Journal
JOURNAL OF MEDICINAL CHEMISTRY
Volume 49, Issue 13, Pages 3872-3887Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jm0601755
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Funding
- NCI NIH HHS [CA 041407] Funding Source: Medline
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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.
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