The effect of the cationic structures of chiral ionic liquids on their antimicrobial activities

Feder‐Kubis, Joanna; Tomczuk, Krzysztof

doi:10.1016/j.tet.2013.03.107

Cited by 53 publications

(39 citation statements)

References 29 publications

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“…On the other hand, 1‐alkyl‐3‐methylimidazolium chlorides possess a broad‐spectrum antibiofilm activity towards clinically significant microbial pathogens81 and the ampicillin ILs display up to 43‐times improved antibacterial activity towards E. coli , Klebsiella pneumoniae ( K. pneumoniae ), S. aureus , and Enterococcus faecium ( E. faecium ) compared to sodium ampicillin 82. The presence of (1 R ,2 S ,5 R )‐(−)‐menthol in the cation moiety increased the antimicrobial activity of ILs and the optically active ILs were significantly more potent than their racemic counterparts, suggesting possible application in antisepsis 83. Bacteria were also used for studying ecotoxicity of ILs.…”

Section: Determination and Analysis Of Eco‐ And Cytotoxicity Of Iomentioning

confidence: 99%

Toxicity of Ionic Liquids: Eco(cyto)activity as Complicated, but Unavoidable Parameter for Task‐Specific Optimization

2014

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Rapid progress in the field of ionic liquids in recent decades led to the development of many outstanding energy-conversion processes, catalytic systems, synthetic procedures, and important practical applications. Task-specific optimization emerged as a sharpening stone for the fine-tuning of structure of ionic liquids, which resulted in unprecedented efficiency at the molecular level. Ionic-liquid systems showed promising opportunities in the development of green and sustainable technologies; however, the chemical nature of ionic liquids is not intrinsically green. Many ionic liquids were found to be toxic or even highly toxic towards cells and living organisms. In this Review, we show that biological activity and cytotoxicity of ionic liquids dramatically depend on the nature of a biological system. An ionic liquid may be not toxic for particular cells or organisms, but may demonstrate high toxicity towards another target present in the environment. Thus, a careful selection of biological activity data is a must for the correct assessment of chemical technologies involving ionic liquids. In addition to the direct biological activity (immediate response), several indirect effects and aftereffects are of primary importance. The following principal factors were revealed to modulate toxicity of ionic liquids: i) length of an alkyl chain in the cation; ii) degree of functionalization in the side chain of the cation; iii) anion nature; iv) cation nature; and v) mutual influence of anion and cation.

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Section: Determination and Analysis Of Eco‐ And Cytotoxicity Of Iomentioning

confidence: 99%

Toxicity of Ionic Liquids: Eco(cyto)activity as Complicated, but Unavoidable Parameter for Task‐Specific Optimization

2014

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“…However, the study conducted on the influence of ionic liquids (ILs) on the aquatic and soil environment gives rise to a serious concern about the possibility of a permanent contamination of these ecosystems with the discussed compounds. IL toxicity has been observed in microorganisms, fungi, algae, terrestrial plants, invertebrates, and vertebrates (Pham et al 2010 ; Petkovic et al 2012 ; Peric et al 2013 ; Cvjetko Bubalo et al 2014b ; Feder-Kubis and Tomczuk 2013 ; Messali et al 2013 ).…”

Section: Introductionmentioning

confidence: 99%

Role of cation structure in the phytotoxicity of ionic liquids: growth inhibition and oxidative stress in spring barley and common radish

Biczak

Pawłowska

Telesiński

et al. 2017

Environ Sci Pollut Res

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The present study determines the influence of three ionic liquids (ILs) containing cations with diversified structure on the growth and development of spring barley seedlings and common radish leaves. Increasing amounts of 1-butyl-1-methylpyrrolidinium hexafluorophosphate [Pyrrol][PF6], 1-butyl-1-methylpiperidinium hexafluorophosphate [Piper][PF6], and 1-butyl-4-methylpyridinium hexafluorophosphate [Pyrid][PF6] were added to the soil on which both plants were cultivated. The results of this studies showed that the applied ILs were highly toxic for plants, demonstrated by the inhibition of length of plant shoots and roots, decrease of fresh mass, and increase of dry weight content. Common radish turned out to be the plant with higher resistance to the used ILs. The differences in the cation structure did not influence phytotoxity of ILs for spring barley. Furthermore, all ILs led to a decrease of photosynthetic pigments, which was directly followed by decreased primary production in plants. Oxidative stress in plants occurred due to the presence of ILs in the soil, which was demonstrated by the increase of malondialdehyde (MDA) content, changes in the H2O2 level, and antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD). The changes in the chlorophyll contents and the increase of POD activity turned out to be the most significant oxidative stress biomarkers in spring barley and common radish. Both spring barley and radish exposed to ILs accumulated a large amount of fluoride ion.Electronic supplementary materialThe online version of this article (doi:10.1007/s11356-017-9439-x) contains supplementary material, which is available to authorized users.

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“…Synthesized chiral chlorides were verified for antimicrobial activity against rods, cocci, bacillus and fungi 35. …”

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Symmetrical Imidazolium Chloride Based on (−)-Menthol: Synthesis, Characterization, and Theoretical Model of the Reaction

2014

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New symmetrical imidazolium chloride from a natural chiral pool of (1R,2S,5R)-(-)-menthol can be efficiently prepared by two different methods. The first method involves a specific type of Menschutkin reaction using novel 1-(1R,2S,5R)-(-)-menthoxymethylimidazole as amine, chloromethyl (1R,2S,5R)-(-)-menthyl ether as quaternization agent, and hexane as solvent. In the second method, imidazole, chloromethyl (1R,2S,5R)-(-)-menthyl ether, and DMF are used. To understand this specific type of the reaction, quantum chemical calculations at the DFT level have been used. The preparation and characterization of 1,3-bis[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium chloride are reported.

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The effect of the cationic structures of chiral ionic liquids on their antimicrobial activities

Cited by 53 publications

References 29 publications

Toxicity of Ionic Liquids: Eco(cyto)activity as Complicated, but Unavoidable Parameter for Task‐Specific Optimization

Toxicity of Ionic Liquids: Eco(cyto)activity as Complicated, but Unavoidable Parameter for Task‐Specific Optimization

Role of cation structure in the phytotoxicity of ionic liquids: growth inhibition and oxidative stress in spring barley and common radish

Symmetrical Imidazolium Chloride Based on (−)-Menthol: Synthesis, Characterization, and Theoretical Model of the Reaction

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