Evidence for Penetration in Liposomes and in Mitochondrial Membranes of a Fluorescent Analogue of Cord Factor

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Abstract
A fluorescent analog of cord factor, a glycolipid toxin of mycobacteria, was synthesized and its interactions with liposomes and isolated mitochondria were studied. This compound, methyl .alpha.-D-6[12-(9-anthroyl)stearoyl]glucoside, is active against oxidative phosphorylation. When spread as a monolayer at the air-water interface, it forms a well organized phase and strongly interacts with phosphatidylcholine. Addition of phosphatidylcholine liposomes or of isolated mitochondria to a water dispersion of this fluorescent cord factor analog results in a large increase of the fluorescence intensity. The glycolipid probes for the temperature-dependent phase transition of the added suspensions. This cord factor analog penetrates within mitochondrial membranes, a result which is discussed with respect to previous conclusions concerning the way natural cord factors interact with these organelles.

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