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C-glycosides fluorés pour le marquage de peptides : Applications en imageries TEP et bimodale TEP/FPIR

Abstract : The work developed in this thesis is based on saccharidic derivatives especially C-glycosides for which new synthetic methodologies and applications in the field of PET and PET/NIRF imaging have been developed. Some peptides play a major role in therapy and diagnosis of various pathologies and their conjugation with a saccharidic derivative significantly improves their biodistribution. The first part of this work concerns the synthesis of fluorinated (19F) and radiofluorinated (18F) C-glycosides fonctionalized in anomeric position by an arm bearing an azide function. These compounds were coupled by 1,3-dipolar cycloaddition to peptides derived from RGD, allowing the labeling of these peptides by an indirect method namely prosthetic strategy. The radiosynthesis of one radiotracer was fully automated. The in vitro biological evaluation on two types of integrins and in vivo by PET imaging showed the interest of these radiotracers in the field of oncology. The second part is closely linked to these first results. To go further in terms of diagnostic tools, dual (radio)fluorinated probes for bimodal PET/NIRF imaging were developed. This required an elaborated synthetic strategy to introduce a fluorine atom and a cyanine dye, both being PET and NIRF specific imaging probes. The coupling of a biomolecule (RGD peptide) was also performed by "Click" reaction. Regiocontrolled functionalization methods enabled the introduction of these various moieties. The perspective is to evaluate the in vitro biological properties of the synthetized tools and to consider this dual probe for diagnostic and theranostic applications in PET/NIRF imaging.
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Timothé Vucko. C-glycosides fluorés pour le marquage de peptides : Applications en imageries TEP et bimodale TEP/FPIR. Chimie organique. Université de Lorraine, 2019. Français. ⟨NNT : 2019LORR0186⟩. ⟨tel-02526487⟩

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