Amphiphilic Deep Eutectic Solvent Based on Lidocaine and Lauric Acid: Formation of Microemulsion and Gel

Wu, Jieyu; Yin, Tianxiang

doi:10.1021/acs.langmuir.1c02837

Cited by 19 publications

(8 citation statements)

References 27 publications

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“…Those are formed by an organic salt (typically ammonium) and a neutral compound, acting as a hydrogen bond donor, at the eutectic ratio of the mixture. Mixing these precursors leads to a highly entropic state stabilized by an extensive hydrogen bond network, often remaining liquid at room temperature. − DESs are compared to ionic liquids since different precursors allow great control over the solvent physicochemical properties, such as polarity, hydrophobicity, and hydrogen potential. ,− Importantly, DESs can be synthesized from bio-derived compounds, such as sugars, carboxylic acids, and ammonium salts, which bestows the system with mild character, thermal and chemical stability, sustainability, and biocompatibility. − Hence, DESs offer a tailorable, suitable environment for biomolecules, probing to be milder alternatives to ionic liquids . Recently, particular emphasis has been placed on developing DESs as solvents for biomolecule assembly, preparation of functional biomaterials, enzymatic catalysis, and preservation of biomolecule integrity, among others. ,,− …”

Section: Introductionmentioning

confidence: 99%

Hydration in Deep Eutectic Solvents Induces Non-monotonic Changes in the Conformation and Stability of Proteins

et al. 2022

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The preservation of labile biomolecules presents a major challenge in chemistry, and deep eutectic solvents (DESs) have emerged as suitable environments for this purpose. However, how the hydration of DESs impacts the behavior of proteins is often neglected. Here, we demonstrate that the amino acid environment and secondary structure of two proteins (bovine serum albumin and lysozyme) and an antibody (immunoglobulin G) in 1:2 choline chloride:glycerol and 1:2 choline chloride:urea follow a re-entrant behavior with solvent hydration. A dome-shaped transition is observed with a folded or partially folded structure at very low (<10 wt % H 2 O) and high (>40 wt % H 2 O) DES hydration, while protein unfolding increases between those regimes. Hydration also affects protein conformation and stability, as demonstrated for bovine serum albumin in hydrated 1:2 choline chloride:glycerol. In the neat DES, bovine serum albumin remains partially folded and unexpectedly undergoes unfolding and oligomerization at low water content. At intermediate hydration, the protein begins to refold and gradually retrieves the native monomer−dimer equilibrium. However, ca. 36 wt % H 2 O is required to recover the native folding fully. The half-denaturation temperature of the protein increases with decreasing hydration, but even the dilute DESs significantly enhance the thermal stability of bovine serum albumin. Also, protein unfolding can be reversed by rehydrating the sample to the high hydration regime, also recovering protein function. This correlation provides a new perspective to understanding protein behavior in hydrated DESs, where quantifying the DES hydration becomes imperative to identifying the folding and stability of proteins.

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Section: Introductionmentioning

confidence: 99%

Hydration in Deep Eutectic Solvents Induces Non-monotonic Changes in the Conformation and Stability of Proteins

et al. 2022

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“…Subsequently, methyltrioctylammonium bromide (MTOAB) was recruited as a representative filmogen to redistribute ZnTPP-C 70 into a uniform sol–gel on the basis of the aforementioned H-bonding network just as the smooth basal plane exemplified (Figure B) . Such a gel phase bears resemblance to the viscous fluid of deep eutectic solvents (DES), which was once observed elsewhere at the mixture of TOAB and zinc meso -tetra(carboxyphenyl)porphine and the likes . As a follow-up, the dropcasts of iPR, a polycyclic ammonium, as well as the urinarily excreted Sel after Se fortification disrupted the former apparent evenness as revealed in Figure C and D, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Since the phenomenological i P ∼ ν 1/2 contradicts the intuitive surface-controlled process, a rationale can be drawn that the easily polarized N + and free Br − of MTOAB rallied an ionotropic medium for realtime relay of reactive charges, 22 which is consistent with our elucidation on the ion-channeled ECL in TOAB. 13 Essentially, this rule pins down the significance of lipoidal DES constructs in the ECL functionality of porphyrinic H-bond donors, 17,30 that is analogously akin to the endomembrane organism of chlorophylls inside a chloroplast. 13 Models for ECL Membrane-Binding Bioassay.…”

Section: ■ Introductionmentioning

confidence: 99%

Sorting and Screening of Quaternary Ammonium Lipoids for Membrane-Binding Assays Based on Electrochemiluminescent Cocrystalline Nanosheets

Chen

Zhu

et al. 2022

Langmuir

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Being synthetic supplements to natural lipids, lipoids now play an increasingly significant role in nanopore sequencing, olfactory sensing, and nanoimpact electrochemistry. Yet, systematic comparisons to sort and screen qualified lipoids are lacking for specific scenario applications. Here, taking the merits of electrochemiluminescence (ECL) in probing biointerfacial events, a new metric was proposed for the evaluation of substrate candidacy in the pool of hyamine bromides (ABs), that are used to cohere with electron-rich porphyrins for deep eutectics-like ECL matrices. Using a state-of-the-art framework emitter, the cocrystalline nanosheet of C70 and zinc meso-tetraphenylporphine (ZnTPP) via simple liquid–liquid interfacial deposition, 6 out of 20 ABs were inspected and identified as not only amenable filmogens but excitonic sensitizers in key terms of ECL strength as well as voltammetric characteristics. Among them, the methyltrioctyl (MTOAB) headgroup stood out; while the ECL activity at ZnTPP-C70@MTOAB was proven to be dictated by ionophoresis across multilamellar lipoidal layers. Thus, target-induced membrane deformation would let coreactant scavengers in to quench ECL, which enabled assays on two less visited bioprocesses regarding (1) the lipid solubility of ipratropium bromide, an aerosol medication for rhinitis treatment; and (2) the resorption of selenosugar as the central metabolite of Se-proteins on kidney glomerular basement barrier. Both resulted in nice membrane-binding measurements with comparable dissociation constants to reported microfluidic ELISA methods. By and large, though still being rudimentary, such parametrization of ECL-able biofilm would set up a basic ECL toolbox for archiving and resourcing multilipoidal even lipid–lipoid combos to handle the realistic (sub)cytomembrane processes in the future.

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“…Excessive dilution of DESs with water can destroy the hydrogen bonds between DES components, resulting in the loss of the supramolecular structure of DESs [ 16 ]. Moreover, additional auxiliary materials (surfactant/co-surfactant or organic solvent) are required to make them miscible with an oil phase when applied to oil-based formulations, which may cause skin irritation and potential toxicity after topical application repeatedly [ 17 – 19 ].…”

Section: Introductionmentioning

confidence: 99%

Deep eutectic solvent self-assembled reverse nanomicelles for transdermal delivery of sparingly soluble drugs

Li,

Jiao,

Guo

et al. 2024

J Nanobiotechnol

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Background Transdermal delivery of sparingly soluble drugs is challenging due to their low solubility and poor permeability. Deep eutectic solvent (DES)/or ionic liquid (IL)-mediated nanocarriers are attracting increasing attention. However, most of them require the addition of auxiliary materials (such as surfactants or organic solvents) to maintain the stability of formulations, which may cause skin irritation and potential toxicity. Results We fabricated an amphiphilic DES using natural oxymatrine and lauric acid and constructed a novel self-assembled reverse nanomicelle system (DES-RM) based on the features of this DES. Synthesized DESs showed the broad liquid window and significantly solubilized a series of sparingly soluble drugs, and quantitative structure-activity relationship (QSAR) models with good prediction ability were further built. The experimental and molecular dynamics simulation elucidated that the self-assembly of DES-RM was adjusted by noncovalent intermolecular forces. Choosing triamcinolone acetonide (TA) as a model drug, the skin penetration studies revealed that DES-RM significantly enhanced TA penetration and retention in comparison with their corresponding DES and oil. Furthermore, in vivo animal experiments demonstrated that TA@DES-RM exhibited good anti-psoriasis therapeutic efficacy as well as biocompatibility. Conclusions The present study offers innovative insights into the optimal design of micellar nanodelivery system based on DES combining experiments and computational simulations and provides a promising strategy for developing efficient transdermal delivery systems for sparingly soluble drugs.

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Amphiphilic Deep Eutectic Solvent Based on Lidocaine and Lauric Acid: Formation of Microemulsion and Gel

Cited by 19 publications

References 27 publications

Hydration in Deep Eutectic Solvents Induces Non-monotonic Changes in the Conformation and Stability of Proteins

Hydration in Deep Eutectic Solvents Induces Non-monotonic Changes in the Conformation and Stability of Proteins

Sorting and Screening of Quaternary Ammonium Lipoids for Membrane-Binding Assays Based on Electrochemiluminescent Cocrystalline Nanosheets

Deep eutectic solvent self-assembled reverse nanomicelles for transdermal delivery of sparingly soluble drugs

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