Synthesis and carbon-11 labeling of (R)- and (S)-thionisoxetine, norepinephrine reuptake inhibitors, potential radioligands for positron emission tomography.
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.
Filannino
Maria Azzurra
MA
Institute of Molecular Bioimaging and Physiology, CNR, University of Milano-Bicocca, San Raffaele Scientific Institute, Via Olgettina 60, 20132 Milan, Italy.
Matarrese
Mario
M
Turolla
Elia Anna
EA
Masiello
Valeria
V
Moresco
Rosa Maria
RM
Todde
Sergio
S
Verza
Elisa
E
Magni
Fulvio
F
Cattaneo
Angela
A
Bachi
Angela
A
Kienle
Marzia Galli
MG
Fazio
Ferruccio
F
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
D002250:Carbon Radioisotopes; D008024:Ligands; D014179:Neurotransmitter Uptake Inhibitors; D019275:Radiopharmaceuticals; D005473:Fluoxetine; C093518:thionisoxetine; D009638:Norepinephrine