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Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds.

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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Joyard Y,Azzouz R,Bischoff L,Papamicaël C,Labar D,Bol A,Bol V,Vera P,Grégoire V,Levacher V,Bohn P

doi

10.1016/j.bmc.2013.04.029

subject

Has Abstract

pub_date

2013-07-01 00:00:00

pages

3680-8

issue

13

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00355-6

journal_volume

21

pub_type

杂志文章

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