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Synthesis of 2-[(4-[18F]Fluorobenzoyloxy)methyl]-1,4-naphthalenedione from 2-hydroxymethyl 1,4-naphthoquinone and 4-[18F]fluorobenzoic acid using dicyclohexyl carbodiimide

✍ Scribed by Uwe Ackermann; Duanne Sigmund; Shinn Dee Yeoh; Angela Rigopoulos; Graeme O'Keefe; Glenn Cartwright; Jonathan White; Andrew M. Scott; Henri J. Tochon-Danguy

Publisher
John Wiley and Sons
Year
2011
Tongue
French
Weight
355 KB
Volume
54
Category
Article
ISSN
0022-2135

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✦ Synopsis

2‐[(4‐[^18^F]Fluorobenzoyloxy)methyl]‐1,4‐naphthalenedione ([^18^F]1) was synthesised as a putative hypoxia imaging agent from 2‐hydroxymethyl 1,4‐naphthoquinone (7) and 4‐[^18^F]fluorobenzoic acid ([^18^F]8) using dicyclohexyl carbodiimide (DCC) to activate [^18^F]8. This coupling reaction was fast and gave quantitative yields. Further investigations are warranted on the use of DCC as a coupling agent in Positron Emission Tomography. The synthesis including HPLC purification and reformulation has been fully automated on a modified FDG synthesiser with two reactor vials. [^18^F]1 was produced in a radiochemical yield of 27 ± 5%, with a radiochemical purity of 97.5% and a specific activity of 78.4–134.5 GBq/µmol at the end of synthesis (n = 23). The total synthesis time including reformulation was 65 min. [^18^F]1 was found to be stable in plasma and saline, but underwent rapid metabolism in a phase 1 metabolite assay using rat S9 liver fractions. An in vivo evaluation of [^18^F]1 in transplanted, hypoxic SK‐RC‐52 tumour‐bearing BALB/c nude mice revealed the tumour‐to‐muscle ratio to be 2.4 ± 0.1 at 2 h post‐injection. Copyright © 2011 John Wiley & Sons, Ltd.

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