Mono-allyloxylated Cucurbit[7]uril Acts as an Unconventional Amphiphile To Form Light-Responsive Vesicles

Kyeng Min Park, Kangkyun Baek, Young Ho Ko, Annadka Shrinidhi, James Murray, Won Hyuk Jang, Ki Hean Kim, Jun Seok Lee, Jejoong Yoo, Sungwan Kim, Kimoon Kim

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

Serendipitously, mono-allyloxylated cucurbit[7]uril (AO1CB[7]) was discovered to act as an unconventional amphiphile which self-assembles into light-responsive vesicles (AO1CB[7]VC) in water. Although the mono-allyloxy group, directly tethered on the periphery of CB[7], is much shorter (C4) than the hydrophobic tails of conventional amphiphiles, it played an important role in vesicle formation. Light-activated transformation of the allyloxy group by conjugation with glutathione was exploited as a remote tool to disrupt the vesicle. The vesicle showed on-demand release of cargo upon irradiation by a laser, after they were internalized into cancer cells. This result demonstrated the potential of AO1CB[7]VC as a new type of light-responsive intracellular delivery vehicle for the release of therapeutic cargo, within cells, on demand.

Original languageEnglish
Pages (from-to)3132-3136
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number12
DOIs
Publication statusPublished - 2018 Mar 12
Externally publishedYes

Keywords

  • amphiphiles
  • cucurbiturils
  • drug delivery
  • supramolecular chemistry
  • vesicles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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