Synergistic behavior of betaine–urea mixture: Formation of deep eutectic solvent

Zeng, Chaoxi; Qi, Suijian; Xin, Ruipu; Yang, Bo; Wang, Yonghua

doi:10.1016/j.molliq.2016.02.076

Cited by 48 publications

(36 citation statements)

References 32 publications

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“…Adding 2 wt % of water lowers the eutectic temperature from 80°C to a temperature lower than 20°C. In fact, the mixtures with a betaine mole fraction of 0.3 or 0.4 did not recrystallize even when kept at a temperature of À 80°C for 72 h. This is consistent with the results of Zeng et al, [10] where it was reported that betaine/urea mixtures (prepared without drying the compounds) did not display crystallization, showing, instead, glass transitions at a temperature of around À 50°C.…”

supporting

confidence: 90%

“…[1,8,9] Trimethylglycine (henceforth called betaine) has been used to prepare DES by some authors. Zeng et al [10] demonstrated the formation of DES by mixing betaine and urea. They were unable to detect the freezing point of several betaine/urea mixtures, observing, instead, glass transitions at a temperature of around À 50°C.…”

mentioning

confidence: 99%

“…Despite its sustainable character, betaine-based DES are still poorly studied, and their intermolecular interactions not explored nor understood. Zeng et al [10] pointed out that typical hydrogen bonds could not account for the formation of the betaine/urea DES. This lack of fundamental knowledge is heightened by the scarcity of solid-liquid equilibrium data for betaine-based systems, which hampers the rational development of novel betaine-based DES, leaving them to the chance of tedious experimental trial and error essays.…”

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confidence: 99%

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Understanding the Formation of Deep Eutectic Solvents: Betaine as a Universal Hydrogen Bond Acceptor

et al. 2020

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The mechanism of formation of betaine‐based deep eutectic solvents (DES) is presented for the first time. Due to its polarity unbalance, it was found that betaine displays strong negative deviations from ideality when mixed with a variety of different organic substances. These results pave the way for a comprehensive design of novel deep eutectic solvents. A connection to biologically relevant systems was made using betaine (osmolyte) and urea (protein denaturant), showing that these two compounds formed a DES, the molecular interactions of which were greatly enhanced in the presence of water.

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confidence: 90%

mentioning

confidence: 99%

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confidence: 99%

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Understanding the Formation of Deep Eutectic Solvents: Betaine as a Universal Hydrogen Bond Acceptor

et al. 2020

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“…The observed chemical shifts also have been previously described in other NADES preparations 30 , 37 . The evidence of hydrogen bonding is supported by the fact that betaine in BU shows a poorer electron density over the nitrogen atom; meanwhile, urea has a higher electron density over its oxygen atom.…”

Section: Resultssupporting

confidence: 83%

“…and Zeng et al . research 28 – 30 , who have described the use of betaine-urea mixtures for stabilization of protein structure. Thus, those substances were selected as the starting point to formulate the solvent and evaluate our hypothesis.…”

Section: Resultsmentioning

confidence: 99%

A Natural Deep Eutectic Solvent Formulated to Stabilize β-Lactam Antibiotics

Olivares

Martínez

Rivas

et al. 2018

Sci Rep

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β-lactam antibiotics, such as penicillin share a very unstable chemical structure. In water-based solutions, such as those used for clinical applications, the β-lactam ring is readily opened due to a nucleophilic or electrophilic attack, leading to the loss of antimicrobial activity. Since the achievement and maintenance of optimum therapeutic levels of β-lactam antibiotics is critical for the resolution of many infectious clinical situations, and to avoid antibiotic resistance generation, the design of new non-aqueous dosage forms is urgent. Recently, natural deep eutectic solvents (NADES) have emerged as alternative non-toxic and non-aqueous solvents for different biomedical applications. In this work, we formulated and characterized a NADES composed by betaine and urea (BU). Using this solvent, we evaluated the stability of clavulanic acid (CLV) and imipenem (IMP) and characterized their antimicrobial activities calculating the minimal inhibitory concentration. Characterization of BU solvent by infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy (NMR) indicated that the obtained solvent has a microstructure mainly based on hydrogen bonding interactions and water addition strongly affects its dynamic. The stability of β-lactam antibiotic IMP and CLV using this solvent was increased by 7 fold and 2.5 fold respectively compared to water when analysed seven days after being dissolved. Microbiological assays showed that antibacterial activity at day seven was significantly decreased for both CLV and IMP when dissolved in water, while no change in their antibacterial properties was observed when antibiotics were dissolved in BU. The increased stability of IMP and CLV in BU may be related to the inert behaviour of the solvent and the higher dynamic restriction that helps antibiotics to maintain a more stable conformation. These data suggest the potential use of BU as a solvent to prevent degradation of β-lactam antibiotics.

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Deep Eutectic Solvents Enable the Enhanced Production of n‐3 PUFA‐Enriched Triacylglycerols

Zhang

et al. 2017

Euro J Lipid Sci & Tech

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Efficient synthesis of n‐3 PUFA‐enriched triacylglycerol (TAG) by the esterification of glycerol with n‐3 PUFA in deep eutectic solvents (DES) is reported. There was a 1.2‐fold increase of TAG yield in DES compared with that in the solvent‐free system. Adsorption of the produced water by DES during esterification contributed to enhance the conversion efficiency by changing the reaction equilibrium. DES also served as an effective solvent for enriching the n‐3 PUFA of TAG in the upper layer of reaction media. A TAG yield of 55% was achieved under the optimal condition. Practical Applications: Enzymatic synthesis of n‐3 PUFA‐enriched triacylglycerol (TAG) is challenged by low yields. Here, deep eutectic solvents show great potential for enhancing the production of n‐3 PUFA‐enriched TAG. The production of n‐3 PUFA‐enriched triacylglycerol is greatly enhanced in deep eutectic solvents.

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Synergistic behavior of betaine–urea mixture: Formation of deep eutectic solvent

Cited by 48 publications

References 32 publications

Understanding the Formation of Deep Eutectic Solvents: Betaine as a Universal Hydrogen Bond Acceptor

Understanding the Formation of Deep Eutectic Solvents: Betaine as a Universal Hydrogen Bond Acceptor

A Natural Deep Eutectic Solvent Formulated to Stabilize β-Lactam Antibiotics

Deep Eutectic Solvents Enable the Enhanced Production of n‐3 PUFA‐Enriched Triacylglycerols

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