Efficient synthesis of the 18F-labelled 3-O-methyl-6-[18F]fluoro-L-DOPA

Appl Radiat Isot. 2003 May;58(5):575-8. doi: 10.1016/s0969-8043(03)00062-9.

Abstract

The 18F-labelled amino acid derivative 3-O-methyl-6-[18F]fluoro-L-DOPA ([18F]OMFD) is a potential radiotracer for imaging tumour tissue using positron emission tomography. The precursor N-formyl-3-O-methyl-4-O-boc-6-trimethyl-stannyl-L-DOPA-ethyl ester enables direct electrophilic radiofluorination by stereoselective destannylation. After partial hydrolysis, optimized HPLC purification and sterile filtration, the [18F]OMFD obtained with high radiochemical purity and ready for use. The total synthesis time is about 50 min and the radiochemical yield achieved is 20-25% (decay corrected, related to [18F]F(2)). It was demonstrated that [18F]OMFD could be produced routinely and reliably for clinical use. [18F]FDOPA-preparation devices can be used with minor modifications.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Dihydroxyphenylalanine / analogs & derivatives*
  • Dihydroxyphenylalanine / chemical synthesis*
  • Dihydroxyphenylalanine / isolation & purification
  • Fluorine Radioisotopes / chemistry*
  • Hydrolysis
  • Isotope Labeling / methods
  • Quality Control
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / isolation & purification
  • Stereoisomerism
  • Tomography, Emission-Computed / methods

Substances

  • Fluorine Radioisotopes
  • Radiopharmaceuticals
  • 3-O-methyl-6-fluoro-dopa
  • Dihydroxyphenylalanine