Synthesis of new sugar-based bolaamphiphilic compounds. Physicochemical study of their molecular aggregation in aqueous solution

We describe the synthesis of new sugar-based bolaamphiphiles having the general structure: [ose derivative]-(Y)-X-(Y)-[ose derivative], where Y=-CONH- or -NHCO- and X is a lipophilic chain of varying length, containing hydrophilic functional groups. The sugar-based polar heads were mono- or diholosides in either the open or closed configuration. Micellization was shown to occur with compounds whose X chain length was above a certain value. Aggregation in micelles was assumed to be the result of chain folding. For compounds with short X, vesicles were obtained under certain conditions. These new synthetic bolaforms may find applications in drug formulation to solubilize hydrophobic compounds such as fatty acids. The globular systems formed do not denature lipoxygenase-type enzymes. The activity of soybean lipoxygenase was examined in the presence of the different bolaforms synthesized and compared to that observed in the presence of Tween 20.