Radiosynthesis and evaluation of 5-methyl-N-(4-[(11)C]methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine ([(11)C]ADX88178) as a novel radioligand for imaging of metabotropic glutamate receptor subtype 4 (mGluR4)

Bioorg Med Chem Lett. 2016 Jan 15;26(2):370-374. doi: 10.1016/j.bmcl.2015.12.008. Epub 2015 Dec 7.

Abstract

ADX88178 (1) has been recently developed as a potent positive allosteric modulator for metabotropic glutamate receptor 4 (mGluR4). The aim of this study was to develop [(11)C]1 as a novel positron emission tomography ligand and to evaluate its binding ability for mGluR4. Using stannyl precursor 3, [(11)C]1 was efficiently synthesized by introducing an [(11)C]methyl group into a pyrimidine ring via C-(11)C coupling and deprotection reactions, in 16±6% radiochemical yield (n=10). At the end of synthesis, 0.54-1.10GBq of [(11)C]1 was acquired with >98% radiochemical purity and 90-120GBq/μmol of specific activity. In vitro autoradiography and ex vivo biodistribution study in rat brains showed specific binding of [(11)C]1 in the cerebellum, striatum, thalamus, cerebral cortex, and medulla oblongata, which showed dose-dependent decreases by administration with multi-dose of unlabeled 1.

Keywords: Autoradiography; PET; [(11)C]ADX88178; mGluR4.

MeSH terms

  • Animals
  • Autoradiography
  • Brain / diagnostic imaging
  • Brain / metabolism*
  • Male
  • Positron-Emission Tomography / methods*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / metabolism*
  • Pyrimidines / pharmacokinetics
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / metabolism*
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Metabotropic Glutamate / analysis
  • Receptors, Metabotropic Glutamate / metabolism*
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / metabolism*
  • Thiazoles / pharmacokinetics
  • Tissue Distribution

Substances

  • 5-methyl-N-(4-methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine
  • Pyrimidines
  • Radiopharmaceuticals
  • Receptors, Metabotropic Glutamate
  • Thiazoles
  • metabotropic glutamate receptor 4