title: Acid-triggered transformation of diortho ester phosphocholine liposome.
abstract: The use of pH-sensitive liposomes for acid-triggered site-specific drug delivery is one of the more promising approaches to improve the therapeutic index of drugs. Here, we report the synthesis, assembly, and hydrolysis of the first ortho ester phosphocholine (OEPC). The acid hydrolysis of OEPC liposomes consists of a lag phase and a burst phase. The lag time is pH-dependent-the lower the pH, the shorter the time. Upon acid hydrolysis, the OEPC liposomes were transformed into leaky metastable vesicles that rapidly collapsed in the presence of albumin. OEPC, when formulated with cationic lipid, significantly enhanced the transfection efficiency compared with that of the pH-insensitive formulation.
authors.affiliation: Department of Biopharmaceutical Sciences, University of California-San Francisco, San Francisco, CA 94143-0446, USA.
authors.forename: Zhaohua
authors.initials: Z
authors.lastname: Huang
authors.forename: Xin
authors.initials: X
authors.lastname: Guo
authors.forename: Weijun
authors.initials: W
authors.lastname: Li
authors.forename: J Andrew
authors.initials: JA
authors.lastname: MacKay
authors.forename: Francis C
authors.initials: FC
authors.lastname: Szoka
mesh_terms: D004952:Esters / Q000737:chemistry; D005233:Fatty Alcohols / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008081:Liposomes / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D010712:Phosphatidic Acids / Q000737:chemistry; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D004952:Esters; D005233:Fatty Alcohols; D008081:Liposomes; D008698:Mesylates; D010712:Phosphatidic Acids; D010767:Phosphorylcholine; C010268:oleyl alcohol