Interaction of imidazolium-based ionic liquids with supported phospholipid bilayers as model biomembranes

Marfori, Lorenzo; Asperti, Stefania; Vita, Alessandro De; Giannangeli, Matteo; Caselli, Alessandro; Milani, P.; Podestà, Alessandro

doi:10.1039/d2cp02866b

Cited by 7 publications

(10 citation statements)

References 95 publications

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“…In the case of C 12 MIm (CF 3 SO 2 ) 2 N), segregated IL droplets were observed at the bilayer surface at concentrations near the IL CMC, which, in turn, led to fast formation of multilayer structures. 350 Among the imidazolium ILs C n MIm Cl (n = 4, 8, 10), C 4 MIm BF 4 , and C 4 MIm (CF 3 SO 2 ) 2 N, the ILs with a short alkyl side chain and a hydrophilic anion induced mild disorder in supported lipid vesicles (SVLs) composed of DMPC, whereas the ILs with long alkyl side chains penetrated SLVs and disrupted them, forming a rigid supported lipid bilayer. The effect depended on the IL concentration, the length of the alkyl side chain in the cation, and the anion hydrophobicity.…”

Section: Interactions With Separate Cellular Organelles and Moleculesmentioning

confidence: 99%

“…The affinity between this side chain and hydrophobic tails of the phospholipids presumably led first to accumulation of the IL cations on the bilayer surface and then to tail-first penetration of the cations into the bilayer, resulting in mechanical and structural weakening and, finally, disruption. In the case of C 12 MIm (CF 3 SO 2 ) 2 N), segregated IL droplets were observed at the bilayer surface at concentrations near the IL CMC, which, in turn, led to fast formation of multilayer structures …”

Section: Mechanisms Of Biological Activity Of Ionic Liquids: State Of...mentioning

confidence: 99%

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Mechanisms of Biological Effects of Ionic Liquids: From Single Cells to Multicellular Organisms

Egorova,

Kibardin,

Posvyatenko

et al. 2024

Chem. Rev.

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The review presents a detailed discussion of the evolving field studying interactions between ionic liquids (ILs) and biological systems. Originating from molten salt electrolytes to present multiapplication substances, ILs have found usage across various fields due to their exceptional physicochemical properties, including excellent tunability. However, their interactions with biological systems and potential influence on living organisms remain largely unexplored. This review examines the cytotoxic effects of ILs on cell cultures, biomolecules, and vertebrate and invertebrate organisms. Our understanding of IL toxicity, while growing in recent years, is yet nascent. The established findings include correlations between harmful effects of ILs and their ability to disturb cellular membranes, their potential to trigger oxidative stress in cells, and their ability to cause cell death via apoptosis. Future research directions proposed in the review include studying the distribution of various ILs within cellular compartments and organelles, investigating metabolic transformations of ILs in cells and organisms, detailed analysis of IL effects on proteins involved in oxidative stress and apoptosis, correlation studies between IL doses, exposure times and resulting adverse effects, and examination of effects of subtoxic concentrations of ILs on various biological objects. This review aims to serve as a critical analysis of the current body of knowledge on IL-related toxicity mechanisms. Furthermore, it can guide researchers toward the design of less toxic ILs and the informed use of ILs in drug development and medicine.

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Section: Interactions With Separate Cellular Organelles and Moleculesmentioning

confidence: 99%

Section: Mechanisms Of Biological Activity Of Ionic Liquids: State Of...mentioning

confidence: 99%

Mechanisms of Biological Effects of Ionic Liquids: From Single Cells to Multicellular Organisms

Egorova,

Kibardin,

Posvyatenko

et al. 2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…Galluzzi et al demonstrated that the length of the alkyl chain of the IL cation dominated the strength of the IL and lipid bilayer interaction and observed the interaction between lipid bilayers deposited on mica surfaces and ILs through atomic force microscopy. 146 An experiment revealed that 1-hexyl-3-methylimidazolium acetate ([HMIM][OAc]) could be inserted into the lipid bilayer in the gel state, causing a more marked influence on the lipid bilayer than 1-butyl-3-methylimidazolium acetate ([BMIM][OAc]). 147 The permeation of the IL cation into the lipid membrane led to the reorganization and softening of the bilayer, ultimately forming an IL/lipid complex.…”

Section: Therapeutic Mechanismsmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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“…AFM analysis indicated the modification of the charge density of a bilayer due to the crowding cations of ILs. 48 Few reports suggested that the insertion of ILs in lipid membranes alters the alkyl chains of lipids relatively more than the polar head group region. 17,20,49−52 Further, the double-chained ILs are relatively less toxic than single-and long-chain ILs.…”

Section: Introductionmentioning

confidence: 99%

“…ILs might interact with a membrane through electrostatic and hydrophobic interactions, which may depend on the charge and hydrophobicity of both the lipids and ILs. , Imidazolium-based ILs reduce the mechanical stability of a supported DOPC lipid bilayer formed on a mica substrate. AFM analysis indicated the modification of the charge density of a bilayer due to the crowding cations of ILs . Few reports suggested that the insertion of ILs in lipid membranes alters the alkyl chains of lipids relatively more than the polar head group region. ,,− Further, the double-chained ILs are relatively less toxic than single- and long-chain ILs. , …”

Section: Introductionmentioning

confidence: 99%

Cholesterol-Controlled Interaction of Ionic Liquids with Model Cellular Membranes

et al. 2023

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While ionic liquids (ILs) are considered as prospective ingredients of new antimicrobial agents, it is important to understand the adverse effects of these molecules on human cells. Since cholesterol is the essential component of a human cell membrane, in the present study, the effect of an imidazolium-based IL has been investigated on the model membrane in the presence of cholesterol. The area per sphingomyelin lipid is found to reduce in the presence of the IL, which is quantified by the area−surface pressure isotherm of the lipid monolayer formed at the air−water interface. The effect is considerably diminished in the cholesterolcontaining monolayer. Further, the IL is observed to decrease the rigidity of the cholesterol-free monolayer. Interestingly, the presence of cholesterol does not allow any change in this property of the layer at lower surface pressure. However, at a higher surface pressure, the IL increases the elasticity in the cholesterol-induced condensed phase of the lipid layer. The X-ray reflectivity measurement on a stack of cholesterol-free lipid bilayers proved the formation of IL-induced phase-separated domains in the matrix of a pure lipid phase. These domains are found to be formed by interdigitating the chains of the lipids, producing a thinner membrane. Such a phase is less intense in the cholesterol-containing membrane. All of these results indicate that the IL molecules may deform the cholesterol-free membrane of a bacterial cell, but the same may not be harmful to human beings as cholesterol could restrict the insertion in the cellular membrane of a human cell.

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Interaction of imidazolium-based ionic liquids with supported phospholipid bilayers as model biomembranes

Abstract: The cytotoxicity of Ionic Liquids (ILs) has been raising attention in the context of the biological and environmental impact of their vast field of applications. It is ascertained that the...

Cited by 7 publications

References 95 publications

Mechanisms of Biological Effects of Ionic Liquids: From Single Cells to Multicellular Organisms

Mechanisms of Biological Effects of Ionic Liquids: From Single Cells to Multicellular Organisms

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Cholesterol-Controlled Interaction of Ionic Liquids with Model Cellular Membranes

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