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

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

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

Author(s): Kyeng Min Park; Kangkyun Baek; Young Ho Ko; Annadka Shrinidhi; James Murray; Jang, WH; Kim, KH; Lee, JS; Jejoong Yoo; Kim, S; Kimoon Kim

Subject: amphiphiles, ; cucurbiturils, ; drug delivery, ; supramolecular chemistry, ; vesicles

Journal: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.12, pp.3132 - 3136

Abstract: Serendipitously, mono-allyloxylated cucurbit[7]uril (AO(1)CB[7]) was discovered to act as an unconventional amphiphile which self-assembles into light-responsive vesicles (AO(1)CB[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 AO(1)CB[7]VC as a new type of light-responsive intracellular delivery vehicle for the release of therapeutic cargo, within cells, on demand T 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim