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Literature DB >> 28662441

An automated synthesizer for electrochemical ¹⁸F-fluorination of organic compounds.

Christopher M Waldmann¹, Artem Lebedev², Nathaniel Allison³, Saman Sadeghi⁴.

Abstract

Electrochemical 18F-fluorination of organic compounds provides a means to synthesize Positron-Emission-Tomography (PET) tracers difficult to obtain otherwise. Here, the first automated synthesizer that enables radiolabeling through carrier-added electrochemical 18F-fluorination is described. The system provides capabilities for all necessary operations such as drying of cyclotron derived [18F]fluoride, electrochemical incorporation of the radioisotope into a precursor molecule, subsequent reactions such as protecting group removals, HPLC-purification and formulation of the final tracer. Demonstrated is the aliphatic electrochemical 18F-fluorination of methyl 2-(phenylthio)acetate.

Entities: Chemical Disease Gene Species

Keywords: Electrochemistry; Late-stage fluorination; PET; Radiosynthesizer; [(18)F]fluoride

Year: 2017 PMID： 28662441 PMCID： PMC5585111 DOI： 10.1016/j.apradiso.2017.06.028

Source DB: PubMed Journal: Appl Radiat Isot ISSN： 0969-8043 Impact factor: 1.513

14 in total

1. Metal-free oxidative fluorination of phenols with [18F]fluoride.

Authors: Zhanghua Gao; Yee Hwee Lim; Matthew Tredwell; Lei Li; Stefan Verhoog; Matthew Hopkinson; Wojciech Kaluza; Thomas Lee Collier; Jan Passchier; Mickael Huiban; Véronique Gouverneur
Journal: Angew Chem Int Ed Engl Date: 2012-05-25 Impact factor: 15.336

2. Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids.

Authors: Toshio Fuchigami; Shinsuke Inagi
Journal: Chem Commun (Camb) Date: 2011-06-25 Impact factor: 6.222

Review 3. (18)F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography.

Authors: Sean Preshlock; Matthew Tredwell; Véronique Gouverneur
Journal: Chem Rev Date: 2016-01-11 Impact factor: 60.622

Review 4. Radiosyntheses using fluorine-18: the art and science of late stage fluorination.

Authors: Erin L Cole; Megan N Stewart; Ryan Littich; Raphael Hoareau; Peter J H Scott
Journal: Curr Top Med Chem Date: 2014 Impact factor: 3.295

5. Positron emission tomography provides molecular imaging of biological processes.

Authors: M E Phelps
Journal: Proc Natl Acad Sci U S A Date: 2000-08-01 Impact factor: 11.205

6. Electrolytic Partial Fluorination of Organic Compounds. 30.(1) Drastic Improvement of Anodic Monofluorination of 2-Substituted 1,3-Oxathiolan-5-ones Using the Novel Fluorine Source Et(4)NF.4HF.

Authors: Seiichiro Higashiya; Satoru Narizuka; Akinori Konno; Tomoko Maeda; Kunitaka Momota; Toshio Fuchigami
Journal: J Org Chem Date: 1999-01-08 Impact factor: 4.354

7. Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF: a high yield synthesis of 6-[18F]Fluoro-L-dopa.

Authors: M Namavari; A Bishop; N Satyamurthy; G Bida; J R Barrio
Journal: Int J Rad Appl Instrum A Date: 1992-08

An automated synthesizer for electrochemical ¹⁸F-fluorination of organic compounds.

1. Metal-free oxidative fluorination of phenols with [18F]fluoride.

2. Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids.

Review 3. (18)F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography.

Review 4. Radiosyntheses using fluorine-18: the art and science of late stage fluorination.

5. Positron emission tomography provides molecular imaging of biological processes.

6. Electrolytic Partial Fluorination of Organic Compounds. 30.(1) Drastic Improvement of Anodic Monofluorination of 2-Substituted 1,3-Oxathiolan-5-ones Using the Novel Fluorine Source Et(4)NF.4HF.

7. Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF: a high yield synthesis of 6-[18F]Fluoro-L-dopa.

8. Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics.

9. Electrochemical radiofluorination. Part 2. Anodic monofluorination of substituted benzenes using [18F]fluoride.

10. Batch-reactor microfluidic device: first human use of a microfluidically produced PET radiotracer.

Review 1. The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Review 2. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

Review 3. Closing the gap between ¹⁹F and ¹⁸F chemistry.

Review 3. (18)F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography.

Review 4. Radiosyntheses using fluorine-18: the art and science of late stage fluorination.

Review 1. The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Review 2. Recent Advances in Synthetic Methodologies to Form C-18F Bonds.

Review 3. Closing the gap between 19F and 18F chemistry.

Review 2. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

Review 3. Closing the gap between ¹⁹F and ¹⁸F chemistry.