ABSTRACT
Novel mandelate ionic liquids with quartenary ammonium cations were synthesized and characterized. The compounds exhibit antimicrobial activity and the most potent one is of similar efficacy against Gram+ bacteria as its counterpart chloride. On the other hand, the mandelates are much less active against Gram-bacteria and fungi. QSAR models suggest that, with respect to cation, their potency depends on lipophilicity. The synthesized ionic liquids are also quite cytotoxic against mammalian cells.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Ionic Liquids/chemistry , Ionic Liquids/pharmacology , Mandelic Acids/chemical synthesis , Mandelic Acids/pharmacology , Crystallography, X-Ray , Gram-Positive Bacteria/drug effects , Microbial Sensitivity Tests , Quantitative Structure-Activity Relationship , SolutionsABSTRACT
A new group of quaternary ammonium lactate based ionic liquids have been prepared and characterized. Didecyldimethylammonium (DDA) and benzalkonium (BA) D,L- and L-lactates are air-stable, hydrophilic, surface-active salts. They are very effective antibacterial and antifungal agents, especially the DDA lactates, against Streptococcus mutants and Candida albicans. Their activities are comparable or more effective than the original benzalkonium chloride. In addition, they have been shown to be good insect-feeding deterrents. However, they are poor antifungal agents for wood preservation. The toxicity of the DDA and BA lactates has also been studied and the results are presented in this paper.
Subject(s)
Alkanes/chemistry , Ionic Liquids/chemistry , Lactic Acid/chemical synthesis , Lactic Acid/pharmacology , Quaternary Ammonium Compounds/chemistry , Animals , Bacteria/drug effects , Feeding Behavior/drug effects , Female , Fungi/drug effects , Insecta/physiology , Ionic Liquids/pharmacology , Ionic Liquids/toxicity , Lactic Acid/chemistry , Lactic Acid/toxicity , Lethal Dose 50 , Rats , Surface Properties , Wood/drug effectsABSTRACT
Different ionic liquids were used as solvents for the effective extraction of the active metabolites of the fruit bodies of C. cibarius. The type of ionic liquid was found to play a significant role in this process. We found that the protic ionic liquid 1-[(nonyloxy)methyl]-1H-imidazol-3-ium salicylate (6) is a most-efficient extracting agent, being superior to classical solvents such as AcOEt or hexane. The obtained extracts generally revealed high insecticidal activities against both house fly and cockroach, with similar potencies as the standard pesticides bromfenvinphos or alphacypermethrin, as well as significant activities against bacteria, yeast, and moulds. Notably, the cidal activities against plant-pathogenic bacteria were stronger than against human bacterial strains.
