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

Abstract

Two novel sorbents based on polydopamine (PDA)-coated magnetic graphite oxide-metal organic frameworks nanoparticles [Cu(L-mal)(bpy)]·H2O (MGO-CuLBH) and [Cu(D-mal)(bpy)]·H2O (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.