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Quantitative relationships between structure and antimicrobial activity of new “Soft” bisquaternary ammonium salts

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Abstract

New surface-active bisquaternary ammonium salts derived from bis-(2-dimethylaminoethyl) ester of glutaric acid are highly effective against representatives of Gram-positive, Gram-negative bacteria and yeasts. Relationships between structure, lipophilicity and antimicrobial effectiveness were demonstrated by quantitative structure-activity methodology. The nonlinear dependence of biological activity on the structure as well as lipophilicity (expressed as critical micelle concentration—CMC) was shown using Kubinyi’s bilinear model. The most effective compounds were those with the alkyl chain of 11–12 carbon atoms and with the CMC values around 0.7−1.0 mmol/L. These derivatives possessed higher antimicrobial activity particularly to Gram-negative bacteria.

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Abbreviations

MIC:

minimum inhibitory concentration

QAS:

quaternary ammonium salts

CMC:

critical micelle concentration

R M :

log (1/R F -1)

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Part 45 of the seriesQuaternary Ammonium Salts; part 44: Brádlerová A.et al., Pharmazie, in press.

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Pavlíková-Mořická, M., Lacko, I., Devínsky, F. et al. Quantitative relationships between structure and antimicrobial activity of new “Soft” bisquaternary ammonium salts. Folia Microbiol 39, 176–180 (1994). https://doi.org/10.1007/BF02814644

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  • DOI: https://doi.org/10.1007/BF02814644

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