Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Exploring the Interactions of Ionic Liquids with Bio-Organic Amphiphiles Using Computational Approaches.

ABSTRACT: Bio-organic amphiphiles have been shown to effectively impart unique physicochemical properties to ionic liquids resulting in the formation of versatile hybrid composites. In this work, we utilized computational methods to probe the formation and properties of hybrids prepared by mixing three newly designed bio-organic amphiphiles with 14 ionic liquids containing cholinium or glycine betaine cations and a variety of anions. The three amphiphiles were designed such that they contain unique biological moieties found in nature by conjugating (a) malic acid with the amino acid glutamine, (b) thiomalic acid with the antiviral, antibacterial pyrazole compound [3-(3,5-dimethyl-1H-pyrazol-1-yl)benzyl]amine, and (c) Fmoc-protected valine with diphenyl amine. Conductor-like screening model for real solvents (COSMO-RS) was used to obtain sigma profiles of the hybrid mixtures and to predict viscosities and mixing enthalpies of each composite. These results were used to determine optimal ionic liquid-bio-organic amphiphile mixtures. Molecular dynamics simulations of three optimal hybrids were then performed, and the interactions involved in the formation of the hybrids were analyzed. Our results indicated that cholinium-based ILs interacted most favorably with the amphiphiles through a variety of inter- and intramolecular interactions. This work serves to illustrate important factors that influence the interactions between bio-organic amphiphiles and bio-ILs and aids in the development of novel ionic liquid-based composites for a wide variety of potential biological applications.

SUBMITTER: Daso RE

PROVIDER: S-EPMC8655765 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

The Proton Dissociation of Bio-Protic Ionic Liquids: [AAE]X Amino Acid Ionic Liquids.

Project description:[AAE]X composed of amino acid ester cations is a sort of typically "bio-based" protic ionic liquids (PILs). They possess potential Brønsted acidity due to the active hydrogens on their cations. The Brønsted acidity of [AAE]X PILs in green solvents (water and ethanol) at room temperature was systematically studied. Various frameworks of amino acid ester cations and four anions were investigated in this work from the viewpoint of structure-property relationship. Four different ways were used to study the acidity. Acid dissociation constants (pKa) of [AAE]X determined by the OIM (overlapping indicator method) were from 7.10 to 7.73 in water and from 8.54 to 9.05 in ethanol. The pKa values determined by the PTM (potential titration method) were from 7.12 to 7.82 in water. Their Hammett acidity function (H0) values (0.05 mol·L-1) were about 4.6 in water. In addition, the pKa values obtained by the DFT (proton-transfer reactions) were from 7.11 to 7.83 in water and from 8.54 to 9.34 in ethanol, respectively. The data revealed that the cationic structures of [AAE]X had little effect and the anions had no effect on the acidity of [AAE]X. At the same time, the OIM, PTM, Hammett method and DFT method were reliable for determining the acidic strength of [AAE]X in this study.

| S-EPMC7795477 | biostudies-literature

Dual Ionic and Organic Nature of Ionic Liquids.

Project description:Inherited the advantages of inorganic salts and organic solvents, ionic liquids (ILs) exhibit many superior properties allowing them promising green solvents for the future. Although it has been widely acknowledged that the unique features of ILs originate from their dual ionic and organic nature, its microscopic physical origin still remains blurry. In this work, by comparing the ion/molecule cage structures obtained from molecular dynamics simulations for seven prototypic liquids--a molten inorganic salt, four ILs, a strongly polar organic solvent, and a weakly polar organic solvent, we have revealed that the depth of the cage energy landscape characterizes the ionic nature of ILs, whereas the slope and curvature of its mimimum determine the organic nature of ILs. This finding advances our understanding of ILs and thus will help their efficient utilization as well as the systematic design of novel functionalized ILs.

| S-EPMC4726069 | biostudies-literature

Exploring the role of ionic liquids to tune the polymorphic outcome of organic compounds.

Project description:While molecular solvents are commonly used in the screening of polymorphs, the choices are often restricted. Ionic liquids (ILs) - also referred as designer solvents - have immense possibility in this regard because of their wide flexibility of tunability. More importantly, the interactions among the IL components are completely unique compared to those present in the molecular solvents. In this context, we have chosen tetrolic acid (TA) and isonicotinamide (INA), which showed solution-structure link in molecular solvents in the past, as probes to investigate the role of imidazolium based ionic liquids in the polymorphism of these two systems and whether the different solute-solvent interactions in ILs affect the polymorphic outcome. It is observed that the selected imidazolium-based ILs, with varying anion basicity have influenced the crystallization outcome by the interaction between ILs and model compounds. Later, we have utilized the concept of double salt ionic liquids (DSIL) for INA, a penta-morphic system, to investigate the variation in the polymorphic outcome. This approach helped to obtain the forms that were otherwise inaccessible in ILs.

| S-EPMC5887107 | biostudies-literature

Quantifying intermolecular interactions of ionic liquids using cohesive energy densities.

Project description:For ionic liquids (ILs), both the large number of possible cation?+?anion combinations and their ionic nature provide a unique challenge for understanding intermolecular interactions. Cohesive energy density, ced, is used to quantify the strength of intermolecular interactions for molecular liquids, and is determined using the enthalpy of vaporization. A critical analysis of the experimental challenges and data to obtain ced for ILs is provided. For ILs there are two methods to judge the strength of intermolecular interactions, due to the presence of multiple constituents in the vapour phase of ILs. Firstly, cedIP, where the ionic vapour constituent is neutral ion pairs, the major constituent of the IL vapour. Secondly, cedC+A, where the ionic vapour constituents are isolated ions. A cedIP dataset is presented for 64 ILs. For the first time an experimental cedC+A, a measure of the strength of the total intermolecular interaction for an IL, is presented. cedC+A is significantly larger for ILs than ced for most molecular liquids, reflecting the need to break all of the relatively strong electrostatic interactions present in ILs. However, the van der Waals interactions contribute significantly to IL volatility due to the very strong electrostatic interaction in the neutral ion pair ionic vapour. An excellent linear correlation is found between cedIP and the inverse of the molecular volume. A good linear correlation is found between IL cedIP and IL Gordon parameter (which are dependent primarily on surface tension). ced values obtained through indirect methods gave similar magnitude values to cedIP. These findings show that cedIP is very important for understanding IL intermolecular interactions, in spite of cedIP not being a measure of the total intermolecular interactions of an IL. In the outlook section, remaining challenges for understanding IL intermolecular interactions are outlined.

| S-EPMC5750021 | biostudies-literature

Integrated Leaching and Separation of Metals Using Mixtures of Organic Acids and Ionic Liquids.

Project description:In this work, the aqueous phase diagram for the mixture of the hydrophilic tributyltetradecyl phosphonium ([P44414]Cl) ionic liquid with acetic acid (CH3COOH) is determined, and the temperature dependency of the biphasic region established. Molecular dynamic simulations of the [P44414]Cl + CH3COOH + H2O system indicate that the occurrence of a closed "type 0" biphasic regime is due to a "washing-out" phenomenon upon addition of water, resulting in solvophobic segregation of the [P44414]Cl. The solubility of various metal oxides in the anhydrous [P44414]Cl + CH3COOH system was determined, with the system presenting a good selectivity for CoO. Integration of the separation step was demonstrated through the addition of water, yielding a biphasic regime. Finally, the [P44414]Cl + CH3COOH system was applied to the treatment of real waste, NiMH battery black mass, being shown that it allows an efficient separation of Co(II) from Ni(II), Fe(III) and the lanthanides in a single leaching and separation step.

| S-EPMC7729566 | biostudies-literature

Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.

2021-08-13 | GSE156769 | GEO

Solubility Studies of Cyclosporine Using Ionic Liquids.

Project description:Six ionic liquids (ILs) were selected based on their chemical and physical properties to study the solubility of cyclosporine A. Of these, cyclosporine exhibited higher room temperature solubility in 1-ethyl-3-methylimidazolium acetate ([C2mim][OAc]) than in acetone, an effective molecular solvent used to solubilize and purify cyclosporine. The solubility of cyclosporine in the ILs dramatically increased at higher temperatures, a critical factor that cannot be varied in a wide range with low boiling molecular solvents. The differences in solubility were explored for cyclosporine purification. Cyclosporine was purified up to ∼93% with n-butylammonium acetate ([C4NH3][OAc]) and could be further purified to 95% using an IL/organic solvent biphasic system. After purification, cyclosporine was recovered as an amorphous solid using the ILs.

| S-EPMC6649182 | biostudies-literature

Hydrogen-Bonding Interactions in Pyridinium-Based Ionic Liquids and Dimethyl Sulfoxide Binary Systems: A Combined Experimental and Computational Study.

Project description:The addition of highly polar and aprotic cosolvents to ionic liquids has proven to considerably decrease the viscosity of the solution and improve mass transfer in many chemical reactions. In this work, the interactions between a representative pyridinium-based ionic liquid, N-butylpyridinium dicyanamide ([Bpy][DCA]), and a cosolvent, dimethylsulfoxide (DMSO), were studied in detail by the combined use of attenuated total reflection Fourier transform infrared spectroscopy, hydrogen nuclear magnetic resonance (1H NMR), and density functional theory calculations. Several species in the [Bpy][DCA]-DMSO mixtures have been identified, that is, ion clusters can translate into ion pairs during the dilution process. DMSO formed hydrogen bonds (H bonds) simultaneously with [Bpy]+ cations and [DCA]- anions but stronger hydrogen-bonding interactions with the [Bpy]+ cations than the [DCA]- anions, and the intrinsic hydrogen-bond networks of IL were difficult to interrupt at low DMSO concentrations. Interestingly, hydrogen-bonding interactions reach the strongest when the molar fraction of DMSO is 0.4-0.5. Hydrogen-bonding interactions are prominent in the chemical shifts of hydrogen atoms in [Bpy]+ cations, and anisotropy is the main reason for the upfield shifts of DMSO in the presence of [Bpy][DCA]. The theoretical calculations offer in-depth studies of the structural evolution and NMR calculation.

| S-EPMC6641321 | biostudies-literature

Synergistic interactions of ionic liquids and antimicrobials improve drug efficacy.

Project description:Combinations of ionic liquids (ILs) with antimicrobial compounds have been shown to produce synergistic activities in model liposomes. In this study, imidazolium chloride-based ILs with alkyl tail length variations are combined with commercially available, small-molecule antimicrobials to examine the potential for combinatorial and synergistic antimicrobial effects on P. aeruginosa, E. coli, S. aureus, and S. cerevisiae. The effects of these treatments in a human cell culture model indicate the cytotoxic limits of ILs paired with antimicrobials. The analysis of these ILs demonstrates that the length of the alkyl chain on the IL molecule is proportional to both antimicrobial activity and cytotoxicity. Moreover, the ILs which exhibit synergy with small-molecule antibiotics appear to be acting in a membrane permeabilizing manner. Collectively, results from these experiments demonstrate an increase in antimicrobial efficacy with specific IL + antimicrobial combinations on microbial cultures while maintaining low cytotoxicity in a mammalian cell culture model.

| S-EPMC7753145 | biostudies-literature

Interactions of Biodegradable Ionic Liquids with a Model Naphthenic Acid.

Project description:Density functional theory models are used to examine five biodegradable ionic liquids (ILs) each one consisting of a substitutional group (-OH, -NH2, -COOH, -COOCH3, and -OCH3) incorporated into the cation of 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4]). The results reveal that hydrogen atoms in -NH2, -COOH, and -COOCH3 form intramolecular hydrogen bonds with fluorine atoms in [BF4]-, whereas hydrogen atoms in -OH and -OCH3 do not form hydrogen bonds with [BF4]-. Further analysis of electron density at bond critical points and noncovalent interactions suggest that [BMIM][BF4] with -COOH has stronger intramolecular hydrogen bonds than other ILs. The extraction mechanism for a model naphthenic acid is hydrogen bonding, with F···H being the strongest hydrogen bond and O···H ranking second. More intermolecular hydrogen bonds occur when model naphthenic acid is adsorbed by [BMIM][BF4] with -COOH and -COOCH3. The interaction energy between model naphthenic acid and ILs with -COOH and -COOCH3 is higher than that with -OH, -NH2, and -OCH3.

| S-EPMC5760565 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data