Synthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate: A novel bifunctional 18F-labelling agent

doi:10.1524/ract.92.4.349.35590

Paper

Synthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate: A novel bifunctional 18F-labelling agent

Published 2004 · F. Wüst, M. Müller, R. Bergmann

Radiochimica Acta

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14

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Abstract

Abstract The one-step radiosynthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate 18F-7 as a novel bifunctional 18F-labelling agent is described. Optimised reaction conditions in a remotely controlled synthesis module gave isothiocyanate 18F-7 in radiochemical yields of 45% (decay-corrected) within 40 min and high radiochemical purity of >95% after solid-phase-extraction. Coupling of compound 18F-7 with the primary amine benzylamine as a model reaction afforded the corresponding ((4-[18F]fluoromethyl)-2-chloro-phenyl)-benzyl thiourea 18F-8 in a high radiochemical yield of >90%. Stability studies of thiourea 18F-8 in terms of radiodefluorination showed appreciable buffer stability at pH 7.4, whereas significant radiodefluorination was observed when 18F-8 was incubated in buffers at pH 3.6 and pH 9.4. Preliminary dynamic PET studies with thiourea 18F-8 in male Wistar rats showed high bone accumulation, indicative of high in vivo radiodefluorination.

Non-RCT

Animal Study

Study Snapshot

The one-step radiosynthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate 18F-7 provides a novel bifunctional 18F-labelling agent with high radiochemical purity and stability, promising potential for radiodefluorination-free imaging.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of 4-([18F]fluoromethyl)-2-chlorophenylisothiocyanate: A novel bifunctional 18F-labelling agent

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References

Rapid solid phase synthesis and biodistribution of 18F-labelled linear peptides

This study developed a rapid method for radiolabelling linear peptides with 18F for PET, enhancing the application of peptides in positron emission tomography.

Automated synthesis of 16 a-[ 18F]fluoroestradiol-3,17 -disulphamate

The automated one-pot procedure for synthesis of 16 a-[18F]fluoroestradiol-3,17 -disulphamate ([18F]FESDS) provides 10 GBq of radiochemically pure material with a radiochemical purity of over 99%, making it a

Recent progress in fluorine-18 labelled peptide radiopharmaceuticals

Fluorine-18-labelled peptides show great promise for diagnostic imaging of various human diseases using PET, with recent developments enabling efficient and site-specific labeling without affecting receptor-binding properties.

Biologically stable [(18)F]-labeled benzylfluoride derivatives.

3-chloro substituted benzylchlorides are the most stable, suggesting 3-chloro benzylfluorides will be the most chemically stable compound for radioligand design.

Performance evaluation of a whole-body PET scanner using the NEMA protocol. National Electrical Manufacturers Association.

The ECAT EXACT HR+ has excellent spatial resolution for brain and small animal studies, with sufficient sensitivity and count rate capacity for fully three-dimensional whole-body imaging.

Labeling proteins at high specific activity using N-succinimidyl 4-[18F](fluoromethyl) benzoate.

N-succinimidyl 4-[18F](fluoromethyl) benzoate, prepared using reversed phase HPLC, effectively labels sensitive proteins like erythropoietin in high yield without aggregation.

A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation.

[18F]SFB is the most suitable fluorine-18 labeling agent for proteins, particularly for antibody labeling, with higher conjugation yields and in vivo stability.

One-step synthesis of 18F labeled [18F]-N-succinimidyl 4-(fluoromethyl)benzoate for protein labeling.

This study successfully synthesized 18F-N-succinimidyl 4-(fluoromethyl)benzoate in one step using Kryptofix 2.2.2/[18F] and acetone at room temperature, resulting in 50-70% protein labeling yields in 15 minutes.

The use of pentafluorophenyl derivatives for the 18F labelling of proteins.

Pentafluorophenyl derivatives provide a fast, one-step method for radiolabelling proteins with 18F, producing low specific activity labelled proteins with reasonable yields.

Citations

Recent progress using the Staudinger ligation for radiolabeling applications.

The Staudinger ligation is a versatile bioorthogonal conjugation technique for radiolabeling biomolecules under mild conditions in radiopharmacy.

Methods to Increase the Metabolic Stability of 18F-Radiotracers

Stabilizing the C-F bond in 18F-radiotracers can improve their metabolic stability and enable their use in pharmaceuticals and biological studies.

Automated preparation of [18F]AFP and [18F]BFP: Two novel bifunctional 18F-labeling building blocks for Huisgen-click

The automated synthesis of [18F]AFP and [18F]BFP, two novel bifunctional 18F-labeling building blocks, enables efficient and stable bioorthogonal labeling of proteins and peptides.

Design and synthesis of novel 18F-radiolabelled glucosamine derivatives for cancer imaging

18F-radiolabelled glucosamine derivatives show potential for cancer imaging by visualizing cancer cells through molecular imaging.

Fluorine‐18 Radiolabeling and Radiopharmacological Characterization of a Benzodioxolylpyrimidine‐based Radiotracer Targeting the Receptor Tyrosine Kinase EphB4

The developed radiotracer shows potential for imaging Eph receptor tyrosine kinases in cancer, but no significant binding or accumulation was observed in EphB4-overexpressing or control tumors.