Bioorthogonal Turn-On Probes for Imaging Small Molecules inside Living Cells

被引:355
作者
Devaraj, Neal K. [1 ]
Hilderbrand, Scott [1 ]
Upadhyay, Rabi [1 ]
Mazitschek, Ralph [1 ]
Weissleder, Ralph [1 ]
机构
[1] Massachusetts Gen Hosp, Ctr Syst Biol, Richard B Simches Res Ctr, Boston, MA 02114 USA
关键词
bioorthogonal; reactions; cycloaddition; fluorogenic tags; imaging; tetrazine; COPPER(I)-CATALYZED AZIDE-ALKYNE; CLICK CHEMISTRY; STAUDINGER LIGATION; FLUORESCENT TAXOIDS; CANCER-CELLS; COPPER-FREE; CYCLOADDITION; SYSTEMS; ABSENCE; DYE;
D O I
10.1002/anie.200906120
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Glowing tags: A series of activatable ("urn-on") tetrazine-conjugated fluorescent probes was developed, which react rapidly in an inverse-electron-demand [4+2] cycloaddition with strained dienophiles such as trans-cyclooctene, thereby strongly increasing the fluorescence intensity (see picture), The novel turn-on probes were applied for intracellular livecell imaging of a microtubuli-binding trans-cyclooctene modified taxol, © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.
引用
收藏
页码:2869 / 2872
页数:4
相关论文
共 46 条
[31]   Inverse-electron-demand Diels-Alder reaction as a highly efficient chemoselective ligation procedure: Synthesis and function of a BioShuttle for temozolomide transport into prostate cancer cells [J].
Pipkorn, Ruediger ;
Waldeck, Waldemar ;
Didinger, Bernd ;
Koch, Mario ;
Mueller, Gabriele ;
Wiessler, Manfred ;
Braun, Klaus .
JOURNAL OF PEPTIDE SCIENCE, 2009, 15 (03) :235-241
[32]   Chemistry in living systems [J].
Prescher, JA ;
Bertozzi, CR .
NATURE CHEMICAL BIOLOGY, 2005, 1 (01) :13-21
[33]  
Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[34]  
2-4
[35]   TAXOL - A NOVEL INVESTIGATIONAL ANTIMICROTUBULE AGENT [J].
ROWINSKY, EK ;
CAZENAVE, LA ;
DONEHOWER, RC .
JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (15) :1247-1259
[36]   TAXOL ASSEMBLES TUBULIN IN THE ABSENCE OF EXOGENOUS GUANOSINE 5'-TRIPHOSPHATE OR MICROTUBULE-ASSOCIATED PROTEINS [J].
SCHIFF, PB ;
HORWITZ, SB .
BIOCHEMISTRY, 1981, 20 (11) :3247-3252
[37]  
Sharpless K.B., 2002, Angew. Chem., V114, P2708, DOI DOI 10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO
[38]  
2-0
[39]   MICROTUBULE ASSEMBLY IN ABSENCE OF ADDED NUCLEOTIDES [J].
SHELANSK.ML ;
GASKIN, F ;
CANTOR, CR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1973, 70 (03) :765-768
[40]   A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes [J].
Sivakumar, K ;
Xie, F ;
Cash, BM ;
Long, S ;
Barnhill, HN ;
Wang, Q .
ORGANIC LETTERS, 2004, 6 (24) :4603-4606