Synthesis, radiolabeling, and in vivo pharmacokinetic evaluation of the amyloid beta radioligand [11C]AZD4694 in nonhuman primates

Mol Imaging Biol. 2014 Apr;16(2):173-9. doi: 10.1007/s11307-013-0666-3.

Abstract

Purpose: [(18)F]AZD4694 (2-(2-(18)F-fluoro-6-(methylamino)-3-pyridyl)benzofuran-5-ol) is a radioligand suitable for imaging of amyloid beta deposits in the living human brain using positron emission tomography (PET). Here, we report the preparation and pharmacokinetic profile of its carbon-11 (t1/2 = 20.4 min) labeled isotopolog [(11)C]AZD4694 and compare [(11)C]AZD4694 with the hitherto most widely applied amyloid PET radioligand [(11)C]Pittsburgh Compound B (PiB).

Procedures: The immediate unlabeled precursor to [(11)C]AZD4694 was prepared in a four-step convergent synthesis. Subsequent N-(11)C-methylation of this precursor with [(11)C]methyl iodide yielded [(11)C]AZD4694, which after isolation and formulation was injected into cynomolgus monkeys. The radioactivity in nonhuman primate brain following injection of [(11)C]AZD4694 and [(11)C]PiB was measured using PET.

Results: [(11)C]AZD4694 was prepared in a 60 % incorporation yield. In a head to head comparison with [(11)C]PiB, it appeared that [(11)C]AZD4694 displayed slightly lower nonspecific binding in white matter than [(11)C]PiB as well as more rapid pharmacokinetics in the brain.

Conclusions: The advantageous pharmacokinetic profile and low nonspecific binding render [(11)C]AZD4694 a promising PET radioligand for imaging of amyloid beta in the human brain with PET.

MeSH terms

  • Amyloid beta-Peptides / chemical synthesis*
  • Amyloid beta-Peptides / pharmacokinetics*
  • Aniline Compounds / blood
  • Aniline Compounds / pharmacokinetics
  • Animals
  • Benzofurans / blood
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacokinetics*
  • Brain / diagnostic imaging
  • Carbon Radioisotopes
  • Humans
  • Hydrocarbons, Fluorinated / blood
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / pharmacokinetics*
  • Macaca fascicularis / metabolism*
  • Magnetic Resonance Imaging
  • Positron-Emission Tomography
  • Radiopharmaceuticals / blood
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics*
  • Thiazoles / blood
  • Thiazoles / pharmacokinetics
  • Time Factors

Substances

  • 2-(4'-(methylamino)phenyl)-6-hydroxybenzothiazole
  • AZD4694
  • Amyloid beta-Peptides
  • Aniline Compounds
  • Benzofurans
  • Carbon Radioisotopes
  • Hydrocarbons, Fluorinated
  • Radiopharmaceuticals
  • Thiazoles