Strain-Promoted Copper-Free "Click" Chemistry for 18F Radiolabeling of Bombesin

被引:107
|
作者
Campbell-Verduyn, Lachlan S. [2 ]
Mirfeizi, Leila [1 ]
Schoonen, Anne K. [2 ]
Dierckx, Rudi A. [1 ]
Elsinga, Philip H. [1 ]
Feringa, Ben L. [2 ]
机构
[1] Univ Groningen, Dept Nucl Med & Mol Imaging, Univ Med Ctr Groningen, NL-9713 GZ Groningen, Netherlands
[2] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
关键词
click chemistry; imaging agents; isotopic labeling; peptides; radiopharmaceuticals; RECEPTOR TARGETED RADIOPHARMACEUTICALS; AZIDE-ALKYNE CYCLOADDITION; PROSTATE-CANCER; 1,3-DIPOLAR CYCLOADDITION; LABELING METHOD; LIVING CELLS; PEPTIDE; ANALOGS; PET; F-18;
D O I
10.1002/anie.201105547
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Click for PET: The GRP-receptor-specific peptide bombesin, which is often used for nuclear imaging of tumors, can be labeled with 18F in a mild and rapid manner by using a copper-free azide-alkyne "click" reaction. A range of azides can be used to provide peptides with different hydrophobicities. The resulting 18F radiopharmaceutical tracers (see scheme) maintain their high affinity for the targeted receptor in vitro in human prostate cancer cells. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11117 / 11120
页数:4
相关论文
共 50 条
  • [1] Evaluation of an integrin αvβ6-specific peptide labeled with [18F]fluorine by copper-free, strain-promoted click chemistry
    Hausner, Sven H.
    Carpenter, Richard D.
    Bauer, Nadine
    Sutcliffe, Julie L.
    NUCLEAR MEDICINE AND BIOLOGY, 2013, 40 (02) : 233 - 239
  • [2] Strain-Promoted Cycloadditions for Development of Copper-Free Click Reactions
    Pigge, F. Christopher
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (18) : 1902 - 1922
  • [3] Preparation of Protein A Membrane Adsorbers Using Strain-Promoted, Copper-Free Dibenzocyclooctyne (DBCO)-Azide Click Chemistry
    Osuofa, Joshua
    Husson, Scott M.
    MEMBRANES, 2023, 13 (10)
  • [4] Fluorine-18 radiolabeling of SCK nanoparticles via copper-free click chemistry
    Zhou, Dong
    Zeng, Dexing
    Lee, Nam
    Dence, Carmen
    Wooley, Karen
    Katzenellenbogen, John
    Welch, Michael
    JOURNAL OF NUCLEAR MEDICINE, 2011, 52
  • [5] Cytocompatible Poly(ethylene glycol)-co-polycarbonate Hydrogels Cross-Linked by Copper-Free, Strain-Promoted Click Chemistry
    Xu, Jianwen
    Filion, Tera M.
    Prifti, Fioleda
    Song, Jie
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2730 - 2737
  • [6] Copper-free click-chemistry with 18F-labeled compounds
    Bouvet, Vincent R.
    Sharma, Sai Kiran
    Wuest, Melinda
    Mavanur, Suresh
    Frank, Wuest
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2011, 54 : S10 - S10
  • [7] Site-specific terminal and internal labeling of RNA by poly(A) polymerase tailing and copper-catalyzed or copper-free strain-promoted click chemistry
    Winz, Marie-Luise
    Samanta, Ayan
    Benzinger, Dirk
    Jaeschke, Andres
    NUCLEIC ACIDS RESEARCH, 2012, 40 (10)
  • [8] Copper-free click chemistry
    Arnaud, Celia
    CHEMICAL & ENGINEERING NEWS, 2007, 85 (43) : 15 - 15
  • [9] Copper-Free Click Biofunctionalization of Silicon Nitride Surfaces via Strain-Promoted Alkyne-Azide Cycloaddition Reactions
    Manova, Radostina K.
    Pujari, Sidharam P.
    Weijers, Carel A. G. M.
    Zuilhof, Han
    van Beek, Tens A.
    LANGMUIR, 2012, 28 (23) : 8651 - 8663
  • [10] [18F]ODIBO: a prosthetic group for bioorthogonal radiolabeling of macromolecules via strain-promoted alkyne-azide cycloaddition
    Boudjemeline, Mehdi
    McNitt, Christopher D.
    Singleton, Thomas A.
    Popik, Vladimir V.
    Kostikov, Alexey P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (03) : 363 - 366