Synthesis of 2-(1,1-dicyanopropen-2-yl)-6-(2-[ 18F]-fluoroethyl)-methylamino-naphthalene ([ 18F]FDDNP)

Abstract

2-(1,1-Dicyanopropen-2-yl)-6-(2-[ 18F]-fluoroethyl)-methylamino-naphthalene ([ 18F]FDDNP) was synthesized in a single step labeling procedure. The precursor, 2-(1,1-dicyanopropen-2-yl)-6-(2-tosyloxyoethyl)-methylamino-naphthalene, was fluorinated with 18F in acetonitrile. After 15 min the reaction mixture was subjected to preparative HPLC purification. The product was isolated from the HPLC eluent with solid-phase extraction, and formulated in an ascorbic acid solution to prevent formation of side products during formulation. Quantitative sticking to tubing and filters was overcome by the addition of polysorbatum-80. This formulation yielded an isotonic, pyrogen-free and sterile solution of [ 18F]FDDNP. The overall decay-corrected radiochemical yield was 41±11% ( n=22). Radiochemical purity was >98% and the specific activity was 102±56 GBq/μmol at the end of synthesis.