title: Automated radiosynthesis of N-succinimidyl 3-(di-tert-butyl[(18)F]fluorosilyl)benzoate ([(18)F]SiFB) for peptides and proteins radiolabeling for positron emission tomography.
abstract: Recently, silicon fluoride building blocks (SiFA) have emerged as valuable and promising tools to overcome challenges in the labeling of peptides and proteins for positron emission tomography (PET). Herein, we report a fully automated synthesis of N-succinimidyl 3-(di-tert-butyl[(18)F]fluorosilyl)benzoate ([(18)F]SiFB) by a commercially available Scintomics Hot Box 3 synthesis module, to be used as a prosthetic group for peptide and protein labeling. The drying of K2.2.2./K (18)F complex was performed according to the Munich method modified by our group (avoiding azeotropic drying) using oxalic acid to neutralize the base from the (18)F(-) containing QMA eluent. This K2.2.2./K (18)F complex was then used for SiFA (18)F-(19)F isotopic exchange followed by a fast purification by a solid-phase-extraction (SPE) to afford [(18)F]SiFB with an average preparative radiochemical yield (RCY) of 24±1% (non-decay corrected (NDC)) within a synthesis time of 30 min. The [(18)F]SiFB produced by automated synthesis was then used for the (18)F-labeling of rat serum albumin (RSA) as a proof of applicability.
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada. Electronic address: radouane.koudih@mail.mcgill.ca.
authors.forename: R
authors.initials: R
authors.lastname: Koudih
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada.
authors.forename: A
authors.initials: A
authors.lastname: Kostikov
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada.
authors.forename: M
authors.initials: M
authors.lastname: Kovacevic
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada.
authors.forename: D
authors.initials: D
authors.lastname: Jolly
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada.
authors.forename: V
authors.initials: V
authors.lastname: Bernard-Gauthier
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada.
authors.forename: J
authors.initials: J
authors.lastname: Chin
authors.affiliation: Department of Inorganic Chemistry II, Faculty of Chemistry, TU Dortmund, Otto-Hahn-Str. 6, 44221 Dortmund, Germany.
authors.forename: K
authors.initials: K
authors.lastname: Jurkschat
authors.affiliation: Biomedical Chemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, Mannheim, Germany.
authors.forename: C
authors.initials: C
authors.lastname: Wängler
authors.affiliation: Molecular Imaging and Radiopharmaceutical Chemistry, Department of Clinical Radiology and Nuclear Medicine, Medical Faculty Mannheim of Heidelberg University, Mannheim, Germany.
authors.forename: B
authors.initials: B
authors.lastname: Wängler
authors.affiliation: McConnell Brain Imaging Centre, Montreal Neurological Institute, McGill University, 3801 University Street, Montreal, Quebec, Canada. Electronic address: ralf.schirrmacher@mcgill.ca.
authors.forename: R
authors.initials: R
authors.lastname: Schirrmacher
mesh_terms: D000818:Animals; D005459:Fluorides / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D007553:Isotope Labeling / Q000295:instrumentation / Q000379:methods; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D011854:Radiochemistry / Q000295:instrumentation / Q000379:methods; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D051381:Rats; D012709:Serum Albumin / Q000737:chemistry; D017655:Silicon Compounds / Q000737:chemistry; D013388:Succinimides / Q000138:chemical synthesis*
chemical_list: D005462:Fluorine Radioisotopes; C572729:N-succinimidyl 3-(di-tert-butylfluorosilyl)benzoate; D017646:Organosilicon Compounds; D019275:Radiopharmaceuticals; D012709:Serum Albumin; D017655:Silicon Compounds; D013388:Succinimides; C054375:silicon fluoride; D005459:Fluorides
keywords: Automated synthesis; Biomolecules labeling; Fluorine 18; PET imaging; SiFA; Silicon–fluoride building blocks