Synthesis, radiolabeling and initial in vivo evaluation of [(11)C]KSM-01 for imaging PPAR-α receptors

Bioorg Med Chem Lett. 2012 Oct 1;22(19):6233-6. doi: 10.1016/j.bmcl.2012.08.010. Epub 2012 Aug 9.

Abstract

Peroxisome proliferator-activated receptor alpha (PPAR-α) is a ligand-activated nuclear receptor transcription factor that regulates the fatty acid β-oxidation. An in vitro assay identified the p-methoxy phenyl ureido thiobutyric acid derivative KSM-01 (IC(50)=0.28±0.09nM) having a higher affinity to activate PPAR-α than the PPAR-α agonist GW7647 (IC(50)=0.46±0.19nM). In this study, we report the synthesis and initial in vivo evaluation of [(11)C]KSM-01. The radiosynthesis was carried out by first alkylating the corresponding p-phenol precursor with [(11)C]MeI in DMF using NaOH, followed by deprotection of the t-butyl ester group by TFA, yielding [(11)C]KSM-01. SUV analysis of dynamic micro PET/CT imaging data showed that [(11)C]KSM-01 accumulation was ∼2.0-fold greater in cardiac-specific PPAR-α overexpressing transgenic mice compared to wild-type littermates. The post-PET biodistribution studies were consistent with these results and demonstrated 2.5-fold greater radiotracer uptake in the heart of transgenic mice compared to the wild-type littermates. These results demonstrate the potential utility of PPAR-α agonists as PET radiopharmaceuticals.

Publication types

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

MeSH terms

  • Animals
  • Butyrates / chemical synthesis
  • Butyrates / chemistry
  • Butyrates / pharmacology*
  • Humans
  • Isotope Labeling*
  • Mice
  • Mice, Transgenic
  • PPAR alpha / agonists*
  • Phenylurea Compounds / chemical synthesis
  • Phenylurea Compounds / chemistry
  • Phenylurea Compounds / pharmacology*
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacology*
  • Tissue Distribution
  • Tomography, X-Ray Computed

Substances

  • ((11)C)KSM-01
  • Butyrates
  • PPAR alpha
  • Phenylurea Compounds
  • Radiopharmaceuticals