Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate

• Published in: Bioorganic & medicinal chemistry letters 2011-12, Vol.21 (23), p.6996-7000
• Main Authors: Anderson, James C., McCarthy, Robert A., Paulin, Sarah, Taylor, Peter W.
• Format: Article
• Language: English
• Subjects: (−)-Epicatechin gallate analogues; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibacterial chemotherapy; antibacterial properties; Antibiotic resistance; Antibiotics. Antiinfectious agents. Antiparasitic agents; beta-Lactam Resistance - drug effects; Biological and medical sciences; Catechin - analogs & derivatives; Catechin - chemistry; Catechin - pharmacology; chemistry; Hydroxylation; Medical sciences; methicillin; Methicillin-Resistant Staphylococcus aureus - drug effects; Microbial Sensitivity Tests; Molecular Structure; MRSA; oxacillin; Oxacillin - pharmacology; Pharmacology. Drug treatments; β-Lactam antibiotics
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2011.09.116

We examined the impact of gradual removal of hydroxyl groups from the A- and B-rings of (−)-epicatechin gallate on antibacterial activity and oxacillin resistance attenuation of an epidemic strain of methicillin resistant Staphylococcus aureus. Removal of both hydroxyls from the B-ring effected a large reduction in oxacillin MIC (from 512 to 0.25 mg/mL at a concentration of 12.5 mg/L); further hydroxyl deletion of the A-ring reduced the oxacillin effect but increased intrinsic anti-staphylococcal activity