Physicochemical and Theoretical Characterization of a New Small Non-Metal Schiff Base with a Differential Antimicrobial Effect against Gram-Positive Bacteria

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dc.contributor.authorGacitua, Manuel
dc.contributor.authorCarreno, Alexander
dc.contributor.authorMorales-Guevara, Rosaly
dc.contributor.authorPaez-Hernandez, Dayan
dc.contributor.authorMartinez-Araya, Jorge I.
dc.contributor.authorAraya, Eyleen
dc.contributor.authorPreite, Marcelo
dc.contributor.authorOtero, Carolina
dc.contributor.authorRivera-Zaldivar, Maria Macarena
dc.contributor.authorSilva, Andres
dc.contributor.authorFuentes, Juan A.
dc.date.accessioned2025-01-20T21:11:57Z
dc.date.available2025-01-20T21:11:57Z
dc.date.issued2022
dc.description.abstractSearching for adequate and effective compounds displaying antimicrobial activities, especially against Gram-positive bacteria, is an important research area due to the high hospitalization and mortality rates of these bacterial infections in both the human and veterinary fields. In this work, we explored (E)-4-amino-3-((3,5-di-tert-butyl-2-hydroxybenzylidene)amino) benzoic acid (SB-1, harboring an intramolecular hydrogen bond) and (E)-2-((4-nitrobenzilidene)amino)aniline (SB-2), two Schiff bases derivatives. Results demonstrated that SB-1 showed an antibacterial activity determined by the minimal inhibitory concentration (MIC) against Staphylococcus aureus, Enterococcus faecalis, and Bacillus cereus (Gram-positive bacteria involved in human and animal diseases such as skin infections, pneumonia, diarrheal syndrome, and urinary tract infections, among others), which was similar to that shown by the classical antibiotic chloramphenicol. By contrast, this compound showed no effect against Gram-negative bacteria (Klebsiella pneumoniae, Escherichia coli, and Salmonella enterica). Furthermore, we provide a comprehensive physicochemical and theoretical characterization of SB-1 (as well as several analyses for SB-2), including elemental analysis, ESMS, H-1 and C-13 NMR (assigned by 1D and 2D techniques), DEPT, UV-Vis, FTIR, and cyclic voltammetry. We also performed a computational study through the DFT theory level, including geometry optimization, TD-DFT, NBO, and global and local reactivity analyses.
dc.fuente.origenWOS
dc.identifier.doi10.3390/ijms23052553
dc.identifier.eissn1422-0067
dc.identifier.issn1661-6596
dc.identifier.urihttps://doi.org/10.3390/ijms23052553
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/93637
dc.identifier.wosidWOS:000768060500001
dc.issue.numero5
dc.language.isoen
dc.revistaInternational journal of molecular sciences
dc.rightsacceso restringido
dc.subjectSchiff bases
dc.subjectintramolecular hydrogen bond
dc.subjectHPLC-MS
dc.subjectcyclic voltammetry
dc.subjectDFT
dc.subjectlocal reactivity analysis
dc.subjectMIC
dc.subjectStaphylococcus aureus
dc.subjectEnterococcus faecalis
dc.subjectBacillus cereus
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titlePhysicochemical and Theoretical Characterization of a New Small Non-Metal Schiff Base with a Differential Antimicrobial Effect against Gram-Positive Bacteria
dc.typeartículo
dc.volumen23
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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