title: Nonelectrolyte permeability of liposomes of hydroxyfatty acid-containing phosphatidylcholines.
abstract: Two phosphatidylcholines containing hydroxylated fatty acids, 1-palmitoyl-2-[5-hydroxy-6,8,11,14-eicosatetraenoyl]-sn-glycero-3- phosphocholine (1-palm-2-5HETE PC) and 1-palmitoyl-2-[15(S)-hydroxy-5,8,11,13- eicosatetraenoyl]-sn-glycero-3-phosphocholine (1-palm-2-15HETE PC), and one phosphatidylcholine containing nonhydroxylated fatty acids, 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphocholine (1-palm-2-arach PC) were synthesized. Permeation of small nonelectrolytes (glycerol, 1,2-propanediol, urea, methylurea, propionamide and dimethylformamide) was assessed in multilamellar liposomes containing these synthetic PCs plus egg yolk phosphatidycholine (EPC) in the presence and absence of cholesterol. In liposomes containing 23% cholesterol, 69.3% EPC and 7.7% of either 1-palm-2-5HETE PC or 1-palm-2-15HETE PC the permeability to small nonelectrolytes was 60 to 400% greater than in liposomes containing 23% cholesterol and 77% EPC. The HETE-containing PCs also increased permeability in liposomes without cholesterol but the effects were less striking. Addition of the synthetic PCs did not affect the energy of activation of permeation.
authors.affiliation: Department of Medicine, Jewish Hospital of St. Louis, MO.
authors.forename: Y
authors.initials: Y
authors.lastname: Isaacson
authors.forename: T E
authors.initials: TE
authors.lastname: Riehl
authors.forename: W F
authors.initials: WF
authors.lastname: Stenson
mesh_terms: D002463:Cell Membrane Permeability / Q000187:drug effects; D002784:Cholesterol / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology; D005990:Glycerol / Q000378:metabolism; D008081:Liposomes / Q000032:analysis / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology*; D010742:Phospholipid Ethers / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology; D013816:Thermodynamics
chemical_list: D005231:Fatty Acids, Unsaturated; D008081:Liposomes; D010713:Phosphatidylcholines; D010742:Phospholipid Ethers; C062037:1-palmitoyl-2-(5-hydroxy-6,8,11,14-eicosatetraenoyl)-glycero-3-phosphocholine; C062038:1-palmitoyl-2-(15-hydroxy-5,8,11,13-eicosatetraenoyl)-glycero-3-phosphocholine; C043051:1-O-hexadecyl-2-arachidonyl-sn-glycero-3-phosphocholine; D002784:Cholesterol; D005990:Glycerol