Role of cationic head-group in cytotoxicity of ionic liquids: Probing changes in bilayer architecture using solid-state NMR spectroscopy

Kaur, Navleen; Fischer, Markus; Kumar, Sandeep; Gahlay, Gagandeep Kaur; Scheidt, Holger A.; Mithu, Venus Singh

doi:10.1016/j.jcis.2020.08.115

Cited by 23 publications

(44 citation statements)

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“…24 In any of these cytotoxicity pathways, interaction of ionic liquid molecules with cellular membranes assumes significant importance. Accordingly, several studies based on molecular dynamics, 25,26 neutron reflectivity, 27 small-angle Xray scattering (SAXS), 28,29 X-ray reflectivity (XRR), 30 quasielastic neutron scattering (QENS), 16,31 and solid-state NMR spectroscopy 21,22,32 have been performed to unveil the mechanism of this interaction of ionic liquids with lipid bilayers. Amphiphilic cations in ionic liquids insert into the lipid bilayer in an orientation parallel to the phospholipids.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Amphiphilic cations in ionic liquids insert into the lipid bilayer in an orientation parallel to the phospholipids. 21,27,33 This intercalation alters the packing and dynamics of the acyl chain and head group region of the phospholipid bilayer 21,22,32 and perturbs the structural and mechano-elastic properties of the lipid bilayer, making it permeable or disrupting it all together in a detergent-like fashion.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Size and ζ-potential studies were performed with POPC and POPG LUVs having lipid concentration fixed at 0.275 ± 0.015 mM according to a procedure already reported. 21 S3. The size of POPC and POPG LUVs before and after the addition of 1 mM ionic liquids remains nearly the same.…”

Section: ■ Introductionmentioning

confidence: 99%

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Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

et al. 2021

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We have evaluated ionic liquids based on double-chained 1-alkyl-3-octylimidazolium cations ([C n C8IM]+, n = 2, 4, 6, 8, 10, 12) for their cytotoxicity toward various cell lines. The toxicity of ionic liquids was correlated to their ability to partition into and permeabilize phosphocholine (POPC)- or phosphoglycerol (POPG)-based large unilamellar vesicles. Membrane partitioning of ionic liquids was assessed using the ζ-potential measurements, and membrane permeability was determined using fluorescence-based dye leakage assays. Both cytotoxicity and membrane permeability of these ILs were found to increase in a sigmoidal fashion with increasing chain length on the N1 atom (n in [C n C8IM]+) cations. These results were compared with those for ionic liquids based on single-chained 1-alkyl-3-methylimidazolium cations ([C n+8C1IM]+), carrying a similar number of carbon atoms but as a single alkyl chain. Our studies show that ionic liquids containing double-chained cations are relatively less cytotoxic and membrane-permeabilizing than the cations bearing a single long alkyl chain.

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Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

et al. 2021

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“…9 The results reveal that [N 2 Py][Ala] was the most toxic among the four ILs, one possible reason was that its structure was well maintained in ethanol, which exacerbated the toxicity of [N 2 Py][Ala], the another reason may be that cations possessing aromatic head-groups are more toxic than the non-aromatic ones. 22 And the ranked degree of toxicity from high to low was:…”

Section: Discussionmentioning

confidence: 99%

Effects of amino acid ionic liquids with different cations ([N₂Py], [N₂₂₂₂], [P₂₂₂₂], and [C₂mim]) on wheat seedlings

Chen

Xiao

et al. 2021

RSC Adv.

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“…Within the different types of model membranes, liposomes are highly suitable for permeability research and drug delivery systems. Additionally, they allow for the use of various thermoanalytical and spectroscopic techniques—such as isothermal titration calorimetry (ITC), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FT-IR), fluorescence spectroscopy, and nuclear magnetic resonance (NMR) methods—to study biophysical interactions of the drug–membrane complex [ 7 , 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes

et al. 2021

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Biological membranes are complex dynamic systems composed of a great variety of carbohydrates, lipids, and proteins, which together play a pivotal role in the protection of organisms and through which the interchange of different substances is regulated in the cell. Given the complexity of membranes, models mimicking them provide a convenient way to study and better understand their mechanisms of action and their interactions with biologically active compounds. Thus, in the present study, a new Schiff base (Bz-Im) derivative from 2-(m-aminophenyl)benzimidazole and 2,4-dihydroxybenzaldehyde was synthesized and characterized by spectroscopic and spectrometric techniques. Interaction studies of (Bz-Im) with two synthetic membrane models prepared with 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and DMPC/1,2-dimyristoyl-sn-glycero-3-phosphoglycerol (DMPG) 3:1 mixture, imitating eukaryotic and prokaryotic membranes, respectively, were performed by applying differential scanning calorimetry (DSC). Molecular dynamics simulations were also developed to better understand their interactions. In vitro and in silico assays provided approaches to understand the effect of Bz-Im on these lipid systems. The DSC results showed that, at low compound concentrations, the effects were similar in both membrane models. By increasing the concentration of Bz-Im, the DMPC/DMPG membrane exhibited greater fluidity as a result of the interaction with Bz-Im. On the other hand, molecular dynamics studies carried out on the erythrocyte membrane model using the phospholipids POPE (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine), SM (N-(15Z-tetracosenoyl)-sphing-4-enine-1-phosphocholine), and POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) revealed that after 30 ns of interaction, both hydrophobic interactions and hydrogen bonds were responsible for the affinity of Bz-Im for PE and SM. The interactions of the imine with POPG (1-Palmitoyl-2-Oleoyl-sn-Glycero-3-Phosphoglycerol) in the E. coli membrane model were mainly based on hydrophobic interactions.

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Role of cationic head-group in cytotoxicity of ionic liquids: Probing changes in bilayer architecture using solid-state NMR spectroscopy

Cited by 23 publications

References 63 publications

Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

Effects of amino acid ionic liquids with different cations ([N₂Py], [N₂₂₂₂], [P₂₂₂₂], and [C₂mim]) on wheat seedlings

A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes

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Role of cationic head-group in cytotoxicity of ionic liquids: Probing changes in bilayer architecture using solid-state NMR spectroscopy

Cited by 23 publications

References 63 publications

Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

Cytotoxicity and Membrane Permeability of Double-Chained 1,3-Dialkylimidazolium Cations in Ionic Liquids

Effects of amino acid ionic liquids with different cations ([N2Py], [N2222], [P2222], and [C2mim]) on wheat seedlings

A Study of the Interaction of a New Benzimidazole Schiff Base with Synthetic and Simulated Membrane Models of Bacterial and Mammalian Membranes

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Product

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Effects of amino acid ionic liquids with different cations ([N₂Py], [N₂₂₂₂], [P₂₂₂₂], and [C₂mim]) on wheat seedlings