title: Single additional methylene group in the head-group region imparts high gene transfer efficacy to a transfection-incompetent cationic lipid.
abstract: In combination with equimolar 1,2-dioleoyl-L-alpha-glycero-3-phosphatidyl ethanolamine, a novel cholesterol-based cationic lipid with beta-alanine head-group (2) has been demonstrated to be strikingly more efficacious (10-24-fold) in transfecting CHO, COS-1 and HepG2 cells than its glycine analog (1) containing just one less methylene unit in its head-group region. Syntheses, characterizations and in vitro transfection biology of lipids 1 and 2 are described. Present findings demonstrate that even truly minor structural alterations, such as inclusion of just one additional methylene functionality in the polar head-group region, can convert an essentially transfection-incompetent cholesterol-based cationic amphiphile to a remarkably efficient cationic transfection lipid.
authors.affiliation: Division of Lipid Science and Technology, Indian Institute of Chemical Technology, 500 007, Hyderabad, India.
authors.forename: Rajkumar Sunil
authors.initials: RS
authors.lastname: Singh
authors.forename: Arabinda
authors.initials: A
authors.lastname: Chaudhuri
mesh_terms: D000818:Animals; D016466:CHO Cells; D019556:COS Cells; D002412:Cations; D045744:Cell Line, Tumor; D002470:Cell Survival; D002784:Cholesterol / Q000031:analogs & derivatives; D006224:Cricetinae; D004247:DNA / Q000737:chemistry; D006801:Humans; D006838:Hydrocarbons; D008055:Lipids / Q000737:chemistry*; D008081:Liposomes / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D014162:Transfection / Q000379:methods*; D001616:beta-Galactosidase / Q000032:analysis / Q000378:metabolism
chemical_list: D002412:Cations; D006838:Hydrocarbons; D008055:Lipids; D008081:Liposomes; C030011:carbene; D004247:DNA; D002784:Cholesterol; D001616:beta-Galactosidase; D008697:Methane