Sulfonamide-salicylaldehyde imines active against methicillin- and trimethoprim/sulfonamide-resistant Staphylococci
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
34633218
DOI
10.4155/fmc-2021-0169
Knihovny.cz E-resources
- Keywords
- Schiff bases, Staphylococcus aureus, antibacterial activity, cytotoxicity, drug resistance, imine, in vitro activity, sulfamethoxazole, sulfonamides,
- MeSH
- Aldehydes chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Drug Resistance, Bacterial drug effects MeSH
- Imines chemistry pharmacology MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Staphylococcus drug effects MeSH
- Sulfonamides chemistry pharmacology MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Aldehydes MeSH
- Anti-Bacterial Agents MeSH
- Imines MeSH
- salicylaldehyde MeSH Browser
- Sulfonamides MeSH
Background: Increasing resistance has resulted in an urgent need for new antimicrobial drugs. A systematic me-too approach was chosen to modify clinically used sulfonamides to obtain their imines. Methods & results: Twenty-five compounds were synthesized and evaluated for their antibacterial activity. The most active compounds were also investigated against methicillin- and trimethoprim/sulfamethoxazole (SMX)-resistant Gram-positive species. Staphylococci shared the highest susceptibility including resistant strains with minimum inhibitory concentrations from 3.91 μM (≥2.39 μg ml-1). Crucially, the compounds inhibit MRSA and trimethoprim/SMX-resistant Staphylococci without any cross-resistance. Modification of parent sulfonamides turned a bacteriostatic effect into a bactericidal effect. Toxicity for HepG2 and hemolytic properties were also determined. Conclusions: The presence of a dihalogenated salicylidene moiety is required for optimal activity. Based on toxicity, promising derivatives for further investigation were identified.
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