title: 18F-fluorothiols: a new approach to label peptides chemoselectively as potential tracers for positron emission tomography.
abstract: [(18)F]Fluorothiols are a new generation of peptide labeling reagents. This article describes the preparation of suitable methanesulfonyl precursors and their use in no-carrier-added radiosyntheses of (18)F-fluorothiols. The preparations of (3-[(18)F]fluoropropylsulfanyl)triphenylmethane, (2-[2-[2-(2-[(18)F]fluoroethoxy)ethoxy]ethoxy]ethylsulfanyl)triphenylmethane, and 4-[(18)F]fluoromethyl-N-[2-triphenylmethanesulfanyl)ethyl]benzamide starting from the corresponding methanesulfonyl precursors were investigated. Following the removal of the triphenylmethane protecting group, the (18)F-fluorothiols were reacted with the N-terminal chloroacetylated model peptide ClCH(2)C(O)-LysGlyPheGlyLys. The corresponding radiochemical yields of (18)F-labeled isolated model peptide, decay-corrected to (18)F fluoride, were 10%, 32%, and 1%, respectively. These results indicate a considerable potential of (18)F-fluorothiols for the chemoselective labeling of peptides as tracers for positron emission tomography (PET).
authors.affiliation: Hammersmith Hospital, Hammersmith Imanet Ltd., Du Cane Road, London W12 0NN, U.K. mglaser@csc.mrc.ac.uk
authors.forename: Matthias
authors.initials: M
authors.lastname: Glaser
authors.forename: Hege
authors.initials: H
authors.lastname: Karlsen
authors.forename: Magne
authors.initials: M
authors.lastname: Solbakken
authors.forename: Joseph
authors.initials: J
authors.lastname: Arukwe
authors.forename: Frank
authors.initials: F
authors.lastname: Brady
authors.forename: Sajinder K
authors.initials: SK
authors.lastname: Luthra
authors.forename: Alan
authors.initials: A
authors.lastname: Cuthbertson
mesh_terms: D005462:Fluorine Radioisotopes / Q000032:analysis* / Q000737:chemistry; D010446:Peptide Fragments / Q000032:analysis* / Q000737:chemistry; D049268:Positron-Emission Tomography / Q000379:methods*; D011849:Radioactive Tracers
chemical_list: D005462:Fluorine Radioisotopes; D010446:Peptide Fragments; D011849:Radioactive Tracers