Evidence for penetration in liposomes and in mitochondrial membranes of a fluorescent analogue of cord factor.
A fluorescent analogue of cord factor, a glycolipid toxin of mycobacteria, has been synthesized and its interactions with liposomes and isolated mitochondria have been studied. This compound, methyl alpha-D-6[12-(9-anthroyl)stearoyl]glucoside, is shown to be active against oxidative phosphorylation. When spread as a monolayer at the air-water interface, it forms a well organized phase and it strongly interacts with phosphatidylcholine. Addition of phosphatidylcholine liposomes or of isolated mitochondria to a water disperson of this fluorescent cord factor analogue results in a large increase of the fluorescence intensity. Moreover, the glycolipid probes for the temperature-dependent phase transition of the added suspensions. It is thus suggested that this cord factor analogue penetrates within mitochondrial membranes, a result which is discussed with respect to our previous conclusions concerning the way natural cord factors can interact with these organelles.
D000818:Animals; D000873:Anthracenes / Q000378:metabolism* / Q000494:pharmacology; D005260:Female; D006017:Glycolipids / Q000378:metabolism* / Q000494:pharmacology; D007425:Intracellular Membranes / Q000378:metabolism*; D007700:Kinetics; D008081:Liposomes; D008930:Mitochondria, Liver / Q000187:drug effects / Q000378:metabolism*; D010085:Oxidative Phosphorylation / Q000187:drug effects; D011312:Pressure; D051381:Rats; D013050:Spectrometry, Fluorescence; D013499:Surface Properties; D013696:Temperature
D000873:Anthracenes; D006017:Glycolipids; D008081:Liposomes; C026694:methyl alpha-D-6-(12-(9-anthroyl)stearoyl)glucoside