Synthesis and preliminary evaluation of 18-(18)F-fluoro-4-thia-oleate as a PET probe of fatty acid oxidation

J Nucl Med. 2010 Aug;51(8):1310-7. doi: 10.2967/jnumed.109.074245. Epub 2010 Jul 21.

Abstract

Fatty acid oxidation (FAO) is a major energy-providing process with important implications in cardiovascular, oncologic, neurologic, and metabolic diseases. A novel 4-thia oleate analog, 18-(18)F-fluoro-4-thia-oleate ((18)F-FTO), was evaluated in relationship to the previously developed palmitate analog 16-(18)F-fluoro-4-thia-palmitate ((18)F-FTP) as an FAO probe.

Methods: (18)F-FTO was synthesized from a corresponding bromoester. Biodistribution and metabolite analysis studies were performed in rats. Preliminary small-animal PET studies were performed with (18)F-FTO and (18)F-FTP in rats.

Results: A practical synthesis of (18)F-FTO was developed, providing a radiotracer of high radiochemical purity (>99%). In fasted rats, myocardial uptake of (18)F-FTO (0.70 +/- 0.30% dose kg [body mass]/g [tissue mass]) was similar to that of (18)F-FTP at 30 min after injection. At 2 h, myocardial uptake of (18)F-FTO was maintained, whereas (18)F-FTP uptake in the heart was 82% reduced. Similar to (18)F-FTP, (18)F-FTO uptake by the heart was approximately 80% reduced at 30 min by pretreatment of rats with the CPT-I inhibitor etomoxir. Folch-type extraction analyses showed 70-90% protein-bound fractions in the heart, liver, and skeletal muscle, consistent with efficient trafficking of (18)F-FTO to the mitochondrion with subsequent metabolism to protein-bound species. Preliminary small-animal PET studies showed rapid blood clearance and avid extraction of (18)F-FTO and of (18)F-FTP into the heart and liver. Images of (18)F-FTO accumulation in the rat myocardium were clearly superior to those of (18)F-FTP.

Conclusion: (18)F-FTO is shown to be a promising metabolically trapped FAO probe that warrants further evaluation.

Publication types

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

MeSH terms

  • Animals
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / pharmacology
  • Epoxy Compounds / pharmacology
  • Fatty Acids / metabolism*
  • Female
  • Heart / diagnostic imaging
  • Myocardium / metabolism
  • Oleic Acids / chemical synthesis*
  • Oxidation-Reduction
  • Palmitates
  • Positron-Emission Tomography / methods*
  • Radiopharmaceuticals / chemical synthesis*
  • Rats
  • Rats, Sprague-Dawley
  • Sulfides / chemical synthesis*
  • Thiones
  • Tissue Distribution

Substances

  • 16-fluoro-4-thiapalmitic acid
  • 18-fluoro-4-thiaoleic acid
  • Enzyme Inhibitors
  • Epoxy Compounds
  • Fatty Acids
  • Oleic Acids
  • Palmitates
  • Radiopharmaceuticals
  • Sulfides
  • Thiones
  • etomoxir