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Journal of Environmental Chemical Engineering · 2025 · IF 7.2

Preparation of hydrophilic and antibacterial nanofiltration membrane by post-grafting N-(3-Aminopropyl)-imidazole

Yu Fu,Fangbo Zhao,Yingzheng Liu,Ruiqi Li,Hongxu Chen,Liu Yang,Zhiguo Li,Mingcong Wu,Dan Wang

In this research, we introduce a novel and efficient approach for enhancing both the antibacterial efficacy and resistance to protein fouling of nanofiltration (NF) membranes, marking the first report of a method capable of concurrently addressing these critical membrane performance parameters. After traditional interface polymerization (IP), NF membranes were post-treated by the antibacterial N-(3-Aminopropyl)-imidazole (ANPI) which can be grafted on the membrane by its amino group reacting with rest acyl chloride in IP on the surface. After parameter optimization of the ANPI concentration, the modified membrane NF-12 demonstrated up to 99% antibacterial activity against two representative pathogens, Escherichia coli and Staphylococcus aureus . Except for this, due to the zwitterionic effect, the modified membrane achieved a remarkable 68.7% enhancement in water flux and the recovery rate of BSA cyclic pollution reached 97.5%. From mechanism analysis, it can be proposed that the post-grafted ANPI brought antibacterial properties to the NF membrane, which was able to kill bacteria attached to the membrane surfaces. Also, the imidazole protonation introduced positive charges to the NF membrane surface, mixing with negative charges produced by acyl chloride hydration, which produced the zwitterionic effect and facilitated the formation of a robust hydrophilic hydration layer, thereby significantly diminishing the adhesion of contaminants.

研究领域: 材料科学 · 环境工程 · 生物医学
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EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY · 2017 ·Vol. 119 ·期 12 ·1700300 · IF 2.145

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

Long Xu,Li Zhang,Daoming Li,Pengzhan Liu,Chin-Ping Tan,Weifei Wang,Xiangqian Liu,Bo Yang,Dongming Lan,Yonghua Wang

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.

CAS / MDL: 67-48-1 57-13-6
研究领域: 生物化学 · 食品科学
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CLINICAL NUTRITION · 2014 · IF 3.94

Particle size determines effects of lipoprotein lipase on the catabolism of n-3 triglyceride-rich particles

Lulu Xia,Chaonan Fan,Hua Dong,Cui Wang,Yuanyuan Lu,Richard J. Deckelbaum,Kemin Qi

Summary Background & aims The catabolic pathways of n-3 triglyceride (TG) rich particles (n-3 TGRP) have not been clearly elucidated. In this study, we investigated the effects of lipoprotein lipase (LPL) on the catabolism of n-3 TGRP compared to n-6 TGRP in vivo and in vitro, and we determined whether particle size affects the biological functions of LPL in n-3 TGRP catabolism. Methods Four types of lipid emulsions , chylomicron (CM)-sized n-3 TG and n-6 TG emulsions, and very low density lipoprotein (VLDL)-sized n-3 TG and n-6 TG emulsions, were labeled with 1,1′-dioctadecy1-3,3,3′,3′-tetramethylindo-carbocyanine perchlorate (DiI) and administered via a bolus injection to LPL gene knockout (LPL+/−) mice in vivo and were added to cultured LPL miRNA-transfected 3T3-L1 adipocytes in vitro. Results With CM-sized emulsions, a reduction in LPL expression in LPL+/− mice had almost no effect on tissue uptake of n-3 TG emulsions with smaller changes in their initial blood clearance ; however, greater effects were observed for VLDL-sized n-3 TG emulsions with respect to tissue uptake with greater changes in their initial blood clearance, compared to n-6 TG emulsions with the same size. In vitro, LPL miRNA transfection had smaller effects on CM-sized and greater effects on VLDL-sized n-3 TG emulsions, with respect to particle uptake, cell TG mass, particle-cell binding and particle lipolysis . Conclusion These results suggested that LPL is more important for catabolism of n-3 TGRP of smaller size; whereas it is essential for catabolism of all sizes of n-6 TGRP.

研究领域: 生物化学 · 营养学
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Journal of Water Process Engineering · 2024 · IF 6.3

N-(3-Aminopropyl)-imidazole modified polyamide reverse osmosis membrane for improved permeability and selectivity

Yingying Liu,Wanjing Cui,Xiuge Chen,Ming Wang,Haifeng Zhang,Zhi Wang

Reverse osmosis (RO) membrane technology is applied widely on the water desalinization for relieving the challenge of freshwater scarcity. Polyamide (PA) membranes with superior water flux and rejection in the RO process are currently in high demand. In this study, a novel reactive additive N-(3-Aminopropyl)-imidazole (N-IM) was utilized to optimize the interfacial polymerization (IP) process and enhance PA-RO membrane performance. N-IM made the nascent film more porous and created an RO membrane with a thicker PA separation layer. The modified membrane exhibited a more hydrophilic surface, ascribing to more carboxylic acid groups. This membrane exhibited an improved water flux, increasing from 59.67 L/(m 2 ∙h) of original membrane to 82.76 L/(m 2 ∙h) of the modified membrane with the addition of 0.5 % w/v N-IM concentration, which was attributed to the enhanced hydrophilicity and increased water trapping capacity provided by the imidazole ring in N-IM. Additionally, the NaCl rejection increased from 98.75 % to 98.97 %, which can be attributed to the thicker separation layer and more carboxylic acid groups. In addition, the membrane showed excellent stability of performance and good pH stability. The study presents a novel approach to producing RO membranes with exceptional performance.

研究领域: 材料科学 · 环境工程
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Journal of Oleo Science · 2021 · IF 1.601

Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents

Xiumei Wang,Xiaoxu Zhao,Xiaoli Qin,Zexin Zhao,Bo Yang,Yonghua Wang

n-3 polyunsaturated fatty acids (PUFA)-rich triacylglycerols (TAG) with many beneficial effects are still difficult to be synthesized efficiently and rapidly by current synthetic techniques. This study reports the fatty acid specificity of immobilized MAS1 lipase and its efficient synthesis of n-3 PUFA-rich TAG by esterification of glycerol with n-3 PUFA in natural deep eutectic solvents (NADES) systems. Immobilized MAS1 lipase showed the highest preference for capric acid [C10:0, the highest specificity constant (1/α)=1] whereas it discriminated strongly against docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) due to their lowest specificity constants (1/α=0.19 and 0.2). Moreover, the highest n-3 PUFA-rich TAG content (55.8%) with similar n-3 PUFA composition to the substrate was obtained in choline chloride/glycerol (CG) system. There was a 1.38-fold increase of TAG content in CG system compared with that in the solvent-free system. Interestingly, immobilized MAS1 lipase exhibited no regiospecificity in the solvent-free and various NADES systems. Besides, the potential reaction mechanism of immobilized MAS1 lipase-catalyzed esterification of glycerol with n-3 PUFA in NADES systems was described. It was found that the use of NADES as solvents could greatly enhance TAG content, and make it easy to separate the product. These results indicated that immobilized MAS1 lipase is a promising biocatalyst for the efficient synthesis of n-3 PUFA-rich TAG by esterification of glycerol with n-3 PUFA in NADES systems.

研究领域: 生物化学 · 食品科学 · 酶工程
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

An Efficient Synthesis of Lysophosphatidylcholine Enriched with n-3 Polyunsaturated Fatty Acids by Immobilized MAS1 Lipase

Xiumei Wang,Xiaoli Qin,Xiuting Li,Zexin Zhao,Bo Yang,Yonghua Wang

n-3 polyunsaturated fatty acid (PUFA)-rich lysophosphatidylcholine (LPC) with many beneficial effects was effectively synthesized by immobilized MAS1 lipase-catalyzed esterification of n-3 PUFA with sn-glycero-3-phosphatidylcholine (GPC) under vacuum in a solvent-free system. Immobilized MAS1 lipase was found to be a more suitable catalyst for the production of n-3 PUFA-rich LPC when compared with Novozym 435. The maximal GPC conversion and LPC content (93.12% and 90.77 mol %) were obtained under the optimized conditions (enzyme loading of 300 U/g substrate, temperature of 55 °C, and n-3 PUFA/GPC molar ratio of 20:1). Moreover, it was observed that 1-acyl-sn-glycero-3-lysophosphatidylcholine (sn-1 acyl LPC) was the main reaction product, as demonstrated by molecular docking. These results showed that immobilized MAS1 lipase had high phospholipase activity with a predominant specificity for the sn-1 hydroxyl position of GPC to efficiently synthesize highly pure n-3 PUFA-rich LPC from GPC for industrial application.

CAS / MDL: 865-49-6 115-86-6
研究领域: 生物化学 · 食品科学 · 酶工程
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FOOD CHEMISTRY · 2024 · IF 8.5

Highly efficient enzymatic enrichment of n-3 polyunsaturated fatty acid glycerides via interfacial biocatalysis in Pickering emulsions

Liumei Wu,Dongming Li,Fuyang Bi,Chao Yu,Yufei Zhang,Mingming Zheng

A novel Pickering interfacial biocatalysis (PIB) system has been, for the first time, successfully applied for the enzymatic selective hydrolysis of algae oils and fish oils to enrich n-3 PUFAs glycerides. Lipase AY 400SD was identified and adsorbed on hydrophobic hollow core-shell silica nanoparticles, resulting in the formation of the immobilized enzyme AY 400SD@HMSS-C 18 . The biocatalyst was employed as an emulsifier to stabilize the water-in-oil Pickering emulsion, resulting in the successful construction of the PIB system. The newly developed PIB system resulted in a notable enhancement of the n-3 PUFAs content of the six oils, with a mean increase ranging from 9.17 % to 23.09 %, and with the recovery rate of n-3 PUFAs exceeded 90 %. The platform demonstrated to be stable and recyclable. The present research illustrated that the PIB has the potential to be a viable alternative for the purpose of enhancing the content of n-3 PUFAs in glycerides.

研究领域: 生物化学 · 食品科学
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JOURNAL OF SURFACTANTS AND DETERGENTS · 2010 ·Vol. 14 ·期 3 ·317-324 · IF 0.795

Synthesis of N-(3-Oxapropanoxyl)dodecanamide and its Application in Surfactant-Polymer Flooding

Cui Zheng-gang,Song Hong-xing,Yu Jun-jie,Jiang Jian-zhong,Wang Feng

Alkali-surfactant-polymer (ASP) flooding has been considered to be one of the useful tertiary oil recovery techniques. However, field tests in China have revealed that serious side effects may occur due to using alkali. Thus alkali-free SP flooding is more favorable in China. Unfortunately, surfactants effective in ASP flooding are usually ineffective in the absence of alkali and new surfactants need to be designed. In this paper N -(3-Oxapropanoxyl)dodecanamide as a pure compound and a mixture of homologues with narrow EO number distribution, synthesized by the reaction of lauroyl chloride with diglycolamine and addition of one ethylene oxide to coconut monoethanolamide respectively, are examined for their adaptability in SP flooding. It is found that, when mixed with betaines, both products can reduce Daqing crude oil/connate water interfacial tension to a magnitude of 10 −3 –10 −4  mNm −1 at 45 °C in a wide surfactant concentration range, 0.01–0.5 wt%, and oil displacement tests using natural cores indicates that a tertiary oil recovery of 18.6 ± 0.4% OOIP can be achieved by SP flooding with the N -(3-Oxapropanoxyl)dodecanamide as the main surfactant without adding any alkaline agent and neutral electrolyte. N -(3-Oxapropanoxyl)dodecanamide, as a nonionic surfactant without a cloud point and producible industrially from renewable materials, is an ideal surfactant for SP flooding in the absence of an alkaline agent.

研究领域: 石油工程 · 化学工程
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FOOD CHEMISTRY · 2016 · IF 4.052

Immobilized MAS1 lipase showed high esterification activity in the production of triacylglycerols with n-3 polyunsaturated fatty acids

Xiumei Wang,Daoming Li,Man Qu,Rabia Durrani,Bo Yang,Yonghua Wang

Immobilization of lipase MAS1 from marine Streptomyces sp. strain W007 and its application in catalyzing esterification of n-3 polyunsaturated fatty acids (PUFA) with glycerol were investigated. The resin XAD1180 was selected as a suitable support for the immobilization of lipase MAS1, and its absorption ability was 75   mg/g (lipase/resin ratio) with initial buffer pH value of 8.0. The thermal stability of immobilized MAS1 was improved significantly compared with that of the free lipase. Immobilized MAS1 had no regiospecificity in the hydrolysis of triolein. The highest esterification degree (99.31%) and TAG content (92.26%) by immobilized MAS1-catalyzed esterification were achieved under the optimized conditions, which were significantly better than those (82.16% and 47.26%, respectively) by Novozym 435. More than 92% n-3 PUFA was incorporated into TAG that had similar fatty acids composition to the substrate (n-3 PUFA). The immobilized MAS1 exhibited 50% of its initial activity after being used for five cycles.

CAS / MDL: 143-07-7
研究领域: 生物化学 · 酶工程 · 食品科学
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Journal of Materials Chemistry B · 2024 · IF 6.1

Enhancing Oncolytic Virus Efficiency with Methionine and N-(3-guanidinopropyl)methacrylamide Modified Acrylamide Cationic Block Polymer

Gong Chen,Yuan Yuan,Ying Li,Zushun Xu,Qianyuan He,Zizhen Qin,Han Hu,Congcong Gao,Qi Xu,Qinglei Gao,Fei Li

Oncolytic virus ablation of tumor cells has the advantages of high tumor selectivity, strong immunogenicity and low side effects. However, the recognition and clearance of oncolytic viruses by the immune system is the main reason that limits their anti-tumor efficiency. As a highly biosafe and highly modifiable oncolytic virus vector, acrylamide can improve the long-term circulation of oncolytic viruses, but it is limited in its uptake efficiency by tumor cells. Herein, we constructed a N- hydroxymethyl acrylamide -b-(N-3- aminopropyl methacrylamide) -b-DMC block copolymers (NMA-b-APMA-b-DMA, NAD) as an oncolytic virus carrier, which not only improves the long-term circulation of oncolytic viruses in the body but also has excellent loading oncolytic virus stability. The data shows that no obvious difference in the transfection effect of the NAD/Ad complex with or without neutralizing antibody in the medium, which meant that the cationic carrier mediated by NAD/Ad had good serum stability. Only 10 micrograms of NAD carrier are needed to load the oncolytic virus, which can increase the transfection efficiency by 50 times. Cell experiments and mouse animal experiments show that NAD vector can significantly enhance the anti-tumor effect of oncolytic viruses. We hope that this work will promote the application of acrylamide as an oncolytic virus vector and provide new ideas for modification methods of acrylamide for biomedical applications.

研究领域: 生物医学 · 肿瘤学 · 病毒学
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Veterinary Sciences · 2025 ·Vol. 12 ·期 3 ·233 · IF 2.3

N-(3-Oxododecanoyl)-Homoserine Lactone Induces Intestinal Barrier Damage in Piglets via the Lipid Raft-Mediated Apoptosis Pathway

Yang Yang,Xin Zhang,Jin Yang,Ziyan Wu,Junpeng Li,Ruilong Song,Chuang Meng,Guoqiang Zhu

Simple SummaryQuorum sensing (QS) not only regulates bacterial virulence through signaling molecules, but is also capable of causing direct damage to host cells. Previous studies have found a high correlation between N-acyl homoserine lactone (AHL) of the QS in the piglet intestine and piglet health. In a mouse model, AHL signaling N-(3-oxododecanoyl)-homoserine lactone (OdDHL) induced apoptosis of intestinal cells and damage to intestinal barrier. In a porcine intestinal epithelial cell model, OdDHL also was confirmed to induce apoptosis. The direct role and mechanism of OdDHL in the digestive tract of porcine animal models have not been elucidated. For the first time in a piglet model, we have verified that AHL induces apoptosis and disrupts the intestinal barrier, and we have also verified the protective effect of QS inhibitors. The present study also investigates the central role of cellular lipid rafts in the critical phase in which OdDHL adheres to cells and exerts functions. In cells where lipid rafts were eliminated, the ability of OdDHL adherence to cell surface was significantly reduced, and apoptosis induction was similarly impaired. This result indicates an important role for lipid rafts in relevant processes. This study provides basic data for the antimicrobial application of QSI in pig farming.Quorum sensing (QS) is a process by which bacteria sense their population density and regulate behavior accordingly. QS not only regulates bacterial virulence but also directly influences host cells. Previous studies have shown that QS is strongly associated with piglet intestinal health, but the mechanism is not yet clear. For the first time, we have confirmed in a piglet animal model that OdDHL directly damages intestinal cells in weaned piglets, disrupting the intestinal barrier. We also provide a preliminary exploration of the underlying mechanism of these effects. TUNEL assays confirmed that damage to the piglet intestinal barrier coincided temporally and spatially with dysregulated apoptosis. Lipid rafts, key components of the cell membrane, are involved in many biological processes, including the activation of apoptosis-related proteins. Following the disruption of the lipid raft structure in IPEC-J2 cells, the apoptosis rate under OdDHL stimulation decreased by 50%. These data demonstrate that lipid rafts mediate the attachment of OdDHL to porcine intestinal cells; then, OdDHL induces apoptosis in porcine intestinal cells through the mitochondrial and death receptor pathways, thereby compromising the integrity of the porcine intestinal barrier. This study provides foundational insights into the role of QS in piglet intestinal diseases.

研究领域: 动物科学 · 微生物学 · 细胞生物学
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Journal of Flow Chemistry · 2022 ·Vol. 12 ·期 3 ·317-325 · IF 3.264

Continuous synthesis of N-(3-Amino-4-methylphenyl)benzamide and its kinetics study in microflow system

Xu Qilin,Li Guosi,Zhu Fucheng,Chen Naidong,Chen Cuiwu,Yu Zhiqun

N -(3-Amino-4-methylphenyl)benzamide ( 1 ) is a crucial building blocks of many drug candidates. In this paper, a continuous flow microreactor system was developed to synthesize 1 and determine intrinsic reaction kinetics parameters. By screening the acylating reagents and reaction conditions, 1 was obtained by the selective acylation of 4-methylbenzene-1,3-diamine ( 2 ) with benzoic anhydride ( 3 ). Since the two amine groups in 2 are in different chemical environments, parallel by-products and serial by-products coexist, which makes the selective monoacylation process relatively complicated. To reveal the reaction process clearly, reaction rate constants and their 95% confidence intervals, activation energies, pre-exponential factors were acquired by kinetics study in microflow system. The established kinetic model can calculate the selectivity and conversion of the acylation reaction, which are in good agreement with the experimental results. Subsequently, the kinetic model was used to optimize reaction conditions, as a result, 1 was synthesized in the microreactor with a yield of 85.7% within 10 min.

研究领域: 化学工程 · 有机化学 · 药学
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