Thermo-triggered release of a Cys probe from the cavity of a water-soluble pillar[5]arene

被引:11
作者
Chi, Xiaodong [1 ]
Wang, Pi [1 ]
Li, Yang [1 ]
Ji, Xiaofan [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
Pillararene; Hydrophobic interaction; Host-guest system; Supramolecular chemistry; RECOGNITION; CHEMISTRY; NETWORKS; BINDING;
D O I
10.1016/j.tetlet.2015.06.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel [2]pseudorotaxane based on thermo-responsive water-soluble pillar[5]arene WP5 and Cys probe 1 was successfully prepared in water. This complex exhibited no responsiveness to Cys at room temperature due to its high stability that inhibited the interaction between probe 1 and Cys. However, the encapsulated 1 could be released from the cavity of WP5 upon heating, leading to the formation of 1-Cys adduct. Moreover, the probe could be used to monitor Cys with high sensitivity. Importantly, WP5, 1, and the [2]pseudorotaxane WP5 superset of 1 showed excellent biocompatibility, making the probe a very attractive candidate for biological applications. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4545 / 4548
页数:4
相关论文
共 43 条
  • [1] A Facile and Efficient Preparation of Pillararenes and a Pillarquinone
    Cao, Derong
    Kou, Yuhui
    Liang, Jianquan
    Chen, Zhizhao
    Wang, Lingyun
    Meier, Herbert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9721 - 9723
  • [2] Biphen[n]arenes
    Chen, Huanqing
    Fan, Jiazeng
    Hu, Xiaoshi
    Ma, Junwei
    Wang, Shilu
    Li, Jian
    Yu, Yihua
    Jia, Xueshun
    Li, Chunju
    [J]. CHEMICAL SCIENCE, 2015, 6 (01) : 197 - 202
  • [3] Multistimuli Responsive Supramolecular Cross-Linked Networks On the Basis of the Benzo-21-Crown-7/Secondary Ammonium Salt Recognition Motif
    Chen, Long
    Tian, Yu-Kui
    Ding, Yue
    Tian, Yu-Jing
    Wang, Feng
    [J]. MACROMOLECULES, 2012, 45 (20) : 8412 - 8419
  • [4] A Dual-Responsive Supra-Amphiphilic Polypseudorotaxane Constructed from a Water-Soluble Pillar[7]arene and an Azobenzene-Containing Random Copolymer
    Chi, Xiaodong
    Ji, Xiaofan
    Xia, Danyu
    Huang, Feihe
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (04) : 1440 - 1443
  • [5] Chemical-responsive control of lower critical solution temperature behavior by pillar[10]arene-based host-guest interactions
    Chi, Xiaodong
    Xue, Min
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (89) : 13754 - 13756
  • [6] LCST-Type Phase Behavior Induced by Pillar[5]arene/Ionic Liquid Host-Guest Complexation
    Dong, Shengyi
    Zheng, Bo
    Yao, Yong
    Han, Chengyou
    Yuan, Jiayin
    Antonietti, Markus
    Huang, Feihe
    [J]. ADVANCED MATERIALS, 2013, 25 (47) : 6864 - 6867
  • [7] Novel [2]pseudorotaxanes constructed by self-assembly of bis-urea-functionalized pillar[5]arene and linear alkyl dicarboxylates
    Duan, Qunpeng
    Xia, Wei
    Hu, Xiaoyu
    Ni, Mengfei
    Jiang, Juli
    Lin, Chen
    Pan, Yi
    Wang, Leyong
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (68) : 8532 - 8534
  • [8] Pillar[5]arene-based polymeric architectures constructed by orthogonal supramolecular interactions
    Guan, Yangfan
    Ni, Mengfei
    Hu, Xiaoyu
    Xiao, Tangxin
    Xiong, Shuhan
    Lin, Chen
    Wang, Leyong
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (68) : 8529 - 8531
  • [9] Calixarene-based supramolecular polymerization in solution
    Guo, Dong-Sheng
    Liu, Yu
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (18) : 5907 - 5921
  • [10] The high yielding synthesis of pillar[5]arenes under Friedel-Crafts conditions explained by dynamic covalent bond formation
    Holler, Michel
    Allenbach, Nicolas
    Sonet, Jordan
    Nierengarten, Jean-Francois
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (20) : 2576 - 2578