Binding Study of Antibacterial Drug Ciprofloxacin with Imidazolium-Based Ionic Liquids Having Different Halide Anions: A Spectroscopic and Density Functional Theory Analysis
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ABSTRACT:
SUBMITTER: Siddiquee A
PROVIDER: S-EPMC10653064 | biostudies-literature | 2023 Nov
REPOSITORIES: biostudies-literature
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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
Project description:We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant π-π stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-% cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs.
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Project description:We report studies of the vacuum interfacial structure of a series of 1-methyl-3-alkylimidazolium bis(perfluoroalkanesulfonyl)imide ionic liquids (ILs) and predict and explain their Fresnel-normalized X-ray reflectivity. To better interpret the results, we use a theory we recently developed dubbed "the peaks and antipeaks analysis of reflectivity" which splits the overall signal into that of different pair subcomponents. Whereas the overall reflectivity signal is not very informative, the peak and trough intensities for the pair subcomponents provide rich information for analysis. When species containing cationic alkyl or anionic fluoroalkyl tails are present at the interface, a tail layer is found next to a vacuum, and this tail layer can be composed of both alkyl and fluoroalkyl moieties. To maintain the positive-negative alternation of charged groups, alkyl and fluoroalkyl tails must necessarily be nearby and cannot segregate. Charged groups are found in the subsequent layer just below the interface and arranged to achieve lateral charge neutrality. In general, fluctuations at and away from the interface are based on polarity (i.e., heads and tails) and not on charge; when there are no significant alkyl or fluoroalkyl moieties in the IL, atomic density fluctuations away from the interface are small and appear to exist for the purpose of achieving lateral charge balance. For all the systems reported here, the persistence length of density fluctuations does not go beyond ∼7 nm.
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Project description:Amyloid fibrils have immense potential to become the basis of modern biomaterials. The formation of amyloid fibrils in vitro strongly depends on the solvent properties. Ionic liquids (ILs), alternative solvents with tunable properties, have been shown to modulate amyloid fibrillization. In this work, we studied the impact of five ILs with 1-ethyl-3-methylimidazolium cation [EMIM+] and anions of Hofmeisterseries hydrogen sulfate [HSO4-], acetate [AC-], chloride [Cl-], nitrate [NO3-], and tetrafluoroborate [BF4-] on the kinetics of insulin fibrillization and morphology, and the structure of insulin fibrils when applying fluorescence spectroscopy, AFM and ATR-FTIR spectroscopy. We found that the studied ILs were able to speed up the fibrillization process in an anion- and IL-concentration-dependent manner. At an IL concentration of 100 mM, the efficiency of the anions at promoting insulin amyloid fibrillization followed the reverse Hofmeister series, indicating the direct binding of ions with the protein surface. At a concentration of 25 mM, fibrils with different morphologies were formed, yet with similar secondary structure content. Moreover, no correlation with the Hofmeister ranking was detected for kinetics parameters. IL with the kosmotropic strongly hydrated [HSO4-] anion induced the formation of large amyloid fibril clusters, while the other kosmotropic anion [AC-] along with [Cl-] led to the formation of fibrils with similar needle-like morphologies to those formed in the IL-free solvent. The presence of the ILs with the chaotropic anions [NO3-] and [BF4-] resulted in longer laterally associated fibrils. The effect of the selected ILs was driven by a sensitive balance and interplay between specific protein-ion and ion-water interactions and non-specific long-range electrostatic shielding.
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Project description:We performed terahertz time-domain spectroscopy and infrared spectroscopy of imidazolium-based, pyridinium-based, and tetraalkylammonium-based tetrafluoroborate ionic liquids to study their characteristic intermolecular and intramolecular vibrational modes to clarify interactions between various cations and the tetrafluoroborate anion. It was found that the central frequency of the intermolecular vibrational band for these ionic liquids has a relatively high frequency, ranging from 90 to 100 cm-1. In the 900-1150 cm-1 range, the intramolecular vibrational absorption band of the 3-fold degenerate mode of tetrafluoroborate anions in the ionic liquids was observed. Although the tetrafluoroborate anion is attributable to one of the weakly coordinated anions, the spectroscopic splitting behavior of the 3-fold degenerate mode differs depending on the cation species. It was revealed that the degenerate mode is very sensitive to local interactions between the tetrafluoroborate anion and each cation.
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Project description:Synthesis of dimeric nitro-substituted imidazolium salts under the conventional/solvent-free method is reported. The solvent-free method is more important than the conventional one because of its shorter reaction time, higher yield from easily available starting material, environmental safety, and so forth. Counter anion exchange is carried out using inorganic salt, which is dissolved in deionized water at room temperature. In antibacterial studies, dimeric nitro-substituted imidazolium cations with bromide counter anions showed excellent inhibition against E. coli and P. aeruginosa bacteria. These experimental results were further supported by molecular docking studies. All the compounds (3-6) (a-d) showed excellent antibacterial activity than the standard drugs (gentamycin, nalidixic acid, oflaxacin, ciproflaxacin, and amikacin). Molecular docking studies showed strong hydrogen bonding, polar and hydrophobic interactions between the dimeric imidazolium salts, and Escherichia coli/Pseudomonas aeruginosa/Proteus vulgaris/Staphylococcus aureus receptors.
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Project description:Cellulose can be dissolved in ionic liquids (ILs), and
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Project description:Green Chemistry involves applying a set of principles aimed at minimizing the use of hazardous substances in the design, production, and application of chemical products. In recent decades, Ionic Liquids (ILs) have emerged as more environmentally friendly substitutes for traditional organic solvents. This preference is primarily due to their low vapor pressure, which results in minimal atmospheric pollution and enhanced industrial safety. However, existing literature highlights the toxicity of ILs towards aquatic invertebrates. Consequently, this study points to assess the biochemical effects of a selection of ILs through an in vitro approach. Specifically, digestive gland and gill cellular fractions (S9) of the marine bivalve Mytilus galloprovincialis were exposed to varying concentrations (0.05-2 μM) of three ILs featuring identical cations but different anions. The ILs tested were 1-ethyl-3-methylimidazolium octanoate ([EMIM][Oct]), 1-ethyl-3-methylimidazolium acetate ([EMIM][OAc]), and 1-ethyl-3-methylimidazolium ethyl sulfate ([EMIM][EtSO4]). The results indicate that [EMIM][Oct] induces higher toxicity in both S9 tissues, highlighting a strong effect of the anion. Overall, antioxidant and biotransformation defenses were significantly altered for all three ILs assessed. While acetylcholinesterase activity was significantly inhibited of about half of control activity, indicating neurotoxic damage as part of the toxicity mode of action of these ILs, neither lipid peroxidation nor alterations to DNA integrity were observed (≥100 %). This study supports the use of in vitro techniques as important tools capable of generating reliable ecotoxicological data, which can be further considered as a screening before in vivo testing and used for in silico modeling.
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Project description:Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids
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Project description:The identification of specific design concepts for the in silico design of ionic liquids (ILs) has been accomplished using theoretical methods. Molecular building blocks, such as interchangeable functional groups, are used to design a priori new ILs which have subsequently been experimentally investigated. The conformational design concepts are developed by separately and systematically changing the central (imide), bridging (sulfonyl) and end (trifluoromethyl) group of the bis(trifluoromethanesulfonyl)imide [N(Tf)2]- anion and examining the resultant potential energy surfaces. It is shown that these design concepts can be used to tune separately the minimum energy geometry, transition state barrier height and relative stability of different conformers. The insights obtained have been used to design two novel anions for ILs, trifluoroacetyl(methylsulfonyl)imide [N(Ms)(TFA)]- and acetyl(trifluoromethanesulfonyl)imide [N(Tf)(Ac)]-. The computationally predicted structures show excellent agreement with experimental structures obtained from X-ray crystallography. [C4C1im][N(Tf)(Ac)] and [C4C1im][N(Ms)(TFA)] ILs have been synthesised and ion diffusion coefficients examined using pulsed field gradient stimulated echo NMR spectroscopy. Significantly increased diffusion was observed for the more flexible [N(Tf)(Ac)]- compared with the more rigid [N(Ms)(TFA)]- analogue. Furthermore, a pronounced impact on the fluidity was observed. The viscosity of the IL with the rigid anion was found to be twice as high as the viscosity of the IL with the flexible anion. The design concepts presented in this work will enable researchers in academia and industry to tailor anions to provide ILs with specific desired properties.
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