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

被引：347
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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 16期
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
    Pipkorn, Ruediger
    Waldeck, Waldemar
    Didinger, Bernd
    Koch, Mario
    Mueller, Gabriele
    Wiessler, Manfred
    Braun, Klaus
    [J]. JOURNAL OF PEPTIDE SCIENCE, 2009, 15 (03) : 235 - 241
  • [32] Chemistry in living systems
    Prescher, JA
    Bertozzi, CR
    [J]. 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
    ROWINSKY, EK
    CAZENAVE, LA
    DONEHOWER, RC
    [J]. 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
    SCHIFF, PB
    HORWITZ, SB
    [J]. 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
    SHELANSK.ML
    GASKIN, F
    CANTOR, CR
    [J]. 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
    Sivakumar, K
    Xie, F
    Cash, BM
    Long, S
    Barnhill, HN
    Wang, Q
    [J]. ORGANIC LETTERS, 2004, 6 (24) : 4603 - 4606
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