Synthesis and preliminary evaluation of (R,R)(S,S) 5-(2-(2-[4-(2-[(18)F]fluoroethoxy)phenyl]-1-methylethylamino)-1-hydroxyethyl)-benzene-1,3-diol ([(18)F]FEFE) for the in vivo visualisation and quantification of the beta2-adrenergic receptor status in lung

The (18)F-labeled beta2-adrenergic receptor ligand (R,R)(S,S) 5-(2-(2-[4-(2-[(18)F]fluoroethoxy)phenyl]-1-methylethylamino)-1-hydroxyethyl)-benzene-1,3-diol, a derivative of the original highly selective racemic fenoterol, was synthesized in an overall radiochemical yield of 20% after 65 min with a...

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Published in:Bioorganic & medicinal chemistry letters 2003-08, Vol.13 (16), p.2687-2692
Main Authors: Schirrmacher, Esther, Schirrmacher, Ralf, Thews, Oliver, Dillenburg, Wolfgang, Helisch, Andreas, Wessler, Ignatz, Buhl, Roland, Höhnemann, Sabine, Buchholz, Hans Georg, Bartenstein, Peter, Machulla, Hans Jürgen, Rösch, Frank
Format: Article
Language:English
Subjects:
Animals
Fenoterol - analogs & derivatives
Fenoterol - metabolism
Fluorine Radioisotopes
In Vitro Techniques
Lung - diagnostic imaging
Lung - metabolism
Models, Chemical
Radiopharmaceuticals - chemical synthesis
Radiopharmaceuticals - pharmacokinetics
Receptors, Adrenergic, beta-2 - analysis
Receptors, Adrenergic, beta-2 - metabolism
Swine
Tissue Distribution
Tomography, Emission-Computed
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Summary:The (18)F-labeled beta2-adrenergic receptor ligand (R,R)(S,S) 5-(2-(2-[4-(2-[(18)F]fluoroethoxy)phenyl]-1-methylethylamino)-1-hydroxyethyl)-benzene-1,3-diol, a derivative of the original highly selective racemic fenoterol, was synthesized in an overall radiochemical yield of 20% after 65 min with a radiochemical purity higher than 98%. The specific activity was in the range of 50-60 GBq/micromol. In vitro testing of the non-radioactive fluorinated fenoterol derivative with isolated guinea pig trachea was conducted to obtain an IC(50) value of 60 nM. Preliminary ex vivo organ distribution and in vivo experiments with positron emission tomography (PET) on guinea pigs were performed to study the biodistribution as well as the displacement of the radiotracer to prove specific binding to the beta2-receptor.
ISSN:0960-894X