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Angew. Chem.-Int. Edit., Accepted manuscript online: 29 JAN 2018, DOI: 10.1002/anie.201713059
Mono-allyloxylated Cucurbit[7]uril Acts as an Unconventional Amphiphile to Form Light-responsive Vesicles
Kyeng Min Park1,6,*, Kangkyun Baek1, Young Ho Ko1, Annadka Shrinidhi1, James Murray1, Won Hyuk Jang4, Ki Hean Kim3,4, Jun-Seok Lee5, Jejoong Yoo1, Sungwan Kim2 and Kimoon Kim1,2,4,*
1Center for Self-assembly and Complexity (CSC), Institute for Basic Science (IBS), Pohang, 37363, Republic of Korea
2Department of Chemistry, POSTECH, Pohang 37363, Republic of Korea
3Department of Mechanical Engineering , POSTECH
4Division of Integrative Biosciences and Biotechnology, POSTECH
5Molecular Recognition Research Center & Department of Biological Chemistry, KIST-School Korea Institute of Science & Technology, Seoul, 02792, Republic of Korea
6Department of Nanomaterials Science and Engineering, University of Science and Technology (UST), Daejeon, 34113, Republic of Korea
*To whom correspondence may be addressed.
1Center for Self-assembly and Complexity (CSC), Institute for Basic Science (IBS), Pohang, 37363, Republic of Korea
2Department of Chemistry, POSTECH, Pohang 37363, Republic of Korea
3Department of Mechanical Engineering , POSTECH
4Division of Integrative Biosciences and Biotechnology, POSTECH
5Molecular Recognition Research Center & Department of Biological Chemistry, KIST-School Korea Institute of Science & Technology, Seoul, 02792, Republic of Korea
6Department of Nanomaterials Science and Engineering, University of Science and Technology (UST), Daejeon, 34113, Republic of Korea
*To whom correspondence may be addressed.
Abstract
Serendipitously, we discovered that mono-allyloxylated cucurbit[7]uril (AO₁CB[7]) acts as an unconventional amphiphile which self-assembles into light-responsible 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 (GSH) was exploited as a remote tool to disrupt the vesicle. The vesicle showed on-demand release of cargo upon irradiation of the laser after they were internalized into cancer cells. This result demonstrated the great potential of AO₁CB[7]VC as a new type of light-responsive intracellular delivery vehicle for the release of therapeutic cargos inside cells on-demand.
Keywords : Supramolecular Chemistry; amphiphile; cucurbituril; vesicle;smart material
Keywords : Supramolecular Chemistry; amphiphile; cucurbituril; vesicle;smart material
논문정보
- Research article
- 2018년 01월 (BRIC 등록일 2018-02-14)
- 국내 연구진
- 바이오·의료융합 > 바이오센싱 및 나노바이오물질
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