Abstract :
[en] Uronic acid derivatives (UAD) constitute a particular class of carbohydrate-based small compounds, which are receiving growing interests today for many reasons. Beyond their excellent environmental compatibility, their potentiality mainly arises from the large abundance of their precursors from renewable resources, and the quasi-unlimited availability of their molecular structure and geometry [1]. Such a structural diversity allows them to be a typical compound class for the structure-activity relationship investigation using simplest models. This approach is very important for predicting their functionalities and activities. Among others, searching specific and potent biological activities against target molecules, cells, and micro-organisms is a big challenge today. In this context, binding interactions of three UAD having different hydrophobic residues (allyl, benzyl, and cyclohexyl) to 1-palmitoyl-2-oleyl-sn-glycerol-3-phosphatidylcholine (POPC) vesicles have been investigated using Isothermal Titration Calorimetry (ITC) technique [2]. The binding affinity (Ka) to the membrane model at 25°C has been determined and compared for the three compounds. Based on thermograms resulting from UAD aqueous solution titration experiments, with and without POPC vesicles, it clearly appears that both derivatives with a cyclic residue interact stronger with the lipid membrane model than their linear derivative counter-part, which exhibits almost no interaction. Moreover, the derivative compound with a cyclohexyl residue saturates faster POPC vesicles than that with a benzyl residue. We conclude that: (a) UAD having a cyclic hydrophobic residue, either saturated or unsaturated, bind more easily to the lipid membrane model than a linear one ending with a double bond; (b) the greater the number of hydrogen in the UAD residue chemical structure (saturated bonds), the stronger their binding affinity to POPC vesicles, suggesting the importance of H-bonding to such a lipid membrane model. The Ka mean value of the best tested UAD, i.e. with a cyclohexyl residue, is about 5.103 M-1.
[1] Razafindralambo, H.; Blecker, C; and M. Paquot., Screening of basic properties of amphiphilic molecular the structures for colloidal system formation and stability: the case of carbohydrate-based surfactants in: Amphiphiles: Molecular Assembly and Applilcations, ed. R. Nagarajan, ACS, Washignton, 2011, (In press).
[2] Razafindralambo, H.; Dufour, S.; Paquot, M.; Deleu, M., Thermodynamic studies of the binding interactions of surfactin analogues to lipid vesicles: application of isothermal titration calorimetry. J. Therm. Anal. Calorim., 2009, 9 (3), 817-821.
Acknowledgment: This work was supported by Belgian Walloon Region with DG06 research project of excellence (TECHNOSE).
