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A facile synthesis of precursor for the σ-1 receptor PET radioligand [18 F]FTC-146 and its radiofluorination

A. Marešová, M. Jurášek, PB. Drašar, B. Dolenský, EA. Prokudina, V. Shalgunov, MM. Herth, P. Cumming, A. Popkov

. 2024 ; 67 (2) : 59-66. [pub] 20240103

Language English Country England, Great Britain

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc24007315

Grant support
A2_FPBT_2022_067 UCT Prague
A1_FPBT_2022_007 UCT Prague

The σ-1 receptor is a non-opioid transmembrane protein involved in various human pathologies including neurodegenerative diseases, inflammation, and cancer. The previously published ligand [18 F]FTC-146 is among the most promising tools for σ-1 molecular imaging by positron emission tomography (PET), with a potential for application in clinical diagnostics and research. However, the published six- or four-step synthesis of the tosyl ester precursor for its radiosynthesis is complicated and time-consuming. Herein, we present a simple one-step precursor synthesis followed by a one-step fluorine-18 labeling procedure that streamlines the preparation of [18 F]FTC-146. Instead of a tosyl-based precursor, we developed a one-step synthesis of the precursor analog AM-16 containing a chloride leaving group for the SN 2 reaction with 18 F-fluoride. 18 F-fluorination of AM-16 led to a moderate decay-corrected radiochemical yield (RCY = 7.5%) with molar activity (Am ) of 45.9 GBq/μmol. Further optimization of this procedure should enable routine radiopharmaceutical production of this promising PET tracer.

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$a Marešová, Anna $u Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Praha 6, Czech Republic $1 https://orcid.org/000000030330810X
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$a The σ-1 receptor is a non-opioid transmembrane protein involved in various human pathologies including neurodegenerative diseases, inflammation, and cancer. The previously published ligand [18 F]FTC-146 is among the most promising tools for σ-1 molecular imaging by positron emission tomography (PET), with a potential for application in clinical diagnostics and research. However, the published six- or four-step synthesis of the tosyl ester precursor for its radiosynthesis is complicated and time-consuming. Herein, we present a simple one-step precursor synthesis followed by a one-step fluorine-18 labeling procedure that streamlines the preparation of [18 F]FTC-146. Instead of a tosyl-based precursor, we developed a one-step synthesis of the precursor analog AM-16 containing a chloride leaving group for the SN 2 reaction with 18 F-fluoride. 18 F-fluorination of AM-16 led to a moderate decay-corrected radiochemical yield (RCY = 7.5%) with molar activity (Am ) of 45.9 GBq/μmol. Further optimization of this procedure should enable routine radiopharmaceutical production of this promising PET tracer.
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$a Jurášek, Michal $u Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Praha 6, Czech Republic $1 https://orcid.org/0000000250699716
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$a Shalgunov, Vladimir $u Department of Drug Design and Pharmacology, University of Copenhagen, Copenhagen, Denmark $u PET and Cyclotron Unit, Copenhagen University Hospital, Copenhagen, Denmark $1 https://orcid.org/0000000189561207
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$a Popkov, Alexander $u Institute of Organic Chemistry, Johannes Kepler University, Linz, Austria $u Samo Biomedical Centre, Pardubice, Czech Republic $1 https://orcid.org/0000000224068005
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