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Synthesis and biological activity of quaternary salts of 3-N-dodecylaminoquinuclidine

In an attempt to identify a new class of antimicrobial agents, the antimicrobial potential of quaternary quinuclidinium derivativeswith N-alkyl substituent on the position 3 of quinuclidine was evaluated.We were guided bythe results of our previouswork which showedthatquaternary derivatives of 3- substituted quinuclidineshavevery good biological activity.1Therefore, newseriesof quaternary quinuclidiniumsalts were designed and synthetized by the quaternization of quinuclidin-3-yl(dodec-1-yl)aminewith different benzyl bromides. All compounds were obtained in very good yields after which they were further characterized by physico-chemical methods includingFTIR, 1H and 13C NMR spectroscopies.The antibacterial activities of all compounds were evaluated against series of recent clinical isolates of antibiotic susceptible Gram-positive and resistant Gram- negative pathogens by determining their minimum inhibitory concentrations. All compounds showed good to strong broad-spectrum activity displaying MIC values between1.95-3.9 μg/mL.Cytotoxicity of compounds with different cell lines in human cell culture was determinedand it was determined that HaCat cell line is less tolerant that RPE1 displaying IC50values between 0.97-24.3 μM/mL. Based on these results, quaternary quinuclidine with long alkyl chain can be considered as promising new class of antimicrobials and further investigations should be performed.

quaternary salts, quinuclidine-3-yl(dodec-1-yl)amine, antimicrobial activity, cytotoxicity

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