title: Synthesis, Structure and Antimicrobial Properties of Novel Benzalkonium Chloride Analogues with Pyridine Rings.
abstract: Quaternary ammonium compounds (QACs) are a group of compounds of great economic significance. They are widely used as emulsifiers, detergents, solubilizers and corrosion inhibitors in household and industrial products. Due to their excellent antimicrobial activity QACs have also gained a special meaning as antimicrobials in hospitals, agriculture and the food industry. The main representatives of the microbiocidal QACs are the benzalkonium chlorides (BACs), which exhibit biocidal activity against most bacteria, fungi, algae and some viruses. However, the misuses of QACs, mainly at sublethal concentrations, can lead to an increasing resistance of microorganisms. One of the ways to avoid this serious problem is the introduction and use of new biocides with modified structures instead of the biocides applied so far. Therefore new BAC analoguesP13-P18with pyridine rings were synthesized. The new compounds were characterized by NMR, FT-IR and ESI-MS methods. PM3 semiempirical calculations of molecular structures and the heats of formation of compoundsP13-P18were also performed. Critical micellization concentrations (CMCs) were determined to characterize the aggregation behavior of the new BAC analogues. The antimicrobial properties of novel QACs were examined by determining their minimal inhibitory concentration (MIC) values against the fungiAspergillus niger,Candida albicans,Penicillium chrysogenumand bacteriaStaphylococcus aureus,Bacillus subtilis,Escherichia coliandPseudomonas aeruginosa. The MIC values ofN,N-dimethyl-N-(4-methylpyridyl)-N-alkylammonium chlorides for fungi range from 0.1 to 12 mM and for bacteria, they range from 0.02 to 6 mM.
authors.affiliation: Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznan, Umultowska 89b, 61-614 Poznań, Poland. brycki@amu.edu.pl.
authors.forename: Bogumił
authors.initials: B
authors.lastname: Brycki
authors.affiliation: Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University in Poznan, Umultowska 89b, 61-614 Poznań, Poland. imalecka@amu.edu.pl.
authors.forename: Izabela
authors.initials: I
authors.lastname: Małecka
authors.affiliation: Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wólczańska 171/173, 90-924 Łódź, Poland. anna.kozirog@p.lodz.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Koziróg
authors.affiliation: Institute of Fermentation Technology and Microbiology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wólczańska 171/173, 90-924 Łódź, Poland. anna.otlewska@p.lodz.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Otlewska
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects / Q000254:growth & development; D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D001548:Benzalkonium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D008823:Micelles; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010408:Penicillium chrysogenum / Q000187:drug effects / Q000254:growth & development; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D011725:Pyridines / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D001548:Benzalkonium Compounds; D008823:Micelles; D011725:Pyridines
keywords: antimicrobial resistance; benzalkonium chlorides; biocides; critical micellization concentrations; minimal inhibitory concentration; quaternary ammonium salts