Literature DB >> 25820685

An evaluation of a high-pressure (11)CO carbonylation apparatus.

Kenneth Dahl1, Oleksiy Itsenko, Obaidur Rahman, Johan Ulin, Carl-Olof Sjöberg, Peter Sandblom, Lars-Anders Larsson, Magnus Schou, Christer Halldin.   

Abstract

[(11)C]Carbon monoxide ((11)CO) is a versatile building block for the synthesis of Positron Emission Tomography (PET) radioligands. However, the difficulty of trapping (11)CO in a small solvent volume has limited its utility. We here report an evaluation of a simple, fully automated high-pressure synthesizer prototype for the use in (11)C-carbonylation reactions. [(11)C]Carbon monoxide was easily prepared by online reduction of [(11)C]carbon dioxide using either Mo(s) or Zn(s) as the reducing agent. The conversion yield of (11)CO was >99% when zinc was used as the reducing agent, and the corresponding value for Mo was approximately 71%. When the Zn or Mo column was constantly kept under inert atmosphere, no significant decrease in reducing properties was observed for more than 100 (11)CO productions. However, in our hands, Mo reductant was much easier to service. A total of nine functional groups were successfully radiolabeled using the (11)CO synthesizer prototype. All measured radiochemical yields exceeded 37%, and the (11)CO trapping efficiency was generally above 90%, except for the Suzuki coupling where the trapping efficiency was 80%. This high-pressure synthesizer using [(11)C]carbon monoxide as the labeling precursor is easy to operate allowing for (11)C-carbonylation reactions to be performed in a high yield and in a routinely fashion.
Copyright © 2015 John Wiley & Sons, Ltd.

Entities:  

Keywords:  carbon-11; carbonylation; isotopic labeling; prototype; radiochemistry

Mesh:

Substances:

Year:  2015        PMID: 25820685     DOI: 10.1002/jlcr.3280

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


  8 in total

Review 1.  Considerations in the Development of Reversibly Binding PET Radioligands for Brain Imaging.

Authors:  Victor W Pike
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530

2.  11C-Labeling of Aryl Ketones as Candidate Histamine Subtype-3 Receptor PET Radioligands through Pd(0)-Mediated 11C-Carbonylative Coupling.

Authors:  Fabrice G Siméon; William J Culligan; Shuiyu Lu; Victor W Pike
Journal:  Molecules       Date:  2017-05-12       Impact factor: 4.411

Review 3.  New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals.

Authors:  Kenneth Dahl; Christer Halldin; Magnus Schou
Journal:  Clin Transl Imaging       Date:  2017-02-25

4.  Instantaneous Conversion of [11 C]CO2 to [11 C]CO via Fluoride-Activated Disilane Species.

Authors:  Carlotta Taddei; Salvatore Bongarzone; Antony D Gee
Journal:  Chemistry       Date:  2017-05-17       Impact factor: 5.236

5.  Recent progress in [11 C]carbon dioxide ([11 C]CO2 ) and [11 C]carbon monoxide ([11 C]CO) chemistry.

Authors:  Carlotta Taddei; Antony D Gee
Journal:  J Labelled Comp Radiopharm       Date:  2018-02-05       Impact factor: 1.921

6.  Development of a fully automated low-pressure [11 C]CO carbonylation apparatus.

Authors:  Mélodie Ferrat; Youssef El Khoury; Peter Larsen; Kenneth Dahl; Christer Halldin; Magnus Schou
Journal:  J Labelled Comp Radiopharm       Date:  2020-08-27       Impact factor: 1.921

7.  Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation.

Authors:  Sara Roslin; Peter Brandt; Patrik Nordeman; Mats Larhed; Luke R Odell; Jonas Eriksson
Journal:  Molecules       Date:  2017-10-10       Impact factor: 4.411

Review 8.  [11C]Carbon monoxide: advances in production and application to PET radiotracer development over the past 15 years.

Authors:  Carlotta Taddei; Victor W Pike
Journal:  EJNMMI Radiopharm Chem       Date:  2019-09-18
  8 in total

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