Membrane penetration depth and lipid phase preference of acyl-labeled dansyl phosphatidylcholines in phosphatidylcholine vesicles.

The dansyl fluors of 1-oleoyl-2-[4-(dansyl)amino]butyl]-sn-glycero-3-phosphocholine (18:1,4-dansyl PC) and 1-palmitoyl-2-[1-[(dansyl)amino)]undecanoyl]-sn-glycero-3-phosphoc holine (16:0,11-dansyl PC) were shown to reside at similar depths in phosphatidylcholine vesicles at pH 7. Analysis of fluorescence emission maxima showed that the dansyl groups of both 18:1,4-dansyl PC and 16:0,11-dansyl PC in phosphatidylcholine vesicles experienced environments more polar than methanol, suggesting that the dansyl group attached to the terminus of the undecanoyl chain must fold back toward the bilayer surface. Fluorescence polarization measurements in solid/fluid lipid mixtures show that both probes partition strongly into fluid phase lipid. The very low polarization values of 16:0,11-dansyl PC in lipid vesicles are consistent with the notion that the dansyl fluor of 16:0,11-dansyl PC existed in an environment allowing a high degree of motional freedom due to folding back of the dansyl group attached to the undecanoyl chain.