Use of 2-[(18)F]fluoroethylazide for the Staudinger ligation - Preparation and characterisation of GABA(A) receptor binding 4-quinolones

Bioorg Med Chem Lett. 2010 Aug 1;20(15):4649-52. doi: 10.1016/j.bmcl.2010.05.106. Epub 2010 Jun 8.

Abstract

The labelling reagent 2-[(18)F]fluoroethylazide was used in a traceless Staudinger ligation. This reaction was employed to obtain the GABA(A) receptor binding 6-benzyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (2-[(18)F]fluoroethyl) amide. The radiotracer was prepared with a non-decay corrected radiochemical yield of 7%, a radiochemical purity >95% and a specific radioactivity of 0.9 GBq/micromol. The compound showed low brain penetration in normal rats. A series of fluoroalkyl 4-quinolone analogues with nanomolar to sub-nanomolar affinity for the GABA(A) receptor has been prepared as well.

MeSH terms

  • 4-Quinolones / chemistry*
  • Animals
  • Azides / chemistry*
  • Brain / diagnostic imaging
  • Fluorine Radioisotopes / chemistry
  • Protein Binding
  • Radiography
  • Radiopharmaceuticals / chemistry*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, GABA-A / chemistry*
  • Receptors, GABA-A / metabolism
  • Tissue Distribution

Substances

  • 4-Quinolones
  • Azides
  • Fluorine Radioisotopes
  • Radiopharmaceuticals
  • Receptors, GABA-A