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

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

37 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

Keywords

amphiphiles
cucurbiturils
drug delivery
supramolecular chemistry
vesicles

UN SDGs

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

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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

U2 - 10.1002/anie.201713059

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

Keywords

UN SDGs

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