Synthèse de groupements prosthétiques glucidiques : vers de nouveaux traceurs peptidiques pour l'imagerie par tomographie par émission de positons (TEP)

Abstract : The use of peptides or proteins labeled with fluorine-18, as agents for Positron Emission Tomography (PET) is a rapidly growing field. Thus, the objective of our work was to create and to synthesize new glycosyl prosthetic groups, which are analogs of 2-deoxy-2-[18F]fluoro-D-glucose ([18F]FDG). The particularity of these compounds is their azide moiety which enables a simple and efficient ligation with alkynylated amino acids via a Huisgen type reaction or "click Chemistry". The first goal was to study the ideal position for the introduction of the azide moiety on the sugar, either at the C-1 or C-6 position. In order to evaluate the incorporation of fluorine-18, two different strategies were developed to obtain two generations of labeled precursors and cold references. The second objective was to synthesize alkynylated phenylalanine, cysteine and gluthation derivatives to test the ?click Chemistry? ligation method with the best prosthetic group.
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Christine Vala. Synthèse de groupements prosthétiques glucidiques : vers de nouveaux traceurs peptidiques pour l'imagerie par tomographie par émission de positons (TEP). Autre. Université Henri Poincaré - Nancy 1, 2009. Français. ⟨NNT : 2009NAN10031⟩. ⟨tel-01748470⟩

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