1. Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds.
- Author
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Joyard Y, Azzouz R, Bischoff L, Papamicaël C, Labar D, Bol A, Bol V, Vera P, Grégoire V, Levacher V, and Bohn P
- Subjects
- Animals, Fluorine Radioisotopes metabolism, Humans, Hypoxia diagnosis, Nitroimidazoles chemical synthesis, Nitroimidazoles metabolism, Positron-Emission Tomography methods, Rats, Rats, Wistar, Silicon metabolism, Tissue Distribution, Fluorine Radioisotopes chemistry, Nitroimidazoles chemistry, Silicon chemistry
- Abstract
The syntheses of new nitroimidazole compounds using silicon-[(18)F]fluorine chemistry for the potential detection of tumor hypoxia are described. [(18)F]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/μmol, however these compounds ([(18)F]7 and [(18)F]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/μmol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/μmol. The labeled compound [(18)F]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [(18)F]18 is suitable for further in vivo assessments., (Copyright © 2013 Elsevier Ltd. All rights reserved.)
- Published
- 2013
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