87803-75-6Relevant academic research and scientific papers
Surface-differentiated model phospholipid bilayers
Moss, Robert A.,Okumura, Yukihisa
, p. 1750 - 1756 (1992)
Dipalmitoylphosphatidylcholine (DPPC) and dioleoylphosphatidylcholine (DOPC) were synthesized in which the head groups were covalently functionalized with p-nitrophenyl benzoate (PNPB) moieties. Liposomes composed of 1 part functional lipid and 7 parts nonfunctional DPPC or DOPC were created at pH 6 and subjected to an exovesicular/endovesicular 12/6 pH gradient. Under these conditions, the exovesicular PNPB groups saponified more rapidly (k ～ 4.5 × 10-2 s-1) than the endovesicular PNPB groups [k ～ 7 × 10-6 s-1 (DPPC) or 7 × 10-5 s-1 (DOPC)], leading to surface-differentiated liposomes with exovesicular p-nitrophenylate labels and intact, endovesicular PNPB groups. The half-times for flip-flop reequilibration of the intact PNPB lipids between the endovesicular and exovesicular leaflets of the liposomal bilayers were (DPPC) ～ 6 min at 65 °C and (DOPC) ～ 20 min at 65 °C. The permeabilities of these liposomes to H+/OH- were also studied. Comparisons of the DPPC and DOPC flip-flop dynamics to those of analogous, cationic, ammonium ion lipids highlight the relative dynamic stability of the zwitterionic phospholipids in liposomal bilayers.
