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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 47期
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
  • [41] Improved synthesis and biological evaluation of chelator-modified α-MSH analogs prepared by copper-free click chemistry
    Baumhover, Nicholas J.
    Martin, Molly E.
    Parameswarappa, Sharavathi G.
    Kloepping, Kyle C.
    O'Dorisio, M. Sue
    Pigge, F. Christopher
    Schultz, Michael K.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (19) : 5757 - 5761
  • [42] Copper-free click chemistry between azides and internal alkynes for triphenylene discotic liquid crystal trimer formation
    Bai, Yue-Feng
    Bao, Long
    Hu, Ping
    Wang, Bi-Qin
    Redshaw, Carl
    Zhao, Ke-Qing
    LIQUID CRYSTALS, 2013, 40 (01) : 97 - 105
  • [43] A novel dibenzoazacyclooctyne precursor in regioselective copper-free click chemistry. An innovative 3-step synthesis
    Starke, Frank
    Walther, Martin
    Pietzsch, Hans-Juergen
    ARKIVOC, 2010, : 350 - 359
  • [44] Copper-Free Click for PET: Rapid 1,3-Dipolar Cycloadditions with a Fluorine-18 Cyclooctyne
    Carpenter, Richard D.
    Hausner, Sven H.
    Sutcliffe, Julie L.
    ACS MEDICINAL CHEMISTRY LETTERS, 2011, 2 (12): : 885 - 889
  • [45] Evaluation of 4-[18F]fluoro-1-butyne as a radiolabeled synthon for click chemistry with azido compounds
    Kim, Dong Hyun
    Choe, Yearn Seong
    Kim, Byung-Tae
    APPLIED RADIATION AND ISOTOPES, 2010, 68 (02) : 329 - 333
  • [46] Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis
    Zheng, Qinheng
    Xu, Hongtao
    Wang, Hua
    Du, Wen-Ge Han
    Wang, Nan
    Xiong, Huan
    Gu, Yuang
    Noodleman, Louis
    Sharpless, K. Barry
    Yang, Guang
    Wu, Peng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (10) : 3753 - 3763
  • [47] 4-[18F]Fluoro-N-methyl-N-(propyl-2-yn-1-yl)benzenesulfonamide ([18F]F-SA): a versatile building block for labeling of peptides, proteins and oligonucleotides with fluorine-18 via Cu(I)-mediated click chemistry
    Ramenda, Theres
    Steinbach, Joerg
    Wuest, Frank
    AMINO ACIDS, 2013, 44 (04) : 1167 - 1180
  • [48] Synthesis and in vitro evaluation of [18F]fluoroethyl triazole labelled [Tyr3]octreotate analogues using click chemistry
    Iddon, Lisa
    Leyton, Julius
    Indrevoll, Bard
    Glaser, Matthias
    Robins, Edward G.
    George, Andrew J. T.
    Cuthbertson, Alan
    Luthra, Sajinder Kaur
    Aboagye, Eric O.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (10) : 3122 - 3127
  • [49] Surface modification for site-directed covalent attachment of molecules via strain-promoted azide-alkyne click-chemistry reaction and photolithography
    Vrettou, Fotini
    Petrou, Panagiota
    Kakabakos, Sotirios
    Argitis, Panagiotis
    Gajos, Katarzyna
    Budkowski, Andrzej
    Chatzichristidi, Margarita
    SURFACES AND INTERFACES, 2023, 36
  • [50] Standardized Method to Functionalize Plasma-Extracellular Vesicles via Copper-Free Click Chemistry for Targeted Drug Delivery Strategies
    Ciferri, Maria Chiara
    Bruno, Silvia
    Rosenwasser, Nicole
    Gorgun, Cansu
    Reverberi, Daniele
    Gagliani, Maria Cristina
    Cortese, Katia
    Grange, Cristina
    Bussolati, Benedetta
    Quarto, Rodolfo
    Tasso, Roberta
    ACS APPLIED BIO MATERIALS, 2024, 7 (02) : 827 - 838
12345