3 years ago

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

Kangkyun Baek, Jejoong Yoo, Young Ho Ko, Sungwan Kim, Kimoon Kim, Annadka Shrinidhi, Won Hyuk Jang, Kyeng Min Park, James Murray, Ki Hean Kim, Jun-Seok Lee
Serendipitously, we discovered that mono-allyloxylated cucurbit[7]uril (AO₁CB[7]) acts as an unconventional amphiphile which self-assembles into light-responsible 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 (GSH) was exploited as a remote tool to disrupt the vesicle. The vesicle showed on-demand release of cargo upon irradiation of the laser after they were internalized into cancer cells. This result demonstrated the great potential of AO₁CB[7]VC as a new type of light-responsive intracellular delivery vehicle for the release of therapeutic cargos inside cells on-demand.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201713059

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