Evidence of a reverse side-chain effect of tris(pentafluoroethyl)trifluorophosphate [FAP]-based ionic liquids against pathogenic bacteria

Weyhing-Zerrer, Nadine; Kalb, Roland; Oßmer, Rolf; Rossmanith, Peter; Mester, Patrick

doi:10.1016/j.ecoenv.2017.10.059

Cited by 23 publications

(16 citation statements)

References 43 publications

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“…In particular, 1-butyl-3methylimidazolium bis(trifluoromethanesulfonyl)imide ( S1) [95]. Interestingly, it was demonstrated that for ILs with tris(pentafluoroethyl)trifluorophosphate anions, the antimicrobial activity decreased upon increasing the alkyl side chain length [96].…”

Section: Common Ionic Liquids and Ionic Liquids With Active Pharmaceutical Ingredients (Api-ils)mentioning

confidence: 99%

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

Vereshchagin

Frolov

Egorova

et al. 2021

IJMS

170

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Quaternary ammonium compounds (QACs) belong to a well-known class of cationic biocides with a broad spectrum of antimicrobial activity. They are used as essential components in surfactants, personal hygiene products, cosmetics, softeners, dyes, biological dyes, antiseptics, and disinfectants. Simple but varied in their structure, QACs are divided into several subclasses: Mono-, bis-, multi-, and poly-derivatives. Since the beginning of the 20th century, a significant amount of work has been dedicated to the advancement of this class of biocides. Thus, more than 700 articles on QACs were published only in 2020, according to the modern literature. The structural variability and diverse biological activity of ionic liquids (ILs) make them highly prospective for developing new types of biocides. QACs and ILs bear a common key element in the molecular structure–quaternary positively charged nitrogen atoms within a cyclic or acyclic structural framework. The state-of-the-art research level and paramount demand in modern society recall the rapid development of a new generation of tunable antimicrobials. This review focuses on the main QACs exhibiting antimicrobial and antifungal properties, commercial products based on QACs, and the latest discoveries in QACs and ILs connected with biocide development.

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Section: Common Ionic Liquids and Ionic Liquids With Active Pharmaceutical Ingredients (Api-ils)mentioning

confidence: 99%

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

Vereshchagin

Frolov

Egorova

et al. 2021

IJMS

170

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“…The use of a hydrophobic anion ([(CF 3 SO 2 ) 2 N]) increased the ILs toxicity, confirming the influence of the hydrophobic anions on the toxic effect of ILs. The increase of the cation alkyl side-chain led to increased ILs hydrophobicity and consequently to a significant increase in their toxicity, as we have seen from the work of Weyhing-Zerrer and coworkers [ 53 , 54 ]. However, hydrophobicity does not tell the whole history.…”

Section: Effect Of Ionic Liquids On Microorganismsmentioning

confidence: 78%

“…The ILs, [N 4,4,4,4 ][OH] and [P 4,4,4,4 ][OH] were considered harmless against all bacteria. The other six ILs were considered practically harmless, and like in the studies presented by Weyin-Zerrer [ 53 , 54 ], no significant distinctions were observed in the toxicities between Gram-positive and -negative bacteria. In this study, the Gram-positive bacteria were also revealed to be more susceptible than Gram-negative bacteria due to the thicker and more lipophilic cell membranes of the Gram-positive.…”

Section: Effect Of Ionic Liquids On Microorganismsmentioning

confidence: 97%

“…However, no explanation was found for this behavior. To better understand the effect of [(C 2 F 5 ) 3 PF 3 ] anion, the authors performed a more focused study [ 54 ], where they confirmed that Gram-positive bacteria were more susceptible to [(C 2 F 5 ) 3 PF 3 ] anion. A. fischeri was the most sensitive and susceptible to ILs from all the bacteria studied.…”

Section: Effect Of Ionic Liquids On Microorganismsmentioning

confidence: 99%

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Ionic Liquids—A Review of Their Toxicity to Living Organisms

Gonçalves

Paredes

Cristino

et al. 2021

IJMS

128

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Ionic liquids (ILs) were initially hailed as a green alternative to traditional solvents because of their almost non-existent vapor pressure as ecological replacement of most common volatile solvents in industrial processes for their damaging effects on the environment. It is common knowledge that they are not as green as desired, and more thought must be put into the biological consequences of their industrial use. Still, compared to the amount of research studying their physicochemical properties and potential applications in different areas, there is a scarcity of scientific papers regarding how these substances interact with different organisms. The intent of this review was to compile the information published in this area since 2015 to allow the reader to better understand how, for example, bacteria, plants, fish, etc., react to the presence of this family of liquids. In general, lipophilicity is one of the main drivers of toxicity and thus the type of cation. The anion tends to play a minor (but not negligible) role, but more research is needed since, owing to the very nature of ILs, except for the most common ones (imidazolium and ammonium-based), many of them are subject to only one or two articles.

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“…It was found that they exhibited different level of sensitivity to ILs in terms of growth kinetics and viability. Three debatable notions have noticed from different studies: i) there are differences between the effects of ILs on Gram-positive and Gram-negative bacteria, [16,26,[74][75][76] ii) no discernible difference between the effects on the two types of bacteria, [3,77,78] iii) insufficient evidence to draw definitive conclusions on the effects on the bacteria types. [25,79] For example, Gram-positive B. subtilis was more resistant to imidazolium-based hydrophilic ILs, whereas Gramnegative Pseudomonas aeruginosa exhibited more tolerance to choline-and phosphonium-based ILs.…”

Section: Toxicity Of Ionic Liquids Toward Microorganismsmentioning

confidence: 99%

An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms

Sivapragasam

Moniruzzaman

Goto

2020

Biotechnology Journal

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Ionic liquids (ILs), a class of materials with unique physicochemical properties, have been used extensively in the fields of chemical engineering, biotechnology, material sciences, pharmaceutics, and many others. Because ILs are very polar by nature, they can migrate into the environment with the possibility of inclusion in the food chain and bioaccumulation in living organisms. However, the chemical natures of ILs are not quintessentially biocompatible. Therefore, the practical uses of ILs must be preceded by suitable toxicological assessments. Among different methods, the use of microorganisms to evaluate IL toxicity provides many advantages including short generation time, rapid growth, and environmental and industrial relevance. This article reviews the recent research progress on the toxicological properties of ILs toward microorganisms and highlights the computational prediction of various toxicity models.

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Evidence of a reverse side-chain effect of tris(pentafluoroethyl)trifluorophosphate [FAP]-based ionic liquids against pathogenic bacteria

Cited by 23 publications

References 43 publications

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

Ionic Liquids—A Review of Their Toxicity to Living Organisms

An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms

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