U. Ackermann, Duanne Sigmund, S. Yeoh
Nov 1, 2011
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Influential Citations
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
2-[(4-[18F]Fluorobenzoyloxy)methyl]-1,4-naphthalenedione ([18F]1) was synthesised as a putative hypoxia imaging agent from 2-hydroxymethyl 1,4-naphthoquinone (7) and 4-[18F]fluorobenzoic acid ([18F]8) using dicyclohexyl carbodiimide (DCC) to activate [18F]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. [18F]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. [18F]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 [18F]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.