Design and applications of biocompatible choline amino acid ionic liquids

Miao, Shurui; Warr, Gregory G.

doi:10.1039/d2gc02282f

Cited by 35 publications

(34 citation statements)

References 194 publications

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“…Water, too, can modulate liquid nanostructure through the polar network. 39,82 Inherently amphiphilic ions with the capacity to sustain a polar network in the solvent may also expand the range of solutes that can behave as surfactants beyond those seen in water. This is illustrated by the unexpected miscibility of nanostructured ILs with aliphatic alcohols.…”

Section: Solventsmentioning

confidence: 99%

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How Does Nanostructure in Ionic Liquids and Hybrid Solvents Affect Surfactant Self-Assembly?

Marlow

Warr

2023

J. Phys. Chem. B

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Ionic liquids (ILs) have recently emerged as novel classes of solvents that support surfactant self-assembly into micelles, liquid crystals, and microemulsions. Their low volatility and wide liquid stability ranges make them attractive for many diverse applications, especially in extreme environments. However, the number of possible ion combinations makes systematic investigations both challenging and rare; this is further amplified when mixtures are considered, whether with water or other H-bonding components such as those found in deep eutectics. In this Perspective we examine what factors determine amphiphilicity, solvophobicity and solvophilicity, in ILs and related exotic environments, in what ways these differ from water, and how the underlying nanostructure of the liquid itself affects the formation and structure of micelles and other self-assembled materials.

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Section: Solventsmentioning

confidence: 99%

“…Surfactant self-assembly structure can be further tuned through the H-bond donor/acceptor capacity of nonamphiphilic ions, e.g., formate versus nitrate or thiocyanate. Water, too, can modulate liquid nanostructure through the polar network. , …”

Section: Amphiphilicity In Ionic and Hybrid Solventsmentioning

confidence: 99%

How Does Nanostructure in Ionic Liquids and Hybrid Solvents Affect Surfactant Self-Assembly?

Marlow

Warr

2023

J. Phys. Chem. B

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“…To date, various solvent systems have been developed to dissolve lignin, including aqueous organic solvents [14][15][16][17] , liquid ammonia 18,19 , ionic liquid (IL)-based systems [20][21][22] , and deep eutectic solvents (DESs) [23][24][25] . Of these developed solvents, DESs are an emerging class of functional solvents, and are generally composed by two components, calling as hydrogenbond donor (HBD) and hydrogen-bond acceptor (HBA), respectively [26][27][28] .…”

Section: Introductionmentioning

confidence: 99%

Biomass-Based Acidic Deep Eutectic Solvents for Efficient Dissolution of Lignin: Towards Performance and Mechanism Elucidation

Huang¹,

Chen²,

Zhao³

et al. 2023

Acta Physico Chimica Sinica

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Lignocellulose utilization has the unique feature of net-zero carbon emissions. Thus, the utilization of lignocellulose as a renewable alternative to fossil-based carbon resources is one of the most promising strategies to achieve "carbon neutrality". Lignin has been recognized as the most abundant aromatic biopolymer on Earth; hence, it could be the most promising alternative to fossil-based aromatics. The efficient dissolution of lignin is crucial for lignin upgrading, which relies on the design of innovative and robust solvents. Herein, we designed several biomass-derived acidic deep eutectic solvents (DESs) using choline chloride, betaine, and L-carnitine as hydrogen bond acceptors (HBAs), and four protic compounds as hydrogen bond donors (HBDs), namely, oxalic acid, benzoic acid, ethyl gallate, and 5-methoxysalicylic acid. The designed DESs can dissolve different types of lignin, including alkali lignin (AL), dealkaline lignin (DAL), enzymatic hydrolysis lignin (EHL), and Kraft lignin (KL). Lignin dissolution was found to be affected by the relative contents of three phenylpropanoid monomers in lignin: syringyl (S), guaiacyl (G), and p-hydroxyphenyl (H) units. More S and fewer H units in lignin could result in higher solubility. G-, S-, and H-type structural units were found in EHL, while AL, KL, and DAL had only G-type structural units. Therefore, EHL could be more easily dissolved than AL, KL, and DAL in the most developed DESs. The hydroxyl group content of the four lignin samples had a significant impact on lignin dissolution. AL (1.98 mmol•g −1 ) and EHL (1.93 mmol•g −1 ) had much higher contents of phenolic hydroxyl groups than DAL (0.62 mmol•g −1 ), implying that AL and EHL had higher polarity than DAL. This resulted in different dissolution behaviors in different DESs with varying polarities. However, the sulfonate groups afforded KL with much higher polarity, thus resulting in the special dissolution behavior of KL. It is to be noted that not all cases of dissolving lignin in the developed DESs conformed to the above rules. Therefore, it is necessary to further explore the effect of the properties of the DESs on the dissolution of different lignins. Choline chloride was the preferred HBA to construct DESs with good performance and adaptability to lignin dissolution, whereas suitable acidity enabled benzoic acid and ethyl gallate to be favorable HBDs. Systematic investigation revealed that an efficient DES for lignin dissolution should possess stronger hydrogen-bonding acidity (α > 0.95) and appropriate polarity matching with the dissolved lignin. In addition, the pKa value of the HBD and the acidity of the DESs were also efficient indices for estimating the performance of an acidic DES in dissolving lignin, and the pKa value and acidity could be well correlated with the polarity. Generally, HBDs (e.g., BA and EG in this study) with moderate pKa values can be employed to construct robust DESs to dissolve lignin with satisfactory solubility. Additionally, the viscosity of the DESs should have an impac...

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“…18−20 ILs (MILs). 21,22 Among these, MILs have received increasing interest in the fields of gas separation, catalytic reactions, and electro-chromic devices due to their strong response to the external magnetic field. 23,24 Some reports mention MILs as a solvent for the storage and extraction of biomolecules and nucleic acids.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The physicochemical properties of ILs can be varied by tuning their cations and anions; thus, they are also known as designer solvents . These properties make them suitable solvents for preserving and extracting proteins and biomolecules. − ILs are also used for the storage, stability, and extraction of proteins and nucleic acids. − The effect of ILs on the function and enzymatic activity of proteins is of paramount importance in chemical biology. − Depending on their physical and chemical properties and applications, ILs are categorized into room-temperature ILs (RTILs), task-specific ILs (TSILs), supported IL membranes (SILMs), and magnetic ILs (MILs). , Among these, MILs have received increasing interest in the fields of gas separation, catalytic reactions, and electro-chromic devices due to their strong response to the external magnetic field. , Some reports mention MILs as a solvent for the storage and extraction of biomolecules and nucleic acids. − Anderson and coworkers reported the efficiency of ammonium-based MILs in the extraction of long and short plasmid DNA from bacterial cell lysate and salmon testes . They have also developed a method to remove DNA from the MIL by designing a Polymerase Chain Reaction (PCR) buffer and on coupling it with the process. , In another report, Anderson and coworkers describe a particle-free approach to sequence-specific DNA extraction using MILs .…”

Section: Introductionmentioning

confidence: 99%

Enhancement of Peroxidase Activity in Magnetic Ionic Liquids

Tulsiyan

Mahalik

Dandekar

et al. 2023

ACS Sustainable Chem. Eng.

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Cytochrome c (Cyt-c) is a heme-containing protein that plays a vital role as an electron carrier in the mitochondrial respiratory chain. Cyt-c possesses peroxidase-like activity in the native state despite its six-coordinated heme iron. In this work, we studied the effect of magnetic ionic liquids (MILs) on the peroxidase activity of Cyt-c. Guaiacol oxidation was used to probe the activity of Cyt-c in the presence of cholinium (Ch)-based MILs such as [Ch][FeCl4] and [Ch]2[MnCl4]. A detailed kinetics and thermodynamics study on the activity of Cyt-c in the presence of MILs was investigated with the help of isothermal titration calorimetry (ITC), UV–vis, circular dichroism (CD), and fluorescence spectroscopy. The peroxidase activity of Cyt-c increases by twofold in the presence of [Ch][FeCl4] and only 20% in the presence of [Ch]2[MnCl4] IL. This correlates with the accessibility of the heme iron of Cyt-c. Molecular docking and molecular dynamic simulations were also employed to explore the mechanism of the interaction. The increase in the peroxidase activity of Cyt-c is attributed to the perturbation in the native sixth coordination bond of methionine-80 associated with the heme region of Cyt-c. Since not much work has been done on the enzymatic activity in the presence of MILs, we hope this will set the platform to use MILs to modulate and control enzymatic activity and catalysis.

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Design and applications of biocompatible choline amino acid ionic liquids

Abstract: Millions of tons of solvents are produced annually and are ubiquitous across many industries ranging from coatings, paintings, textiles, pharmaceuticals, extraction of resources, to chemical synthesis. The global market for...

Cited by 35 publications

References 194 publications

How Does Nanostructure in Ionic Liquids and Hybrid Solvents Affect Surfactant Self-Assembly?

How Does Nanostructure in Ionic Liquids and Hybrid Solvents Affect Surfactant Self-Assembly?

Biomass-Based Acidic Deep Eutectic Solvents for Efficient Dissolution of Lignin: Towards Performance and Mechanism Elucidation

Enhancement of Peroxidase Activity in Magnetic Ionic Liquids

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