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Molecules. 2018 Sep 14;23(9). pii: E2354. doi: 10.3390/molecules23092354.

Novel Alkylimidazolium Ionic Liquids as an Antibacterial Alternative to Pathogens of the Skin and Soft Tissue Infections.

Author information

1
Instituto de Química de Recursos Naturales, Universidad de Talca, P.O. Box 747, Talca 3460000, Chile. oforero@utalca.cl.
2
Multidisciplinary Agroindustry Research Laboratory, Universidad Autónoma de Chile, Talca 3460000, Chile. ricastro@utalca.cl.
3
Carrera de Ingeniería en Construcción e Instituto de Ciencias Químicas Aplicadas, Universidad Autónoma de Chile, Talca 3460000, Chile. ricastro@utalca.cl.
4
Instituto de Química de Recursos Naturales, Universidad de Talca, P.O. Box 747, Talca 3460000, Chile. mgutierrez@utalca.cl.
5
Departamento de Salud Municipal de Hualañe, Maule 3530000, Chile. dgonzalez@ssmaule.cl.
6
Instituto de Química de Recursos Naturales, Universidad de Talca, P.O. Box 747, Talca 3460000, Chile. lssantos@utalca.cl.
7
Instituto de Ciencias Biomédicas, Universidad Autónoma de Chile, Talca 3460000, Chile. damach.david@gmail.com.
8
Departamento de Bioquímica Clínica e Inmunohematología, Facultad de Ciencias de la Salud, Universidad de Talca, P.O. Box 747, Talca 3460000, Chile. lguzman@utalca.cl.

Abstract

Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (IC50) of the different ILs were determined by microdilution in broth, also Molecular dynamics simulations were performed to study the interaction mechanism between ILs and membranes. The MIC value in Gram-positive bacteria showed that as the hydrocarbon chain increases, the MIC value decreases with a dose-dependent effect. Furthermore, Gram-negative bacteria showed high MIC values, which were also evidenced in the antibacterial screening. The molecular dynamics showed an incorporation of the ILs with the longer chain (10 C), corresponding to a passive diffusion towards the membrane surface, for its part, the ILs with the shorter chain due to its lack of hydrophobicity was not incorporated into the bilayer. Finally, the new ILs synthesized could be an alternative for the treatment of Gram-positive bacteria causative of SSTIs.

KEYWORDS:

antibacterial; ionic liquids; skin and soft tissue infections

PMID:
30223457
PMCID:
PMC6225289
DOI:
10.3390/molecules23092354
[Indexed for MEDLINE]
Free PMC Article

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