title: Design and synthesis of an ¹⁸F-labeled version of phenylethyl orvinol ([¹⁸F]FE-PEO) for PET-imaging of opioid receptors.
abstract: 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.
authors.affiliation: ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany.
authors.forename: János
authors.initials: J
authors.lastname: Marton
authors.forename: Gjermund
authors.initials: G
authors.lastname: Henriksen
mesh_terms: D005462:Fluorine Radioisotopes / Q000737:chemistry*; D008024:Ligands; D057054:Molecular Imaging / Q000379:methods; D009019:Morphinans / Q000138:chemical synthesis* / Q000494:pharmacology*; D049268:Positron-Emission Tomography / Q000379:methods; D011957:Receptors, Opioid / Q000819:agonists* / Q000378:metabolism
chemical_list: D005462:Fluorine Radioisotopes; D008024:Ligands; D009019:Morphinans; D011957:Receptors, Opioid; C544195:phenylethyl orvinol