Synthesis, 18F-Radiolabelling and Biological Characterization of Novel Fluoroalkylated Triazine Derivatives for in Vivo Imaging of Phosphodiesterase 2A in Brain via Positron Emission Tomography

Molecules. 2015 May 26;20(6):9591-615. doi: 10.3390/molecules20069591.

Abstract

Phosphodiesterase 2A (PDE2A) is highly and specifically expressed in particular brain regions that are affected by neurological disorders and in certain tumors. Development of a specific PDE2A radioligand would enable molecular imaging of the PDE2A protein via positron emission tomography (PET). Herein we report on the syntheses of three novel fluoroalkylated triazine derivatives (TA2-4) and on the evaluation of their effect on the enzymatic activity of human PDE2A. The most potent PDE2A inhibitors were 18F-radiolabelled ([18F]TA3 and [18F]TA4) and investigated regarding their potential as PET radioligands for imaging of PDE2A in mouse brain. In vitro autoradiography on rat brain displayed region-specific distribution of [18F]TA3 and [18F]TA4, which is consistent with the expression pattern of PDE2A protein. Metabolism studies of both [18F]TA3 and [18F]TA4 in mice showed a significant accumulation of two major radiometabolites of each radioligand in brain as investigated by micellar radio-chromatography. Small-animal PET/MR studies in mice using [18F]TA3 revealed a constantly increasing uptake of activity in the non-target region cerebellum, which may be caused by the accumulation of brain penetrating radiometabolites. Hence, [18F]TA3 and [18F]TA4 are exclusively suitable for in vitro investigation of PDE2A. Nevertheless, further structural modification of these promising radioligands might result in metabolically stable derivatives.

Keywords: Alzheimer’s disease; PDE2A; PET imaging in brain; micellar HPLC.

MeSH terms

  • Animals
  • Autoradiography
  • Brain / metabolism
  • Brain / ultrastructure
  • Cyclic Nucleotide Phosphodiesterases, Type 2 / antagonists & inhibitors
  • Cyclic Nucleotide Phosphodiesterases, Type 2 / metabolism*
  • Female
  • Fluorine Radioisotopes
  • Humans
  • Isotope Labeling / methods*
  • Mice
  • Neuroimaging / methods*
  • Permeability
  • Phosphodiesterase Inhibitors / chemistry
  • Phosphodiesterase Inhibitors / metabolism
  • Phosphodiesterase Inhibitors / pharmacokinetics*
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / metabolism
  • Radiopharmaceuticals / pharmacokinetics*
  • Rats
  • Rats, Sprague-Dawley
  • Triazines / chemistry
  • Triazines / metabolism
  • Triazines / pharmacokinetics*

Substances

  • Fluorine Radioisotopes
  • Phosphodiesterase Inhibitors
  • Radiopharmaceuticals
  • Triazines
  • Cyclic Nucleotide Phosphodiesterases, Type 2
  • PDE2A protein, human