Synthesis and biological evaluation of pyridazinone analogues as potential cardiac positron emission tomography tracers

J Med Chem. 2008 May 22;51(10):2954-70. doi: 10.1021/jm701443n. Epub 2008 Apr 19.

Abstract

A series of fluorinated pyridazinone derivatives with IC50 values ranging from 8 to 4000 nM for the mitochondrial complex 1 (MC1) have been prepared. Structure-activity relationship (SAR) assessment indicated preference of the fluorine label to be incorporated on an alkyl side chain rather than directly on the pyridazinone moiety. Tissue distribution studies of a series of analogues ([18F] 22-28) in Sprague-Dawley (SD) rats identified [18F]27 as the most promising radiotracer with high uptake in cardiac tissue (3.41%ID/g; 30 min post injection) in addition to favorable heart to nontarget organ distribution ratios. MicroPET images of SD rats and nonhuman primates after [18F]27 administration allowed easy assessment of the myocardium through 60 min with minimal lung or liver interference.

MeSH terms

  • Animals
  • Cattle
  • Electron Transport Complex I / antagonists & inhibitors
  • Female
  • Fluorine Radioisotopes
  • Heart / diagnostic imaging*
  • In Vitro Techniques
  • Macaca mulatta
  • Male
  • Mitochondria, Heart / enzymology
  • Positron-Emission Tomography
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry
  • Pyridazines / pharmacokinetics
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • 2-tert-butyl-4-chloro-5-(4-(2-fluoroethoxymethyl)benzyloxy)-3-(2H)-pyridazinone
  • Fluorine Radioisotopes
  • Pyridazines
  • Radiopharmaceuticals
  • Electron Transport Complex I