Structure--activity relationship and preclinical evaluation of carbon-11-labeled ammonium salts as PET--myocardial perfusion imaging agents

Mol Imaging Biol. 2012 Oct;14(5):625-36. doi: 10.1007/s11307-011-0539-6.

Abstract

Background: Due to the limited availability of suitable positron emission tomography (PET) tracers, the majority of myocardial perfusion imaging (MPI) scans is performed using SPECT rather than PET.

Aim: The aim of this study is to design and synthesize carbon-11-labeled ammonium salt derivatives and explore their structure–activity relationship (SAR) and their potential as PET–MPI agents.

Methods and results: Three carbon-11-labeled ammonium salts were developed. SAR of the labeled compounds were explored vis-à-vis the effects of charge density and lipophilicity on the distribution kinetics in mice. These studies pointed at [11C]4 as the lead compound. Comparative microPET/CT scans in healthy rats, using both [11C]4 and [13 N]–NH3, substantiated the potential of [11C]4 ([11C]-DMDPA). A proof of concept for the potential of radiolabeled ammonium salts as MPI agents has been demonstrated in a newly developed swine model of permanent partial coronary artery occlusion.

Conclusions: SAR studies of 11C-labeled ammonium salts suggest that both lipophilicity and charge density affect the performance of these compounds as MPI probes. In a swine model, the labeled lead successfully visualized the defect regions in the myocardium. The data presented call for the development of fluorine-18 analogues, to increase clinical impact.

MeSH terms

  • Animals
  • Carbon Radioisotopes* / pharmacokinetics
  • Isotope Labeling*
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Myocardial Infarction / diagnostic imaging
  • Myocardial Ischemia / diagnostic imaging
  • Myocardial Perfusion Imaging*
  • Positron-Emission Tomography*
  • Quaternary Ammonium Compounds / chemistry*
  • Rats
  • Salts* / chemistry
  • Structure-Activity Relationship
  • Sus scrofa
  • Time Factors
  • Tissue Distribution

Substances

  • Carbon Radioisotopes
  • Quaternary Ammonium Compounds
  • Salts