Dansyl lysine: a structure-selective fluorescent membrane stain?

Dansyl lysine (DL) is a fluorescent compound that has significantly higher solubility in synthetic phosphatidylcholine (PC) membranes with a low cholesterol content than it does in water or in membranes having a high cholesterol content. Its fluorescence intensity is enhanced at least 50-fold when dissolved in PC membranes. Therefore, membranes with mole fractions of cholesterol (Xch) less than or equal to 0.5-0.3 are stained by aqueous solutions of DL: those with a higher cholesterol content, 0.3-0.4 less than or equal to Xch less than or equal to 0.5, are not. It is proposed that DL selects for a structural feature of membranes: cholesterol-free domains. The phenomenon has provided evidence for long-lived compositional heterogeneity in large multilamellar PC-cholesterol liposomes having Xch less than or equal to 0.2. This is not consistent with a model in which the homogeneous state is thermodynamically favored and both intermembrane transfer and transmembrane transfer (flip-flop) of cholesterol are fast. These studies are of potential importance for understanding cell membrane structure, in particular lipid-phase equilibria and the maintenance of compositional heterogeneity between the different membranes of cells.