Synthesis and Evaluation of a Novel PET Radioligand for Imaging Glutaminyl Cyclase Activity as a Biomarker for Detecting Alzheimer's Disease

ACS Sens. 2024 May 24;9(5):2605-2613. doi: 10.1021/acssensors.4c00313. Epub 2024 May 8.

Abstract

Several new lines of research have demonstrated that a significant number of amyloid-β peptides found in Alzheimer's disease (AD) are truncated and undergo post-translational modification by glutaminyl cyclase (QC) at the N-terminal. Notably, QC's products of Abeta-pE3 and Abeta-pE11 have been active targets for investigational drug development. This work describes the design, synthesis, characterization, and in vivo validation of a novel PET radioligand, [18F]PB0822, for targeted imaging of QC. We report herein a simplified and robust chemistry for the synthesis of the standard compound, [19F]PB0822, and the corresponding [18F]PB0822 radioligand. The PET probe was developed with 99.9% radiochemical purity, a molar activity of 965 Ci.mmol-1, and an IC50 of 56.3 nM, comparable to those of the parent PQ912 inhibitor (62.5 nM). Noninvasive PET imaging showed that the probe is distributed in the brain 5 min after intravenous injection. Further, in vivo PET imaging with [18F]PB0822 revealed that AD 5XFAD mice harbor significantly higher QC activity than WT counterparts. The data also suggested that QC activity is found across different brain regions of the tested animals.

Keywords: Alzheimer’s disease; PET imaging; [18F]PB0822; glutaminyl cyclase; pyroglutamate Abeta.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • Alzheimer Disease* / diagnostic imaging
  • Alzheimer Disease* / metabolism
  • Aminoacyltransferases* / antagonists & inhibitors
  • Aminoacyltransferases* / metabolism
  • Amyloid beta-Peptides / analysis
  • Amyloid beta-Peptides / metabolism
  • Animals
  • Biomarkers / metabolism
  • Brain / diagnostic imaging
  • Brain / enzymology
  • Brain / metabolism
  • Fluorine Radioisotopes / chemistry
  • Humans
  • Ligands
  • Mice
  • Positron-Emission Tomography* / methods
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / chemistry

Substances

  • glutaminyl-peptide cyclotransferase
  • Aminoacyltransferases
  • Fluorine Radioisotopes
  • Radiopharmaceuticals
  • Biomarkers
  • Amyloid beta-Peptides
  • Ligands