Synthesis and characterization of (18)F-labeled active site inhibited factor VII (ASIS)

J Labelled Comp Radiopharm. 2015 May 15;58(5):196-201. doi: 10.1002/jlcr.3282. Epub 2015 Mar 27.

Abstract

Activated factor VII blocked in the active site with Phe-Phe-Arg-chloromethyl ketone (active site inhibited factor VII (ASIS)) is a 50-kDa protein that binds with high affinity to its receptor, tissue factor (TF). TF is a transmembrane glycoprotein that plays an important role in, for example, thrombosis, metastasis, tumor growth, and tumor angiogenesis. The aim of this study was to develop an (18)F-labeled ASIS derivative to assess TF expression in tumors. Active site inhibited factor VII was labeled using N-succinimidyl-4-[(18)F]fluorobenzoate, and the [(18)F]ASIS was purified on a PD-10 desalting column. The radiochemical yield was 25 ± 6%, the radiochemical purity was >97%, and the pseudospecific radioactivity was 35 ± 9 GBq/µmol. The binding efficacy was evaluated in pull-down experiments, which monitored the binding of unlabeled ASIS and [(18)F]ASIS to TF and to a specific anti-factor VII antibody (F1A2-mAb). No significant difference in binding efficacy between [(18)F]ASIS and ASIS could be detected. Furthermore, [(18)F]ASIS was relatively stable in vitro and in vivo in mice. In conclusion, [(18)F]ASIS has for the first time been successfully synthesized as a possible positron emission tomography tracer to image TF expression levels. In vivo positron emission tomography studies to evaluate the full potential of [(18)F]ASIS are in progress.

Keywords: 18F; PET; [18F]SFB; active site inhibited factor VII; molecular imaging; protein labeling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Chloromethyl Ketones / chemistry*
  • Amino Acid Chloromethyl Ketones / pharmacology
  • Animals
  • Catalytic Domain
  • Factor VII / antagonists & inhibitors
  • Factor VII / chemistry*
  • Fluorine Radioisotopes / chemistry
  • Mice
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Tissue Distribution

Substances

  • Amino Acid Chloromethyl Ketones
  • Fluorine Radioisotopes
  • Radiopharmaceuticals
  • phenylalanyl-phenylalanyl-arginine chloromethyl ketone
  • Factor VII