Synthesis and biological evaluation of radioiodinated 2,5-diphenyl-1,3,4-oxadiazoles for detecting beta-amyloid plaques in the brain

Bioorg Med Chem. 2009 Sep 1;17(17):6402-6. doi: 10.1016/j.bmc.2009.07.020. Epub 2009 Jul 17.

Abstract

This paper describes the synthesis and biological evaluation of a new series of 2,5-diphenyl-1,3,4-oxadiazole (1,3,4-DPOD) derivatives for detecting beta-amyloid plaques in Alzheimer's brains. The affinity for beta-amyloid plaques was assessed by an in vitro binding assay using pre-formed synthetic Abeta42 aggregates. The new series of 1,3,4-DPOD derivatives showed affinity for Abeta42 aggregates with K(i) values ranging from 20 to 349 nM. The 1,3,4-DPOD derivatives clearly stained beta-amyloid plaques in an animal model of Alzheimer's disease, reflecting the affinity for Abeta42 aggregates in vitro. Compared to 3,5-diphenyl-1,2,4-oxadiazole (1,2,4-DPOD) derivatives, they displayed good penetration of and fast washout from the brain in biodistribution experiments using normal mice. The novel radioiodinated 1,3,4-DPOD derivatives may be useful probes for detecting beta-amyloid plaques in the Alzheimer's brain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alzheimer Disease / diagnosis
  • Amyloid beta-Peptides / analysis*
  • Amyloid beta-Peptides / chemistry
  • Amyloid beta-Peptides / metabolism
  • Animals
  • Brain / pathology*
  • Iodine Radioisotopes / chemistry
  • Mice
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacokinetics
  • Plaque, Amyloid / chemistry*
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics
  • Tissue Distribution

Substances

  • Amyloid beta-Peptides
  • Iodine Radioisotopes
  • Oxadiazoles
  • Radiopharmaceuticals