Development of fluorescent probes based on protection-deprotection of the key functional groups for biological imaging

被引:380
作者
Tang, Yonghe [1 ]
Lee, Dayoung [2 ]
Wang, Jiaoliang [3 ]
Li, Guanhan [1 ]
Yu, Jinghua [1 ]
Lin, Weiying [1 ,3 ]
Yoon, Juyoung [2 ]
机构
[1] Univ Jinan, Sch Biol Sci & Technol, Sch Chem & Chem Engn, Inst Fluorescent Probes Biol Imaging, Jinan 250022, Shandong, Peoples R China
[2] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea
[3] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemobiosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
基金
新加坡国家研究基金会;
关键词
SE-N BOND; TURN-ON; HYDROGEN-PEROXIDE; LIVING CELLS; COLORIMETRIC CHEMOSENSORS; RATIOMETRIC DETECTION; THIOLS; HYDRAZINE; FLUORIDE; CYSTEINE;
D O I
10.1039/c5cs00103j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recently, the strategy of protection-deprotection of functional groups has been widely employed to design fluorescent probes, as the protection-deprotection of functional groups often induces a marked change in electronic properties. Significant advances have been made in the development of analyte-responsive fluorescent probes based on the protection-deprotection strategy. In this tutorial review, we highlight the representative examples of small-molecule based fluorescent probes for bioimaging, which are operated via the protection-deprotection of key functional groups such as aldehyde, hydroxyl, and amino functional groups reported from 2010 to 2014. The discussion includes the general protection-deprotection methods for aldehyde, hydroxyl, or amino groups, as well as the design strategies, sensing mechanisms, and deprotection modes of the representative fluorescent imaging probes applied to bio-imaging.
引用
收藏
页码:5003 / 5015
页数:13
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[1]   Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-On Fluorescent Probe [J].
Au-Yeung, Ho Yu ;
Chan, Jefferson ;
Chantarojsiri, Teera ;
Chang, Christopher J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (40) :15165-15173
[2]   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
[3]  
Chan J, 2012, NAT CHEM, V4, P973, DOI [10.1038/NCHEM.1500, 10.1038/nchem.1500]
[4]   Construction of a near-infrared fluorescence turn-on and ratiometric probe for imaging palladium in living cells [J].
Chen, Hua ;
Lin, Weiying ;
Yuan, Lin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (12) :1938-1941
[5]   Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species [J].
Chen, Xiaoqiang ;
Tian, Xizhe ;
Shin, Injae ;
Yoon, Juyoung .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4783-4804
[6]   A highly specific BODIPY-based probe localized in mitochondria for HClO imaging [J].
Cheng, Guanghui ;
Fan, Jiangli ;
Sun, Wen ;
Sui, Kun ;
Jin, Xin ;
Wang, Jingyun ;
Peng, Xiaojun .
ANALYST, 2013, 138 (20) :6091-6096
[7]   A "turn-on" fluorescent probe for hypochlorous acid: convenient synthesis, good sensing performance, and a new design strategy by the removal of C=N isomerization [J].
Cheng, Xiaohong ;
Jia, Huizhen ;
Long, Teng ;
Feng, Jun ;
Qin, Jingui ;
Li, Zhen .
CHEMICAL COMMUNICATIONS, 2011, 47 (43) :11978-11980
[8]   Modern reaction-based indicator systems [J].
Cho, Dong-Gyu ;
Sessler, Jonathan L. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (06) :1647-1662
[9]   A two-photon fluorescent probe for ratiometric imaging of hydrogen peroxide in live tissue [J].
Chung, Chul ;
Srikun, Duangkhae ;
Lim, Chang Su ;
Chang, Christopher J. ;
Cho, Bong Rae .
CHEMICAL COMMUNICATIONS, 2011, 47 (34) :9618-9620
[10]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566