β-Cyclodextrin-ionic liquid functionalized chiral composite membrane for enantioseparation of drugs and molecular simulation

With the development of pharmaceutical field, the demand for single enantiomer drugs is gradually increasing. Recently, chiral membrane separation technology has great potential in the field of enantioseparation due to its simple preparation, continuous operation and easy scale-up. In this study, a novel β-cyclodextrin-ionic liquid thin film composite membrane (β-CD-IL TFCM) was fabricated by interfacial polymerization method to achieve the enantioseparation of chiral drugs. Various fabrication conditions of the membrane were optimized with tryptophan as a model molecule to improve its enantioselectivity. Under optimal fabrication conditions, the percent enantiomeric excess (e.e.%) of tryptophan was 100.0% and the solute flux (J S ) was 8.0 nmol cm −2 h −1 . Enantioseparation of various chiral drugs was achieved using β-CD-IL TFCM, including propranolol (e.e.% = 73.4%), warfarin (e.e.% = 11.4%), metoprolol (e.e.% = 3.4%), ibuprofen (e.e.% = 17.8%) and terbutaline (e.e.% = 3.3%). In addition, molecular docking simulation was applied to investigate the separation mechanism of chiral drugs, demonstrating that multiple interactions promote the separation of drug enantiomers. These results reveal the excellent enantioseparation performance of β-CD-IL TFCM, which has a wide prospect in realizing industrial application of chiral membranes. • Novel β-CD-IL TFCM was designed and fabricated by interfacial polymerization. • The membrane performed excellent enantioselectivity and permeability. • Optical separations of propranolol, ibuprofen and warfarin were achieved. • The chiral recognition mechanism was investigated by molecular docking simulation.