Bicephalic amphiphile architecture affects antibacterial activity
| Autor: | Christian R. Schwantes, Kelsey L. Wilson-Henjum, Devon Flaherty, Kristina M. Hamill, David C. Warnock, Kaitlin L. Simmons, Kevin P. C. Minbiole, Robert W. Davis, Kyle Seifert, Jade E. LaDow, Jon A. L. Willcox, Kevin L. Caran |
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| Rok vydání: | 2011 |
| Předmět: |
Pharmacology
Lysis biology Chemistry medicine.drug_class Organic Chemistry Cationic polymerization Microbial Sensitivity Tests General Medicine Gram-Positive Bacteria Antimicrobial biology.organism_classification Combinatorial chemistry Anti-Bacterial Agents Structure-Activity Relationship Antiseptic Biochemistry Gram-Negative Bacteria Drug Discovery Amphiphile medicine Alkoxy group Antibacterial activity Bacteria |
| Zdroj: | European Journal of Medicinal Chemistry. 46:4219-4226 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2011.06.026 |
| Popis: | A series of cationic amphiphiles, each with an aromatic core, was prepared and investigated for antimicrobial properties. The synthesized amphiphiles in this study are bicephalic (double-headed) in that they each possess two trimethylammonium head groups and a single linear alkoxy tail. Minimum inhibitory and minimum bactericidal concentrations of these amphiphiles were in the low micromolar range. Antimicrobial activities are highly sensitive to the chain length of the hydrophobic region, and modestly reliant on the relative positioning of the head groups on the aromatic core. These trends were more pronounced in time kill assays, wherein longer chain compounds required significantly shorter times to completely kill bacteria. Microscopy suggested that the mode of cell death was lysis. Strong inhibition was observed with both biscationic compounds and monocationic comparisons against Gram-positive bacteria; only biscationic amphiphiles maintained good activity versus the Gram-negative bacteria tested. These observations provide direction for future antimicrobial structural investigations. |
| Databáze: | OpenAIRE |
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