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| Hauptseite > Publikationsdatenbank > Radiosynthesis and stability evaluation of [18F]sulfonimidoyl fluorides |
| Hauptseite > Publikationsdatenbank > Radiosynthesis and stability evaluation of [18F]sulfonimidoyl fluorides |
| Contribution to a conference proceedings/Journal Article | FZJ-2026-03769 |
; ; ;
2025
Elsevier Science
Amsterdam [u.a.]
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Please use a persistent id in citations: doi:10.1016/j.nucmedbio.2025.109206
Abstract: Introduction: Alkyl-substituted sulfonimidoyl fluorides [R-(O=)S(=N-Alk)-F; ASIFs] have been reported to be hydrolytically stable compounds, making them promising lead structures for the development of novel PET tracers. However, unlike 18F-labeled aryl fluorosulfates and sulfamoyl fluorides, radiofluorinated ASIFs have not been described in the literature (1, 2). Hence, this work aimed to apply a SuFEx-based protocol developed by our group for the radiosynthesis of [18F]ASIFs and to evaluate their stability. Methods: Sulfonimidoyl fluorides 1–4 were synthesized in four steps as follows. Tosyl chloride was reduced to the corresponding sulfinyl chloride, which was reacted with a primary amine to yield the respective sulfinamide. Subsequent oxidation with N-chlorosuccinimide generated the respective sulfonimidoylchloride, which was in turn converted to the corresponding ASIF via halogen exchange. For radiofluorination via 18F/19F isotopic exchange (Scheme 1), [18F]fluoride was trapped on a QMA cartridge and eluted with a solution of Et4NOTf in MeOH. After removal of the solvent, a solution of the respective ASIF (1 μmol) in MeCN was added and the mixture was heated for 10 minutes at 70 °C. The reaction was quenched by addition of water and the radiolabeled products were isolated by HPLC. Hydrolytic stability was assessed in aqueous solutions at pH 5, 7.4, and 9. Results: 1–4 were obtained in overall yields of 32–54%. The corresponding [18F]ASIFs were produced within 40 min in radiochemical yields of 39–77% with (radio)chemical purities of >97%. Stability tests revealed rapid radiodefluorination of all four [18F]ASIFs, with release of more than 10% free [18F]fluoride during the first 10 minutes and full degradation within one hour. Conclusions: The protocol for SuFEx 18F-fluorination was successfully adapted for the radiosynthesis of [18F]ASIFs. However, insufficient hydrolytic stability indicates the necessity for further structural optimization before [18F]ASIFs can be used as viable PET tracers.
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