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Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine

  • Research Article
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Central European Journal of Chemistry

Abstract

We synthesized nine quaternary ammonium compounds (QUATs) starting from phenylalanine, N-alkyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromides, which were prepared as optically pure substances. Five compounds were prepared as S-enantiomers and four compounds as R-enantiomers. These compounds were evaluated by their activities against bacteria and fungi. Three microbial strains were used in the study: the gram-negative bacteria Escherichia coli, the gram-positive bacteria Staphylococcus aureus and the fungi Candida albicans. The activities were expressed as minimum bactericidal or fungicidal concentrations (MBC). The most active compounds were (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide and (2R)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide, with MBC values exceeding those of commercial benzalkoniumbromide (BAB) used as standard. The relationships between structure and biological activity of the tested QUATs were quantified by the bilinear model (QSAR) and are discussed.

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Authors and Affiliations

  1. Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia

    Miloš Lukáč, Ivan Lacko, Zuzana Kyselová & Ferdinand Devínsky

  2. Department of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia

    Marián Bukovský

  3. Department of Physical Chemistry of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, 832 32, Slovakia

    Janka Karlovská

  4. Institute of Chemistry, Faculty of Natural Science, Comenius University, Bratislava, 842 15, Slovakia

    Branislav Horváth

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  1. Miloš Lukáč
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  2. Ivan Lacko
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  7. Ferdinand Devínsky
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Correspondence to Miloš Lukáč.

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Lukáč, M., Lacko, I., Bukovský, M. et al. Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. cent.eur.j.chem. 8, 194–201 (2010). https://doi.org/10.2478/s11532-009-0126-8

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  • DOI: https://doi.org/10.2478/s11532-009-0126-8

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