Phosphonium pillar[5]arenes as a new class of efficient biofilm inhibitors: importance of charge cooperativity and the pillar platform
| Autor: | Roymon Joseph, Yoram Cohen, Micha Fridman, Maya Hadar, Dana Kaizerman, Mark Feldman, Ido M. Herzog |
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| Rok vydání: | 2016 |
| Předmět: |
Staphylococcus aureus
Stereochemistry Cooperativity 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Organophosphorus Compounds Calixarene Materials Chemistry Enterococcus faecalis Humans Ammonium Phosphonium Gram-Positive Bacterial Infections 010405 organic chemistry Metals and Alloys Biofilm General Chemistry Pillararene Staphylococcal Infections Combinatorial chemistry 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Anti-Bacterial Agents Quaternary Ammonium Compounds Monomer Membrane chemistry Biofilms Ceramics and Composites Calixarenes |
| Zdroj: | Chemical communications (Cambridge, England). 52(70) |
| ISSN: | 1364-548X |
| Popis: | Biofilm formation, which frequently occurs in microbial infections and often reduces the efficacy of antibiotics, also perturbs many industrial and domestic processes. We found that a new class of water soluble pillar[5]arenes bearing phosphonium moieties (1, 2) and their respective ammonium analogues (3, 4) inhibit biofilm formation with IC50 values in the range of 0.67–1.66 μM. These compounds have no antimicrobial activity, do not damage red blood cell membranes, and do not affect mammalian cell viability in culture. Comparison of the antibiofilm activities of the phosphonium-decorated pillar[5]arene derivatives 1 and 2 with their respective ammonium counterparts 3 and 4 and their monomers 5 and 6, demonstrate that while positive charges, charge cooperativity and the pillararene platform are essential for the observed antibiofilm activity the nature of the charges is not. |
| Databáze: | OpenAIRE |
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