Self-assembly of chiral foldamers with alternating hydrophilic and hydrophobic side chains into acid-sensitive and solvent-exchangeable vesicular particles.

Abstract

It is difficult for the same molecule to self-assemble into stable vesicular particles in water and aliphatic hydrocarbon (oil), respectively. Here we demonstrated that chiral oligo(methylene-<i>p</i>-phenyleneethynylene)s with alternating hydrophilic and hydrophobic side chains were able to self-assemble into vesicular particles independent of solvent polarity. These particles were well dispersed in aliphatic hydrocarbon, alcohol or water for at least one month at room temperature, and readily transferred from organic to aqueous phases <i>via</i> dialysis. They displayed a noticeable response to the acidity of the aqueous phase, and could be used as simple cargos for loading hydrophilic or hydrophobic molecules in aqueous cores, which were different from loading in polymersomes. The vesicular particles loaded with hydrophobic paclitaxel exhibited comparable anti-HeLa cell activity to free paclitaxel <i>in vitro</i>.