Novel chiral metal organic frameworks functionalized composites for facile preparation of optically pure propranolol hydrochlorides

Two novel sorbents based on polydopamine (PDA)-coated magnetic graphite oxide-metal organic frameworks nanoparticles [Cu( L -mal)(bpy)]·H 2 O (MGO-CuLBH) and [Cu( D -mal)(bpy)]·H 2 O (MGO-CuDBH) possessing of both magnetic property and excellent enantioselective ability were prepared and characterized. Solutions of racemic propranolol hydrochloride ( Rac -PRO) were chosen to investigate the enantioselective performance of MGO-CuLBH and MGO-CuDBH by dispersive magnetic nanoparticle solid phase extraction (d-MNSPE). The results showed that the nanocomposites have excellent enantioselectivity to PROs with enantiomeric excess ( ee ) values reaching up to 98%. The entire process with PROs by the d-MNSPE method was fast, convenient and the collected composites could be easily recycled. Multi-stage operations using MGO-CuLBH and MGO-CuDBH were scaled up to obtain milligram quantities of R -propranolol hydrochloride ( R -PRO) and S -propranolol hydrochloride ( S -PRO). Furthermore, on the basis of the successful preparations, the differences in the cytotoxicity of Rac -PRO, R -PRO and S -PRO on A549 cells in vitro were all evaluated.