Caffeic and 3-(3,4-dihydroxyphenyl)glyceric acid derivatives as antimicrobial agent: biological evaluation and molecular docking studies

• Published in: SAR and QSAR in environmental research Vol. 33; no. 4; pp. 307 - 321
• Main Authors: Merlani, M., Barbakadze, V., Amiranashvili, L., Gogilashvili, L., Petrou, A., Geronikaki, A., Ćirić, A., Glamočlija, J., Soković, M.
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 03.04.2022
• Subjects: 14a-lanosterol demethylase; Anti-Bacterial Agents - pharmacology; Anti-Infective Agents; Antibacterial; antifungal; docking; Escherichia coli; Glyceric Acids; Ketoconazole; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Molecular Docking Simulation; Quantitative Structure-Activity Relationship; Structure-Activity Relationship; antifungal; docking; 14a-lanosterol demethylase; Antibacterial
• ISSN: 1062-936X; 1029-046X
• DOI: 10.1080/1062936X.2022.2066173

Herein we report the evaluation of the antimicrobial activity of some previously synthesized 3-(3,4-dihydroxyphenyl)glyceric acid in benzylated and in free 3,4 hydroxy groups in catechol moiety along with some caffeic and 3-(3,4-dihydroxyphenyl)glyceric acid amides using the microdilution method. The evaluation revealed that compounds showed in general moderate to low activity with MIC in range of 0.36-4.5 mg/mL. Compounds were also studied against three resistant bacteria strains MRSA (Methicillin-resistant Staphylococcus aureus), E. coli and P. aeruginosa. Seven out of ten compounds were more potent than reference drugs ampicillin and streptomycin against MRSA, while against another two resistant strains seven compounds showed low activity and the rest were inactive. Antifungal activity of the tested compounds was much better than antibacterial, with MIC in the range of 0.019-3.0 mg/mL. Compounds #7 and 15 showed good activity against all fungi tested, being more potent than ketoconazole and in some case even better than bifonazole used as reference drugs. Docking studies revealed that the most active compound #7 binds to the haem group of the enzyme in the same way as ketoconazole.