title: Synthesis and biological activity of carbamate-linked cationic lipids for gene delivery in vitro.
abstract: We have introduced a convenient synthesis method for carbamate-linked cationic lipids. Two cationic lipids N-[1-(2,3-didodecylcarbamoyloxy)propyl]-N,N,N-trimethylammonium iodide (DDCTMA) and N-[1-(2,3-didodecyl carbamoyloxy)propyl]-N-ethyl-N,N-dimethylammonium iodide (DDCEDMA), with identical length of hydrocarbon chains, alternative quaternary ammonium heads, carbamate linkages between hydrocarbon chains and quaternary ammonium heads, were synthesized for liposome-mediated gene delivery. Liposomes composed of DDCEDMA and DOPE in 1:1 ratio exhibited a lower zeta potential as compared to those made of pure DDCEDMA alone, which influences their DNA-binding ability. pGFP-N2 plasmid was transferred by cationic liposomes formed from the above cationic lipids into Hela and Hep-2 cells, and the transfection efficiency of some of cationic liposomes was superior or parallel to that of two commercial transfection agents, Lipofectamine2000 and DOTAP. Combined with the results of the agarose gel electrophoresis and transfection experiment, the DNA-binding ability of cationic lipids was too strong to release DNA from complex in the transfection, which could lead to relative low transfection efficiency and high cytotoxicity.
authors.affiliation: State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China.
authors.forename: Defu
authors.initials: D
authors.lastname: Zhi
authors.forename: Shubiao
authors.initials: S
authors.lastname: Zhang
authors.forename: Farooq
authors.initials: F
authors.lastname: Qureshi
authors.forename: Yinan
authors.initials: Y
authors.lastname: Zhao
authors.forename: Shaohui
authors.initials: S
authors.lastname: Cui
authors.forename: Bing
authors.initials: B
authors.lastname: Wang
authors.forename: Huiying
authors.initials: H
authors.lastname: Chen
authors.forename: Yinhuan
authors.initials: Y
authors.lastname: Wang
authors.forename: Defeng
authors.initials: D
authors.lastname: Zhao
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D002219:Carbamates / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D004587:Electrophoresis, Agar Gel; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D008081:Liposomes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D010316:Particle Size; D010714:Phosphatidylethanolamines / Q000737:chemistry; D010957:Plasmids / Q000737:chemistry / Q000378:metabolism; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D014162:Transfection
chemical_list: C410262:1,2-dioleoyl-glycero-3-phosphatidyl ethanolamine; D002219:Carbamates; D002412:Cations; D008081:Liposomes; D010714:Phosphatidylethanolamines; D000644:Quaternary Ammonium Compounds