Synthesis and properties of a novel bolaamphiphile surfactant derived from proline

A novel bolaamphiphile surfactant N,N′-(octane-1,8-diyl)bis(pyrrolidine-2-carboxamide) (DAOP), was designed and synthesized from proline and 1,8-diaminooctane, as the hydrophilic part and hydrophobic part, respectively. After separation and purification, the structures of the synthesized bola surfactants were verified by IR, MS and 1H NMR. The pKa was measured by a titration experiment, the turbidity was determined using a Shimadzu UV-1750 spectrophotometer, and the critical micelle concentration (CMC) values of the synthesized surfactants in water were obtained using the conductivity and fluorescence probe measurements. The synthesized bolaamphiphile surfactants demonstrate the ability of self-assemble to form vesicles that were confirmed with dynamic light scattering and transmission electron microscopy. The results showed that the novel bolaamphiphile surfactant derived from proline might potentially be an excellent carrier for drug delivery.

Graphical abstractA novel bolaamphiphile was synthesized from proline and 1,8-diaminooctane, and its physicochemical properties were investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide