title: In vitro lipofection with novel series of symmetric 1,3-dialkoylamidopropane-based cationic surfactants containing single primary and tertiary amine polar head groups.
abstract: A novel series of symmetric double-chained primary and tertiary 1,3-dialkoylamido monovalent cationic lipids were synthesized and evaluated for their transfection activities. In the absence of the helper lipid DOPE (1,2-dioleoyl-sn-glycero-3-phosphoethanolamine), only the primary and tertiary dioleoyl derivatives 1,3lmp5 and 1,3lmt5, respectively elicited transfection activity. This is a striking difference between symmetrical 1,2-diacyl glycerol-based monovalent cationic lipids that always found both dioleoyl and dimyristoyl analogues being efficient transfection reagents. In the presence of helper lipid, all cationic derivatives induced marker gene expression, except the dilauroyl analogues 1,3lmp1 and 1,3lmt1 that elicited no transfection activity. Combining electrophoretic mobility data of the lipoplexes at different charge ratios with transfection activity suggested two requirements for high transfection activity with monovalent double-chained cationic lipids, that is, binding/association of the lipid to the plasmid DNA and membrane fusion properties of the lipid layers surrounding the DNA.
authors.affiliation: Division of Pharmaceutics, Arnold & Marie Schwartz College of Pharmacy and Health Sciences, Long Island University, 75 Dekalb Avenue, Brooklyn, NY 11201, USA.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Sheikh
authors.forename: Jennifer
authors.initials: J
authors.lastname: Feig
authors.forename: Becky
authors.initials: B
authors.lastname: Gee
authors.forename: Song
authors.initials: S
authors.lastname: Li
authors.forename: Michalakis
authors.initials: M
authors.lastname: Savva
mesh_terms: D000588:Amines / Q000737:chemistry*; D000818:Animals; D002412:Cations; D045744:Cell Line, Tumor; D004587:Electrophoresis, Agar Gel / Q000379:methods; D004926:Escherichia coli / Q000235:genetics; D006651:Histocytochemistry; D006801:Humans; D008055:Lipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D051379:Mice; D010957:Plasmids / Q000235:genetics; D011407:Propane / Q000031:analogs & derivatives*; D013501:Surface-Active Agents / Q000737:chemistry*; D014162:Transfection / Q000379:methods*; D001616:beta-Galactosidase / Q000235:genetics / Q000378:metabolism
chemical_list: D000588:Amines; D002412:Cations; D008055:Lipids; D013501:Surface-Active Agents; D001616:beta-Galactosidase; D011407:Propane