Radiosynthesis of 6-([18F]fluoroacetamido)-1-hexanoicanilide ([18F]FAHA) for PET imaging of histone deacetylase (HDAC)

✍ Scribed by Uday Mukhopadhyay; William P. Tong; Juri G. Gelovani; Mian M. Alauddin

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: French
• Weight: 290 KB
• Volume: 49
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1122

✦ Synopsis

Abstract

Radiosynthesis of a novel substrate for histone deacetylase (HDAC), 6‐([^18^F]fluoroacetamido)‐1‐hexanoicanilide ([^18^F]FAHA, [^18^F]‐3) is reported. For precursor synthesis, compound 1 (6‐amino‐1‐hexanoicanilide) was prepared by the reaction of 6‐amino hexanoic acid with thionyl chloride in dichloroethane followed by addition of aniline. Compound 1 was reacted with bromoacetic anhydride in tetrahydrofuran (THF) in the presence of triethylamine to produce the precursor compound 6‐(bromoacetamido)‐1‐hexanoicanilide 2. Fluorination reactions were performed using tetrabutylammonium fluoride in various solvents at 80°C to prepare the unlabeled reference compound 3. Radiofluorinations were performed using either n‐Bu~4~N^18^F or K^18^F/kryptofix, and the crude product was purified by high performance liquid chromatography (HPLC). The radiochemical yields were 9–13% decay corrected (d.c.) with an average of 11% using K^18^F/kryptofix, and specific activity >2 GBq/µmol at the end of synthesis. The synthesis time was 67–75 min from the end of bombardment (EOB). Copyright © 2006 John Wiley & Sons, Ltd.