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Abstract :
[en] Sugar-based surfactants are natural and biocompatible compounds. Among sugar-based surfactants, there is an increase of interest for the xylose-based bolaforms because of their potential applications in pharmaceutical and cosmetic fields and of their original physicochemical properties.
Xylose-based bolaforms have interfacial and membrane-interacting properties making them potential molecules for drug delivery systems. For this work, we chemically synthetized by metathesis in the presence of Grubbs I catalyzer, a novel symmetric bolaform composed of two xylose polar heads connected by an ether link to a hydrocarbon chain having 18 carbon atoms with an unsaturation (BolaX). We were able to obtain two bolaforms differing only at the level of the anomeric configuration of the xylose moieties, or orBolaX).
The surface activities of both compounds were analyzed. The anomeric configuration gives interfacial properties at the air-water interface contrary to the one. The interactions of the BolaX with model membranes were then analyzed in order to determine if it can be used for drug delivery systems.
Our results show that BolaX were able to interact and insert within lipid monolayers containing phospholipids and sterols. In order to have informations at the molecular level of these interactions, another model membrane, called multilamellar vesicles (MLVs), containing phospholipids and sterols with or without BolaX were prepared. Both MLVs were analyzed by the means of the FTIR spectroscopy.
In parallel, we have calculated the interaction energy of the BolaX with different lipid molecules by the means of the Hypermatrix method developed at our laboratory. Moreover, the insertion of the BolaX within the lipid bilayers was simulated using our IMPALA method.
Taking together, our findings indicate that BolaX would be a potential candidate for drug delivery systems because of its surface active properties and its ability to insert within membranes.
