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] [18F]FPyZIDE: A versatile prosthetic reagent for the fluorine-18 radiolabeling of biologics via copper-catalyzed or strain-promoted alkyne-azide cycloadditions
    Roche, Melanie
    Specklin, Simon
    Richard, Mylene
    Hinnen, Francoise
    Genermont, Kevin
    Kuhnast, Bertrand
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2019, 62 (02): : 95 - 108
  • [5] Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions
    Knight, James C.
    Richter, Susan
    Wuest, Melinda
    Way, Jenilee D.
    Wuest, Frank
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (23) : 3817 - 3825
  • [6] 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)
  • [7] Genetically Encoded Copper-Free Click Chemistry
    Plass, Tilman
    Milles, Sigrid
    Koehler, Christine
    Schultz, Carsten
    Lemke, Edward A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3878 - 3881
  • [8] [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
  • [9] Strain-Promoted "Click" Chemistry for Terminal Labeling of DNA
    Marks, Isaac S.
    Kang, Jun Sung
    Jones, Brady T.
    Landmark, Kevin J.
    Cleland, Andrew J.
    Taton, T. Andrew
    BIOCONJUGATE CHEMISTRY, 2011, 22 (07) : 1259 - 1263
  • [10] Thiacycloalkynes for Copper-Free Click Chemistry
    de Almeida, Gabriela
    Sletten, Ellen M.
    Nakamura, Hitomi
    Palaniappan, Krishnan K.
    Bertozzi, Carolyn R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) : 2443 - 2447