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

^*Corresponding author for this work

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

37 Citations (Scopus)

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
Publication status	Published - 2018 Mar 12
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by the Institute for Basic Science (IBS) ([IBS-R007-D1] and [IBS-R007-Y1]), intramural funding from KIST (2E28030/CAP-17-01-KISTEurope), and the National Research Foundation funded by the Korean Government (MEST; No. NRF-2017R1A2A1A18070960).

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

amphiphiles
cucurbiturils
drug delivery
supramolecular chemistry
vesicles

ASJC Scopus subject areas

Catalysis
General Chemistry

UN SDGs

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

Access to Document

10.1002/anie.201713059

Cite this

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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.",

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note = "Funding Information: This work was supported by the Institute for Basic Science (IBS) ([IBS-R007-D1] and [IBS-R007-Y1]), intramural funding from KIST (2E28030/CAP-17-01-KISTEurope), and the National Research Foundation funded by the Korean Government (MEST; No. NRF-2017R1A2A1A18070960). Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/anie.201713059",

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AU - Baek, Kangkyun

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AU - Shrinidhi, Annadka

AU - Murray, James

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AU - Kim, Ki Hean

AU - Lee, Jun Seok

AU - Yoo, Jejoong

AU - Kim, Sungwan

AU - Kim, Kimoon

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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.

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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