RSC Advances
·
2015
·Vol. 5
·期 86
·69939-69947
·
IF 3.84
Qin Yan,Hong-Ning Zheng,Chuan Jiang,Kun Li,Shou-Jun Xiao
Polymer brushes of polymethacrylic acid (PMAA) and PMAA-associated polymer blends of PMAA/PNIPAM (poly-N-isopropylacrylamide) were prepared on porous silicon for further investigation of the EDC/NHS (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide/N-hydroxysuccinimide) activation mechanisms by infrared spectroscopy. When the fragmentation degree of PMAA blocks in PMAA-associated polymer blends is increased, the production of anhydride wanes from dominant to recessive, whereas a complementary product of the NHS-ester waxes from recessive to dominant. The Thorpe–Ingold effect was applied to explain the formation of anhydride: the gem-dialkyl groups of PMAA next to the carboxylic acids compress the acid side chains close to each other; thus, once the intermediate of O-acylisourea forms, it will be attacked by the intramolecular neighboring acid much faster than any other nucleophiles such as NHS and water, and therefore the six-membered ring of the anhydride will be formed. All acid side chains in PMAA standing next to each other will form an anhydride, primarily due to the Thorpe–Ingold effect, unless they are sterically hindered, whereas only isolated acid side chains form the NHS-ester. The EDC/NHS activation results for four small molecules of dicarboxylic acids in aqueous media, namely, glutaric acid and 2,2-dimethyl glutaric acid, which generate disuccinimidyl ester with high yield, and succinic acid and 2,2-dimethyl succinic acid, which remain intact, can also be explained by the Thorpe–Ingold effect. A clear understanding of the EDC/NHS activation mechanisms of PMAA will take us a step closer for resolving the mechanistic ambiguity of the carbodiimide/additive coupling reactions for amide bond formation.
研究领域:
高分子化学
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生物材料科学
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DOI
高影响因子
FOOD CHEMISTRY
·
2023
·
IF 8.8
Huan Gong,Ye Zi,Guangyi Kan,Li Li,Cuiping Shi,Xichang Wang,Jian Zhong
Herein, a safe desolvation and crosslinking method was developed to prepare food-grade bovine bone gelatin (BBG) nanoparticles for Pickering emulsion stabilization. The nanoparticle-like structures were formed by adjusting pH 9.0 and adding ethanol, and then stable nanoparticles were formed by using N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) and N -hydroxysuccinimide (NHS) as crosslinker. Compared with other pH (2.5, 5.0, 7.0, and 12.0), pH 9.0 was the appropriate pH to prepare BBG nanoparticles. Individual nanoparticles (6.50 nm in height), oligomeric nanoparticles (13.42–22.52 nm in height), and polymeric nanoparticles (obvious liquid-precipitate separation) were formed at EDC·HCl/NHS concentrations of 6, 9–12, and 15–20 mg/mL, respectively. The oligomeric nanoparticles induced the highest emulsion creaming stability. The emulsion creaming ability increased with the increase of BBG nanoparticle concentrations. Low NaCl concentration (e.g., 100 mmol/L) could increase the emulsion creaming stability. Finally, 4 °C was the best storage temperature for fish oil-loaded Pickering emulsions.
研究领域:
食品科学
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材料科学
·
化学工程
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PubMed
高影响因子
JOURNAL OF APPLIED POLYMER SCIENCE
·
2022
·Vol. 140
·期 3
·e53318
·
IF 3.057
Aoqi Li,Yingqing Ye,Peixin Gong,Bo Xiao,Bo Jiang
Compared with traditional conjugates 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide (EDC) and N-hydroxysuccinimide (NHS), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) is an emerging biological coupling reagent and has been used in the amidation of hyaluronic acid. In this paper, DMTMM was used to achieve the amidation of chitosan (CS) with glucuronic acid (GA) in an aqueous medium to generate a GA-CS derivative. The grafting efficacy was preliminarily compared with the EDC/NHS-mediated reaction. As a result, the substitution degree of 17.6% for DMTMM-mediated grafting and 13.1% for EDC/NHS chemistry indicated that DMTMM-mediated synthesis of GA-CS appeared to be more efficient. The reaction kinetics experiments showed that GA-CS derivative with a degree of substitution up to about 26.1% was obtained using equal molar ratios of DMTMM and GA exceeding CS at room temperature. These results indicate that employing DMTMM as a coupling agent is a feasible and promising strategy for the amidation modification of chitosan.
研究领域:
生物化学
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材料科学
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DOI
高影响因子
LANGMUIR
·
2011
·
IF 4.269
Cuie Wang,Qin Yan,Hong-Bo Liu,Xiao-Hui Zhou,Shou-Jun Xiao
Infrared spectroscopy was applied to investigate the well-known EDC/NHS (N-ethyl-N′-(3-(dimethylamino)propyl)carbodiimide/N-hydroxysuccinimide) activation details of poly(acrylic acid) (PAA) and poly(methacrylic acid) (PMAA) brushes grafted on porous silicon. Succinimidyl ester (NHS-ester) is generally believed to be the dominant intermediate product, conveniently used to immobilize biomolecules containing free primary amino groups via amide linkage. To our surprise, the infrared spectral details revealed that the EDC/NHS activation of PMAA generated anhydride (estimated at around 76% yield and 70% composition), but not NHS-ester (around 5% yield and 11% composition) under the well-documented reaction conditions, as the predominant intermediate product. In contrast, EDC/NHS activation of PAA still follows the general rule, i.e., the expected NHS-ester is the dominant intermediate product (around 45% yield and 57% composition), anhydride the side product (40% yield and 28% composition), under the optimum reaction conditions. The following amidation on PAA-based NHS-esters with a model amine-containing compound, l-leucine methyl ester, generated approximately 70% amides and 30% carboxylates. In contrast, amidation of PAA- or PMAA-based anhydrides with l-leucine methyl ester only produced less than 30% amides but more than 70% carboxylates. The above reaction yields and percentage compositions were estimated by fitting the carbonyl stretching region with 5 possible species, NHS-ester, anhydride, N-acylurea, unreacted acid, unhydrolyzed tert-butyl ester, and using the Beer–Lambert law. The different surface chemistry mechanisms will bring significant effects on the performance of surface chemistry-derived devices such as biochips, biosensors, and biomaterials.
研究领域:
表面化学
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高分子化学
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生物偶联
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材料科学
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生物传感器
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高影响因子
CHINESE JOURNAL OF ANALYTICAL CHEMISTRY
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2017
·
IF 0.795
Qiang ZHANG,Rui-Xue LI,Xin CHEN,Xing-Xing HE,Ai-Ling HAN,Guo-Zhen FANG,Ji-Feng LIU,Shuo WANG
Fluorescence spectroscopy was used to investigate the efficiency of coupling peptides to gold nanoparticles via 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride- N -hydroxysuccinimide (EDC-NHS). In this study, the effects of experiment conditions including the buffer solution (PBS, HEPES, Tris-HCl, and borate buffer solution), pH (6.5–9.0) and concentrations of buffer solution (10, 25, 40 and 50 mM), concentrations of NHS and EDC (from 0.2 M NHS-0.01 M EDC to 1.0 M NHS-0.5 M EDC), ratios of NHS to EDC (0, 0.5, 1.0, 2.0 and 2.5), and the coupling reaction time (4, 8, 12, 24 and 36 h) on the coupling efficiency were investigated and the optimized conditions were developed. These results indicated that the optimal experimental conditions were: pH 7.0 and 25 mM of the HEPES buffer solution, the concentrations ratios of NHS to EDC of 2:1 (0.4 M NHS-0.2 M EDC), and coupling reaction time of 24 h.
研究领域:
生物化学
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纳米生物学
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高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
·
IF 8.5
Zelin Liao,Hui Yu,Gaohong He,Xuehua Ruan,Hailong Li,Jinhui Dou,Xiujuan Zhang
Blood-contacting membranes require hydrophobicity to prevent leakage but suffer from poor hemocompatibility. Hydrophilic modification represents a key strategy to address this limitation. Herein, hydrophilic carboxymethyl-chitosan (CMCS) modification onto polyethersulfone (PES) membrane (CMCS-PES) was achieved via thermal-crosslinking and amidation reaction, followed by characterization through SEM, AFM, FTIR, XPS, BET, as well as water contact angle measurements, and systematic evaluation for its performance in hemocompatibility, antibacterial activity, long-term stability, and gas permeation. Compared with unmodified PES membranes, CMCS-PES membrane showed excellent hydrophilicity with surface water contact angle reduced from 84.3° to 30.9°, displayed improved hemocompatibility with bovine serum albumin adsorption decreased from 57.76 to 31.32 μg/cm 2 , bovine γ-globulin from 47.26 to 27.45 μg/cm 2 , hemolysis rate reduced from 0.9 % to 0.3 %, prolonged activated partial thromboplastin time by 12.4 s, lower blood fibrinogen level by 20 %, and exhibited good antibacterial activity with inhibition on E. coli growth by 28.9 % and S. aureus by 42.76%. Moreover, the CMCS-PES membrane still presents competitive gas permeation in comparison to other membranes investigated under similar conditions, and demonstrated excellent long-term stability in preventing blood leakage and platelet adhesion. This research provides an effective modification strategy for hemocompatibility improvement on blood-contacting membranes.
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PubMed
高影响因子
MICROCHEMICAL JOURNAL
·
2025
·
IF 5.1
Jingyi Guo,Xi Cheng,Huiyan Cao,Youping Deng,Fang Wang
N6-methyladenosine (m6A) is the most prevalent epigenetic RNA modification in eukaryotes, playing critical roles in RNA metabolism and disease progression. Current detection methods for m6A, such as mass spectrometry and antibody-based assays, face limitations in sensitivity, cost, or complexity. Electrochemical biosensors offer a promising alternative but struggle with nonspecific binding and low signal-to-noise ratios. This work addresses these challenges by developing a highly sensitive and selective electrochemical sensor for m6A quantification in complex biological samples. We designed a laser-induced graphene electrode (AuNPs/LIG) functionalized with gold nanoparticles and 11-mercaptoundecanoic acid (MUA) to immobilize anti-m6A antibodies via Protein A (PrA)-directed coupling. The sensor exploited steric hindrance and electrostatic repulsion from m6A-bound RNA to suppress electron transfer of the Fe[(CN) 6 ] 3− redox probe, yielding a current response proportional to m6A concentration. The assay achieved a linear range of 0.001–10 nM with a detection limit of 0.284 pM, surpassing our previous work by a large margin in terms of sensitivity. Validation in HeLa cell RNA and undiluted human serum confirmed high accuracy and minimal interference from nonspecific RNA. This method of m6A detection offers unparalleled advantages in sensitivity, real-time quantification, and cost-effective miniaturization, while future advancements in material science and multiplexed detection integration could revolutionize its clinical translation for point-of-care diagnostics in m6A-related diseases, such as cancer and metabolic disorders.
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高影响因子
Materials Today Chemistry
·
2026
·
IF 7.4
Congyi Mao,Hock Eng Khoo,Di Huang,Xiuwen Li,Caiying Li,Xiaobo Chen,Fang Liu,Xia Li
Valorization of sugarcane bagasse xylan, an agricultural byproduct, for sustainable material design. • CXY–CS hydrogel fabricated via EDC/NHS-mediated covalent crosslinking between carboxymethyl xylan and chitosan. • The polysaccharide-based hydrogel effectively adsorbs three heavy metal ions: Cr(VI), Cu(II), and Zn(II). • A unique reduction-coordination mechanism is revealed for Cr(VI) removal, distinguishing it from typical cation adsorption. The development of high-performance adsorbents from agricultural waste is hindered by the limited solubility and the absence of functional groups in native polymers. To address these challenges, this study fabricated a novel hydrogel by crosslinking carboxymethylated xylan (CXY) with chitosan (CS) via an environmentally benign amidation reaction. A series of systematic batch adsorption experiments was performed at low concentrations (0–20 mg L −1 ) to investigate the adsorption kinetics and thermodynamics. A series of high-concentration tests (500 mg L −1 ) was conducted to ascertain the maximum adsorption capacities and cyclic regeneration performance for Cu 2+ , Zn 2+ , and Cr(VI). The underlying mechanism was elucidated through X-ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations. The adsorption process exhibited conformance with the pseudo-second-order kinetic model and Langmuir isotherm, thereby indicating monolayer chemisorption. The thermodynamic parameters confirmed the spontaneity and exothermic nature of the process. In conditions of high concentration (500 mg L −1 ), the hydrogel exhibited noteworthy maximum adsorption capacities (Q max ) of 129.23, 123.24, and 126.19 mg g −1 for Cu 2+ , Zn 2+ , and Cr(VI), respectively, demonstrating over 85% adsorption efficiency following five regeneration cycles. Mechanistic analysis revealed a synergistic “reduction-coordination” pathway, while the highly toxic Cr(VI) undergoes unique surface reduction to less hazardous Cr(III). The integration of experimental and theoretical approaches in this study provides a systematic clarification of the adsorption performance and the dual-function “reduction-coordination” mechanism of the hydrogel toward multiple heavy metals. The study provides a robust scientific foundation for the development of sustainable, waste-derived materials for the remediation of complex heavy metal pollution. Download: Download high-res image (317KB) Download: Download full-size image
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高影响因子
JOURNAL OF MEMBRANE SCIENCE
·
2024
·
IF 8.4
Shichen Zeng,Xu Liang,Mingang Zhao,Yanxiong Ren,Hanze Ma,Ziting Zhu,Yuhan Wang,Shaoyu Wang,Junyi Zhao,Guangzhaoyao Yang,Xuerui Wang,Fusheng Pan,Guangwei He,Zhongyi Jiang
Covalent organic frameworks (COF) are deemed as disruptive membrane materials owing to their versatile functionalities, high stability and ordered nanochannels. However, the size mismatch between the COF intrinsic pore and gas molecules becomes a grand challenge when using COF membrane for carbon capture. Herein, we propose a new type of polymer-functionalized COF laminar membranes through grafting CO 2 -phlic polyethyleneimine (PEI) polymer onto carboxylic acid COF (cCOF) laminar membranes. The cCOF nanosheets with high density of carboxyl groups are prepared via modified single phase solution method and then assembled to fabricate membranes. Further, the cCOF membranes are functionalized with PEI using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide/N-Hydroxysuccinimide (EDC/NHS) coupling chemistry. The introduction of abundant amino groups from PEI afford the affinity of membranes toward CO 2 . Meanwhile, the graft of the PEI polymers reduces the defects or pinholes on the membrane surface. As a result, the PEI functionalized cCOF membranes exhibit a high CO 2 permeance of 1004 GPU and a CO 2 /N 2 selectivity of 33.7, which reach the carbon capture target performance and show great prospect for treating real flue gas. Our approach of functionalizing cCOF membranes with tailored functionalities may inspire the design of molecule-selective COF membranes.
研究领域:
材料科学
·
环境科学
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高影响因子
JOURNAL OF FOOD BIOCHEMISTRY
·
2017
·Vol. 41
·期 5
·e12395
·
IF 1
Shuai Cui,Qin-Wei Zhou,Xiao-Ling Wang,Si-Qi Yang,Kai Chen,Zhi-Yuan Dai,Yao-Wen Huang,Tao Zhou
Bovine pancreatic lipase was immobilized onto N -succinyl-chitosan beads by using N -(3-dimethylaminopropyl)- N ′-ethylcarbodiimide (EDC)/ N -hydroxysuccinimide (NHS) as the activating agent. The immobilized lipase was characterized by Fourier transform infrared spectra and scanning electron microscopy. The activity of the immobilized lipase obtained under the optimized immobilization conditions was found to reach 1,480 U/g, with enzyme activity recovery of 74.5%. Compared to the free lipase, thermal stability of the immobilized lipase was greatly improved. The reusability study indicated that the immobilized lipase retained 76.6% of its initial activity after being recycled five times. A preliminary study indicated that the prepared immobilized lipase can effectively enrich the polyunsaturated fatty acid in fish oil (increasing from 45.1 to 67.7%), of which the combined docosahexaenoic acid and eicosapentaenoic acid contents increased from 16.3 to 27.1%. Practical applications To overcome the drawbacks of using free lipase, an effective method was developed by immobilization of lipase onto N -succinyl-chitosan beads using EDC/NHS as the activating agent. The immobilized lipase prepared by this method may find application in the enrichment of polyunsaturated fatty acids of fish oil.
研究领域:
生物化学
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食品科学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2024
·
IF 7.7
Shengyu Li,Lihong Gong,Xijin Wu,Xianli Liu,Ningning Bai,Yingxue Guo,Xia Liu,Hong Zhang,Huiying Fu,Qiyang Shou
Currently, protein-based hydrogels are widely applied in soft materials, tissue engineering and implantable scaffolds owing to their excellent biocompatibility, and degradability. However, most protein-based hydrogels are soft brittle. In this study, a ductile and mechanically enhanced bovine serum albumin (BSA) hydrogel is fabricated by soaking the a 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride/N-hydroxysuccinimide (EDC/NHS) induced BSA hydrogel in (NH 4 ) 2 SO 4 solution. An EDC/NHS coupling reaction induce protein coupling reactions that cause the BSA skeleton to resemble architectural load-bearing walls, protecting the integrity of the hydrogel and preventing collapse. The effects of the BSA and (NH 4 ) 2 SO 4 concentrations on the hydrogel mechanics are evaluated, and the possible strengthening mechanism is discussed. Besides, the highly kosmotropic ions greatly enhance the hydrophobic interaction within BSA gels and dehydration effect and their mechanical properties were significantly enhanced. The various mechanical properties of hydrogels can be regulated over a large window by soaking hydrogels into various ions. And most of them can be washed away, maintaining high biocompatibility of the protein. Importantly, the protein hydrogels prepared by this strategy could also be modified as strain sensors. In a word, this work demonstrates a new, universal method to provide multi-functional, biocompatible, strength enhanced and regulable mechanical pure protein hydrogel, combining the Hofmeister effect with -NH 2 /-COOH association groups.
研究领域:
生物材料学
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组织工程学
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DOI
PubMed
高影响因子
Foods
·
2026
·Vol. 15
·期 12
·2117
·
IF 6
Jiarun Gao,Le Yu,Xiang Wan,Leilei Sun,Wenkui Song
Ready-to-eat sea cucumbers (RSC) cannot be preserved at room temperature due to autolysis, which is closely related to the instability of collagen resulting from the disruption of hydrogen bonds. To investigate the protective effect ofN-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide (EDC/NHS) cross-linking against disruption of hydrogen bonds and its role in stabilizing RSC quality at room temperature, this study designed comparative experiments involving EDC/NHS cross-linking treatments with varying sequences of hydrogen bonds disruption. The results indicated that EDC/NHS positively affects the stabilization of the collagen structure in RSC. The various quality parameters of both groups of RSC that underwent cross-linking treatment before and after hydrogen bonds disruption were significantly better than those of the control group, which only experienced the breaking of hydrogen bonds. Notably, the Eb group, which underwent EDC/NHS cross-linking treatment prior to the disruption of the hydrogen bonds network, yielded even more favorable results. Preliminary analyses of textural properties and moisture content suggested that EDC/NHS helps delay the deterioration of RSC quality. The levels of soluble components and carbonyl groups indicated that prior cross-linking treatment is more effective in mitigating collagen degradation and oxidation. Differential scanning calorimetry revealed that the reduction in ΔH for the Eb group was only 2.4%. Furthermore, fluorescence spectroscopy, Fourier transform infrared spectroscopy, and circular dichroism spectroscopy, examined from the perspectives of secondary and tertiary structures respectively, indicated that the cross-linking mechanism of EDC/NHS involves the formation of a more robust network of amide bonds, thereby preventing the disruption of hydrogen bonds and enhancing collagen stability, enabling it to better resist the cleavage of hydrogen bonds due to urea. The scanning electron microscope and Van Gieson’s staining techniques offer a clearer illustration of this point from a microscopic perspective. Moreover, molecular docking simulations have indicated the cross-linking mechanism of EDC/NHS at the atomic level, thereby establishing a scientific foundation for the potential application and development of EDC/NHS in room-temperature storage technologies for RSC.
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PubMed
高影响因子
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