Synthesis and in vivo evaluation of 18F-desbromo-DuP-697 as a PET tracer for cyclooxygenase-2 expression

J Nucl Med. 2003 Oct;44(10):1700-6.

Abstract

Cyclooxygenase-2 (COX-2) overexpression has been observed in various pathologies, such as inflammation, cancer, ischemia, and Alzheimer's disease. As an initial step toward a noninvasive PET technique to assay COX-2 expression, this study describes the synthesis and preliminary evaluation of the radiolabeled COX-2 inhibitor (18)F-desbromo-DuP-697.

Methods: Desbromo-DuP-697 was radiolabeled by a nucleophilic aromatic substitution reaction of the nitro precursor with (18)F-fluoride. Biodistribution studies of the tracer were performed in a carrageenan-induced hyperalgesia rat model. Brain uptake was investigated with autoradiography. To confirm the results of the biodistribution, COX activity was determined by a peroxidase assay.

Results: Biodistribution studies showed specific binding of the tracer to COX-2 in heart, kidney, brain, and blood cells, but not in the inflamed paw, which was probably due to low COX-2 expression. In the brain, regional differences in tracer uptake were observed, with high uptake in cortical regions. (18)F-Desbromo-DuP-697 did not show any binding to COX-1. Nonspecific uptake was high in fat and intestines.

Conclusion: Because of its ability to cross the blood-brain barrier, (18)F-desbromo-DuP-697 appears to be suitable for COX-2 imaging in the brain. Its high nonspecific uptake in the intestines may limit its use for imaging in the abdominal region.

Publication types

  • Comparative Study
  • Evaluation Study
  • Validation Study

MeSH terms

  • Animals
  • Brain / diagnostic imaging*
  • Brain / metabolism*
  • Cyclooxygenase 2
  • Fluorine Radioisotopes / pharmacokinetics*
  • Fluorine Radioisotopes / therapeutic use*
  • Hyperalgesia / diagnostic imaging*
  • Hyperalgesia / metabolism*
  • Isoenzymes / biosynthesis*
  • Isotope Labeling / methods*
  • Male
  • Organ Specificity
  • Prostaglandin-Endoperoxide Synthases / biosynthesis*
  • Radionuclide Imaging
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Thiophenes / chemical synthesis
  • Thiophenes / pharmacokinetics*
  • Thiophenes / therapeutic use*
  • Tissue Distribution

Substances

  • 18F-2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene
  • Fluorine Radioisotopes
  • Isoenzymes
  • Radiopharmaceuticals
  • Thiophenes
  • DuP 697
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases