Folate-PEG-NOTA-Al18F: A New Folate Based Radiotracer for PET Imaging of Folate Receptor-Positive Tumors

Mol Pharm. 2017 Dec 4;14(12):4353-4361. doi: 10.1021/acs.molpharmaceut.7b00415. Epub 2017 Nov 1.

Abstract

The folate receptor (FR) has been established as a promising target for imaging and therapy of cancer (FR-α), inflammation, and autoimmune diseases (FR-β). Several folate based PET radiotracers have been reported in the literature, but an 18F-labeled folate-PET imaging agent with optimal properties for clinical translation is still lacking. In the present study, we report the design and preclinical evaluation of folate-PEG12-NOTA-Al18F (1), a new folate-PET agent with improved potential for clinical applications. Radiochemical synthesis of 1 was achieved via a one-pot labeling process by heating folate-PEG12-NOTA in the presence of in situ prepared Al18F for 15 min at 105 °C, followed by HPLC purification. Specific binding of 1 to FR was evaluated on homogenates of KB (FR-positive) and A549 (FR-deficient) tumor xenografts in the presence and absence of excess folate. In vivo tumor imaging with folate-PEG12-NOTA-Al18F was compared to imaging with 99mTc-EC20 using nu/nu mice bearing either KB or A549 tumor xenografts. Specific accumulation of 1 in tumor and other tissues was assessed by high-resolution micro-PET and ex vivo biodistribution in the presence and absence of excess folate. Radiosynthesis of 1 was accomplished within ∼35 min, affording pure radiotracer 1 in 8.4 ± 1.3% (decay corrected) radiochemical yield with ∼100% radiochemical purity after HPLC purification and a specific activity of 35.8 ± 15.3 GBq/mmol. Further in vitro and in vivo examination of 1 demonstrated highly specific FR-mediated uptake in FR+ tumor, with Kd of ∼0.4 nM (KB), and reduced accumulation in liver. Given its facile preparation and improved properties, the new radiotracer, folate-PEG12-NOTA-Al18F (1), constitutes a promising tool for identification and classification of patients with FR overexpressing cancers.

Keywords: 18F-PET imaging; Al18F-NOTA; cancer imaging; folate conjugate; folate receptor.

Publication types

  • Comparative Study

MeSH terms

  • A549 Cells
  • Aluminum Compounds / chemistry
  • Aluminum Compounds / pharmacokinetics
  • Animals
  • Drug Evaluation, Preclinical
  • Female
  • Fluorides / chemistry
  • Fluorides / pharmacokinetics
  • Fluorine Radioisotopes / chemistry
  • Fluorine Radioisotopes / pharmacokinetics
  • Folate Receptors, GPI-Anchored / metabolism*
  • Folic Acid / analogs & derivatives
  • Folic Acid / chemistry
  • Folic Acid / pharmacokinetics
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacokinetics
  • Heterocyclic Compounds, 1-Ring
  • Humans
  • Isotope Labeling / methods
  • KB Cells
  • Mice
  • Mice, Nude
  • Neoplasms / diagnostic imaging*
  • Neoplasms / pathology
  • Organotechnetium Compounds
  • Polyethylene Glycols / chemistry
  • Polyethylene Glycols / pharmacokinetics
  • Positron-Emission Tomography / methods*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics*
  • Tissue Distribution
  • X-Ray Microtomography / methods
  • Xenograft Model Antitumor Assays

Substances

  • Aluminum Compounds
  • Fluorine Radioisotopes
  • Folate Receptors, GPI-Anchored
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 1-Ring
  • Organotechnetium Compounds
  • Radiopharmaceuticals
  • poly(ethylene glycol)-folate
  • technetium 99m EC20 folate peptide
  • Polyethylene Glycols
  • 1,4,7-triazacyclononane-N,N',N''-triacetic acid
  • Folic Acid
  • Fluorine-18
  • Fluorides
  • aluminum fluoride