title: Cholesterol interactions with tetracosenoic acid phospholipids in model cell membranes: role of the double-bond position.
abstract: The synthesis and thermotropic properties of 1,2-di-(9Z)-9-tetracosenoylphosphatidylcholine [delta 9-PC(24:1,24:1), 1], 1,2-di-(5Z)-5-tetracosenoylphosphatidylcholine [delta 5-PC(24:1,24:1), 2], and 1,2-di-(15Z)-15- tetracosenoylphosphatidylcholine [delta 15-PC(24:1,24:1), 3] are reported. Liposomes prepared from these phospholipids differ from those of the natural sponge phospholipids, 1,2-di-(5Z,9Z)-5,9-hexacosadienoylphosphatidylcholine (4a) and the corresponding ethanolamine (4b), both of which virtually exclude cholesterol from their bilayers. The behavior of 1 and 2 is similar to that of 1,2-di-(6Z,9Z)-6,9-hexacosadienoylphosphatidylcholine (5), which exhibits a partial molecular interaction with cholesterol. In the case of 3, cholesterol appears to interact with the saturated acyl chain regions of this phospholipid in a manner similar to that of its interaction with DPPC acyl chains. This study delineates the effect of the double-bond location in long fatty acyl chains of phospholipids on their interactions with cholesterol.
authors.affiliation: Department of Chemistry, Stanford University, California 94305.
authors.forename: E
authors.initials: E
authors.lastname: Ayanoglu
authors.forename: B H
authors.initials: BH
authors.lastname: Chiche
authors.forename: M
authors.initials: M
authors.lastname: Beatty
authors.forename: C
authors.initials: C
authors.lastname: Djerassi
authors.forename: N
authors.initials: N
authors.lastname: Düzgüneş
mesh_terms: D002152:Calorimetry, Differential Scanning; D002462:Cell Membrane / Q000378:metabolism*; D002784:Cholesterol; D005229:Fatty Acids, Monounsaturated; D007202:Indicators and Reagents; D008051:Lipid Bilayers; D008081:Liposomes; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D010713:Phosphatidylcholines / Q000138:chemical synthesis; D010743:Phospholipids / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
chemical_list: D005229:Fatty Acids, Monounsaturated; D007202:Indicators and Reagents; D008051:Lipid Bilayers; D008081:Liposomes; D010713:Phosphatidylcholines; D010743:Phospholipids; C064583:tetracosenoic acid; D002784:Cholesterol