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Open AccessArticle
Antimicrobial Activity of Anionic Bis(N-Heterocyclic Carbene) Silver Complexes
1
Departamento de Química Inorgánica, Facultad de Química, Universidad de Sevilla, 41012 Sevilla, Spain
2
Departamento de Microbiología, Facultad de Biología, Universidad de Sevilla, 41012 Sevilla, Spain
3
Servicio de Resonancia Magnética Nuclear, CITIUS, Universidad de Sevilla, 41012 Sevilla, Spain
4
Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, 41092 Sevilla, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(19), 4608; https://doi.org/10.3390/molecules29194608 (registering DOI)
Submission received: 7 September 2024
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Revised: 20 September 2024
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Accepted: 23 September 2024
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Published: 27 September 2024
Abstract
The antimicrobial properties of a series of anionic bis(carbene) silver complexes Na3[Ag(NHCR)2] were investigated (2a–2g and 2c′, where NHCR is a 2,2′‑(imidazol-2-ylidene)dicarboxylate-type N‑heterocyclic carbene). The complexes were synthesized by the interaction of imidazolium dicarboxylate compounds with silver oxide in the presence of aqueous sodium hydroxide. Complexes 2f,g were characterized analytically and spectroscopically, and the ligand precursor 1f and complexes 2c and 2g were structurally identified by X-ray diffraction methods. The anions of 2c and 2g, [Ag(NHCR)2]3−, showed a typical linear disposition of Ccarbene-Ag-Ccarbene atoms and an uncommonly eclipsed conformation of carbene ligands. The antimicrobial properties of complexes 2a–g, which contains chiral (2b–2e and 2c′) and non-chiral derivatives (2a,f,g), were evaluated against Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa, and a Gram‑positive bacterium, Staphylococcus aureus. From the observed values of the minimal inhibitory concentration and minimal bactericidal concentration, complexes 2a and 2b showed the best antimicrobial activity against all strains. An interesting chirality–antimicrobial relationship was found, and eutomer 2c′ showed better activity than its enantiomer 2c against the three bacteria. Furthermore, these complexes were investigated experimentally and theoretically by 109Ag nuclear magnetic resonance, and the electronic and steric characteristics of the dianionic carbene ligands were also examined.
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MDPI and ACS Style
Carrasco, C.J.; Montilla, F.; Villalobo, E.; Angulo, M.; Álvarez, E.; Galindo, A.
Antimicrobial Activity of Anionic Bis(N-Heterocyclic Carbene) Silver Complexes. Molecules 2024, 29, 4608.
https://doi.org/10.3390/molecules29194608
AMA Style
Carrasco CJ, Montilla F, Villalobo E, Angulo M, Álvarez E, Galindo A.
Antimicrobial Activity of Anionic Bis(N-Heterocyclic Carbene) Silver Complexes. Molecules. 2024; 29(19):4608.
https://doi.org/10.3390/molecules29194608
Chicago/Turabian Style
Carrasco, Carlos J., Francisco Montilla, Eduardo Villalobo, Manuel Angulo, Eleuterio Álvarez, and Agustín Galindo.
2024. "Antimicrobial Activity of Anionic Bis(N-Heterocyclic Carbene) Silver Complexes" Molecules 29, no. 19: 4608.
https://doi.org/10.3390/molecules29194608
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