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            <title xml:lang="en">Nanoparticles based on different generation adamantane dendrons : design, synthesis and self-assembly studies</title>
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                <title xml:lang="en">Nanoparticles based on different generation adamantane dendrons : design, synthesis and self-assembly studies</title>
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                <authority type="supervisor">Alberto Bianco</authority>
                <authority type="jury">Jean-François Nierengarten [Président]</authority>
                <authority type="jury">Eric Doris [Rapporteur]</authority>
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                <term xml:lang="en">Foldamers</term>
                <term xml:lang="en">Therapeutic application</term>
                <term xml:lang="en">Dendrons</term>
                <term xml:lang="en">Adamantane</term>
                <term xml:lang="fr">Applications thérapeutiques</term>
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              <p>Adamantane is a polycyclic hydrocarbon, rigid and quite bulky. In medicine, several adamantane-based derivatives have been developed especially as antiviral agents. Easily functionalized, its 3D well-defined structure considerably decrease the sterical hindrance between its different functional groups. In this context, we decided to use adamantane to build more complex structures such as dendrons and foldamers. Dendrons are synthetic polymers with interesting properties. Because of their size, they are considered as nanoparticles and possess a passive cancer cell targeting. In addition,they are easily functionalized and can be use as vector of drugs. Indeed, the dendrons improve the physochemical properties of a drug (absorption, distribution, metabolism, elimination and toxicity). We decided to combine adamantane and dendrons to build adamantane-based dendrons. However, these dendrons have the particularity of not having spacer between the adamantane moieties, thus, they are highly rigid. Transmission electron microscopy analysis of the different functionalized dendrons allowed to study their self-assembly capacity and their morphology according to their functional groups,the solvent, the concentration and the support. In a second step, we designed an amino acid based on adamantane. This g-amino acid has been introduced in a peptide backbone using solid phase peptide synthesis. Then, the effects of adamantane onto peptide secondary structures have been studied by circular dichroism.</p>
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              <p>L’adamantane est un hydrocarbure polycyclique, rigide et assez encombrant. En médecine, plusieurs dérivés à base d’adamantane ont été développés notamment comme agent antiviraux. Facilement fonctionnalisés, sa conformation 3D permet d’amoindrir les encombrements stériques entre les différents groupements fonctionnels. Nous avons décidé d’utiliser ses propriétés pour concevoir des structures plus complexes, à savoir, des dendrons et des foldamers. Les dendrons sont des polymères synthétiques possédant des propriétés intéressantes. De par leurs tailles, ils sont considérés comme des nanoparticules et possèdent un ciblage passif des cellules cancéreuses. De plus, facilement fonctionnalisés ils peuvent être utilisés comme molécule cargo dans la vectorisation de principes actifs. Outre la vectorisation, les dendrons permettent d’améliorer les propriétés physico-chimiques d’un médicament (absorption, distribution, métabolisme, élimination et toxicité). Nous avons alors choisi de concevoir des dendrons à base d’adamantane. Ces derniers ont la particularité de ne pas posséder d’espaceur entre les molécules d'adamantane se qui les rend hautement rigides. L’analyse par microscopie électronique à transmission de différents dendrons a permis d’étudier leurs morphologies selon leurs fonctionnalisations ainsi que l’effet du solvant, de la concentration et du support sur leurs auto-assemblages. Dans un second temps, nous avons conçu un acide aminé basé sur l’adamantane. Cet acide g-aminé a ensuite été incorporé dans des séquences peptidiques et les effets de l’adamantane sur la structure secondaire des peptides ont été étudiés par dichroïsme circulaire.</p>
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