Radioiodinated aza-diphenylacetylenes as potential SPECT imaging agents for beta-amyloid plaque detection

Bioorg Med Chem Lett. 2007 Jul 1;17(13):3581-4. doi: 10.1016/j.bmcl.2007.04.062. Epub 2007 Apr 25.

Abstract

Two new iodinated fluoro- and hydroxy-pegylated aza-diphenylacetylene derivatives, 1 and 2, targeting beta-amyloid (Abeta) plaques have been successfully prepared. In vitro binding carried out in tissue homogenates prepared from postmortem AD brains with [(125)I]IMPY (6-iodo-2-(4'-dimethylamino)phenyl-imidazo[1,2-a]pyridine) as the radioligand indicated good binding affinities (K(i)=9.2 and 16.8 nM for 1 and 2, respectively). Brain penetrations of the corresponding radioiodinated ligands, evaluated in the normal mice, showed good initial brain penetrations (3.55% and 5.67% ID/g for [(125)I]1 and [(125)I]2 at 2 min post-injection). The washout from normal mice brain was relatively fast (0.33% and 0.91% ID/g at 2h post-injection). The specific binding of these radioiodinated ligands to beta-amyloid plaques was clearly demonstrated using film autoradiography of AD brain sections. Taken together, these preliminary results strongly suggest that these novel iodinated aza-diphenylacetylenes may be potentially useful for imaging Abeta plaques in the living human brain.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemical synthesis
  • Acetylene / pharmacology
  • Alzheimer Disease / drug therapy
  • Alzheimer Disease / pathology
  • Amyloid beta-Peptides / chemistry*
  • Animals
  • Brain / metabolism
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Humans
  • Iodine Radioisotopes / pharmacology*
  • Kinetics
  • Ligands
  • Mice
  • Models, Chemical
  • Tissue Distribution
  • Tomography, Emission-Computed, Single-Photon / instrumentation*
  • Tomography, Emission-Computed, Single-Photon / methods

Substances

  • Amyloid beta-Peptides
  • Iodine Radioisotopes
  • Ligands
  • biphenylacetylene
  • Acetylene