Simplified fast and high yielding automated synthesis of [18F]fluoroethylcholine for prostate cancer imaging

Bioorg Med Chem. 2008 Oct 15;16(20):9121-6. doi: 10.1016/j.bmc.2008.09.031. Epub 2008 Sep 13.

Abstract

(11)C- and (18)F-labeled choline analogues are successful tracers for prostate cancer imaging using positron emission tomography (PET). Due to the practical advantages of the longer-living radioisotope (18)F (t(1/2)=110 min) instead of (11)C (t(1/2)=20 min), [(18)F]fluoroethylcholine has been introduced to increase the opportunity of widespread clinical application. Nevertheless, the various known synthetic methods provide [(18)F]fluoroethylcholine for human use only in moderate overall yields of up to 30% so far. Here, a new simplified and high yield two-step-synthesis for [(18)F]fluoroethylcholine is described for potential clinical applications starting from 2-bromoethyl triflate (BETfO) using a modified, commercially available fully automated synthesis module. All synthesis parameters were subsequently optimized resulting in a total yield of 47+/-5% (not decay corrected) in only 40min. [(18)F]fluoroethylcholine could be obtained ready for human use as physiological solution after fixation on Sep-Pak Accell Light cartridges (waters((R))) and formulation with saline without the need of GC or HPLC purification. Radiochemical purity was >99.9% and no contamination of the sterile solution with chemicals used during the synthesis was detected.

MeSH terms

  • Automation
  • Choline / analogs & derivatives*
  • Choline / chemical synthesis
  • Choline / chemistry
  • Humans
  • Male
  • Molecular Structure
  • Prostatic Neoplasms / diagnosis*
  • Radiochemistry
  • Time Factors

Substances

  • fluoroethylcholine
  • Choline