A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

被引：9
作者：
Tanaka, Katsunori [1 ]
Kitadani, Masataka [2 ]
Tsutsui, Ayumi [1 ]
Pradipta, Ambara R. [1 ]
Imamaki, Rie [3 ]
Kitazume, Shinobu [3 ]
Taniguchi, Naoyuki [3 ]
Fukase, Koichi [2 ]
机构：
[1] RIKEN, Biofunct Synthet Chem Lab, Wako, Saitama 3510198, Japan
[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
[3] RIKEN, RIKEN Global Res Cluster, RIKEN Max Planck Joint Res Ctr Syst Chem Biol, Dis Glyc Team,Syst Glycobiol Res Grp, Wako, Saitama 3510198, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 09期
基金：
日本学术振兴会;
关键词：
STEREOSELECTIVE ASYMMETRIC 6-PI-AZAELECTROCYCLIZATION; PHOTOAFFINITY-LABELING MODIFICATION; COPPER(I)-CATALYZED AZIDE-ALKYNE; IN-VIVO DYNAMICS; CLICK CHEMISTRY; SACCHARIDE-BIOSENSORS; FORMAL SYNTHESIS; COPPER-FREE; SELECTIVE MODIFICATION; PHOTOCLICK CHEMISTRY;
D O I：
10.1039/c3ob42267d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized. The cascading reaction sequence involved (i) ligand-directed azaelectrocyclization with lysine and (ii) the autooxidation-induced release of a fluorescence quencher from the labeled protein. The probe was linked to a cyclic RGDyK peptide to enable the selective visualization of integrin alpha(V)beta(3) on the surfaces of live cells.
引用
收藏
页码：1412 / 1418
页数：7
相关论文
共 56 条
  • [1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems
    Agard, NJ
    Prescher, JA
    Bertozzi, CR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15046 - 15047
  • [2] Copper-free click chemistry for dynamic in vivo imaging
    Baskin, Jeremy M.
    Prescher, Jennifer A.
    Laughlin, Scott T.
    Agard, Nicholas J.
    Chang, Pamela V.
    Miller, Isaac A.
    Lo, Anderson
    Codelli, Julian A.
    Bertozzi, Carolyn R.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) : 16793 - 16797
  • [3] Imaging cell surface glycans with bioorthogonal chemical reporters
    Chang, Pamela V.
    Prescher, Jennifer A.
    Hangauer, Matthew J.
    Bertozzi, Carolyn R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (27) : 8400 - +
  • [4] Metabolic Labeling of Sialic Acids in Living Animals with Alkynyl Sugars
    Chang, Pamela V.
    Chen, Xing
    Smyrniotis, Chris
    Xenakis, Alexander
    Hu, Tianshun
    Bertozzi, Carolyn R.
    Wu, Peng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (22) : 4030 - 4033
  • [5] MicroPET and autoradiographic imaging of breast cancer αv-integrin expression using 18F- and 64Cu-labeled RGD peptide
    Chen, XY
    Park, R
    Tohme, M
    Shahinian, AH
    Bading, JR
    Conti, PS
    [J]. BIOCONJUGATE CHEMISTRY, 2004, 15 (01) : 41 - 49
  • [6] Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae
    Deiters, A
    Cropp, TA
    Mukherji, M
    Chin, JW
    Anderson, JC
    Schultz, PG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) : 11782 - 11783
  • [7] Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes
    Fernandez-Suarez, Marta
    Baruah, Hemanta
    Martinez-Hernandez, Laura
    Xie, Kathleen T.
    Baskin, Jeremy M.
    Bertozzi, Carolyn R.
    Ting, Alice Y.
    [J]. NATURE BIOTECHNOLOGY, 2007, 25 (12) : 1483 - 1487
  • [8] Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA
    Gierlich, Johannes
    Burley, Glenn A.
    Gramlich, Philipp M. E.
    Hammond, David M.
    Carell, Thomas
    [J]. ORGANIC LETTERS, 2006, 8 (17) : 3639 - 3642
  • [9] A general semisynthetic method for fluorescent saccharide-biosensors based on a lectin
    Hamachi, I
    Nagase, T
    Shinkai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12065 - 12066
  • [10] Development of a Bioorthogonal and Highly Efficient Conjugation Method for Quantum Dots Using Tetrazine-Norbornene Cycloaddition
    Han, Hee-Sun
    Devaraj, Neal K.
    Lee, Jungmin
    Hilderbrand, Scott A.
    Weissleder, Ralph
    Bawendi, Moungi G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) : 7838 - +
123456