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

doi:10.1002/anie.201713059

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

Institute for Basic Science
University of Science and Technology UST
Pohang University of Science and Technology
Korea Institute of Science and Technology

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

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 language	English
Pages (from-to)	3132-3136
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	12
DOIs	https://doi.org/10.1002/anie.201713059
State	Published - 12 Mar 2018
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

amphiphiles
cucurbiturils
drug delivery
supramolecular chemistry
vesicles

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10.1002/anie.201713059

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

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.",

keywords = "amphiphiles, cucurbiturils, drug delivery, supramolecular chemistry, vesicles",

author = "Park, \{Kyeng Min\} and Kangkyun Baek and Ko, \{Young Ho\} and Annadka Shrinidhi and James Murray and Jang, \{Won Hyuk\} and Kim, \{Ki Hean\} and Lee, \{Jun Seok\} and Jejoong Yoo and Sungwan Kim and Kimoon Kim",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = mar,

day = "12",

doi = "10.1002/anie.201713059",

language = "English",

volume = "57",

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journal = "Angewandte Chemie - International Edition",

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T1 - Mono-allyloxylated Cucurbit[7]uril Acts as an Unconventional Amphiphile To Form Light-Responsive Vesicles

AU - Park, Kyeng Min

AU - Baek, Kangkyun

AU - Ko, Young Ho

AU - Shrinidhi, Annadka

AU - Murray, James

AU - Jang, Won Hyuk

AU - Kim, Ki Hean

AU - Lee, Jun Seok

AU - Yoo, Jejoong

AU - Kim, Sungwan

AU - Kim, Kimoon

PY - 2018/3/12

Y1 - 2018/3/12

N2 - 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.

AB - 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.

KW - amphiphiles

KW - cucurbiturils

KW - drug delivery

KW - supramolecular chemistry

KW - vesicles

UR - https://www.scopus.com/pages/publications/85042217290

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DO - 10.1002/anie.201713059

M3 - Article

C2 - 29377454

AN - SCOPUS:85042217290

SN - 1433-7851

VL - 57

SP - 3132

EP - 3136

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

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

Abstract

UN SDGs

Keywords

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