Quantifying the hydrogen-bonding interaction between cation and anion of pure [EMIM][Ac] and evidencing the ion pairs existence in its extremely diluted water solution: Via 13 C, 1 H, 15 N and 2D NMR

Chen, Yu; Li, Shehong; Xue, Zhimin; Hao, Ming-Yang; Mu, Tiancheng

doi:10.1016/j.molstruc.2014.09.023

Cited by 22 publications

(20 citation statements)

References 66 publications

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“…Acetate ILs induced more shifts than those paired with strong anions. [Emim]Ac dissociated insufficiently into isolated ions in aqueous solution [ 31 ]. It acted as a basic IL and could be acidified with pressurized CO 2 [ 32 ].…”

Section: Discussionmentioning

confidence: 99%

Molecular Mechanisms Underlying Inhibitory Binding of Alkylimidazolium Ionic Liquids to Laccase

et al. 2017

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Water-miscible alkylimidazolium ionic liquids (ILs) are “green” co-solvents for laccase catalysis, but generally inhibit enzyme activity. Here, we present novel insights into inhibition mechanisms by a combination of enzyme kinetics analysis and molecular simulation. Alkylimidazolium cations competitively bound to the TI Cu active pocket in the laccase through hydrophobic interactions. Cations with shorter alkyl chains (C2~C6) entered the channel inside the pocket, exhibiting a high compatibility with laccase (competitive inhibition constant Kic = 3.36~3.83 mM). Under the same conditions, [Omim]Cl (Kic = 2.15 mM) and [Dmim]Cl (Kic = 0.18 mM) with longer alkyl chains bound with Leu296 or Leu297 near the pocket edge and Leu429 around TI Cu, which resulted in stronger inhibition. Complexation with alkylimidazolium cations shifted the pH optima of laccase to the right by 0.5 unit, and might, thereby, lead to invalidation of the Hofmeister series of anions. EtSO4− showed higher biocompatibility than did Ac− or Cl−, probably due to its binding near the TI Cu and its hindering the entry of alkylimidazolium cations. In addition, all tested ILs accelerated the scavenging of 2, 2′-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals, which, however, did not play a determining role in the inhibition of laccase.

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Section: Discussionmentioning

confidence: 99%

Molecular Mechanisms Underlying Inhibitory Binding of Alkylimidazolium Ionic Liquids to Laccase

et al. 2017

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“…The amphiphilic nature of the acetate anion may also allow long-range non-specific interactions with the non-polar groups on the protein surface, interfering with hydrophobic intermolecular contacts responsible for aggregation. Acetate is also known to dissociate insufficiently from the EMIM cation into isolated ions even in diluted solutions [ 66 ]. These properties might contribute to the milder effect of EMIM-ac on lysozyme stability compared to EMIM-BF 4 .…”

Section: Discussionmentioning

confidence: 99%

Effect of 1-Ethyl-3-methylimidazolium Tetrafluoroborate and Acetate Ionic Liquids on Stability and Amyloid Aggregation of Lysozyme

Fedunova

Antošová

Marek

et al. 2022

IJMS

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Amyloid fibrils draw attention as potential novel biomaterials due to their high stability, strength, elasticity or resistance against degradation. Therefore, the controlled and fast fibrillization process is of great interest, which raises the demand for effective tools capable of regulating amyloid fibrillization. Ionic liquids (ILs) were identified as effective modulators of amyloid aggregation. The present work is focused on the study of the effect of 1-ethyl-3-methyl imidazolium-based ILs with kosmotropic anion acetate (EMIM-ac) and chaotropic cation tetrafluoroborate (EMIM-BF4) on the kinetics of lysozyme amyloid aggregation and morphology of formed fibrils using fluorescence and CD spectroscopy, differential scanning calorimetry, AFM with statistical image analysis and docking calculations. We have found that both ILs decrease the thermal stability of lysozyme and significantly accelerate amyloid fibrillization in a dose-dependent manner at concentrations of 0.5%, 1% and 5% (v/v) in conditions and time-frames when no fibrils are formed in ILs-free solvent. The effect of EMIM-BF4 is more prominent than EMIM-ac due to the different specific interactions of the anionic part with the protein surface. Although both ILs induced formation of amyloid fibrils with typical needle-like morphology, a higher variability of fibril morphology consisting of a different number of intertwining protofilaments was identified for EMIM-BF4.

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“…[5][6][7][8][9][10][11] Subsequently the anion can be changed by an ion exchange column according to Alcalde et al (Chart 1). 12 To verify the completeness of the exchange we analyzed the NMR Spectra and perform a silver test.…”

Section: Chartmentioning

confidence: 99%

Analyzing the solution behavior of hygroscopic Imidazolium and Choline based ILs for optimizing liquid sorption media

Brünig

Pietschnig

2016

Proceedings of the 20th International Electronic Conference on Synthetic Organic Chemistry

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Analyzing the solution behavior of hygroscopic Imidazolium and Choline based ILs for optimizing liquid sorption media.Thorge Brünig, Rudolf Pietschnig* Abstract:Absorption storage systems in combination with solar thermal systems are a potential attempt for the reduction of greenhouse gases.1 The currently used sorption media like LiCl or LiBr show problems concerning crystallization, corrosion or low storage capacity.2, 3 Imidazolium and Choline based ILs in combination with organic anions may be an alternative to the classical hygroscopic salt solutions, because they are able to quickly absorb large amounts of water in an exothermic process. To optimize the sorption system we have screened the latter device parameters, especially the solution behavior of the ILs to determine structure-property relationships and improve the performance. Therefore, a calorimetric analysis offers an insight in the interaction between cation, anion and water. 4 In combination with other investigation, we hope to obtain a simulation of the sorption process.

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Quantifying the hydrogen-bonding interaction between cation and anion of pure [EMIM][Ac] and evidencing the ion pairs existence in its extremely diluted water solution: Via 13 C, 1 H, 15 N and 2D NMR

Cited by 22 publications

References 66 publications

Molecular Mechanisms Underlying Inhibitory Binding of Alkylimidazolium Ionic Liquids to Laccase

Molecular Mechanisms Underlying Inhibitory Binding of Alkylimidazolium Ionic Liquids to Laccase

Effect of 1-Ethyl-3-methylimidazolium Tetrafluoroborate and Acetate Ionic Liquids on Stability and Amyloid Aggregation of Lysozyme

Analyzing the solution behavior of hygroscopic Imidazolium and Choline based ILs for optimizing liquid sorption media

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