The traceless Staudinger ligation for indirect 18F-radiolabelling

被引:36
作者
Carroll, Laurence [1 ]
Boldon, Sophie [1 ]
Bejot, Romain [1 ]
Moore, Jane E. [2 ]
Declerck, Jerome [3 ]
Gouverneur, Veronique [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
[2] AstraZeneca UK, Alderley Pk SK10 4TG, Cheshire, England
[3] Siemens Mol Imaging, Oxford OX1 2EP, England
关键词
POSITRON-EMISSION-TOMOGRAPHY; FREE CLICK CHEMISTRY; FLUOROUS SYNTHESIS; DETAGGING PROCESS; F-18; ION; PET;
D O I
10.1039/c0ob00564a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Staudinger ligation of phosphine-substituted thioesters with F-18-fluoroethylazide has been successfully applied to access F-18-labelled molecules in radiochemical yields superior to 95%; the first fluorous variant of a Staudinger radio-ligation has been validated.
引用
收藏
页码:136 / 140
页数:5
相关论文
共 30 条
[1]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[2]   Bioorthogonal click chemistry: Covalent labeling in living systems [J].
Baskin, Jeremy M. ;
Bertozzi, Carolyn R. .
QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12) :1211-1219
[3]   Fluorous Synthesis of 18F Radiotracers with the [18F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process [J].
Bejot, Romain ;
Fowler, Thomas ;
Carroll, Laurence ;
Boldon, Sophie ;
Moore, Jane E. ;
Declerck, Jerome ;
Gouverneur, Veronique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :586-589
[4]   Use of perfluoro groups in nucleophilic 18F-fluorination [J].
Blom, Elisabeth ;
Karimi, Farhad ;
Langstrom, Bengt .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (1-2) :24-30
[5]   Fluorous synthesis of allylic fluorides: C-F bond formation as the detagging process [J].
Boldon, Sophie ;
Moore, Jane E. ;
Gouverneur, Veronique .
CHEMICAL COMMUNICATIONS, 2008, (31) :3622-3624
[6]   Chemistry with [18F]fluoride ion [J].
Cai, Lisheng ;
Lu, Shuiyu ;
Pike, Victor W. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (17) :2853-2873
[7]   Copper-free click chemistry in living animals [J].
Chang, Pamela V. ;
Prescher, Jennifer A. ;
Sletten, Ellen M. ;
Baskin, Jeremy M. ;
Miller, Isaac A. ;
Agard, Nicholas J. ;
Lo, Anderson ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (05) :1821-1826
[8]   Robust Fluorescent Detection of Protein Fatty-Acylation with Chemical Reporters [J].
Charron, Guillaume ;
Zhang, Mingzi M. ;
Yount, Jacob S. ;
Wilson, John ;
Raghavan, Anuradha S. ;
Shamir, Eliah ;
Hang, Howard C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) :4967-4975
[9]   Light, medium, and heavy fluorous triarylphosphines exhibit comparable reactivities to triphenylphosphine in typical reactions of triarylphosphines [J].
Curran, DP ;
Wang, XA ;
Zhang, QS .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3716-3719
[10]   Use of 2-[18F]fluoroethylazide for the Staudinger ligation - Preparation and characterisation of GABAA receptor binding 4-quinolones [J].
Gaeta, Alessandra ;
Woodcraft, John ;
Plant, Stuart ;
Goggi, Julian ;
Jones, Paul ;
Battle, Mark ;
Trigg, William ;
Luthra, Sajinder K. ;
Glaser, Matthias .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (15) :4649-4652