High-contrast and real-time visualization of membrane proteins in live cells with malachite green-based fluorogenic probes

被引:9
作者
Chen, Yefeng [1 ]
Xue, Chenghong [1 ]
Wang, Jie [1 ]
Xu, Minqiu [1 ]
Li, Yuyao [1 ]
Ding, Yiru [1 ]
Song, Heng [1 ]
Xu, Weipan [1 ]
Xie, Hexin [1 ]
机构
[1] East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Frontiers Sci Ctr Materiobiol & Dynam Chem, Shanghai Key Lab New Drug Design,Sch Pharm, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
Cellular imaging; Fluorogenic probe; Environment-sensitive fluorophore; Alkaline phosphatase; Integrin; AGGREGATION-INDUCED EMISSION; ALKALINE-PHOSPHATASE; FLUORESCENT-PROBES; APTAMER; BINDING;
D O I
10.1016/j.cclet.2021.09.088
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Imaging dynamics of membrane proteins of live cells in a wash-free and real-time manner has been a challenging task. Herein, we report unprecedented applications of malachite green (MG), an organic dye widely used in pigment industry, as a switchable fluorophore to monitor membrane enzymes or noncatalytic proteins in live cells. Conformationally flexible MG is non-fluorescent in aqueous solution, yet covalent binding with endogenous proteins of cells significantly enhances its fluorescence at 670 nm by restricting flexibility of dye. Integrating a phosphate-caged quinone methide precursor with MG yielded a covalent labeling fluorogenic probe, allowing real-time imaging of membrane alkaline phosphatase (ALP, a model catalytic protein) activity in live cells with over 100-fold enhancement of fluorescence intensity. Moreover, MG is also applicable to image non-catalytic protein by conjugation with protein-specific ligand. A fluorogenic probe consisted of c-RGDfK peptide and MG proved to be compatible with wash-free and real-time visualization of non-catalytic integrin alpha(v)beta(3) in live cells with high contrast. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
引用
收藏
页码:1637 / 1642
页数:6
相关论文
共 51 条
[1]   Aptamers switch on fluorescence of triphenylmethane dyes [J].
Babendure, JR ;
Adams, SR ;
Tsien, RY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14716-14717
[2]   Effect of BSA binding on photophysical and photochemical properties of triarylmethane dyes [J].
Baptista, MS ;
Indig, GL .
JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (23) :4678-4688
[3]   Recent progress in two-photon small molecule fluorescent probes for enzymes [J].
Chen, Ding ;
Qin, Wenjing ;
Fang, Haixiao ;
Wang, Lan ;
Peng, Bo ;
Li, Lin ;
Huang, Wei .
CHINESE CHEMICAL LETTERS, 2019, 30 (10) :1738-1744
[4]   S-Cis Diene Conformation: A New Bathochromic Shift Strategy for Near-Infrared Fluorescence Switchable Dye and the Imaging Applications [J].
Chen, Hsiang-Jung ;
Chew, Chee Ying ;
Chang, En-Hao ;
Tu, Yu-Wei ;
Wei, Li-Yu ;
Wu, Bo-Han ;
Chen, Chien-Hung ;
Yang, Ya-Ting ;
Huang, Su-Chin ;
Chen, Jen-Kun ;
Chen, I-Chia ;
Tan, Kui-Thong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (15) :5224-5234
[5]   Enzyme-Activated Fluorogenic Probes for Live-Cell and in Vivo Imaging [J].
Chyan, Wen ;
Raines, Ronald T. .
ACS CHEMICAL BIOLOGY, 2018, 13 (07) :1810-1823
[6]   Integrin adhesion receptors in tumor metastasis [J].
Felding-Habermann, B .
CLINICAL & EXPERIMENTAL METASTASIS, 2003, 20 (03) :203-213
[7]   A new fluorometric turn-on assay for alkaline phosphatase and inhibitor screening based on aggregation and deaggregation of tetraphenylethylene molecules [J].
Gu, Xinggui ;
Zhang, Guanxin ;
Wang, Zhuo ;
Liu, Wenwen ;
Xiao, Le ;
Zhang, Deqing .
ANALYST, 2013, 138 (08) :2427-2431
[8]  
GUILBAULT GG, 1968, ANAL LETT, V1, P333
[9]   ORTHO-(DIFLUOROMETHYL)ARYL-BETA-D-GLUCOSIDES AND PARA-(DIFLUOROMETHYL)ARYL-BETA-D-GLUCOSIDES - A NEW CLASS OF ENZYME-ACTIVATED IRREVERSIBLE INHIBITORS OF BETA-GLUCOSIDASES [J].
HALAZY, S ;
BERGES, V ;
EHRHARD, A ;
DANZIN, C .
BIOORGANIC CHEMISTRY, 1990, 18 (03) :330-344
[10]   Aggregation-induced emission [J].
Hong, Yuning ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (11) :5361-5388