A two-step fluorinase enzyme mediated (18)F labelling of an RGD peptide for positron emission tomography

Chem Commun (Camb). 2015 Sep 11;51(70):13542-5. doi: 10.1039/c5cc05013h.

Abstract

A two-step radiolabelling protocol of a cancer relevant cRGD peptide is described where the fluorinase enzyme is used to catalyse a transhalogenation reaction to generate [(18)F]-5'-fluoro-5'-deoxy-2-ethynyladenosine, [(18)F]FDEA, followed by a 'click' reaction to an azide tethered cRGD peptide. This protocol offers efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37 °C in 2 hours, which was metabolically stable in rats and retained high affinity for αVβ3 integrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Proteins / metabolism*
  • Bacterial Proteins / pharmacokinetics
  • Click Chemistry
  • Fluorine Radioisotopes / pharmacokinetics
  • Male
  • Molecular Structure
  • Oligopeptides / chemistry*
  • Oxidoreductases / metabolism*
  • Oxidoreductases / pharmacokinetics
  • Peptides / chemistry*
  • Peptides / metabolism
  • Positron-Emission Tomography / methods*
  • Rats

Substances

  • Bacterial Proteins
  • Fluorine Radioisotopes
  • Oligopeptides
  • Peptides
  • arginyl-glycyl-aspartic acid
  • Oxidoreductases
  • fluorinase