Site-Specific 64Cu Labeling of the Serine Protease, Active Site Inhibited Factor Seven Azide (FVIIai-N3), Using Copper Free Click Chemistry

Bioconjug Chem. 2018 Jan 17;29(1):117-125. doi: 10.1021/acs.bioconjchem.7b00649. Epub 2017 Dec 21.

Abstract

A method for site-specific radiolabeling of the serine protease active site inhibited factor seven (FVIIai) with 64Cu has been applied using a biorthogonal click reaction. FVIIai binds to tissue factor (TF), a trans-membrane protein involved in hemostasis, angiogenesis, proliferation, cell migration, and survival of cancer cells. First a single azide moiety was introduced in the active site of this 50 kDa protease. Then a NOTA moiety was introduced via a strain promoted azide-alkyne reaction and the corresponding conjugate was labeled with 64Cu. Binding to TF and the stability was evaluated in vitro. TF targeting capability of the radiolabeled conjugate was tested in vivo by positron emission tomography (PET) imaging in pancreatic human xenograft cancer mouse models with various TF expressions. The conjugate showed good stability (>91% at 16 h), an immunoreactivity of 93.5%, and a mean tumor uptake of 2.1 ± 0.2%ID/g at 15 h post injection. In conclusion, FVIIai was radiolabeled with 64Cu in single well-defined position of the protein. This method can be utilized to prepare conjugates from serine proteases with the label at a specific position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Azides / chemistry*
  • Catalytic Domain
  • Cell Line, Tumor
  • Click Chemistry / methods*
  • Copper Radioisotopes / chemistry*
  • Factor VII / chemistry*
  • Factor VII / pharmacology
  • Female
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds, 1-Ring
  • Humans
  • Isotope Labeling / methods
  • Mice
  • Mice, Nude
  • Pancreatic Neoplasms / diagnostic imaging*
  • Positron Emission Tomography Computed Tomography / methods
  • Serine Proteases / chemistry*
  • Serine Proteases / pharmacology
  • Thromboplastin / analysis*

Substances

  • Azides
  • Copper Radioisotopes
  • Copper-64
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 1-Ring
  • 1,4,7-triazacyclononane-N,N',N''-triacetic acid
  • Factor VII
  • Thromboplastin
  • Serine Proteases