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Synthesis and characterization of surface‐active compounds derived from cholesterol derivatives and glucose
Author(s) -
Piispanen Peter S.,
Byström Styrbjörn,
Svensson Martin,
Kronberg Bengt,
Blute Irena,
Norin Torbjörn
Publication year - 2002
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-002-0232-y
Subject(s) - chemistry , pulmonary surfactant , solubility , critical micelle concentration , micelle , liposome , membrane , aqueous solution , molar ratio , chromatography , organic chemistry , catalysis , biochemistry
The synthesis and characterization of surface‐active compounds based on various steroid derivatives and glucose are presented. The hydrophobic and hydrophilic parts of the compounds were linked via glucosidic bonds. All compounds were found to have very low water solubility and only limited solubility in various organic solvents. The compounds were investigated according to their ability to interact with an anionic surfactant, sodium dodecylsulfate (SDS), in order to induce a decrease in the critical micelle concentration (CMC) of the surfactants. This synergistic effect was pronounced for cholestanol‐6‐on‐β‐ D ‐glucopyranoside and for cholestan‐3,6‐diol‐β‐ D ‐glucopyranoside. These two compounds lowered the CMC from 8 to 6 and 0.6 mM, respectively, for water solutions of SDS/glucoside with a molar ratio of 92∶8. Furthermore, the ability of the compounds to stabilize lipid membranes, in liposomes, at varying concentrations of Ca 2+ , was studied. The compounds were, as expected, found to induced stabilization similar to that of cholesterol.