phase (EDACD) was synthesized by the reaction of mono-6-ethylenediamine-β-cyclodextrin with the active alkyl isocyanate, anchoring to silica gel. After the successful analysis and characterization using scanning electron microscopy, Fourier transform infrared spectra, solid-state nuclear magnetic resonance spectra, elemental analysis, and thermogravimetric analysis techniques, the enantioselective performance of the as-prepared EDACD column was evaluated by non-steroidal antiinflammatory drugs and flavonoids under the reversed-phase HPLC condition. The factors that affected enantioseparation including mobile phase compositions and buffers were investigated in more detail. As a result, EDACD showed a satisfactory enantioselectivity for the tested drugs. With the mobile phase of acetonitrile and 20-mM ammonium formate adjusted to pH 4.0 using formic acid (85:15, v/v) at the flow rate of 0.6 mL min-1, the enantiomers of ibuprofen, carprofen, naproxen, indoprofen, ketoprofen, eriocitrin, naringin, and narirutin were separated with the best resolutions of 1.53, 1.64, 3.72, 2.40, 0.50, 0.61, 0.58, and 0.52. To adjust the proportion of acetonitrile to 80% (by volume), the enantiomers of pranoprofen and flurbiprofen were completely resolved with the best resolutions of 1.60 and 1.59. Additionally, by the study of the molecular docking, hydrogen bonding and inclusion complexation were believed to play an important role in chiral recognition. As a new material, EDACD will have a wider application in the analysis of chiral compounds.
Keywords: Chiral stationary phase; Enantioseparation; HPLC; Molecular docking; β-Cyclodextrin derivative.