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Theses

Dérivés C-glycosidiques pour l’imagerie bimodale TEP/FPIR. Applications au marquage de dérivés peptidiques RGD

Abstract : The work developed in this thesis deals with C-glycosyl compounds for which new synthetic methodologies and applications in PET/NIRF imaging have been developed. Some peptides have a major role in the therapy and diagnostic of diverse pathologies and their conjugation with a fluorophore and a radioelement allow precise diagnostic and potential theranostic applications by surgery. The goal was to develop the synthesis of (radio)fluorinated and fluorescent dual probes for bimodal PET/NIRF imaging. An elaborated synthetic strategy was required to introduce a fluorine atom and a cyanine-type fluorophore, both being the specific probes of PET and NIRF imaging. Two main strategies were developed for the synthesis of these tools: the functionalization of C-glycosyl derivative including a [3.3.0]furofuranone scaffold and the functionalization of polyhydroxylated C-glycosyl compound. The protection/deprotection synthetic strategies have made possible the setting up of these various elements followed by the conjugation of two peptidic RGD derivatives by CuAAC “Click” reaction. The affinity of the two fluorinated and fluorescent derivatives for the integrins was in the same range (40 nM) than the RGD peptide alone, highlighting the benefit of the divalence of the agent. The radiofluorination of a dual PET/NIRF probe have been successfully achieved, allowing application for in vivo PET and NIRF imaging as well as NIRF-guided surgery.
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https://hal.univ-lorraine.fr/tel-03356421
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Submitted on : Tuesday, September 28, 2021 - 9:40:05 AM
Last modification on : Sunday, June 26, 2022 - 3:13:58 AM
Long-term archiving on: : Wednesday, December 29, 2021 - 6:11:54 PM

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  • HAL Id : tel-03356421, version 1

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Julen Ariztia. Dérivés C-glycosidiques pour l’imagerie bimodale TEP/FPIR. Applications au marquage de dérivés peptidiques RGD. Chimie organique. Université de Lorraine, 2021. Français. ⟨NNT : 2021LORR0097⟩. ⟨tel-03356421⟩

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