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Journal of Materials Chemistry B · 2015 ·Vol. 4 ·期 4 ·760-767 · IF 4.726

Reverse micelles-in-microspheres with sustained release of water-soluble combretastatin A4 phosphate for S180 tumor treatment

Liping wu,Liyan Qiu

Combretastatin A4 phosphate (CA4P), the water-soluble phosphate pro-drug of combretastatin A4 (CA4), acts as a novel vascular disrupting agent (VDA). It strongly inhibits tubulin polymerization and selectively exerts action against tumor blood vessels. However, its quite short half-life (∼30 min) results in a short action time and consequently limits its application. Therefore, it is beneficial to develop a sustained-release preparation of CA4P for relatively long action duration. On the other hand, conventional PLGA microspheres display poor encapsulation capability for water-soluble small molecules due to rapid diffusion outside. Hence, we developed CA4P-loaded microspheres (CA4P-MS) composed of methoxy poly(ethylene glycol)-b-polylactide (PELA) reverse micelles and PLGA with a nano-in-micro sea-island structure. The CA4P encapsulation efficiency of CA4P-MS reached 92.88%. More interestingly, sustained drug release was achieved, which contributed to the prolonged inhibition effect on S180 tumor during a 30-day period with one-time subcutaneous administration. In conclusion, our study established a biodegradable polymer based platform to construct microspheres for water-soluble small molecular compounds with sustained release and a long-lasting action.

CAS / MDL: 616-38-6 9002-89-5
研究领域: 药剂学 · 肿瘤学 · 生物材料
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Analytical Methods · 2014 ·Vol. 6 ·期 21 ·8627-8632 · IF 1.938

Determination of rhodamine B in lipsticks by high performance liquid chromatography after extraction with AOT reversed micelles

Jinjiao Shi,Ligang Chen

In this study, we investigated the possibility of reverse micelles which were used for the determination of rhodamine B in lipsticks followed by high performance liquid chromatography (HPLC). The reverse micelle of surfactant sodium 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate (AOT) was formed in n-hexane. First, the samples were preprocessed by reverse micelle extraction, and then rhodamine B was extracted from the mixture with methanol by back-extraction. The effects of different parameters including the concentration of surfactant, pH, amount of potassium chloride, ultrasonic time and type of organic solvents were evaluated and optimized during reverse micelle formation. The limit of detection of rhodamine B was 0.01 μg g−1. The intra-day and inter-day precisions expressed as relative standard deviations were 3.6% and 4.5%, respectively. The recovery of rhodamine B obtained was 95.0%. The reverse micelle method proposed for the determination of rhodamine B in real samples of lipsticks has the advantages of simplicity, speed, high precision, low detection limit and the use of inexpensive equipment.

研究领域: 分析化学 · 食品与化妆品安全 · 药物分析 · 分子检测 · 环境与健康
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Effect of CHAPS on the selective synthesis of (S)-n-octyl ibuprofen ester in AOT reverse micelle catalyzed by lipase

Yu Chen,Xirong Huang

CHAPS (3-[(3-cholamidopropyl) dimethylammonio]-1-propane sulfonate), a biocompatible zwitterionic surfactant derived from bile salt, has attracted great attention due to its distinct molecular structure and aggregation behavior. Addition of a low level of CHAPS to AOT (sodium bis(2-ethylhexyl) sulfosuccinate) reverse micelles has been found to be able to enhance the catalytic activity of the solubilized lipase. In this study, the effect of CHAPS on the lipase-catalyzed selective synthesis of (S)-n-octyl ibuprofen ester was investigated in AOT reverse micelles at 37 °C. The results demonstrate that the presence of CHAPS in AOT reverse micelle enhances both the yield and the enantiomeric excess (ee) value of (S)-n-octyl ibuprofen ester, especially at low water content. With 8 mM CHAPS in AOT reverse micelle ([AOT] = 100 mM, [H 2 O]/[AOT] = 12, pH = 7.0), a 48-hour yield of 34.2 % could be obtained, which is approximately twice that without CHAPS. In addition, the ee value of the product is increased from 89.1 % to 98.2 %. To understand the mechanism of the CHAPS effect, dynamic light scattering, fluorescence emission spectroscopy and Fourier transform infrared spectroscopy techniques were used to characterize the size of the reverse micelle, the conformation of the solubilized lipase and the activity of the bulk water in the reverse micelle. It reveals that at low water content, the addition of CHAPS enlarges the size of AOT reverse micelle, stabilizes the lipase conformation and reduces the nucleophilicity of bulk water in AOT reverse micelle. The synergistic effect of the aforementioned factors results in the improvement of the enzymatic synthesis of the ester. The above research provides scientific support for the lipase-based preparation of chiral acids/alcohols in the reverse micellar system.

CAS / MDL: 540-84-1 15687-27-1
研究领域: 生物化学 · 酶工程 · 有机合成
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Materials · 2024 ·Vol. 17 ·期 12 ·2901 · IF 3.1

Reverse Micelles Extraction of Prolamin from Baijiu Jiuzao: Impact of Isolation Process on Protein Structure and Morphology

Ting-Ting Yu,Fu-Rong Yang,Yao Su,Yi-Heng Qi,Yi Liu,Nan Hu

Prolamins, proteins derived from plants, have extensive applications in pharmaceutics and food science. Jiuzao is a byproduct of the Baijiu brewing industry, and is a great source of prolamin. Despite its importance, knowledge regarding the extraction techniques and the properties of prolamin derived from Baijiu Jiuzao (PBJ) remains limited. Reverse micelles (RMs) extraction offers an efficient and cost-effective method for purifying proteins. In the present study, prolamin was extracted from Baijiu Jiuzao using RMs extraction and subsequently characterized in terms of its secondary structure, morphology, and particle size distribution. Our findings indicate that the purified prolamin extracted using further RMs extraction possessed higher α-helix content (+13.25%), forming a large-scale protein network, and narrower particle size distributions compared to the crude prolamin obtained by NaOH-ethanol method. This research suggests that RMs extraction has potential applications in extracting prolamin from brewing industry byproducts, offering an environmentally friendly approach to Baijiu Jiuzao recycling.

CAS / MDL: 57-09-0
研究领域: 食品科学 · 蛋白质化学 · 环境科学
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Journal of Materials Chemistry B · 2014 ·Vol. 3 ·期 2 ·316-322 · IF 0

Reverse micelles based on biocompatible β-cyclodextrin conjugated polyethylene glycol block polylactide for protein delivery

Wen-Xing Gu,Mingran Zhu,Nan Song,Xiaoxu Du,Ying-Wei Yang,Hui Gao

A series of linear and star-shaped amphiphilic polyethylene glycol block polylactide (PEG-b-PLA) and β-cyclodextrin (CD) conjugated PEG-b-PLA (PEG-b-PLA-CD) copolymers were synthesized. Bovine serum albumin (BSA) aqueous solution was emulsified in the copolymer organic solutions to fabricate reverse micelles (RMs), and was then further transferred into ethyl oleate (EO), a pharmaceutically acceptable vehicle, by the RMs. As identified by 1H NMR, the RMs were formed with a hydrophilic core of PEG and CD, covered with a hydrophobic corona of PLA moiety, and were spherical in shape, as observed by a scan electronic microscope. Compared with the PEG-b-PLA RMs, the PEG-b-PLA-CD RMs presented higher encapsulation efficiency. The release of BSA was influenced by the copolymer composition and architecture. BSA stability in the release aqueous phase was confirmed by circular dichroism spectroscopy. The oil-based formulation fabricated from biodegradable copolymers with high drug loading showed a great potential for protein delivery.

CAS / MDL: 9048-46-8
研究领域: 生物材料 · 药物递送
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LANGMUIR · 2017 · IF 3.833

Confined Pool-Buried Water-Soluble Nanoparticles from Reverse Micelles

Yong Liu,Ying Chen,Yongchao Yao,Kui Luo,Shiyong Zhang,Zhongwei Gu

With the special nature of confined water pools, reverse micelles (RMs) have shown potential for a wide range of applications. However, the inherent water insolubility of RMs hinders their further application prospect especially for applications related to biology. We present herein the first successful transformation of water-insoluble RMs into water-soluble nanoparticles without changing the confined aqueous interiors by hydrolysis/aminolysis of arm-cleavable interfacial cross-linked reverse micelles formed from diester surfactant 1. The unique properties exhibited by the aqueous interiors of the resulting pool-buried water-soluble nanoparticles (PWNPs) were demonstrated both by the template synthesis of gold nanoparticles in the absence of external reductants and by the fluorescence enhancement of encapsulated thioflavin T (ThT). Importantly, the unique potential for PWNPs in biological applications was exemplified by the use of ThT@PWNPs and “cell targeted” ThT@PWNPs as effective optical imaging agents of living cells. This work conceptually overcomes the application bottleneck of RMs and opens an entry to a new class of functional materials.

研究领域: 化学 · 生物学 · 材料科学
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CHEMICAL ENGINEERING RESEARCH & DESIGN · 2022 · IF 4.119

Proposal and application of a novel extraction and purification technology for juglone from Juglans mandshurica waste branches: Reverse micellar microemulsion combined with magnetic solid phase extraction

Mengfei Tian,Chunyu Liang,Naveed Ahmad,Chunying Li,Weihao Wang,Yu Zhang,Zidan Luo,Lequn Qiu,Chunjian Zhao

A reverse micellar microemulsion combined with magnetic solid phase extraction (RMM-MSPE) technology was developed for the extraction and purification of juglone from Juglans mandshurica . Reverse micellar microemulsion (RMM) (Tween 80: n-propanol: n-hexane: 0.05 mol/L KCl aqueous solution = 27:13.5:4.5:55; w/w/w/w) was used to extract juglone based on microwave. The optimum conditions were a pH of 5.6, a liquid-solid ratio of 20:1 (mL/g), temperature of 40 °C, time of 63 s, and power of 400 W. Graphene oxide/nano diamonds/ Fe 3 O 4 (GO/ND/Fe 3 O 4 ) was prepared as adsorbent and applied to purify juglone by magnetic solid-phase extraction (MSPE). The optimum adsorption conditions were time of 14 h, solid to liquid ratio of 30 mg/mL, pH of 5.5 and shaker speed of 200 r/min. Anhydrous methanol provided the best desorption of juglone and the optimum conditions were a desorption time of 16 h, pH of 8, and the solid-liquid ratio of 40 mg/mL. The purity of juglone was 69.08% and the recovery yield was 78.67%. RMM and GO/ND/Fe 3 O 4 could be reused three times and eight times after the first use, respectively. The proposed RMM-MSPE is a green and efficient alternative method for extraction and purification of juglone.

CAS / MDL: 481-39-0
研究领域: 植物化学 · 环境科学 · 药用植物学
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INSTRUMENTATION SCIENCE & TECHNOLOGY · 2021 · IF 1.584

Three phase dispersive liquid-liquid microextraction (DLLME) based on reverse micelles for the enrichment of Q-markers of cinnamic acids in traditional Chinese medicine

Zhao-chan Liu,Li Yang,Rong-rong Xing,Xuan Chen,Xiao-hong Bai,Shuang Hu

This work describes three phase dispersive liquid-liquid microextraction based on reverse micelles for the determination of Q-markers of cinnamic acids (caffeic acid, p-hydroxycinnamic acid, ferulic acid, and cinnamic acid) in traditional Chinese medicine followed by high performance liquid chromatography (HPLC) analysis. The variables influencing the procedure were optimized separately. Enrichment factors from 110 to 189, linearities from 1.2 to 960 ng mL−1 with r2 exceeding 0.9943, detection limits from 0.1 to 0.6 ng mL−1, excellent precision with relative standard deviations below 5.6%, and good relative recoveries from 80.0% to 113.3% were achieved. In addition, the mechanism of the procedure was explored by comparison with conventional dispersive liquid-liquid microextraction at the optimum conditions. The results showed that the developed microextraction procedure improved the sensitivity and consumed less organic solvent and is a greener approach.

研究领域: 分析化学 · 中药学
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SCIENCE OF THE TOTAL ENVIRONMENT · 2019 · IF 5.589

Degradation of several polycyclic aromatic hydrocarbons by laccase in reverse micelle system

Pengfei Xu,Hao Du,Xin Peng,Yu Tang,Yaoyu Zhou,Xiangyan Chen,Jia Fei,Yong Meng,Lu Yuan

Remediation of polycyclic aromatic hydrocarbons (PAHs) in oily sludge has become the focus of attention. UV spectrophotometer analysis showed that four types of PAHs were found in sample, which including phenanthrene, anthracene, benzo( a )anthracene and benzo( b )fluoranthene. In order to degrade PAH effectively, the laccase reverse micelles system was proposed. The system protects laccase from being affected by organic phase. Reverse micelles were prepared by using isooctane to simulate oil. The optimum water content W 0 was 10 by measuring the electrical conductivity of the system. Under this condition, the effects of pH, temperature and ionic strength on the degradation rate of PAHs were investigated. Also, compared with that of non-immobilized laccase, the ratio between the secondary structures of laccase under different conditions was studied. The results showed that the highest laccase activity was obtained at pH 4.2 and 30 °C with 60 mmol/L KCl. Meanwhile, the structure of α-helix accounts for the largest proportion, and the ratio of α-helix in the laccase secondary structure in the laccase-reverse micelle system was higher than that of the non-immobilized one under this condition. Finally, predicting the reactive site of the degradation of polycyclic aromatic hydrocarbons was simulated by ORCA (Version 4.2.0). The application in oily sludge was further conducted. This study provides an effective method and basis for the degradation of PAHs in oily sludge.

研究领域: 环境生物技术 · 污染生态学 · 酶工程 · 有机污染物降解 · 土壤修复
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Journal of Environmental Chemical Engineering · 2024 · IF 7.4

Solving the problem of the 'third phase' in the extraction process by regulating the formation of micelles

Ting Li,Shishun Dong,Qifeng Wei,Xiulian Ren

Based on the theory of critical micelle , a Gemini type amide based ionic liquid system was developed to effectively extract Zr(IV) and Hf(IV) dispersed in an acidic chloride solution from the liquid phase into the organic phase through a coordination driven process. We focused on the effect of the reverse micelles formed during the extraction process of the extracted compound on the stability of the coordination system. The 'third phase' problem in the organic phase during the extraction process was analyzed from the perspective of molecular polarity. Thus, the strategy of Gemini amide ionic liquid applied to the extraction of metal ions in an acidic chloride system was improved.

CAS / MDL: 7647-01-0
研究领域: 化学 · 环境科学
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JOURNAL OF SEPARATION SCIENCE · 2019 ·Vol. 42 ·期 18 ·2977-2984 · IF 2.516

Comparison of three-phase hollow fiber liquid-phase microextraction based on reverse micelle with conventional two-phase hollow fiber liquid-phase microextraction and their applications for analysis of cinnamic acids in traditional Chinese medicines

Zhao-chan Liu,Shu-mei Zhang,Run-qin Wang,Xuan Chen,Shuang Hu,Xiao-hong Bai

A novel three-phase hollow fiber liquid-phase microextraction was developed based on reverse micelle as extraction solvent and acceptor phase, and compared with conventional two-phase hollow fiber liquid-phase microextraction. Both procedures were used in the extraction and concentration of four cinnamic acids (caffeic acid, p -hydroxycinnamic acid, ferulic acid, and cinnamic acid) in traditional Chinese medicines prior to high-performance liquid chromatography analysis. Parameters affecting the two procedures were investigated and optimized to obtain the optimum enrichment factors. The mechanism of the developed procedure was explored and elucidated by comparison with conventional two-phase hollow fiber liquid-phase microextraction. Under the optimized conditions, the analytes’ enrichment factors were between 50 and 118 for the proposed procedure, and 31–96 for conventional two-phase mode. Satisfactory linear ranges ( r 2 ≥ 0.99), detection limits (0.1–0.6 ng/mL), precisions (<9.2%), and accuracies (recoveries: 80–123.1%) were observed for the two procedures. The results showed that the enrichment capacity of the proposed procedure for the cinnamic acids is better than that of conventional two-phase procedure, and both are eco-friendly, simple, and effective for the enrichment and detection of cinnamic acids in traditional Chinese medicines.

研究领域: 分析化学 · 药物分析
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JOURNAL OF SEPARATION SCIENCE · 2025 ·Vol. 48 ·期 8 ·e70242 · IF 2.8

Chain Length-Dependent Reverse Micelle Extraction of Prolamins From Baijiu Jiuzao: Synergistic Effects of Ethanol, Ionic Strength, and Chaotropic Agent

TingTing Yu,FuRong Yang,Fang Wang,YongMei Chen,Yi Liu,Nan Hu

This study investigated the chain length-dependent extraction efficiency of two cationic surfactants—dodecyltrimethylammonium bromide (C12, 12-carbon chain) and cetyltrimethylammonium bromide (C16, 16-carbon chain)—for reverse micelle extraction of prolamins from Baijiu Jiuzao (Chinese Baijiu distillers' grains). Although pH variations (4.0–9.0) had negligible effects, ethanol, ionic strength, and chaotropic agent demonstrated distinct chain length-dependent behaviors: ethanol increased C12's forward extraction efficiency by 10.6% (absolute) while enhancing C16's backward efficiency by 8.7%. Potassium chloride enhanced C16's forward efficiency by 4.7%, while potassium bromide significantly improved C12's backward efficiency by 15.9%. Guanidine hydrochloride consistently promoted C16 in both extraction phases. Dynamic light scattering demonstrated significant differences ( p < 0.05) in reverse micelle sizes: C12 formed smaller empty reverse micelles (1.5 ± 0.2 nm) compared to C16 (2.5 ± 0.5 nm). During forward extraction, reverse micelles expanded significantly to 217.9 ± 6.3 nm (C12) and 311.2 ± 43.2 nm (C16). Backward extraction released prolamin particles of 449.0 ± 16.2 nm (C12) and 650.4 ± 29.7 nm (C16), confirming the size-exclusion-driven release mechanism. The more compact C12 reverse micelles correlated with lower total prolamin yield (26.6 ± 0.1% vs. 32.2 ± 0.1% for C16, p < 0.01) and substantially diminished bovine serum albumin recovery (5.2 ± 0.2% vs. 45.3 ± 2.5%, p < 0.01). Sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis corroborated these findings, further demonstrating that reverse micelle-extracted prolamins formed thermally stable dimers resistant to reductive cleavage. Combined with dynamic light scattering data (particle size range: 400–700 nm in the backward-extraction aqueous phase), these findings demonstrate that prolamin aggregates after reverse micelle extraction. These findings demonstrate that surfactant chain length as a key parameter for optimizing reverse micellar systems, where shorter-chain surfactants facilitate selective extraction, whereas longer chains enhance yields.

CAS / MDL: 1119-94-4 57-09-0
研究领域: 食品科学 · 胶体与界面科学 · 蛋白质提取 · 生物技术 · 化学工程
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