Effects of phosphonium-based ionic liquids on phospholipid membranes studied by small-angle X-ray scattering

Kontro, Inkeri; Svedström, Kirsi; Duša, Filip; Ahvenainen, Patrik; Ruokonen, Suvi-Katriina; Witos, Joanna; Wiedmer, Susanne Κ.

doi:10.1016/j.chemphyslip.2016.11.003

Cited by 42 publications

(45 citation statements)

References 34 publications

(37 reference statements)

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“…Based on our earlier results, we assume that the main endotherm corresponds to the pure lipid bilayer without a remarkable amount of surfactants included, and the second endotherm at a lower temperature corresponds to newly formed mixed lipid–surfactant vesicles or a heterogeneous lipid–surfactant area in the otherwise pure liposome. In our previous study, we have shown that the lamellar distances of 1‐palmitoyl‐2‐oleyl‐phosphatidylcholine (POPC) multilamellar vesicles (MLVs) decrease and the lamellar disorder increases when [P 14 444 ][OAc] was added to the dispersion. The IL at a concentration of 0.4 m m caused also uneven lamellar spacing in the MLVs, suggesting that the effect of the IL is possibly different on the outer and inner lamellae.…”

Section: Resultsmentioning

confidence: 99%

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Ruokonen

Sanwald

Robciuc

et al. 2018

Chemistry A European J

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This study aims at extending the understanding of the toxicity mechanism of ionic liquids (ILs) using various analytical methods and cytotoxicity assays. The cytotoxicity of eight ILs and one zwitterionic compound was determined using mammalian and bacterial cells. The time dependency of the IL toxicity was assessed using human corneal epithelial cells. Hemolysis was performed using human red blood cells and the results were compared with destabilization data of synthetic liposomes upon addition of ILs. The effect of the ILs on the size and zeta potential of liposomes revealed information on changes in the lipid bilayer. Differential scanning calorimetry was used to study the penetration of the ILs into the lipid bilayer. Pulsed field gradient nuclear magnetic resonance spectroscopy was used to determine whether the ILs occurred as unimers, micelles, or if they were bound to liposomes. The results show that the investigated ILs can be divided into three groups based on the cytotoxicity mechanism: cell wall disrupting ILs, ILs exerting toxicity through both cell wall penetration and metabolic alteration, and ILs affecting solely on cell metabolism.

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Section: Resultsmentioning

confidence: 99%

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Ruokonen

Sanwald

Robciuc

et al. 2018

Chemistry A European J

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“…5 Schematic view of one of the sample configurations used in our MD simulations (Benedetto et al 2015). POPC domains in gray, water layers in red, [C 4 Shrinkage of the phospholipid bilayer thickness upon interaction with RTILs with water has been also confirmed by X-ray experiments (Bhattacharya et al 2017, Kontro et al 2016). In one case (Bhattacharya et al 2017), single supported bilayers of DPPC (a zwitterionic lipid) interacting with aqueous solutions of [bmim] [BF 4 ] have been measured by means of X-ray reflectivity at several RTIL concentrations.…”

Section: Introductionmentioning

confidence: 99%

“…NPS is a label-free optical technique that allows the study of surfaces and interfaces of metals, relying on surface plasmons, with a penetration depth of~10 nm (the quartz crystal microbalance has a penetration depth of about 250 nm). Wiedmer et al have also studied how the addition of cholesterol in the lipid phase changes the RTIL-biomembrane interaction (Kontro et al 2016). This is quite important, since it is well known that cholesterol is present in several biomembranes and stabilizes them.…”

Section: Introductionmentioning

confidence: 99%

“…7), so it is clear that in this case RTILs pass through the phospholipids multilayer superstructures. In the same study, Wiedmer and co-workers (Kontro et al 2016) probed the effect of RTILs using dynamic light scattering (DLS) and zeta potential measurements on large uni-lamellar vesicles. They concluded that the ability of RTILs to affect liposomes is related to the length of the hydrocarbon chains of their cations.…”

Section: Introductionmentioning

confidence: 99%

“…The second X-ray study cited above (Kontro et al 2016) used small-angle X-ray scattering (SAXS) to study multilamellar liposomes of eggPC and eggPG (80:20 mol%) -and with cholesterol (60:20:20 mol%) -in interaction with water solutions of phosphonium-based RTILs. The results were compared with those of the more common imidazolium-based RTILs.…”

Section: Introductionmentioning

confidence: 99%

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Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Benedetto

2017

Biophys Rev

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Room-temperature ionic liquids (RTIL) are a new class of organic salts whose melting temperature falls below the conventional limit of 100°C. Their low vapor pressure, moreover, has made these ionic compounds the solvents of choice of the so-called green chemistry. For these and other peculiar characteristics, they are increasingly used in industrial applications. However, studies of their interaction with living organisms have highlighted mild to severe health hazards. Since their cytotoxicity shows a positive correlation with their lipophilicity, several chemical-physical studies of their interactions with biomembranes have been carried out in the last few years, aiming to identify the molecular mechanisms behind their toxicity. Cation chain length and anion nature of RTILs have seemed to affect lipophilicity and, in turn, their toxicity. However, the emerging picture raises new questions, points to the need to assess toxicity on a case-by-case basis, but also suggests a potential positive role of RTILs in pharmacology, bio-medicine and bio-nanotechnology. Here, we review this new subject of research, and comment on the future and the potential importance of this emerging field of study.

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Water‐Based Synthesis of Hydrophobic Ionic Liquids [N₈₈₈₈][oleate] and [P_666,14][oleate] and their Bioprocess Compatibility

et al. 2018

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The conversion of organic waste streams into carboxylic acids as renewable feedstocks results in relatively dilute aqueous streams. Carboxylic acids can be recovered from such streams by using liquid–liquid extraction. Hydrophobic ionic liquids (ILs) are novel extractants that can be used for carboxylic acid recovery. To integrate these ILs as in situ extractants in several biotechnological applications, the IL must be compatible with the bioprocesses. Herein the ILs [P666,14][oleate] and [N8888][oleate] were synthesized in water and their bioprocess compatibility was assessed by temporary exposure to an aqueous phase that contained methanogenic granular sludge. After transfer of the sludge into fresh medium, [P666,14][oleate]‐exposed granules were completely inhibited. Granules exposed to [N8888][oleate] sustained anaerobic digestion activity, albeit moderately reduced. The IL contaminants, bromide (5–500 ppm) and oleate (10–4000 ppm), were shown not to inhibit the methanogenic conversion of acetate. [P666,14] was identified as a bioprocess‐incompatible component. However, our results showed that [N8888][oleate] was bioprocess compatible and, therefore, has potential applications in bioprocesses.

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Effects of phosphonium-based ionic liquids on phospholipid membranes studied by small-angle X-ray scattering

Cited by 42 publications

References 34 publications

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Water‐Based Synthesis of Hydrophobic Ionic Liquids [N₈₈₈₈][oleate] and [P_666,14][oleate] and their Bioprocess Compatibility

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Effects of phosphonium-based ionic liquids on phospholipid membranes studied by small-angle X-ray scattering

Cited by 42 publications

References 34 publications

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Correlation between Ionic Liquid Cytotoxicity and Liposome–Ionic Liquid Interactions

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Water‐Based Synthesis of Hydrophobic Ionic Liquids [N8888][oleate] and [P666,14][oleate] and their Bioprocess Compatibility

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Product

Resources

About

Water‐Based Synthesis of Hydrophobic Ionic Liquids [N₈₈₈₈][oleate] and [P_666,14][oleate] and their Bioprocess Compatibility