Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives
文献信息
Justyna Łuczak, Christian Jungnickel, Izabela Łącka, Stefan Stolte, Jan Hupka
Knowledge of the structure–activity relationship (SAR) allows for the possibility to design and synthesize new cationic amphiphiles with optimized antimicrobial activities for future development of new disinfectants, sanitizers or preservatives. The need to design and identify new compounds, possessing antimicrobial properties, results from the emergence of more resistant micro-organisms in our globalized society. Hitherto, most studies which analyse the biological activity of ionic liquids (ILs) investigate the effect of the cation, whereas the knowledge of the effect of the anion is limited. The present study confirms the existence of a strong relationship among structure, surface activity and biological action of imidazolium ionic liquids on bacteria and fungi. The dependence of the antimicrobial activity on chemical structure–chain length and anion type of 30 compounds was determined. The anion is an important structural element which partakes in the definition of the phyiscochemical properties of the IL, and in consequence the technological applications and mode of action of the compound. The introduction of a longer substituent on the imidazolium cation results in a lower minimal inhibitory concentration (MIC). Thus, antifungal and antibacterial activities were found to increase with chain length, very often up to a point exhibiting a cut-off effect at chain lengths of 16 or 18 for the imidazolium cation and the [Cl] anion. The efficiency of surface tension reduction circumscribed by the pC20 and the relationship between antimicrobial activity and pC20 is described herein. The relationship indicates an antimicrobial mode of action dependant on the surface activity of the molecule, inferring that surface activity may contribute to the cut-off effect in the biological activity of ILs.
期刊推荐

Proceedings of the National Academy of Sciences of the United States of America

Organic Preparations and Procedures International

Journal of Medicinal Chemistry

Science

Pure and Applied Chemistry

Journal of Catalysis

European Journal of Wood and Wood Products

Planta Medica

Russian Chemical Reviews

Fibre Chemistry
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Green Chemistry

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.



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