Resveratrol-Schiff Base Hybrid Compounds with Selective Antibacterial Activity: Synthesis, Biological Activity, and Computational Study

Sanchez-Gonzalez, Rodrigo; Leyton, Patricio; Aguilar, Luis F.; Reyna-Jeldes, Mauricio; Coddou, Claudio; Diaz, Katy; Mellado, Marco


Nowadays, antimicrobial resistance is a serious concern associated with the reduced efficacy of traditional antibiotics and an increased health burden worldwide. In response to this challenge, the scientific community is developing a new generation of antibacterial molecules. Contributing to this effort, and inspired by the resveratrol structure, five new resveratrol-dimers (9a-9e) and one resveratrol-monomer (10a) were synthetized using 2,5-dibromo-1,4-diaminobenzene (8) as the core compound for Schiff base bridge conformation. These compounds were evaluated in vitro against pathogenic clinical isolates of Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus sp., and Listeria monocytogenes. Antibacterial activity measurements of resveratrol-Schiff base derivatives (9a-9e) and their precursors (4-8) showed high selectivity against Listeria monocytogenes, being 2.5 and 13.7 times more potent than chloramphenicol, while resveratrol showed an EC50 > 320 mu g/mL on the same model. Moreover, a prospective mechanism of action for these compounds against L. monocytogenes strains was proposed using molecular docking analysis, finding a plausible inhibition of internalin C (InlC), a surface protein relevant in bacteria-host interaction. These results would allow for the future development of new molecules for listeriosis treatment based on compound 8.

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Título según WOS: ID WOS:000845516500001 Not found in local WOS DB
Título de la Revista: MICROORGANISMS
Volumen: 10
Número: 8
Editorial: MDPI
Fecha de publicación: 2022


Notas: ISI