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

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...