Development of an 18F-Labeled Irreversible Inhibitor of Transglutaminase 2 as Radiometric Tool for Quantitative Expression Profiling in Cells and Tissues

J Med Chem. 2021 Mar 25;64(6):3462-3478. doi: 10.1021/acs.jmedchem.1c00096. Epub 2021 Mar 11.

Abstract

The transamidase activity of transglutaminase 2 (TGase 2) is considered to be important for several pathophysiological processes including fibrotic and neoplastic tissue growth, whereas in healthy cells this enzymatic function is predominantly latent. Methods that enable the highly sensitive detection of TGase 2, such as application of radiolabeled activity-based probes, will support the exploration of the enzyme's function in various diseases. In this context, the radiosynthesis and detailed in vitro radiopharmacological evaluation of an 18F-labeled Nε-acryloyllysine piperazide are reported. Robust and facile detection of the radiotracer-TGase 2 complex by autoradiography of thin layer plates and polyacrylamide gels after chromatographic and electrophoretic separation owing to irreversible covalent bond formation was demonstrated for the isolated protein, cell lysates, and living cells. By use of this radiotracer, quantitative data on the expression profile of activatable TGase 2 in mouse organs and selected tumors were obtained for the first time by autoradiography of tissue sections.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Fluorine Radioisotopes / chemistry*
  • GTP-Binding Proteins / analysis*
  • GTP-Binding Proteins / antagonists & inhibitors
  • Humans
  • Lysine / analogs & derivatives*
  • Lysine / chemical synthesis
  • Mice
  • Neoplasms / enzymology
  • Neoplasms / pathology
  • Piperazines / chemical synthesis
  • Piperazines / chemistry*
  • Protein Glutamine gamma Glutamyltransferase 2
  • Transglutaminases / analysis*
  • Transglutaminases / antagonists & inhibitors

Substances

  • Fluorine Radioisotopes
  • Piperazines
  • Protein Glutamine gamma Glutamyltransferase 2
  • Transglutaminases
  • GTP-Binding Proteins
  • Fluorine-18
  • Lysine