Design and synthesis of an ¹⁸F-labeled version of phenylethyl orvinol ([¹⁸F]FE-PEO) for PET-imaging of opioid receptors

The semisynthetic oripavine derivative phenethyl orvinol (PEO), a full agonist at opioid receptors (OR), is an attractive structural motif for developing ¹⁸F-labeled PET tracers with a high degree of sensitivity for competition between endogenous and exogenous OR-ligands. The target cold reference c...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2012-09, Vol.17 (10), p.11554-11569
Main Authors: Marton, János, Henriksen, Gjermund
Format: Article
Language:English
Subjects:
18F-fluorination
agonist
automated radiosynthesis
Fluorine Radioisotopes - chemistry
Ligands
Molecular Imaging - methods
Morphinans - chemical synthesis
Morphinans - pharmacology
Narcotics
opioid receptors
PET
Positron-Emission Tomography - methods
Receptors, Opioid - agonists
Receptors, Opioid - metabolism
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Summary:The semisynthetic oripavine derivative phenethyl orvinol (PEO), a full agonist at opioid receptors (OR), is an attractive structural motif for developing ¹⁸F-labeled PET tracers with a high degree of sensitivity for competition between endogenous and exogenous OR-ligands. The target cold reference compound 6-O-(2-fluoroethyl)-6-O-desmethylphenylethyl orvinol (FE-PEO) was obtained via two separate reaction routes. A three-step synthesis was developed for the preparation of a tosyloxyethyl precursor (TE-TDPEO), the key precursor for a direct, nucleophilic radiofluorination to yield [¹⁸F]FE-PEO. The developed radiosynthesis provides the target compound in relevantly high yield and purity, and is adaptable to routine production.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules171011554