title: Synthesis and application of 4-[(18)F]fluorobenzylamine: A versatile building block for the preparation of PET radiotracers.
abstract: A novel synthesis of 4-[(18)F]fluorobenzylamine ([(18)F]FBA) by means of transition metal-assisted sodium borohydride reduction of 4-[(18)F]fluorobenzonitrile ([(18)F]FBN) is described. This approach could successfully be extended to borohydride exchange resin (BER) enabling a viable option for use in automated syntheses. [(18)F]FBA was used for the synthesis of 4-[(18)F]fluorobenzylamine-based thiol group-reactive prosthetic groups 4-[(18)F]fluorobenzyl-2-bromoacetamide ([(18)F]FBBA) and 4-[(18)F]fluorobenzylamidopropionyl maleimide ([(18)F]FBAPM). [(18)F]FBBA and [(18)F]FBAPM were obtained in radiochemical yields of 75% and 55%, respectively. Feasibility of using [(18)F]FBAPM as novel prosthetic group for peptide and protein labelling was demonstrated with cysteine-containing tripeptide glutathione (GSH). [(18)F]FBBA was used for labelling of a fully phosphorothioated 20mer oligodesoxynucleotide (ODN).
authors.affiliation: Department of Oncology, University of Alberta, 11560 University Ave, Edmonton, AB T6G 1Z2, Canada.
authors.forename: Ingrid
authors.initials: I
authors.lastname: Koslowsky
authors.forename: John
authors.initials: J
authors.lastname: Mercer
authors.forename: Frank
authors.initials: F
authors.lastname: Wuest
mesh_terms: D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D001894:Borohydrides / Q000737:chemistry; D005462:Fluorine Radioisotopes; D007553:Isotope Labeling; D015345:Oligonucleotide Probes / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry; D049268:Positron-Emission Tomography; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*
chemical_list: D001549:Benzamides; D001894:Borohydrides; D005462:Fluorine Radioisotopes; D015345:Oligonucleotide Probes; D009842:Oligopeptides; D019275:Radiopharmaceuticals; C114760:4-fluorobenzylamine; C025364:sodium borohydride