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

Oscar Forero-Doria,Luis Guzmán,Anggela Barrientos-Retamal,Ramiro Araya-Maturana,Luis Morales-Quintana

doi:10.3390/molecules24193484

Oscar Forero-Doria, Luis Guzmán + Show 3 more

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https://doi.org/10.3390/molecules24193484

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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.

Highlights

Many applications and innovations have been reported in the field of ionic liquids (ILs), which are salts composed of ions that exist in the liquid state at room temperature [1]
Given that ILs can show a broad spectrum of activity, affecting Gram-positive and -negative bacteria, the aim of this work was to determine the antibacterial and antibiofilm activity of N-alkylimidazolium salts functionalized with p-coumaric and cinnamic acid, and to evaluate the minimum inhibitory concentration (MIC) of these derivatives with different chain lengths and their action on the formation of a biofilm in pathogenic bacteria
The synthesized salts showed good antibacterial activity against Gram-positive bacteria, and activity that decreased against the studied Gram-negative bacteria, and a better antibacterial effect was found when an OH group was presented in the structure of the salt, as observed in the salt 8c, which presented the best Minimum Inhibitory Concentration (MIC) value against S. epidermidis and S. aureus

Summary

Introduction

Many applications and innovations have been reported in the field of ionic liquids (ILs), which are salts composed of ions that exist in the liquid state at room temperature [1]. They are formed by organic cations that are linked with an organic or inorganic anion [2]. IL solutions share structural and mechanical analogies with established biocides and cationic surfactants, such as quaternary ammonium compounds [7,8]

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