N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects

Molecules. 2019 Sep 26;24(19):3484. doi: 10.3390/molecules24193484.

Abstract

The bacterial resistance to antibiotics has compromised the therapies used for bacterial infections. Nowadays, many strategies are being carried out to address this problem. Among them, the use of natural compounds like cinnamic and p-coumaric acids stands out. Nevertheless, their utilization is limited because of their unfavorable physicochemical properties. Due to the lack of new therapeutic alternatives for bacterial infections, novel strategies have emerged, such as the use of ionic liquids; given that they can show a broad spectrum of antibacterial activity, this is why we herein report the antibacterial and antibiofilm activity of a series of N-alkylimidazolium salts functionalized with p-coumaric and cinnamic acids. The results from this study showed better antibacterial activity against Gram-positive bacteria, with a predominance of the salts derived from coumaric acid and a correlation with the chain length. Additionally, a lower efficacy was observed in the inhibition of biofilm formation, highlighting the antibiofilm activity against Staphylococcus aureus, which decreased the production of the biofilm by 52% over the control. In conclusion, we suggest that the salts derived from p-coumaric acid are good alternatives as antibacterial compounds. Meanwhile, the salt derived from cinnamic acid could be a good alternative as an antibiofilm compound.

Keywords: Antibiofilm effects; antimicrobial agents; cinnamoylimidazole salts; ionic liquids.

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Biofilms / drug effects*
  • Cinnamates / chemistry*
  • Coumaric Acids
  • Imidazoles / chemistry*
  • Imidazoles / pharmacology*
  • Ionic Liquids
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Dynamics Simulation
  • Propionates / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Cinnamates
  • Coumaric Acids
  • Imidazoles
  • Ionic Liquids
  • Propionates
  • cinnamic acid
  • imidazole
  • p-coumaric acid