Effect of choline carboxylate ionic liquids on biological membranes

Rengstl, Doris; Kraus, Birgit; Vorst, Matthew Van; Elliott, Gloria D.; Kunz, Werner

doi:10.1016/j.colsurfb.2014.09.057

Cited by 47 publications

(42 citation statements)

References 44 publications

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“…Such an effect has also been detected in other studies, for instance, for choline carboxylates79. In the present study, the cation affected the EC 50 values only within the neodecanoate analogues: surprisingly, GND and TMG cations decreased the toxicity of the ILs when compared to their Na and Ch equivalents.…”

Section: Resultssupporting

confidence: 88%

“…The CMC for Na decanoate is in line with widely accepted value of ~100 mM48. Interestingly the CMC for Ch decanoate is somewhat lower than the value of 75 mM determined in a previous study7. For neodecanoates, the average values are notably higher – roughly between 100 and 450 mM.…”

Section: Resultssupporting

confidence: 88%

“…There are only a few studies investigating the effect of the alkyl chains in the IL anions and particularly the impact of the carboxylate ILs. Based on these studies the elongation of the carboxylate alkyl chain increases the toxic effect in similar way as for cations6789. However, this relationship between anion chain length and toxicity does not seem to be as widely recognized as the effect of the cation chain length, and therefore it needs to be further investigated.…”

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confidence: 98%

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Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Rantamäki

Ruokonen

Sklavounos

et al. 2017

Sci Rep

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We investigated the toxicological effect of seven novel cholinium, guanidinium, and tetramethylguanidinium carboxylate ionic liquids (ILs) from an ecotoxicological point of view. The emphasis was on the potential structure-toxicity dependency of these surface-active ILs in aqueous environment. The median effective concentrations (EC50) were defined for each IL using Vibrio (Aliivibrio) fischeri marine bacteria. Dipalmitoylphosphatidylcholine (DPPC) liposomes were used as biomimetic lipid membranes to study the interactions between the surface-active ILs and the liposomes. The interactions were investigated by following the change in the DPPC phase transition behaviour using differential scanning calorimetry (DSC). Critical micelle concentrations for the ILs were determined to clarify the analysis of the toxicity and the interaction results. Increasing anion alkyl chain length increased the toxicity, whereas branching of the chain decreased the toxicity of the ILs. The toxicity of the ILs in this study was mainly determined by the surface-active anions, while cations induced a minor impact on the toxicity. In the DSC experiments the same trend was observed for all the studied anions, whereas the cations seemed to induce more variable impact on the phase transition behaviour. Toxicity measurements combined with liposome interaction studies can provide a valuable tool for assessing the mechanism of toxicity.

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Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 88%

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confidence: 98%

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Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Rantamäki

Ruokonen

Sklavounos

et al. 2017

Sci Rep

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“…Aiming at better understanding the role played by surfaceactive ILs in the extraction process, the critical micellar concentration (CMC) of the studied ILs, when unavailable in the literature (Bai et al 2008;Łuczak et al 2008Rengstl et al 2014;El Seoud et al 2007;Smirnova and Safonova 2012), was determined by electric conductivity (Inoue et al 2007). The conductivity of several aqueous solutions of different concentrations of IL was determined by continuous dilution of an IL concentrated solution in water using a Russel RL105 Conductivity Meter at 25°C.…”

Section: Determination Of Critical Micellar Concentration (Cmc)mentioning

confidence: 99%

Extraction and recovery processes for cynaropicrin from Cynara cardunculus L. using aqueous solutions of surface-active ionic liquids

et al. 2018

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Due to the wide range of relevant biological activities and high commercial value of cynaropicrin, and aiming at developing cost-effective processes, aqueous solutions of ionic liquids (ILs) were investigated for the extraction and recovery of cynaropicrin from the leaves of Cynara cardunculus L. Both cationic (1-alkyl-3-methylimidazolium chloride) and anionic (cholinium carboxylate) surface-active ILs were investigated, as well as a wide range of conventional surfactants and molecular organic solvents, allowing us to conclude that aqueous solutions of cationic surface-active ILs display a better performance for the extraction of cynaropicrin. Operational conditions were optimized, leading to a cynaropicrin extraction yield of 3.73 wt%. The recycling of both the biomass and the solvent were further investigated to appraise the extraction media saturation and to achieve a higher cynaropicrin extraction yield (6.47 wt%). Finally, it was demonstrated that 65 wt% of the extracted cynaropicrin can be efficiently recovered by precipitation from the IL aqueous extract through the addition of water as anti-solvent, allowing us to put forward both the extraction and recovery processes of the target value-added compound from biomass followed by solvent recycling. This approach opens the door to the development of more sustainable processes using aqueous solutions of ILs instead of the volatile organic solvents commonly used in biomass processing.

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“…This is why a more detailed investigation of choline salts is highly interesting. Based on the available literature, choline salts are characterized by their low toxicity for different cell-lines [15,16], bacteria [17], and other organisms [18]. Moreover, choline salts are industrially available on a large scale.The most widely studied choline salt used in eutectic mixtures is choline chloride [19][20][21][22][23][24][25][26].…”

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confidence: 99%

Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

et al. 2020

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Mixing ionic liquids is a suitable strategy to tailor properties, e.g., to reduce melting points. The present study aims to widen the application range of low-toxic choline-based ionic liquids by studying eight binary phase diagrams of six different choline carboxylates. Five of them show eutectic points with melting points dropping by 13 to 45 • C. The eutectic mixtures of choline acetate and choline 2-methylbutarate were found to melt at 45 • C, which represents a remarkable melting point depression compared to the pure compounds with melting points of 81 (choline acetate) and 90 • C (choline 2-methylbutarate), respectively. Besides melting points, the thermal stabilities of the choline salt mixtures were investigated to define the thermal operation range for potential practical applications of these mixtures. Typical decomposition temperatures were found between 165 and 207 • C, with choline lactate exhibiting the highest thermal stability.Advantages of DESs compared to pure ILs include easy preparation and therefore low production costs, increased biocompatibility in case of certain components, and bigger variety for customization concerning acidity, hydrophobicity, or polarity. DES systems have demonstrated their practical use in several applications, such as interfacial polymerizations [7], electrochemistry [8], and organic reactions [9].So far, the published research describing IL mixtures has mainly focused on imidazolium [10,11], pyrrolidinium [12], and pyridinium [13] ILs. In these works, significant melting point suppression effects were found for the respective eutectic mixtures. However, imidazolium, pyrrolidinium, and pyridinium ILs and their mixtures face some limitations when it comes to large-scale applications in contact with microorganisms or living matter [14]. Challenges include toxicity aspects and the cost for the organic cation synthesis. This is why a more detailed investigation of choline salts is highly interesting. Based on the available literature, choline salts are characterized by their low toxicity for different cell-lines [15,16], bacteria [17], and other organisms [18]. Moreover, choline salts are industrially available on a large scale.The most widely studied choline salt used in eutectic mixtures is choline chloride [19][20][21][22][23][24][25][26]. One of the first reported DESs was a mixture of choline chloride (liquefaction temperature 302 • C), and urea (melting point 134 • C) that resulted in a 2:1 molar mixture with a remarkable melting point suppression to 12 • C [4]. The typical strategy was to combine choline ILs with molecular compounds such as carboxylic acids, alcohols, and urea derivates [27], and such choline-based DESs have been used in various applications, e.g., as drug solubilization vehicles [28][29][30]. Note, however, that by mixing a choline IL with molecular substances, some of the very attractive IL properties, e.g., non-volatility, non-flammability, and high ionic conductivity can get lost to a large extent. This is why the mixing of two choline ILs is ...

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Effect of choline carboxylate ionic liquids on biological membranes

Cited by 47 publications

References 44 publications

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Impact of Surface-Active Guanidinium-, Tetramethylguanidinium-, and Cholinium-Based Ionic Liquids on Vibrio Fischeri Cells and Dipalmitoylphosphatidylcholine Liposomes

Extraction and recovery processes for cynaropicrin from Cynara cardunculus L. using aqueous solutions of surface-active ionic liquids

Influence of Carboxylate Anions on Phase Behavior of Choline Ionic Liquid Mixtures

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