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-p-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 via dialysis. They displayed a noticeable response to the acidity of 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 in vitro.

Supplementary files

Article information

Article type
Paper
Submitted
13 Sep 2021
Accepted
13 Oct 2021
First published
13 Oct 2021

Soft Matter, 2021, Accepted Manuscript

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

Z. Zhao, B. Zheng, Y. Chen, Z. Xie, C. Kang, L. Gao and Z. Guangshan, Soft Matter, 2021, Accepted Manuscript , DOI: 10.1039/D1SM01321A

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