• Home
  • Search Results
  • Convenient synthesis of 18F-radiolabeled R-(-)-N-n-propyl-2-(3-fluoropropanoxy-11-hydroxynoraporphine.

Convenient synthesis of 18F-radiolabeled R-(-)-N-n-propyl-2-(3-fluoropropanoxy-11-hydroxynoraporphine.

Journal of labelled compounds & radiopharmaceuticals (2014-11-18)
Anna W Sromek, Shaohui Zhang, Vamsidhar Akurathi, Alan B Packard, Wei Li, David Alagille, Thomas J Morley, Ronald Baldwin, Gilles Tamagnan, John L Neumeyer
PMID25400260
ABSTRACT

Aporphines are attractive candidates for imaging D2 receptor function because, as agonists rather than antagonists, they are selective for the receptor in the high affinity state. In contrast, D2 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 D2 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.

MATERIALS
Product Number
Brand
Product Description
721964
Supelco
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 5 mm × 8 in.
721956
Sigma-Aldrich
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 3 mm × 8 in.
632546
Supelco
Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, suitable for mass spectrometry (MS), ≥99.5%
650188
Sigma-Aldrich
Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))
PHR1316
Supelco
Residual Solvent - Chloroform, Pharmaceutical Secondary Standard; Certified Reference Material
PHR1557
Supelco
Methylene Chloride, Pharmaceutical Secondary Standard; Certified Reference Material
PHR1551
Supelco
Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material
1424109
USP
Methyl alcohol, United States Pharmacopeia (USP) Reference Standard
06735
Supelco
tert-Butyldimethylsilyl chloride, for GC derivatization, LiChropur™, ≥99.0% (GC)
733466
Sigma-Aldrich
Acetonitrile, electronic grade, 99.999% trace metals basis
1601340
USP
Residual Solvent Class 2 - Acetonitrile, United States Pharmacopeia (USP) Reference Standard
M1550000
Methylene chloride, European Pharmacopoeia (EP) Reference Standard
P1472
Sigma-Aldrich
Potassium carbonate, meets USP testing specifications
675415
Sigma-Aldrich
Acetonitrile, HPLC Plus, ≥99.9%, poly-coated bottles
723851
Supelco
Dichloromethane solution, contains 10 % (v/v) methanol
40042
Supelco
Dichloromethane solution, certified reference material, 5000 μg/mL in methanol
372951
Sigma-Aldrich
tert-Butyldimethylsilyl chloride solution, 1.0 M in THF
270563
Supelco
Dichloromethane, ≥99.9%
240877
Sigma-Aldrich
p-Toluenesulfonyl chloride, ReagentPlus®, ≥99%
270717
Supelco
Acetonitrile, HPLC grade, ≥99.93%
609765
Sigma-Aldrich
Sodium hydroxide-16O solution, 20 wt. % in H216O, 99.9 atom % 16O
686530
Supelco
Acetone solution, contains 20.0 % (v/v) acetonitrile, suitable for HPLC
590681
Sigma-Aldrich
Potassium carbonate, anhydrous, powder, 99.99% trace metals basis
606723
Sigma-Aldrich
Methanol-12C, 99.95 atom % 12C
48358
Supelco
Acetone solution, certified reference material, 2000 μg/mL in methanol: water (9:1)
48538
Supelco
Dichloromethane, analytical standard, stabilized
48600
Supelco
Dichloromethane solution, certified reference material, 200 μg/mL in methanol
667390
Supelco
Methanol solution, contains 0.1 % (v/v) trifluoroacetic acid, 5 % (v/v) water, suitable for HPLC
437557
Sigma-Aldrich
Acetonitrile, ≥99.5%, ACS reagent
270997
Sigma-Aldrich
Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer