Design, synthesis, and biological evaluation of β-lactam antibiotic-based imidazolium- and pyridinium-type ionic liquids

Chem Biol Drug Des. 2011 Jul;78(1):33-41. doi: 10.1111/j.1747-0285.2011.01114.x. Epub 2011 May 25.

Abstract

We herein report the preparation and investigation of antibacterial activity of biocidal ionic liquids (ILs) consisting of cationic imidazolium or pyridinium and an anionic β-lactam antibiotic. The antibacterial properties were quantified by measuring the minimum inhibitory concentration and minimum bactericidal concentration against Escherichia coli O157:H7, Klebsiella pneumoniae, Staphylococcus aureus, and Enterococcus faecium. In general, the ILs had improved antibacterial activity than their parent materials, whether individually or in combination. In 83% of the experiments, the ampicillin ILs (Amp-ILs) had better antibacterial activities than their quaternary halide parent materials, whereas in 92% of the experiments, Amp-ILs outperformed the commercially available sodium ampicillin salt. Amp-ILs had up to 43 times improved antibacterial activity than sodium ampicillin. Overall, when normalized for ampicillin content, ILs had greater antimicrobial activity against E. coli O157:H7, K. pneumoniae, S. aureus, and E. faecium than sodium ampicillin alone.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Drug Design*
  • Drug Evaluation, Preclinical*
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Imidazoles / chemistry*
  • Inhibitory Concentration 50
  • Ions
  • Magnetic Resonance Spectroscopy
  • Micelles
  • Microbial Sensitivity Tests
  • Pyridinium Compounds / chemistry*
  • Solubility
  • beta-Lactams / chemical synthesis*
  • beta-Lactams / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Imidazoles
  • Ions
  • Micelles
  • Pyridinium Compounds
  • beta-Lactams