Probing the Transport of Ionic Liquids in Aqueous Solution through Nanopores

Modi, Niraj; Singh, Pratik Raj; Mahendran, Kozhinjampara R.; Schulz, Robert; Winterhalter, Mathias; Kleinekathöfer, Ulrich

doi:10.1021/jz201006b

Cited by 29 publications

(44 citation statements)

References 38 publications

(52 reference statements)

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“…To be noted, both IL-effects have shown to increase with increasing concentration and alkyl chain length. Diffusion through biological nanopores, such as OmpF and its mutant D113A, has been observed for [C 4 mim][Cl] (Modi et al 2011 ). Diffusion into the cytoplasm via special membrane transporter proteins (e.g., PEPT1 transporter), similar to some amino acid prodrugs, has been suggested as a MoA of amino acid–based ILs, showing a much higher toxicity against NIH/3T3 cells in comparison with the equivalent most common imidazolium ILs (Egorova et al 2015 ).…”

Section: Mechanisms Of Action Of Ilsmentioning

confidence: 99%

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Mechanisms of action of ionic liquids on living cells: the state of the art

2020

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Ionic liquids (ILs) are a relatively new class of organic electrolytes composed of an organic cation and either an organic or inorganic anion, whose melting temperature falls around room-temperature. In the last 20 years, the toxicity of ILs towards cells and micro-organisms has been heavily investigated with the main aim to assess the risks associated with their potential use in (industrial) applications, and to develop strategies to design greener ILs. Toxicity, however, is synonym with affinity, and this has stimulated, in turn, a series of biophysical and chemical-physical investigations as well as few biochemical studies focused on the mechanisms of action (MoAs) of ILs, key step in the development of applications in bio-nanomedicine and bio-nanotechnology. This review has the intent to present an overview of the state of the art of the MoAs of ILs, which have been the focus of a limited number of studies but still sufficient enough to provide a first glimpse on the subject. The overall picture that emerges is quite intriguing and shows that ILs interact with cells in a variety of different mechanisms, including alteration of lipid distribution and cell membrane viscoelasticity, disruption of cell and nuclear membranes, mitochondrial permeabilization and dysfunction, generation of reactive oxygen species, chloroplast damage (in plants), alteration of transmembrane and cytoplasmatic proteins/enzyme functions, alteration of signaling pathways, and DNA fragmentation. Together with our earlier review work on the biophysics and chemical-physics of IL-cell membrane interactions (Biophys. Rev. 9:309, 2017), we hope that the present review, focused instead on the biochemical aspects, will stimulate a series of new investigations and discoveries in the still new and interdisciplinary field of “ILs, biomolecules, and cells.”

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Section: Mechanisms Of Action Of Ilsmentioning

confidence: 99%

“…Diffusion through biological nanopores, such as OmpF and its mutant D113A, has been observed for [C 4 mim][Cl] (Modi et al 2011 ).…”

Section: Mechanisms Of Action Of Ilsmentioning

confidence: 99%

Mechanisms of action of ionic liquids on living cells: the state of the art

2020

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“…The trimeric OmpF (Protein Data Bank: 2OMF) was embedded into a 1-palmitoyl-2-oleoylsn-glycero-3-phosphoethanolamine bilayer and solvated with TIP3P water on both sides of the membrane. The protonation states of the titrable amino residues (Glu296, Asp312) in the OmpF channel were set as in previous studies (30,43). Depending on the actual approach, the final system setup varied slightly.…”

Section: Details Of the System Setupmentioning

confidence: 99%

Fosfomycin Permeation through the Outer Membrane Porin OmpF

Golla

Sans-Serramitjana

Pothula

et al. 2019

Biophysical Journal

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Fosfomycin is a frequently prescribed drug in the treatment of acute urinary tract infections. It enters the bacterial cytoplasm and inhibits the biosynthesis of peptidoglycans by targeting the MurA enzyme. Despite extensive pharmacological studies and clinical use, the permeability of fosfomycin across the bacterial outer membrane is largely unexplored. Here, we investigate the fosfomycin permeability across the outer membrane of Gram-negative bacteria by electrophysiology experiments as well as by all-atom molecular dynamics simulations including free-energy and applied-field techniques. Notably, in an electrophysiological zero-current assay as well as in the molecular simulations, we found that fosfomycin can rapidly permeate the abundant Escherichia coli porin OmpF. Furthermore, two triple mutants in the constriction region of the porin have been investigated. The permeation rates through these mutants are slightly lower than that of the wild type but fosfomycin can still permeate. Altogether, this work unravels molecular details of fosfomycin permeation through the outer membrane porin OmpF of E. coli and moreover provides hints for understanding the translocation of phosphonic acid antibiotics through other outer membrane pores.

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“…In Lim et al, for example, the mutual interaction between RTIL cations once absorbed into the membrane has been studied, and the measured increment of permeability due to the absorption of RTILs has been related to their antibacterial activity. Investigations focused on specific cases and more complex systems, moreover, have enriched even more the broad and diverse panorama presented above (Patel et al 2016;Modi et al 2011;Jeong et al 2012;Ryu et al 2015;Lee et al 2015). An interesting example is the study of Jeon, Lee and co-workers on the effect of RTILs on the ion channel function of Gramicidin A embedded in a phospholipid bilayer (Jeong et al 2012;Ryu et al 2015;Lee et al 2015).…”

Section: Introductionmentioning

confidence: 99%

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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Probing the Transport of Ionic Liquids in Aqueous Solution through Nanopores

Cited by 29 publications

References 38 publications

Mechanisms of action of ionic liquids on living cells: the state of the art

Mechanisms of action of ionic liquids on living cells: the state of the art

Fosfomycin Permeation through the Outer Membrane Porin OmpF

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

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