Radiosynthesis and preclinical evaluation of 11C-ABP688 as a probe for imaging the metabotropic glutamate receptor subtype 5

J Nucl Med. 2006 Apr;47(4):698-705.

Abstract

(11)C-ABP688 (3-(6-methyl-pyridin-2-ylethynyl)-cyclohex-2-enone-O-(11)C-methyl-oxime), a noncompetitive and highly selective antagonist for the metabotropic glutamate receptor subtype 5 (mGluR5), was evaluated for its potential as a PET agent.

Methods: ABP688 was radiolabeled with (11)C by reacting (11)C-methyl iodide with the sodium salt of desmethyl-ABP688 (3-(6-methyl-pyridin-2-ylethynyl)-cyclohex-2-enone oxime). The affinity of (11)C-ABP688 for mGluR5 was determined by Scatchard analysis using rat whole-brain membranes (without cerebellum). Ex vivo autoradiography, biodistribution, and PET studies with (11)C-ABP688 were performed on rats, wild-type mice, and mGluR5-knock-out mice.

Results: The overall synthesis time was 45-50 min from the end of radionuclide production. (11)C-ABP688 was obtained in good radiochemical yield (35% +/- 8%, n = 17, decay corrected), and the specific radioactivity was 150 +/- 50 GBq/mumol (n = 17) at the end of the synthesis. Scatchard analysis revealed a single high-affinity binding site with a dissociation constant of 1.7 +/- 0.2 nmol/L and a maximum number of binding sites of 231 +/- 18 fmol/mg of protein. Ex vivo autoradiography in wild-type mice and rats showed a heterogeneous distribution pattern consistent with the known distribution of mGluR5 in the brain, with the highest uptake in hippocampus, striatum, and cortex. Blocking studies by coinjection of (11)C-ABP688 and unlabeled 2-methyl-6-(3-methoxyphenyl)ethynyl-pyridine (1 mg/kg), an antagonist for mGluR5, revealed up to 80% specific binding in rat brain. In mGluR5-knock-out mouse brain, a homogeneous and markedly reduced accumulation of (11)C-ABP688 was observed. PET studies on rats and mice using a small-animal PET scanner also demonstrated radioactivity uptake in the brain regions known to be rich in mGluR5. In contrast, radioactivity uptake in mGluR5-knock-out mice was fairly uniform, substantiating the specificity of (11)C-ABP688 binding to mGluR5.

Conclusion: (11)C-ABP688 is a selective tracer for imaging mGluR5 in vivo in rodents and may offer a future tool for imaging mGluR5 in humans using PET.

MeSH terms

  • Animals
  • Brain / diagnostic imaging
  • Brain / metabolism*
  • Carbon Radioisotopes
  • Female
  • Male
  • Membranes / metabolism
  • Mice
  • Mice, Inbred C57BL
  • Mice, Knockout
  • Oximes / chemical synthesis*
  • Oximes / pharmacokinetics
  • Positron-Emission Tomography
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacokinetics
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Metabotropic Glutamate 5
  • Receptors, Metabotropic Glutamate / antagonists & inhibitors
  • Receptors, Metabotropic Glutamate / metabolism*
  • Tissue Distribution

Substances

  • 3-(6-methylpyridin-2-ylethynyl)cyclohex-2-enone-O-methyloxime
  • Carbon Radioisotopes
  • GRM5 protein, human
  • Grm5 protein, mouse
  • Grm5 protein, rat
  • Oximes
  • Pyridines
  • Radiopharmaceuticals
  • Receptor, Metabotropic Glutamate 5
  • Receptors, Metabotropic Glutamate