Synthesis and evaluation of 2-(3'-iodo-4'-aminophenyl)-6-hydroxybenzothiazole for in vivo quantitation of amyloid deposits in Alzheimer's disease

J Mol Neurosci. 2002 Aug-Oct;19(1-2):11-6. doi: 10.1007/s12031-002-0004-8.

Abstract

A potent and brain permeable amyloid ligand has been identified as a lead compound capable of I-123/125-labelling for single photon emission computed tomography (SPECT) imaging. In this study, we report the synthesis and I-125-radiolabelling of Compound 6 and its in vitro and in vivo properties. Compound 6 [2-(3'-iodo-4'-aminophenyl)-6-hydroxybenzothiazole] bound to synthetic A beta(1-40) fibrils in a saturable manner, exhibiting an affinity (Ki) of 11+/-1.1 nM in a competitive binding assay using a tritiated thioflavin T analog ([3H]BTA-1) as radioligand. [125I]6 binding to synthetic A beta(1-40) fibrils fit a single-site model. [125I]6 exhibited several-fold higher binding to homogenates of frontal cortex from post-mortem Alzheimer's disease brain relative to age-matched control brain homogenates. No difference in binding was observed in cerebellum. The ratio of radioactivity concentration between frontal cortex and cerebellum was 6-fold higher in AD brain homogenates than the age-matched control. [125I]6 also readily penetrated the blood-brain barrier in normal control mice with an average radioactivity concentration of 6.43+/-0.62%ID/g detected in the whole brain at 2 min post i.v. injection. At 30 min, the radioactivity concentration decreased to 0.40+/-0.05%ID/g, indicating good clearance in the absence of amyloid deposits in the brain.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alzheimer Disease / diagnostic imaging*
  • Alzheimer Disease / metabolism
  • Amyloid beta-Peptides / analysis*
  • Aniline Compounds* / chemical synthesis
  • Animals
  • Benzothiazoles
  • Benzoxazoles / chemical synthesis
  • Brain / diagnostic imaging*
  • Brain / metabolism
  • Evaluation Studies as Topic
  • Humans
  • Iodine Radioisotopes
  • Mice
  • Neurofibrillary Tangles / diagnostic imaging*
  • Neurofibrillary Tangles / metabolism
  • Protein Binding
  • Radiopharmaceuticals / chemical synthesis*
  • Thiazoles* / chemical synthesis
  • Tomography, Emission-Computed, Single-Photon / methods*

Substances

  • 2-(3'-iodo-4'-aminophenyl)-6-hydroxybenzothiazole
  • 2-(4'-dimethylaminophenyl)-6-iodobenzoxazole
  • Amyloid beta-Peptides
  • Aniline Compounds
  • Benzothiazoles
  • Benzoxazoles
  • Iodine Radioisotopes
  • Radiopharmaceuticals
  • Thiazoles
  • benzothiazole