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Literature DB >> 27578168

One-step synthesis of 4-[(18) F]fluorobenzyltriphenylphosphonium cation for imaging with positron emission tomography.

Zhengxing Zhang¹, Chengcheng Zhang¹, Joseph Lau¹, Nadine Colpo¹, François Bénard^1,2, Kuo-Shyan Lin^3,4.

Abstract

4-[(18) F]Fluorobenzyltriphenylphosphonium cation ((18) F-FBnTP) is a promising negative membrane potential targeting positron emission tomography tracer. However, the reported multistep radiolabeling approach for the synthesis of (18) F-FBnTP poses a challenge for routine clinical applications. In this study, we demonstrated that (18) F-FBnTP can be prepared in good conversion yields (~60%, nondecay corrected) in just one step via a copper-mediated (18) F-fluorination reaction using a pinacolyl arylboronate precursor. In addition, our data suggest that (18) F-labeled (phosphonium) cations can be efficiently prepared via a copper-mediated (18) F-fluoronation by using triflate as the counterion.

Entities: Chemical

Keywords: 18F-FBnTP, copper-mediated 18F-fluorination; counterion; fluorine-18; phosphonium cation; positron emission tomography

Mesh：

Substances：

Year: 2016 PMID： 27578168 DOI： 10.1002/jlcr.3436

Source DB: PubMed Journal: J Labelled Comp Radiopharm ISSN： 0362-4803 Impact factor: 1.921

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Cited

7 in total

1. Automated synthesis of PET radiotracers by copper-mediated ¹⁸ F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation.

Authors: Andrew V Mossine; Allen F Brooks; Vadim Bernard-Gauthier; Justin J Bailey; Naoko Ichiishi; Ralf Schirrmacher; Melanie S Sanford; Peter J H Scott
Journal: J Labelled Comp Radiopharm Date: 2018-02-02 Impact factor: 1.921

2. An Automated Multidose Synthesis of the Potentiometric PET Probe 4-[¹⁸F]Fluorobenzyl-Triphenylphosphonium ([¹⁸F]FBnTP).

Authors: Christopher M Waldmann; Adrian Gomez; Phillip Marchis; Sean T Bailey; Milica Momcilovic; Anthony E Jones; David B Shackelford; Saman Sadeghi
Journal: Mol Imaging Biol Date: 2018-04 Impact factor: 3.488

3. Synthesis of high-molar-activity [¹⁸F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

Authors: Andrew V Mossine; Sean S Tanzey; Allen F Brooks; Katarina J Makaravage; Naoko Ichiishi; Jason M Miller; Bradford D Henderson; Thomas Erhard; Christian Bruetting; Marc B Skaddan; Melanie S Sanford; Peter J H Scott
Journal: Nat Protoc Date: 2020-04-08 Impact factor: 13.491

One-step synthesis of 4-[(18) F]fluorobenzyltriphenylphosphonium cation for imaging with positron emission tomography.

1. Automated synthesis of PET radiotracers by copper-mediated ¹⁸ F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation.

2. An Automated Multidose Synthesis of the Potentiometric PET Probe 4-[¹⁸F]Fluorobenzyl-Triphenylphosphonium ([¹⁸F]FBnTP).

3. Synthesis of high-molar-activity [¹⁸F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

4. Copper(II)-Mediated [¹¹C]Cyanation of Arylboronic Acids and Arylstannanes.

5. Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Review 6. Research Progress on ¹⁸F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography.

7. Design, synthesis and evaluation of ¹⁸F-labeled cationic carbonic anhydrase IX inhibitors for PET imaging.

One-step synthesis of 4-[(18) F]fluorobenzyltriphenylphosphonium cation for imaging with positron emission tomography.

1. Automated synthesis of PET radiotracers by copper-mediated 18 F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation.

2. An Automated Multidose Synthesis of the Potentiometric PET Probe 4-[18F]Fluorobenzyl-Triphenylphosphonium ([18F]FBnTP).

3. Synthesis of high-molar-activity [18F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

4. Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes.

5. Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Review 6. Research Progress on 18F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography.

7. Design, synthesis and evaluation of 18F-labeled cationic carbonic anhydrase IX inhibitors for PET imaging.

1. Automated synthesis of PET radiotracers by copper-mediated ¹⁸ F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation.

2. An Automated Multidose Synthesis of the Potentiometric PET Probe 4-[¹⁸F]Fluorobenzyl-Triphenylphosphonium ([¹⁸F]FBnTP).

3. Synthesis of high-molar-activity [¹⁸F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

4. Copper(II)-Mediated [¹¹C]Cyanation of Arylboronic Acids and Arylstannanes.

Review 6. Research Progress on ¹⁸F-Labeled Agents for Imaging of Myocardial Perfusion with Positron Emission Tomography.

7. Design, synthesis and evaluation of ¹⁸F-labeled cationic carbonic anhydrase IX inhibitors for PET imaging.