title: Synthesis and carbon-11 labeling of (R)- and (S)-thionisoxetine, norepinephrine reuptake inhibitors, potential radioligands for positron emission tomography.
abstract: Standards and des-methyl precursors of (R)- and (S)-thionisoxetine, potent and selective norepinephrine reuptake inhibitors, were synthesized and radiolabeled with carbon-11. Both enantiomers of the N-methyl-3-(2-thiomethylphenoxy)-3-phenylpropanamine and the 3-(2-thiomethylphenoxy)-3-phenylpropylamine were obtained via multi-step syntheses, while the radiosyntheses were carried out using [11C]CH3I. The radiochemical yields were 26%, decay corrected and the specific radioactivity ranging from 2 to 3 Ci/micromol. The HPLC analyses were performed using a chiral column: during the radiolabeling, no racemization occurred and the isomers were synthesized with high enantiomeric purity.
authors.affiliation: Institute of Molecular Bioimaging and Physiology, CNR, University of Milano-Bicocca, San Raffaele Scientific Institute, Via Olgettina 60, 20132 Milan, Italy.
authors.forename: Maria Azzurra
authors.initials: MA
authors.lastname: Filannino
authors.forename: Mario
authors.initials: M
authors.lastname: Matarrese
authors.forename: Elia Anna
authors.initials: EA
authors.lastname: Turolla
authors.forename: Valeria
authors.initials: V
authors.lastname: Masiello
authors.forename: Rosa Maria
authors.initials: RM
authors.lastname: Moresco
authors.forename: Sergio
authors.initials: S
authors.lastname: Todde
authors.forename: Elisa
authors.initials: E
authors.lastname: Verza
authors.forename: Fulvio
authors.initials: F
authors.lastname: Magni
authors.forename: Angela
authors.initials: A
authors.lastname: Cattaneo
authors.forename: Angela
authors.initials: A
authors.lastname: Bachi
authors.forename: Marzia Galli
authors.initials: MG
authors.lastname: Kienle
authors.forename: Ferruccio
authors.initials: F
authors.lastname: Fazio
mesh_terms: D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D005473:Fluoxetine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006801:Humans; D007553:Isotope Labeling; D008024:Ligands; D014179:Neurotransmitter Uptake Inhibitors / Q000138:chemical synthesis*; D009638:Norepinephrine / Q000502:physiology*; D049268:Positron-Emission Tomography / Q000379:methods*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis
chemical_list: D002250:Carbon Radioisotopes; D008024:Ligands; D014179:Neurotransmitter Uptake Inhibitors; D019275:Radiopharmaceuticals; D005473:Fluoxetine; C093518:thionisoxetine; D009638:Norepinephrine