F. Brisset et al., SYNTHESIS OF NEW SUGAR-BASED BOLAAMPHIPHILIC COMPOUNDS - PHYSICOCHEMICAL STUDY OF THEIR MOLECULAR AGGREGATION IN AQUEOUS-SOLUTION, New journal of chemistry, 20(5), 1996, pp. 595-605
We describe the synthesis of new sugar-based bolaamphiphiles having th
e general structure: [ose derivative]-(Y)-X-(Y)-[ose derivative], wher
e Y=-CONH- or -NHCO- and X is a lipophilic chain of varying length, co
ntaining hydrophilic functional groups. The sugar-based polar heads we
re mono- or diholosides in either the open or closed configuration. Mi
cellization 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 obt
ained 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 lipox
ygenase-type enzymes. The activity of soybean lipoxygenase was examine
d in the presence of the different bolaforms synthesized and compared
to that observed in the presence of Tween 20.