Application of a novel phenylpiperazine formation reaction to the radiosynthesis of a model fluorine-18-labeled radiopharmaceutical (18FTFMPP)

Nucl Med Biol. 1997 Apr;24(3):269-73. doi: 10.1016/s0969-8051(97)00063-2.

Abstract

The labeled serotonin agonist 3-[18F]fluoro-N-(alpha,alpha,alpha-trifluoro-m-tolyl)piperazine (18FTFMPP) was prepared rapidly using the labeling procedure for trifluorotoluenes, [18F]fluoro-for-nitro exchange, followed by an alumina-supported bis-alkylation. After normal-phase HPLC purification, the labeled product was obtained in 20-32% (n = 20) decay-corrected radiochemical yield with a radiochemical purity > 98% and a specific activity of 100 GBq/mumol. The synthesis time including purification was 3 h. The receptor binding affinity of FTFMPP to rat brain membranes was found to be similar to that of the nonfluorinated parent compound (TFMPP). Although TFMPP has been proposed by others as an agent for the imaging of serotonin receptors, only minimal receptor-mediated uptake was observed.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Brain / metabolism
  • Fluorine Radioisotopes
  • In Vitro Techniques
  • Isotope Labeling
  • Ligands
  • Membranes / metabolism
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry*
  • Piperazines / pharmacokinetics
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Receptors, Serotonin / metabolism
  • Serotonin Agents / chemical synthesis*
  • Serotonin Agents / pharmacokinetics
  • Tissue Distribution

Substances

  • 3-fluoro-N-(alpha,alpha,alpha-trifluoro-3-tolyl)piperazine
  • Fluorine Radioisotopes
  • Ligands
  • Piperazines
  • Radiopharmaceuticals
  • Receptors, Serotonin
  • Serotonin Agents