Premium
Mono‐allyloxylated Cucurbit[7]uril Acts as an Unconventional Amphiphile To Form Light‐Responsive Vesicles
Author(s) -
Park Kyeng Min,
Baek Kangkyun,
Ko Young Ho,
Shrinidhi Annadka,
Murray James,
Jang Won Hyuk,
Kim Ki Hean,
Lee JunSeok,
Yoo Jejoong,
Kim Sungwan,
Kim Kimoon
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713059
Subject(s) - vesicle , amphiphile , chemistry , glutathione , biophysics , intracellular , biochemistry , biology , membrane , copolymer , organic chemistry , enzyme , polymer
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.