Synthesis and Evaluation of
Three Structurally Related 18F‑Labeled Orvinols
of Different Intrinsic Activities:
6‑O‑[18F]Fluoroethyl-diprenorphine
([18F]FDPN), 6‑O‑[18F]Fluoroethyl-buprenorphine ([18F]FBPN), and 6‑O‑[18F]Fluoroethyl-phenethyl-orvinol ([18F]FPEO)

Schoultz, Bent W.; Hjørnevik, Trine; Reed, Brian
J.; Marton, János; Coello, Christopher
S.; Willoch, Frode; Henriksen, Gjermund

doi:10.1021/jm500503k.s001

Synthesis and Evaluation of Three Structurally Related ¹⁸F‑Labeled Orvinols of Different Intrinsic Activities: 6‑O‑[¹⁸F]Fluoroethyl-diprenorphine ([¹⁸F]FDPN), 6‑O‑[¹⁸F]Fluoroethyl-buprenorphine ([¹⁸F]FBPN), and 6‑O‑[¹⁸F]Fluoroethyl-phenethyl-orvinol ([¹⁸F]FPEO)

journal contribution

posted on 2014-06-26, 00:00 authored by Bent W. Schoultz, Trine Hjørnevik, Brian J. Reed, János Marton, Christopher S. Coello, Frode Willoch, Gjermund Henriksen

We report the synthesis and biological evaluation of a triplet of 6-O-¹⁸F-fluoroethylated derivatives of structurally related orvinols that span across the full range of intrinsic activities, the antagonist diprenorphine, the partial agonist buprenorphine, and the full agonist phenethyl-orvinol. [¹⁸F]fluoroethyl-diprenorphine, [¹⁸F]fluoroethyl-buprenorphine, and [¹⁸F]fluoroethyl-phenethyl-orvinol were prepared in high yields and quality from their 6-O-desmethyl-precursors. The results indicate suitable properties of the three 6-O-¹⁸F-fluoroethylated derivatives as functional analogues to the native carbon-11 labeled versions with similar pharmacological properties.