Synthesis and biological evaluation of novel carbon-11 labeled pyridyl ethers: candidate ligands for in vivo imaging of alpha4beta2 nicotinic acetylcholine receptors (alpha4beta2-nAChRs) in the brain with positron emission tomography

Bioorg Med Chem. 2009 Jul 1;17(13):4367-77. doi: 10.1016/j.bmc.2009.05.021. Epub 2009 May 15.

Abstract

The most abundant subtype of cerebral nicotinic acetylcholine receptors (nAChR), alpha4beta2, plays a critical role in various brain functions and pathological states. Imaging agents suitable for visualization and quantification of alpha4beta2 nAChRs by positron emission tomography (PET) would present unique opportunities to define the function and pharmacology of the nAChRs in the living human brain. In this study, we report the synthesis, nAChR binding affinity, and pharmacological properties of several novel 3-pyridyl ether compounds. Most of these derivatives displayed a high affinity to the nAChR and a high subtype selectivity for alpha4beta2-nAChR. Three of these novel nAChR ligands were radiolabeled with the positron-emitting isotope (11)C and evaluated in animal studies as potential PET radiotracers for imaging of cerebral nAChRs with improved brain kinetics.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Brain Chemistry*
  • Carbon Radioisotopes
  • Humans
  • Lipids / chemistry
  • Male
  • Mice
  • Papio
  • Positron-Emission Tomography / methods*
  • Protein Binding
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Radiopharmaceuticals / pharmacology*
  • Rats
  • Rats, Wistar
  • Receptors, Nicotinic / analysis*
  • Receptors, Nicotinic / metabolism*
  • Structure-Activity Relationship

Substances

  • Carbon Radioisotopes
  • Lipids
  • Radiopharmaceuticals
  • Receptors, Nicotinic
  • nicotinic receptor alpha4beta2