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

S Thompson; M Onega; S Ashworth; I N Fleming; J Passchier; D O'Hagan

doi:10.1039/c5cc05013h

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.

Authors

S Thompson¹, M Onega, S Ashworth, I N Fleming, J Passchier, D O'Hagan

Affiliation

¹ School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. do1@st-andrews.ac.uk.

PMID: 26221637
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