title: Lipophilic pyrylium salts in the synthesis of efficient pyridinium-based cationic lipids, gemini surfactants, and lipophilic oligomers for gene delivery.
abstract: Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.
authors.affiliation: Texas A & M University at Galveston, MARS, 5007 Avenue U, Galveston, Texas 77551, USA.
authors.forename: Marc Antoniu
authors.initials: MA
authors.lastname: Ilies
authors.forename: William A
authors.initials: WA
authors.lastname: Seitz
authors.forename: Betty H
authors.initials: BH
authors.lastname: Johnson
authors.forename: Edward L
authors.initials: EL
authors.lastname: Ezell
authors.forename: Aaron L
authors.initials: AL
authors.lastname: Miller
authors.forename: E Brad
authors.initials: EB
authors.lastname: Thompson
authors.forename: Alexandru T
authors.initials: AT
authors.lastname: Balaban
mesh_terms: D002412:Cations; D045744:Cell Line, Tumor; D004337:Drug Carriers / Q000138:chemical synthesis* / Q000737:chemistry; D018014:Gene Transfer Techniques; D006801:Humans; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D008081:Liposomes / Q000737:chemistry; D009861:Onium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002412:Cations; D004337:Drug Carriers; D008055:Lipids; D008081:Liposomes; D009861:Onium Compounds; D011108:Polymers; D011725:Pyridines; D011753:Pyrones; D013501:Surface-Active Agents