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Molecules 2015, 20(3), 3681-3696; doi:10.3390/molecules20033681

Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts

1
Department of Medicinal Chemistry and Drug Analysis, Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 500 05, Czech Republic
2
Department of Epidemiology, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, Hradec Kralove 500 01, Czech Republic
3
Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, Hradec Kralove 500 05, Czech Republic
4
Department of Cybernetics and Biomedical Engineering, Faculty of Electrical Engineering and Computer Science, VSB-Technical University of Ostrava, 17. Listopadu 15, Ostrava-Poruba 708 33, Czech Republic
5
Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, Hradec Kralove 500 01, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Peter J. Rutledge
Received: 4 January 2015 / Revised: 6 February 2015 / Accepted: 12 February 2015 / Published: 24 February 2015
View Full-Text   |   Download PDF [765 KB, uploaded 24 February 2015]   |  

Abstract

A set of new quaternary ammonium compounds based on pyridine-4-aldoxime was synthesized, characterized with analytical data (NMR, EA, HPLC, MS) and tested for in vitro antimicrobial activity (antibacterial, antifungal) and cytotoxicity. Quaternary pyridinium-4-aldoxime salts with length of alkyl side chain from C8 to C20 and belonging to the group of cationic surfactants were investigated in this work. An HPLC experimental protocol for characterization of mixtures of all homologues has been found. Antimicrobial evaluation found that yeast-type fungi were most sensitive towards C14 and C16 analogues, whereas the C16 analogue was completely ineffective against filamentous fungi. Antibacterial assessment showed versatility of C14 and relatively high efficacy of C16 against G+ strains and C14 against G− strains. Notably, none of the studied compounds exceeded the efficacy and versatility of the benzalkonium C12 analogue, and benzalkonium analogues also exhibited lower cytotoxicity in the cell viability assay. View Full-Text
Keywords: pyridinium-4-aldoxime salts; synthesis; analysis; antimicrobial activity; surfactants; cytotoxicity pyridinium-4-aldoxime salts; synthesis; analysis; antimicrobial activity; surfactants; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Marek, J.; Malinak, D.; Dolezal, R.; Soukup, O.; Pasdiorova, M.; Dolezal, M.; Kuca, K. Synthesis and Disinfection Effect of the Pyridine-4-aldoxime Based Salts. Molecules 2015, 20, 3681-3696.

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