Site-specific fluorescence labelling of RNA using bio-orthogonal reaction of trans-cyclooctene and tetrazine

被引:46
作者
Asare-Okai, P. N. [1 ]
Agustin, E. [1 ]
Fabris, D. [1 ]
Royzen, M. [1 ]
机构
[1] SUNY Albany, Dept Chem, Albany, NY 12222 USA
关键词
CLICK CHEMISTRY; LIVING CELLS; ENZYMATIC INCORPORATION; DNA; TRANSCRIPTION; POLYMERASE; FUNCTIONALIZATION; CYCLOADDITION; CONJUGATION; MOLECULES;
D O I
10.1039/c4cc02435d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This communication describes a general approach for site-specific fluorescence labelling of RNA using a cytidine triphosphate (CTP) analogue derivatized with a trans-cyclooctene group. The analogue was efficiently incorporated into a model RNA strand using in vitro transcription. Bio-orthogonal reaction with fluorescein-labelled tetrazine was utilized to fluorescently tag the synthetic RNA strand.
引用
收藏
页码:7844 / 7847
页数:4
相关论文
共 37 条
[1]   Chemical Approaches To Perturb, Profile, and Perceive Glycans [J].
Agard, Nicholas J. ;
Bertozzi, Carolyn R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (06) :788-797
[2]   Autotransfecting Short Interfering RNA through Facile Covalent Polymer Escorts [J].
Averick, Saadyah E. ;
Paredes, Eduardo ;
Dey, Sourav K. ;
Snyder, Kristin M. ;
Tapinos, Nikos ;
Matyjaszewski, Krzysztof ;
Das, Subha R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (34) :12508-12511
[3]   Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic "Click" Modification of DNA with Base-Labile Fluorescent Probes [J].
Berndl, Sina ;
Herzig, Nadine ;
Kele, Peter ;
Lachmann, Daniel ;
Li, Xiaohua ;
Wolfbeis, Otto S. ;
Wagenknecht, Hans-Achim .
BIOCONJUGATE CHEMISTRY, 2009, 20 (03) :558-564
[4]   Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity [J].
Blackman, Melissa L. ;
Royzen, Maksim ;
Fox, Joseph M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13518-+
[5]   Click-click chemistry on a peptidic scaffold for easy access to tetrameric DNA structures [J].
Bonnet, Romaric ;
Murat, Pierre ;
Spinelli, Nicolas ;
Defrancq, Eric .
CHEMICAL COMMUNICATIONS, 2012, 48 (48) :5992-5994
[6]   Single β-Actin mRNA Detection in Neurons Reveals a Mechanism for Regulating Its Translatability [J].
Buxbaum, Adina R. ;
Wu, Bin ;
Singer, Robert H. .
SCIENCE, 2014, 343 (6169) :419-422
[7]   Fluorescent Live-Cell Imaging of Metabolically Incorporated Unnatural Cyclopropene-Mannosamine Derivatives [J].
Cole, Christian M. ;
Yang, Jun ;
Seckute, Jolita ;
Devaraj, Neal K. .
CHEMBIOCHEM, 2013, 14 (02) :205-208
[8]   Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells [J].
Devaraj, Neal K. ;
Hilderbrand, Scott ;
Upadhyay, Rabi ;
Mazitschek, Ralph ;
Weissleder, Ralph .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2869-2872
[9]   Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition [J].
Devaraj, Neal K. ;
Upadhyay, Rabi ;
Hatin, Jered B. ;
Hilderbrand, Scott A. ;
Weissleder, Ralph .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :7013-7016
[10]   Quantitative Imaging of Transcription in Living Drosophila Embryos Links Polymerase Activity to Patterning [J].
Garcia, Hernan G. ;
Tikhonov, Mikhail ;
Lin, Albert ;
Gregor, Thomas .
CURRENT BIOLOGY, 2013, 23 (21) :2140-2145