title: Synthesis of new hypoxia markers EF1 and [18F]-EF1.
abstract: We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl)-N-(3-fluoropropyl)acetamide (EF1) and its 18F analog, 2-(2-nitroimidazol-1[H]-yl)-N- (3-[18F]fluoropropyl)acetamide ([18F]-EF1). Two methods for the preparation of 3-fluoropropylamine, the EF1 side chain, are described. [18F]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic substitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl)acetamide (EBr1) by carrier-added 18F in DMSO at 120 degrees C. Our results demonstrate the preparation of clinically relevant amounts of [18F]-EF1 for use as a non-invasive hypoxia marker with detection using positron emission tomography (PET).
authors.affiliation: Department of Radiation Oncology, University of Pennsylvania, Philadelphia 19104, USA.
authors.forename: A V
authors.initials: AV
authors.lastname: Kachur
authors.forename: W R
authors.initials: WR
authors.lastname: Dolbier
authors.forename: S M
authors.initials: SM
authors.lastname: Evans
authors.forename: C Y
authors.initials: CY
authors.lastname: Shiue
authors.forename: G G
authors.initials: GG
authors.lastname: Shiue
authors.forename: K A
authors.initials: KA
authors.lastname: Skov
authors.forename: I R
authors.initials: IR
authors.lastname: Baird
authors.forename: B R
authors.initials: BR
authors.lastname: James
authors.forename: A R
authors.initials: AR
authors.lastname: Li
authors.forename: A
authors.initials: A
authors.lastname: Roche
authors.forename: C J
authors.initials: CJ
authors.lastname: Koch
mesh_terms: D015415:Biomarkers / Q000032:analysis; D005462:Fluorine Radioisotopes / Q000737:chemistry; D000860:Hypoxia / Q000175:diagnosis* / Q000378:metabolism; D007553:Isotope Labeling / Q000379:methods; D009593:Nitroimidazoles / Q000138:chemical synthesis*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D014055:Tomography, Emission-Computed
chemical_list: C402596:2-(2-nitroimidazol-1H-yl)-N-(3-fluoropropyl)acetamide; D015415:Biomarkers; D005462:Fluorine Radioisotopes; D009593:Nitroimidazoles; D019275:Radiopharmaceuticals