Synthesis and evaluation of 18F-labeled PPARγ antagonists

Nucl Med Biol. 2012 Jan;39(1):77-87. doi: 10.1016/j.nucmedbio.2011.07.002. Epub 2011 Sep 9.

Abstract

Introduction: Peroxisome proliferator-activated receptor gamma (PPARγ) transcriptionally modulates fat metabolism and also plays a role in pathological conditions such as cancer, neurodegenerative disease and inflammation. PPARγ imaging agents are potential tools for investigating these diseases.

Methods: Four analogs of GW9662, a PPARγ antagonist, with different fluorine-containing substituents at the para-position of the aniline ring were synthesized and evaluated using two different receptor binding assays for measuring PPARγ affinity. Micro-positron emission tomography (PET) imaging studies were performed in a transgenic mouse model having a heart-specific overexpression of PPARγ.

Results: All four analogs were found to have binding affinities that were comparable to or better than the reference antagonist, GW9662, using a scintillation proximity assay (SPA). However, only the chloro-based analogs (compounds 3 and 4) had activity in a whole-cell assay measuring activation of the PPARγ/retinoid X receptor complex. The microPET imaging studies in an MHC-PPARγ transgenic mouse model showed high uptake and PPARγ-specific binding for the irreversible antagonist [(18)F]3, whereas the corresponding reversible methoxy analog ([(18)F]5) displayed only nonspecific uptake in heart.

Conclusions: The results of this preliminary study show that the irreversible antagonist [(18)F]3 may represent a novel strategy for imaging PPARγ in vivo with PET.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anilides / chemical synthesis
  • Anilides / pharmacokinetics*
  • Animals
  • Biological Assay / methods
  • Disease Models, Animal
  • Female
  • Fluorine Radioisotopes / pharmacokinetics*
  • Heart / diagnostic imaging
  • Heart Diseases / diagnostic imaging*
  • Ligands
  • Male
  • Mice
  • Mice, Transgenic
  • PPAR gamma / antagonists & inhibitors*
  • PPAR gamma / metabolism
  • Positron-Emission Tomography / methods
  • Rats
  • Rats, Zucker
  • Retinoid X Receptors
  • Tissue Distribution

Substances

  • 2-chloro-5-nitrobenzanilide
  • Anilides
  • Fluorine Radioisotopes
  • Ligands
  • PPAR gamma
  • Retinoid X Receptors