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

Appl Radiat Isot. 2008 Feb;66(2):203-7. doi: 10.1016/j.apradiso.2007.10.008. Epub 2007 Oct 30.

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/micromol at the end of synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alzheimer Disease / diagnostic imaging
  • Amyloid beta-Peptides / metabolism
  • Chromatography, High Pressure Liquid
  • Fluorine Radioisotopes / chemistry*
  • Humans
  • Nitriles / chemical synthesis*
  • Nitriles / isolation & purification
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / isolation & purification

Substances

  • 2-(1-(6-((2-fluoroethyl)(methyl)amino)-2-naphthyl)ethylidene)malononitrile
  • Amyloid beta-Peptides
  • Fluorine Radioisotopes
  • Nitriles
  • Radiopharmaceuticals