An ortho-activation strategy to develop NIR fluorescent probe for rapid imaging of biothiols in vivo

被引:5
|
作者
Yu, Lu [1 ]
Xie, Mingli [2 ]
Chen, Min [2 ]
Yang, Huiru [1 ]
Chen, Liang [2 ]
Xing, Panfei [2 ]
Tian, Zhiyong [1 ]
Wang, Chaojie [2 ]
机构
[1] Henan Univ, Sch Pharm, Kaifeng 475004, Peoples R China
[2] Henan Univ, Key Lab Nat Med & Immuno Engn, Kaifeng 475004, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
Near-infrared (NIR) fluorescence imaging; Ortho-activation; Rapidly detecting; Biothiols; In vivo; CYSTEINE; GLUTATHIONE; DESIGN; THIOLS; SHIFT;
D O I
10.1016/j.talanta.2023.125110
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Biothiols are the main antioxidants in regulating the redox balance and resisting oxidative stress in various biological processes, but the long detection time of current fluorescent probes hinders their rapid imaging in vitro and in vivo. To reveal the influx of biothiols, we rationally develop an ortho-activation approach to accelerate the reaction between the probe and biothiols, by introducing electron-withdrawing fluorine atom into the ortho-site of the phenolic hydroxyl group in the NIR probe to generate an ortho-inductive effect. The ortho-fluorine helps to increase the chemical reactivity of the molecular structure, resulting in a significantly shorter detection time (within 5 min) as compared to previous reports (> 20 min for acrylates-based probes in aqueous solution). Based on this approach, our near-infrared probe 2F-RBX can sensitively and efficiently detect endogenous biothiols in living HepG2 cells and in vivo. These data suggest that ortho-activation is a simple and flexible approach to construct sensitive fluorescent probes for rapid imaging of biothiols, and perhaps other molecules in future, under biological circumstances.
引用
收藏
页数:7
相关论文
共 50 条
  • [1] A new fluorescent 'turn on' probe for rapid detection of biothiols
    Ucuncu, Muhammed
    Zeybek, Huseyin
    Karakus, Erman
    Ucuncu, Canan
    Emrullahoglu, Mustafa
    SUPRAMOLECULAR CHEMISTRY, 2020, 32 (12) : 634 - 641
  • [2] Visualizing biothiols in vivo using a dual-channel sensitive fluorescent probe
    Peng, Zixiong
    Li, Zheng
    Zhou, Tianshuo
    Wu, Dian
    Wang, Erfei
    Ma, Chao
    Lu, Cuifen
    Nie, Junqi
    Fan, Guorun
    Yang, Guichun
    Wang, Feiyi
    Ren, Jun
    DYES AND PIGMENTS, 2023, 214
  • [3] A near-infrared fluorescent probe with a large Stokes shift for the detection and imaging of biothiols in vitro and in vivo
    Wu, Zhengjun
    Zhao, Taotao
    Jiang, Xingyue
    Zhang, Dan
    Wang, Feiyi
    Ren, Xiaoming
    Wang, Zhao
    Wang, Erfei
    Ren, Jun
    ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2024, 416 (28) : 6485 - 6495
  • [4] A Turn-On Fluorescent Probe for Live-Cell Imaging of Biothiols
    Hong, Jong-Ah
    Kim, Min-Ji
    Eo, Jinny
    Lee, Jiyoun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (04) : 425 - 426
  • [5] A Green-emitting Fluorescent Probe Based on a Benzothiazole Derivative for Imaging Biothiols in Living Cells
    Ma, Xiaohua
    Hao, Yuanqiang
    Liu, Jiaxiang
    Wu, Guoguang
    Liu, Lin
    MOLECULES, 2019, 24 (03)
  • [6] A novel near-infrared fluorescent probe with a large stokes shift for the detection and imaging of biothiols
    Wang, Kai
    Leng, Taohua
    Liu, Yajing
    Wang, Chengyun
    Shi, Ping
    Shen, Yongjia
    Zhu, Wei-Hong
    SENSORS AND ACTUATORS B-CHEMICAL, 2017, 248 : 338 - 345
  • [7] A new quinoxaline-based fluorescent probe capable of naked eye recognition and cell imaging for biothiols
    Zhang, Yong
    Zhu, Bin
    Sun, Lan
    Yan, Yanning
    Sun, Ying
    Zhang, Mengyuan
    Huang, Liwei
    Fei, Haiyang
    Yang, Chengyun
    Chen, Yang
    Hao, Cheng
    Ma, Shenao
    Zhu, Jin
    Wang, Zixuan
    Han, Xintong
    Ji, Min
    MICROCHEMICAL JOURNAL, 2024, 199
  • [8] A NIR fluorescent probe for the rapid detection of Hg2+ in living cells and in vivo mice imaging
    Wang, Jiaoliang
    Long, Liping
    Xia, Li
    Fang, Fang
    METHODS AND APPLICATIONS IN FLUORESCENCE, 2017, 5 (02):
  • [9] An ESIPT coupled AIE fluorescent probe for biothiols detection and imaging based on a chalcone fluorophore
    Dai, Fangfang
    Zhao, Min
    Yang, Fangzhou
    Wang, Tingting
    Wang, Chao
    DYES AND PIGMENTS, 2020, 183
  • [10] A lysosome-targeted fluorescent probe with large Stokes shift for visualizing biothiols in vivo and in vitro
    Zhao, Taotao
    Zhang, Tong
    Tao, Zijun
    Zhou, Zhe
    Xia, Xiaofeng
    Wu, Zhengjun
    Wang, Feiyi
    Ren, Jun
    Wang, Erfei
    ISCIENCE, 2024, 27 (12)