Steroid-lipid interactions in sonicated dipalmitoyl phosphatidyl choline vesicles: a steady-state and time-resolved fluorescence anisotropy study with all trans-1,6-diphenyl-1,3,5-hexatriene as probe.

The effect of steroid chemical structure on steroid-lipid interaction is studied in sonicated dipalmitoyl phosphatidylcholine vesicles by steady-state and time-resolved fluorescence anisotropy techniques using diphenylhexatriene as probe. A large number of cholesterol derivatives and steroids, some of them being precursors involved in corticosteroids biosynthesis, has been studied. Addition of a polar group on the side chain in carbon-20 or 22 position evokes considerable difference for the interaction with the bilayer. The carbon-22 position appears to be of critical importance. This observation may be relevant for the functioning of mitochondria from steroid producing tissues, where a stereospecific hydroxylation of cholesterol at the carbon-22R position is required for pregnenolone synthesis.