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Convenient synthesis of 18 F‐radiolabeled R‐(−)‐N‐ n ‐propyl‐2‐(3‐fluoropropanoxy‐11‐hydroxynoraporphine
Author(s) -
Sromek Anna W.,
Zhang Shaohui,
Akurathi Vamsidhar,
Packard Alan B.,
Li Wei,
Alagille David,
Morley Thomas J.,
Baldwin Ronald,
Tamagnan Gilles,
Neumeyer John L.
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3246
Subject(s) - chemistry , specific activity , in vitro , radiochemistry , tosyl , stereochemistry , biochemistry , enzyme
Aporphines are attractive candidates for imaging D 2 receptor function because, as agonists rather than antagonists, they are selective for the receptor in the high affinity state. In contrast, D 2 antagonists do not distinguish between the high and low affinity states, and in vitro data suggests that this distinction may be important in studying diseases characterized by D 2 dysregulation, such as schizophrenia and Parkinson's disease. Accordingly, MCL‐536 (R‐(−)‐N‐n‐propyl‐2‐(3‐[ 18 F]fluoropropanoxy‐11‐hydroxynoraporphine) was selected for labeling with 18 F based on in vitro data obtained for the non‐radioactive ( 19 F) compound. Fluorine‐18‐labeled MCL‐536 was synthesized in 70% radiochemical yield, >99% radiochemical purity, and specific activity of 167 GBq/µmol (4.5 Ci/µmol) using p ‐toluenesulfonyl (tosyl) both as a novel protecting group for the phenol and a leaving group for the radiofluorination.