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. Epub 2014 Sep 28.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • CHO Cells
  • Cell Survival / drug effects
  • Cricetinae
  • Cricetulus
  • Fungi / drug effects*
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Quaternary Ammonium Compounds / chemistry
  • Quinolinium Compounds / chemical synthesis*
  • Quinolinium Compounds / chemistry*
  • Quinolinium Compounds / pharmacology
  • Quinolinium Compounds / toxicity
  • Salts / chemistry

Substances

  • Anti-Infective Agents
  • Quaternary Ammonium Compounds
  • Quinolinium Compounds
  • Salts