Abstract
We report the synthesis and biological evaluation of a triplet of 6-O-(18)F-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. [(18)F]fluoroethyl-diprenorphine, [(18)F]fluoroethyl-buprenorphine, and [(18)F]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-(18)F-fluoroethylated derivatives as functional analogues to the native carbon-11 labeled versions with similar pharmacological properties.
MeSH terms
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Animals
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Brain / diagnostic imaging
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Brain / metabolism
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Buprenorphine / analogs & derivatives*
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Buprenorphine / chemical synthesis
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Buprenorphine / chemistry
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Buprenorphine / pharmacokinetics
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CHO Cells
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Carbon Radioisotopes
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Cricetulus
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Diprenorphine / analogs & derivatives*
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Diprenorphine / chemical synthesis
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Diprenorphine / chemistry
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Diprenorphine / pharmacokinetics
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Fluorine Radioisotopes
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Humans
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Morphinans / chemical synthesis*
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Morphinans / chemistry
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Morphinans / pharmacokinetics
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Narcotic Antagonists
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Positron-Emission Tomography
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Radioligand Assay
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Radiopharmaceuticals / chemical synthesis*
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Radiopharmaceuticals / chemistry
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Radiopharmaceuticals / pharmacokinetics
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Rats
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Receptors, Opioid / agonists
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Receptors, Opioid / metabolism
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Structure-Activity Relationship
Substances
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6-O-(2-fluoroethyl)buprenorphine
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6-O-(2-fluoroethyl)diprenorphine
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6-O-(2-fluoroethyl)phenethylorvinol
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Carbon Radioisotopes
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Fluorine Radioisotopes
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Morphinans
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Narcotic Antagonists
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Radiopharmaceuticals
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Receptors, Opioid
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Diprenorphine
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Buprenorphine