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二氧化钛催化的对甲苯磺酰化前体在高水介质中的放射性氟化反应。

Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium.

作者信息

Sergeev Maxim E, Morgia Federica, Lazari Mark, Wang Christopher, van Dam R Michael

机构信息

Department of Molecular and Medical Pharmacology and Crump Institute for Molecular Imaging, David Geffen School of Medicine at University of California, Los Angeles, 570 Westwood Plaza, Los Angeles, California 90095, United States.

出版信息

J Am Chem Soc. 2015 May 6;137(17):5686-94. doi: 10.1021/jacs.5b02659. Epub 2015 Apr 22.

Abstract

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [(18)F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of (18)F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [(18)F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

摘要

亲核放射性氟化是合成许多正电子发射断层扫描(PET)探针的有效途径,但在反应前必须除去水分以活化回旋加速器产生的[¹⁸F]氟化物,这显著增加了整体放射性标记时间并导致放射性损失。在本报告中,我们证明了在高水介质中进行¹⁸F放射性氟化的可能性。该方法利用二氧化钛纳米颗粒、1:1(v/v)乙腈 - 叔戊醇溶剂混合物和碳酸氢四丁铵作为相转移剂。使用含水的[¹⁸F]氟化物可直接进行高效放射性标记,无需干燥/共沸步骤,从而显著缩短放射合成时间。还实现了目标化合物的高放射化学纯度。通过一系列芳香族、脂肪族和脂环族甲苯磺酸酯前体证明了该合成策略的底物范围。

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本文引用的文献

1
A Review on Adsorption of Fluoride from Aqueous Solution.
Materials (Basel). 2014 Sep 5;7(9):6317-6366. doi: 10.3390/ma7096317.
2
Late-stage [F]Fluorination: New Solutions to Old Problems.
Chem Sci. 2014 Dec 1;5(12):4545-4553. doi: 10.1039/C4SC02099E.
3
4
A general copper-mediated nucleophilic 18F fluorination of arenes.
Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7751-5. doi: 10.1002/anie.201404436. Epub 2014 Jun 10.
5
Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts.
Org Lett. 2014 Jun 20;16(12):3224-7. doi: 10.1021/ol501243g. Epub 2014 Jun 3.
6
Late stage benzylic C-H fluorination with [¹⁸F]fluoride for PET imaging.
J Am Chem Soc. 2014 May 14;136(19):6842-5. doi: 10.1021/ja5039819. Epub 2014 May 6.
7
Efficient radiosynthesis of 3'-deoxy-3'-18F-fluorothymidine using electrowetting-on-dielectric digital microfluidic chip.
J Nucl Med. 2014 Feb;55(2):321-8. doi: 10.2967/jnumed.113.121053. Epub 2013 Dec 23.
10
Radiofluorination of diaryliodonium tosylates under aqueous-organic and cryptand-free conditions.
Org Biomol Chem. 2013 Aug 21;11(31):5094-9. doi: 10.1039/c3ob40742j. Epub 2013 Jun 26.

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