title: Last-Step Enzymatic [(18) F]-Fluorination of Cysteine-Tethered RGD Peptides Using Modified Barbas Linkers.
abstract: We report a last-step fluorinase-catalyzed [(18) F]-fluorination of a cysteine-containing RGD peptide. The peptide was attached through sulfur to a modified and more hydrophilic variant of the recently disclosed Barbas linker which was itself linked to a chloroadenosine moiety via a PEGylated chain. The fluorinase was able to use this construct as a substrate for a transhalogenation reaction to generate [(18) F]-radiolabeled RGD peptides, which retained high affinity to cancer-cell relevant αv β3 integrins.
authors.affiliation: School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK.
authors.forename: Qingzhi
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: John Mallard Scottish PET Centre, School of Medicine, Medical Sciences and Nutrition, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, UK.
authors.forename: Sergio
authors.initials: S
authors.lastname: Dall'Angelo
authors.affiliation: Aberdeen Biomedical Imaging Centre, Institute of Medical Sciences, Foresterhill, Aberdeen, AB25 2ZD, UK.
authors.forename: Ian N
authors.initials: IN
authors.lastname: Fleming
authors.affiliation: John Mallard Scottish PET Centre, School of Medicine, Medical Sciences and Nutrition, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, UK.
authors.forename: Lutz F
authors.initials: LF
authors.lastname: Schweiger
authors.affiliation: John Mallard Scottish PET Centre, School of Medicine, Medical Sciences and Nutrition, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, UK. m.zanda@abdn.ac.uk.
authors.forename: Matteo
authors.initials: M
authors.lastname: Zanda
authors.affiliation: School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK. do1@st-andrews.ac.uk.
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D010455:Peptides
chemical_list: D005462:Fluorine Radioisotopes; D010455:Peptides; D003545:Cysteine
keywords: 18F labeling; Barbas linker; RGD peptide; bioconjugation; chemical biology