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
相关论文
共 50 条
[21]   In vivo two-photon fluorescent imaging of fluoride with a desilylation-based reactive probe [J].
Kim, Dokyoung ;
Singha, Subhankar ;
Wang, Taejun ;
Seo, Eunseok ;
Lee, Jun Ho ;
Lee, Sang-Joon ;
Kim, Ki Hean ;
Ahn, Kyo Han .
CHEMICAL COMMUNICATIONS, 2012, 48 (82) :10243-10245
[22]   A boronate-based fluorescent probe for the selective detection of cellular peroxynitrite [J].
Kim, Jiyoung ;
Park, Jeesook ;
Lee, Hawon ;
Choi, Yongdoo ;
Kim, Youngmi .
CHEMICAL COMMUNICATIONS, 2014, 50 (66) :9353-9356
[23]   Highly sensitive fluorescent probe for thiols based on combination of PET and ESIPT mechanisms [J].
Lan, Minhuan ;
Wu, Jiasheng ;
Liu, Weimin ;
Zhang, Hongyan ;
Zhang, Wenjun ;
Zhuang, Xiaoqing ;
Wang, Pengfei .
SENSORS AND ACTUATORS B-CHEMICAL, 2011, 156 (01) :332-337
[24]   A Two-Photon Fluorescent Probe for Thiols in Live Cells and Tissues [J].
Lee, Jun Han ;
Lim, Chang Su ;
Tian, Yu Shun ;
Han, Ji Hee ;
Cho, Bong Rae .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1216-+
[25]   Hepatocyte-Targeting Single Galactose-Appended Naphthalimide: A Tool for Intracellular Thiol Imaging in Vivo [J].
Lee, Min Hee ;
Han, Ji Hye ;
Kwon, Pil-Seung ;
Bhuniya, Sankarprasad ;
Kim, Jin Young ;
Sessler, Jonathan L. ;
Kang, Chulhun ;
Kim, Jong Seung .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1316-1322
[26]   Design and synthesis of a highly selective fluorescent turn-on probe for thiol bioimaging in living cells [J].
Li, Xin ;
Qian, Shijing ;
He, Qiaojun ;
Yang, Bo ;
Li, Jia ;
Hu, Yongzhou .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (16) :3627-3630
[27]   Ratiometric Detection of Mitochondrial Thiols with a Two-Photon Fluorescent Probe [J].
Lim, Chang Su ;
Masanta, Goutam ;
Kim, Hyung Joong ;
Han, Ji Hee ;
Kim, Hwan Myung ;
Cho, Bong Rae .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (29) :11132-11135
[28]   A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells [J].
Lin, Weiying ;
Long, Lingliang ;
Tan, Wen .
CHEMICAL COMMUNICATIONS, 2010, 46 (09) :1503-1505
[29]   Boronate Oxidation as a Bioorthogonal Reaction Approach for Studying the Chemistry of Hydrogen Peroxide in Living Systems [J].
Lippert, Alexander R. ;
De Bittner, Genevieve C. Van ;
Chang, Christopher J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (09) :793-804
[30]   A "Turn-on" Fluorescent Hg2+ Chemosensor Based on Ferrier Carbocyclization [J].
Ma, Xing ;
Wang, Jing ;
Shan, Qiuli ;
Tan, Zhuowei ;
Wei, Guohua ;
Wei, Dongbin ;
Du, Yuguo .
ORGANIC LETTERS, 2012, 14 (03) :820-823