6-Hydroxyquinolinium salts differing in the length of alkyl side-chain: synthesis and antimicrobial activity

  • Bioorg Med Chem Lett. 2014 Nov 15;24(22):5238-41. doi: 10.1016/j.bmcl.2014.09.060.
David Malinak  1 ,  Rafael Dolezal  2 ,  Jan Marek  3 ,  Sarka Salajkova  4 ,  Ondrej Soukup  4 ,  Marcela Vejsova  5 ,  Jan Korabecny  4 ,  Jan Honegr  1 ,  Marek Penhaker  6 ,  Kamil Musilek  7 ,  Kamil Kuca  8
Affiliations
  • 1. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic; Department of Cybernetics and Biomedical Engineering, Faculty of Electrical Engineering and Computer Science, VSB-Technical University of Ostrava, 17. Listopadu 15, 708 33 Ostrava-Poruba, Czech Republic.
  • 2. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic; Center for Basic and Applied Research, FIM, University of Hradec Kralove, Rokitanskeho 62, Hradec Kralove 500 03, Czech Republic.
  • 3. Department of Epidemiology, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, 500 01 Hradec Kralove, Czech Republic; Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic.
  • 4. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic; Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Trebesska 1575, 500 01 Hradec Kralove, Czech Republic.
  • 5. Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic.
  • 6. Department of Cybernetics and Biomedical Engineering, Faculty of Electrical Engineering and Computer Science, VSB-Technical University of Ostrava, 17. Listopadu 15, 708 33 Ostrava-Poruba, Czech Republic.
  • 7. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic.
  • 8. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic. Electronic address: [email protected].
PMID: 25442318 DOI: 10.1016/j.bmcl.2014.09.060
Abstract

Quaternary ammonium salts substituted with a long alkyl chain exemplify a trustworthy group of medicinal compounds frequently employed as Antifungal and Antibacterial agents. A great asset of these Surfactants underlying their widespread use is low local and system toxicity in humans. In this Letter, a series of novel quaternary 6-hydroxyquinolinium salts with varying length of N-alkyl chain (from C10 to C18) was synthesized and tested for in vitro activity against pathogenic Bacterial and Fungal strains. 6-Hydroxyquinolinium salt with C12 alkyl chain seems to be very interesting candidate due to a high antimicrobial efficacy and cytotoxic safety.

Keywords
6-Hydroxyquinolinium salts; Antimicrobial activity; LC–MS; Surfactants; Synthesis.