BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine

被引:868
作者
Niu, Li-Ya [1 ,2 ]
Guan, Ying-Shi [1 ,2 ]
Chen, Yu-Zhe [1 ]
Wu, Li-Zhu [1 ]
Tung, Chen-Ho [1 ]
Yang, Qing-Zheng [1 ]
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
LIVING CELLS; CELLULAR GLUTATHIONE; HYDROGEN-SULFIDE; PROBE; DYES; THIOLS; FUNCTIONALIZATION; NAPHTHALIMIDE; RHODAMINE; REDUCTASE;
D O I
10.1021/ja309079f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.
引用
收藏
页码:18928 / 18931
页数:4
相关论文
共 41 条
[1]  
BECKER PS, 1986, J BIOL CHEM, V261, P4620
[2]   Fluorescent indicators based on BODIPY [J].
Boens, Noel ;
Leen, Volker ;
Dehaen, Wim .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172
[3]   A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether [J].
Cao, Xiaowei ;
Lin, Weiying ;
Zheng, Kaibo ;
He, Longwei .
CHEMICAL COMMUNICATIONS, 2012, 48 (85) :10529-10531
[4]   Fluorescent and colorimetric probes for detection of thiols [J].
Chen, Xiaoqiang ;
Zhou, Ying ;
Peng, Xiaojun ;
Yoon, Juyoung .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135
[5]   Intracellular Glutathione Detection Using MnO2-Nanosheet-Modified Upconversion Nanoparticles [J].
Deng, Renren ;
Xie, Xiaoji ;
Vendrell, Marc ;
Chang, Young-Tae ;
Liu, Xiaogang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20168-20171
[6]   Visualizing Ascorbate-Triggered Release of Labile Copper within Living Cells using a Ratiometric Fluorescent Sensor [J].
Domaille, Dylan W. ;
Zeng, Li ;
Chang, Christopher J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1194-+
[7]   Highly selective fluorescent OFF-ON thiol probes based on dyads of BODIPY and potent intramolecular electron sink 2,4-dinitrobenzenesulfonyl subunits [J].
Guo, Huimin ;
Jing, Yingying ;
Yuan, Xiaolin ;
Ji, Shaomin ;
Zhao, Jianzhang ;
Li, Xiaohuan ;
Kan, Yanyan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (10) :3844-3853
[8]   A disulfide bound-molecular beacon as a fluorescent probe for the detection of reduced glutathione and its application in cells [J].
Guo, Yingshu ;
Wang, Hao ;
Sun, Yuanshun ;
Qu, Bin .
CHEMICAL COMMUNICATIONS, 2012, 48 (26) :3221-3223
[9]   A Fast Response Highly Selective Probe for the Detection of Glutathione in Human Blood Plasma [J].
Guo, Yixing ;
Yang, Xiaofeng ;
Hakuna, Lovemore ;
Barve, Aabha ;
Escobedo, Jorge O. ;
Lowry, Mark ;
Strongin, Robert M. .
SENSORS, 2012, 12 (05) :5940-5950
[10]   A highly selective ratiometric near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging [J].
Guo, Zhiqian ;
Nam, SeongWon ;
Park, Sungsu ;
Yoon, Juyoung .
CHEMICAL SCIENCE, 2012, 3 (09) :2760-2765