Synthesis of [¹⁸F]-labeled (2-(2-fluoroethoxy)ethyl)triphenylphosphonium cation as a potential agent for myocardial imaging using positron emission tomography

Bioorg Med Chem Lett. 2012 Jan 1;22(1):319-22. doi: 10.1016/j.bmcl.2011.11.005. Epub 2011 Nov 10.


[(18)F]-labeled molecular probe for the detection of myocardial perfusion deficit is driving particular interest due to its high clinical applicability. Thus, we synthesized (2-(2-[(18)F]fluoroethoxy)ethyl)triphenylphosphonium salt ([(18)F]3) that specifically accumulates in myocardium according to mitochondrial membrane potential. Here, we evaluated the performance of [(18)F]3 as a mitochondrial voltage sensor in vitro and in vivo. The [(18)F]3 was synthesized with 20∼30% radiochemical yield and radiochemical purity was >98% by analytical HPLC. Specific activity was >6.7TBq/μmol. The cellular uptake assay showed preferential uptake of [(18)F]3 in cardiomyocytes. The results of biodistribution and micro-PET imaging studies of [(18)F]3 in mice and rats showed preferential accumulation in the myocardium. The results suggest that this compound would be a promising candidate for myocardial imaging.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cations
  • Chromatography, High Pressure Liquid / methods
  • Drug Design
  • Fluorine Radioisotopes / pharmacology
  • Ions
  • Magnetic Resonance Spectroscopy / methods
  • Mitochondria / metabolism
  • Mitochondrial Membranes / metabolism
  • Models, Chemical
  • Myocardium / pathology*
  • Myocytes, Cardiac / cytology
  • Organophosphorus Compounds / chemistry*
  • Perfusion
  • Positron-Emission Tomography / methods*
  • Rats
  • Time Factors
  • Tissue Distribution


  • Cations
  • Fluorine Radioisotopes
  • Ions
  • Organophosphorus Compounds