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Amphiphiles azobenzéniques : potentiel et relations structure-activité pour la lyse cellulaire

Abstract : The emergence of bacterial and fungal strains more and more resistant to disinfection is a threat to the development of nations and human health around the world. Amongst the mechanism of action, we will focus on the interaction between the molecule and the plasmic membrane for the lysis of the microorganism. The first goal of this work is to synthetize amphiphilic molecules to interact with bacterial membrane Azobenzene are interesting because their two phenyl group give them an apolar moiety, the next step is a grafting of a polar head to make them become an amphiphile molecule. Three types of azobenzene were synthetized to evaluate their antibacterial properties and their antifungal properties. The second goal of this work is tounderstand how they interact with the plasmic membranes. To perform this, we tested the azobenzenes on biomimetic models of plasmic membranes. The first group of compounds (AzoOH) with an alcohol group as polar head showed good biological properties but have a poor potential to interact with plasmic membrane. The second group of compounds (AzoPEG) with a triethylene-glycol type polar head have mediocre biological activities, and their ability to interact with the membrane were not enhanced. The third group of compounds (AzoTAI) with a trimethylammonium type polar head showed very good biological activities, and strong interaction with bacterial membrane lipid. These antibacterial activities are correlated to their interaction with bacterial lipids. It also has good abilities to adsorb themselves to hydrophilic/hydrophobic interfaces. However, their cytotoxic activity on human cells can be a severe drawback with their use.
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Antoine Franche. Amphiphiles azobenzéniques : potentiel et relations structure-activité pour la lyse cellulaire. Génie chimique. Université de Technologie de Compiègne; Université de Liège, 2019. Français. ⟨NNT : 2019COMP2523⟩. ⟨tel-02615459⟩

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