Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented.
A few classes of ionic liquids were synthesized and investigated for their physical properties as a function of structural variation. Bis(oxalato)borate (BOB) and bis(trifluoromethylsulfonyl)imide (NTf 2 ) ionic liquids (ILs) containing pyridinium, 4-dimethylaminopyridinium (DMAP) and pyrrolidinium cations bearing alkyl, benzyl, hydroxyalkyl and alkoxy substituents, were prepared from the corresponding halide salts. The physical properties of the DMAP based ionic liquids including viscosity, conductivity and thermal profiles were compared to those of their unsubstituted pyridinium analogues. The properties of the BOB and NTf 2 salts bearing similar cations were also compared. It was found that the DMAP salts were easier to synthesize and purify and have higher thermal decomposition points compared to their pyridinium and pyrrolidinium analogues. The BOB salts were found to be higher melting and more viscous than the NTf 2 salts. The synthesis and physical properties of the various ILs are discussed.
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