Synthesis and evaluation of radioiodinated 1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging

Bioorg Med Chem. 2017 Oct 15;25(20):5576-5585. doi: 10.1016/j.bmc.2017.08.025. Epub 2017 Aug 16.

Abstract

Platelet-derived growth factor receptor β (PDGFRβ) is a transmembrane tyrosine kinase receptor and it is upregulated in various malignant tumors. Radiolabeled PDGFRβ inhibitors can be a convenient tool for the imaging of tumors overexpressing PDGFRβ. In this study, [125I]-1-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinoline-8-yl}piperidin-4-amine ([125I]IIQP) and [125I]-N-3-iodobenzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}-piperidin-4-amine ([125I]IB-IQP) were designed and synthesized, and their potential as PDGFRβ imaging agents was evaluated. In cellular uptake experiments, [125I]IIQP and [125I]IB-IQP showed higher uptake by PDGFRβ-positive cells than by PDGFRβ-negative cells, and the uptake in PDGFRβ-positive cells was inhibited by co-culture with PDGFRβ ligands. The biodistribution of both radiotracers in normal mice exhibited hepatobiliary excretion as the main route. In mice inoculated with BxPC3-luc (PDGFRβ-positive), the tumor uptake of radioactivity at 1h after the injection of [125I]IIQP was significantly higher than that after the injection of [125I]IB-IQP. These results indicated that [125I]IIQP can be a suitable PDGFRβ imaging agent. However, further modification of its structure will be required to obtain a more appropriate PDGFRβ-targeted imaging agent with a higher signal/noise ratio.

Keywords: Molecular imaging; PDGFRβ; Radiotracer; Tyrosine kinase inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Female
  • Humans
  • Iodine Radioisotopes
  • MCF-7 Cells
  • Mammary Neoplasms, Experimental / diagnosis*
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Molecular Imaging*
  • Molecular Probes / chemical synthesis
  • Molecular Probes / chemistry*
  • Molecular Probes / pharmacokinetics
  • Molecular Structure
  • Receptor, Platelet-Derived Growth Factor beta / analysis*
  • Tissue Distribution

Substances

  • Iodine Radioisotopes
  • Molecular Probes
  • PDGFRB protein, human
  • Receptor, Platelet-Derived Growth Factor beta