Synthesis of S-([18F]fluoromethyl)-(+)-McN5652 as a potential PET radioligand for the serotonin transporter

Nucl Med Biol. 2001 Oct;28(7):857-63. doi: 10.1016/s0969-8051(01)00248-7.

Abstract

The present study describes the synthesis of the [18F]fluoromethyl analogue of (+)-McN5652 ([18F]FMe-McN) as a new potential tracer for the serotonin transporter. In vitro binding studies have shown that FMe-McN displays only slightly lower affinity for the serotonin transporter (K(i) = 2.3 +/- 0.1 nM) than (+)-McN5652 (K(i) = 0.72 +/- 0.2 nM). The radiofluorinated tracer [18F]FMe-McN was prepared by reaction of normethyl (+)-McN5652 with the fluoromethylation agent [18F]bromofluoromethane in an overall radiochemical yield of 5 +/- 1% (decay-corrected, related to [18F]fluoride) and with high specific radioactivity (200-2,000 GBq/micromol at the end of synthesis).

MeSH terms

  • Animals
  • Carrier Proteins / metabolism*
  • Caudate Nucleus / metabolism
  • Drug Stability
  • Fluorine Radioisotopes
  • In Vitro Techniques
  • Indicators and Reagents
  • Isoquinolines / chemical synthesis*
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy
  • Membrane Glycoproteins / metabolism*
  • Membrane Transport Proteins*
  • Nerve Tissue Proteins*
  • Paroxetine / metabolism
  • Radioligand Assay
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacology
  • Selective Serotonin Reuptake Inhibitors / metabolism
  • Serotonin Antagonists / chemical synthesis*
  • Serotonin Plasma Membrane Transport Proteins
  • Solvents
  • Swine
  • Tomography, Emission-Computed

Substances

  • Carrier Proteins
  • Fluorine Radioisotopes
  • Indicators and Reagents
  • Isoquinolines
  • Membrane Glycoproteins
  • Membrane Transport Proteins
  • Nerve Tissue Proteins
  • Radiopharmaceuticals
  • Serotonin Antagonists
  • Serotonin Plasma Membrane Transport Proteins
  • Serotonin Uptake Inhibitors
  • Solvents
  • Paroxetine
  • McN 5652