Synthesis of photoactivatable azido-acyl caged oxazine fluorophores for live-cell imaging

被引:17
作者
Anzalone, Andrew V. [1 ,2 ]
Chen, Zhixing [1 ,3 ]
Cornish, Virginia W. [1 ,2 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Columbia Univ, Dept Syst Biol, New York, NY 10032 USA
[3] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
基金
美国国家卫生研究院;
关键词
FLUORESCENT-PROBES; GENERAL-METHOD; CHEMICAL TAGS; LIVING CELLS; IN-VIVO; DYES; MICROSCOPY; DERIVATIVES; PROTEINS;
D O I
10.1039/c6cc04882j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the design and synthesis of a photoactivatable azidoacyl oxazine fluorophore. Photoactivation is achieved cleanly and rapidly with UV light, producing a single fluorescent oxazine photoproduct. We demonstrate the utility of azido-acyl caged oxazines for protein specific labeling in living mammalian cells using the TMP-tag technology.
引用
收藏
页码:9442 / 9445
页数:4
相关论文
共 29 条
[1]   A RAPID CELL-MEMBRANE PERMEABILITY TEST USING FLUORESCENT DYES AND FLOW-CYTOMETRY [J].
AESCHBACHER, M ;
REINHARDT, CA ;
ZBINDEN, G .
CELL BIOLOGY AND TOXICOLOGY, 1986, 2 (02) :247-255
[2]   Formation of oxazine dye by photochemical reaction of N-acyl oxazine derivatives [J].
Akiba, Masaharu ;
Dvornikov, Alexander S. ;
Rentzepis, Peter M. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2007, 190 (01) :69-76
[3]   A Common Diaryl Ether Intermediate for the Gram-Scale Synthesis of Oxazine and Xanthene Fluorophores [J].
Anzalone, Andrew V. ;
Wang, Tracy Y. ;
Chen, Zhixing ;
Cornish, Virginia W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :650-654
[4]   Imaging intracellular fluorescent proteins at nanometer resolution [J].
Betzig, Eric ;
Patterson, George H. ;
Sougrat, Rachid ;
Lindwasser, O. Wolf ;
Olenych, Scott ;
Bonifacino, Juan S. ;
Davidson, Michael W. ;
Lippincott-Schwartz, Jennifer ;
Hess, Harald F. .
SCIENCE, 2006, 313 (5793) :1642-1645
[5]  
Chan J, 2012, NAT CHEM, V4, P973, DOI [10.1038/nchem.1500, 10.1038/NCHEM.1500]
[6]   Chemical tags: inspiration for advanced imaging techniques [J].
Chen, Zhixing ;
Cornish, Virginia W. ;
Min, Wei .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2013, 17 (04) :637-643
[7]   Monoalkoxy BODIPYs-A Fluorophore Class for Bioimaging [J].
Courtis, Alexandra M. ;
Santos, Sofia A. ;
Guan, Yinghua ;
Hendricks, J. Adam ;
Ghosh, Balaram ;
Szantai-Kis, D. Miklos ;
Reis, Surya A. ;
Shah, Jagesh V. ;
Mazitschek, Ralph .
BIOCONJUGATE CHEMISTRY, 2014, 25 (06) :1043-1051
[8]   The fluorescent protein palette: tools for cellular imaging [J].
Day, Richard N. ;
Davidson, Michael W. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (10) :2887-2921
[9]   Fluorescent probes for super-resolution imaging in living cells [J].
Fernandez-Suarez, Marta ;
Ting, Alice Y. .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2008, 9 (12) :929-943
[10]  
Grimm JB, 2015, NAT METHODS, V12, P244, DOI [10.1038/NMETH.3256, 10.1038/nmeth.3256]