Enabling [18F]-bicyclo[6.1.0]nonyne for oligonucleotide conjugation for positron emission tomography applications: [18F]-anti-microRNA-21 as an example

被引:15
作者
Li, Xiang-Guo [1 ,2 ,3 ]
Roivainen, Anne [1 ,2 ,4 ]
Bergman, Jorgen [1 ,2 ,3 ]
Heinonen, Arttu [5 ]
Bengel, Frank [6 ]
Thum, Thomas [7 ]
Knuuti, Juhani [1 ,2 ]
机构
[1] Univ Turku, Turku PET Ctr, FI-20521 Turku, Finland
[2] Turku Univ Hosp, FI-20521 Turku, Finland
[3] Abo Akad Univ, Accelerator Lab, FI-25200 Turku, Finland
[4] Univ Turku, Turku Ctr Dis Modeling, FI-20014 Turku, Finland
[5] Turku Ctr Biotechnol, Prote Facil, FI-20014 Turku, Finland
[6] Hannover Med Sch, Dept Nucl Med, Hannover, Germany
[7] Hannover Med Sch, IMTTS, Hannover, Germany
基金
芬兰科学院;
关键词
AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; PEPTIDE; PET; BIOCONJUGATION; BICYCLONONYNES; MICRORNA; CELLS;
D O I
10.1039/c5cc02618k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A bicyclononyne-based prosthetic group has been developed for F-18-labeling of anti-microRNA-21, an oligonucleotide, in a near-stoichiometric manner.
引用
收藏
页码:9821 / 9824
页数:4
相关论文
共 32 条
  • [1] Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates
    Chen, Weixuan
    Wang, Danzhu
    Dai, Chaofeng
    Hamelberg, Donald
    Wang, Binghe
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (12) : 1736 - 1738
  • [2] Oxidation of single-stranded oligonucleotides by carbonate radical anions: generating intrastrand cross-links between guanine and thymine bases separated by cytosines
    Crean, Conor
    Uvaydov, Yuriy
    Geacintov, Nicholas E.
    Shafirovich, Vladimir
    [J]. NUCLEIC ACIDS RESEARCH, 2008, 36 (03) : 742 - 755
  • [3] Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells
    Dommerholt, Jan
    Schmidt, Samuel
    Temming, Rinske
    Hendriks, Linda J. A.
    Rutjes, Floris P. J. T.
    van Hest, Jan C. M.
    Lefeber, Dirk J.
    Friedl, Peter
    van Delft, Floris L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) : 9422 - 9425
  • [4] 18F-labelling of oligonucleotides using succinimido 4-[18F]fluorobenzoate
    Hedberg, E
    Langstrom, B
    [J]. ACTA CHEMICA SCANDINAVICA, 1998, 52 (08): : 1034 - 1039
  • [5] Synthesis of 4-([F-18]fluoromethyl)phenyl isothiocyanate and its use in labelling oligonucleotides
    Hedberg, E
    Langstrom, B
    [J]. ACTA CHEMICA SCANDINAVICA, 1997, 51 (12): : 1236 - 1240
  • [6] Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation
    Hong, Vu
    Presolski, Stanislav I.
    Ma, Celia
    Finn, M. G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9879 - 9883
  • [7] LABELING OF AN ANTISENSE OLIGONUCLEOTIDE WITH [18F]FPy5yne
    Inkster, James A. H.
    Adam, Michael J.
    Storr, Tim
    Ruth, Thomas J.
    [J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (11-12) : 1131 - 1143
  • [8] Treatment of HCV Infection by Targeting MicroRNA
    Janssen, Harry L. A.
    Reesink, Hendrik W.
    Lawitz, Eric J.
    Zeuzem, Stefan
    Rodriguez-Torres, Maribel
    Patel, Keyur
    van der Meer, Adriaan J.
    Patick, Amy K.
    Chen, Alice
    Zhou, Yi
    Persson, Robert
    King, Barney D.
    Kauppinen, Sakari
    Levin, Arthur A.
    Hodges, Michael R.
    [J]. NEW ENGLAND JOURNAL OF MEDICINE, 2013, 368 (18) : 1685 - 1694
  • [9] Solid-Supported NOTA and DOTA Chelators Useful for the Synthesis of 3′-Radiometalated Oligonucleotides
    Kiviniemi, Anu
    Makela, Joonas
    Makila, Jussi
    Saanijoki, Tiina
    Liljenback, Heidi
    Poijarvi-Virta, Paivi
    Lonnberg, Harri
    Laitala-Leinonen, Tuna
    Roivainen, Anne
    Virta, Pasi
    [J]. BIOCONJUGATE CHEMISTRY, 2012, 23 (09) : 1981 - 1988
  • [10] Inverse electron demand Diels-Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme
    Knall, Astrid-Caroline
    Slugovc, Christian
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 5131 - 5142