Cyanine polyene reactivity: scope and biomedical applications

被引:143
作者
Gorka, Alexander P. [1 ]
Nani, Roger R. [1 ]
Schnermann, Martin J. [1 ]
机构
[1] NCI, Biol Chem Lab, Ctr Canc Res, Frederick, MD 21702 USA
基金
美国国家卫生研究院;
关键词
INFRARED FLUORESCENT-PROBES; BIOMATERIAL-ASSOCIATED INFLAMMATION; DYE LABELING REAGENTS; IN-VIVO; LIVING CELLS; HYDROGEN-SULFIDE; ORGANIC FLUOROPHORES; PHOTOACTIVATABLE FLUOROPHORES; IMPROVED PHOTOSTABILITY; NIR FLUORESCENCE;
D O I
10.1039/c5ob00788g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyanines are indispensable fluorophores that form the chemical basis of many fluorescence-based applications. A feature that distinguishes cyanines from other common fluorophores is an exposed polyene linker that is both crucial to absorption and emission and subject to covalent reactions that dramatically alter these optical properties. Over the past decade, reactions involving the cyanine polyene have been used as foundational elements for a range of biomedical techniques. These include the optical sensing of biological analytes, super-resolution imaging, and near-IR light-initiated uncaging. This review surveys the chemical reactivity of the cyanine polyene and the biomedical methods enabled by these reactions. The overarching goal is to highlight the multifaceted nature of cyanine chemistry and biology, as well as to point out the key role of reactivity-based insights in this promising area.
引用
收藏
页码:7584 / 7598
页数:15
相关论文
共 142 条
[1]   Toxicity of Organic Fluorophores Used in Molecular Imaging: Literature Review [J].
Alford, Raphael ;
Simpson, Haley M. ;
Duberman, Josh ;
Hill, G. Craig ;
Ogawa, Mikako ;
Regino, Celeste ;
Kobayashi, Hisataka ;
Choyke, Peter L. .
MOLECULAR IMAGING, 2009, 8 (06) :341-354
[2]   Enhanced photostability of cyanine fluorophores across the visible spectrum (vol 9, pg 428, 2012) [J].
Altman, Roger B. ;
Zheng, Qinsi ;
Zhou, Zhou ;
Terry, Daniel S. ;
Warren, J. David ;
Blanchard, Scott C. .
NATURE METHODS, 2012, 9 (06) :626-626
[3]   Cysteine-mediated redox signalling in the mitochondria [J].
Bak, D. W. ;
Weerapana, E. .
MOLECULAR BIOSYSTEMS, 2015, 11 (03) :678-697
[4]   Short-range spectroscopic ruler based on a single-molecule optical switch [J].
Bates, M ;
Blosser, TR ;
Zhuang, XW .
PHYSICAL REVIEW LETTERS, 2005, 94 (10)
[5]   Multicolor super-resolution imaging with photo-switchable fluorescent probes [J].
Bates, Mark ;
Huang, Bo ;
Dempsey, Graham T. ;
Zhuang, Xiaowei .
SCIENCE, 2007, 317 (5845) :1749-1753
[6]   Rational Design of a Colorimetric pH Sensor from a Soluble Retinoic Acid Chaperone [J].
Berbasova, Tetyana ;
Nosrati, Meisam ;
Vasileiou, Chrysoula ;
Wang, Wenjing ;
Sing, Kin ;
Lee, Stephen ;
Yapici, Ipek ;
Geiger, James H. ;
Borhan, Babak .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16111-16119
[7]   Light-Controlled Tools [J].
Brieke, Clara ;
Rohrbach, Falk ;
Gottschalk, Alexander ;
Mayer, Guenter ;
Heckel, Alexander .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) :8446-8476
[8]  
Busch D. R., 2010, MOL IMAGING PRINCIPL, P214
[9]   DIRECT AND SENSITIZED PHOTOOXIDATION OF CYANINE DYES [J].
BYERS, GW ;
GROSS, S ;
HENRICHS, PM .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1976, 23 (01) :37-43
[10]   FRET spectral unmixing: a ratiometric fluorescent nanoprobe for hypochlorite [J].
Chen, Gengwen ;
Song, Fengling ;
Wang, Jingyun ;
Yang, Zhigang ;
Sun, Shiguo ;
Fan, Jiangli ;
Qiang, Xinxin ;
Wang, Xu ;
Dou, Bairui ;
Peng, Xiaojun .
CHEMICAL COMMUNICATIONS, 2012, 48 (24) :2949-2951