1356855-53-2Relevant academic research and scientific papers
Synthesis of 2-[(4-[18F]Fluorobenzoyloxy)methyl]-1,4- naphthalenedione from 2-hydroxymethyl 1,4-naphthoquinone and 4-[ 18F]fluorobenzoic acid using dicyclohexyl carbodiimide
Ackermann, Uwe,Sigmund, Duanne,Yeoh, Shinn Dee,Rigopoulos, Angela,O'Keefe, Graeme,Cartwright, Glenn,White, Jonathan,Scott, Andrew M.,Tochon-Danguy, Henri J.
, p. 788 - 794 (2011)
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.
