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

• Published in: Applied radiation and isotopes 2008-02, Vol.66 (2), p.203-207
• Main Authors: Klok, R.P., Klein, P.J., van Berckel, B.N.M., Tolboom, N., Lammertsma, A.A., Windhorst, A.D.
• Format: Article
• Language: English
• Subjects: [ 18F]FDDNP; Alzheimer disease; Alzheimer Disease - diagnostic imaging; Amyloid beta-Peptides - metabolism; Chromatography, High Pressure Liquid; F-18; Fluorine Radioisotopes - chemistry; Humans; Nitriles - chemical synthesis; Nitriles - isolation & purification; Positron emission tomography; Radiopharmaceuticals - chemical synthesis; Radiopharmaceuticals - isolation & purification; β-Amyloid
• ISSN: 0969-8043; 1872-9800
• DOI: 10.1016/j.apradiso.2007.10.008

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.