Chemical reactivity and antimicrobial activity of N-substituted maleimides
| Autor: | Michal Sabisz, Natalia Salewska, Izabela Lącka, Joanna Boros-Majewska, Maria J. Milewska, Sławomir Milewski, Katarzyna Chylińska |
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| Rok vydání: | 2011 |
| Předmět: |
Staphylococcus aureus
Antifungal Agents Stereochemistry Microbial Sensitivity Tests Maleimides Structure-Activity Relationship chemistry.chemical_compound Chitin Biosynthesis Candida albicans Drug Discovery Escherichia coli Humans Organic chemistry Enzyme Inhibitors Cell Proliferation Glucan Pharmacology chemistry.chemical_classification Dose-Response Relationship Drug Molecular Structure biology General Medicine Cytostatic Agents biology.organism_classification Antimicrobial Anti-Bacterial Agents Enzyme chemistry Glucosyltransferases Lipophilicity Antibacterial activity Bacillus subtilis HeLa Cells |
| Zdroj: | Journal of Enzyme Inhibition and Medicinal Chemistry. 27:117-124 |
| ISSN: | 1475-6374 1475-6366 |
| Popis: | Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.5-4 µg ml(-1) range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC(50) values below 0.1 µg ml(-1). Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells. |
| Databáze: | OpenAIRE |
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