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
Sensors & Diagnostics
·
2025
·
IF 4.1
Teody Gumabat,Jeanne Phyre Lagare Oracion,Jolina Fedelis,Ethel Keleste,Rey Capangpangan,Noel Lito Sayson,Gerard Dumancas,Arnold Alguno,Felmer Latayada
Spermine, a key biogenic amine indicating food freshness, is typically detected using costly and time-consuming chromatographic methods. This study introduces a more efficient, eco-friendly alternative—a label-free colorimetric sensing platform using gold nanoparticles (AuNPs) functionalized with 11-mercaptoundecanoic acid and capped with an N-hydroxysuccinimide (NHS)-ester. Transmission electron microscopy revealed monodisperse, spherical AuNPs (13 nm), with an increase in size upon functionalization. Fourier transform infrared spectra confirmed successful functionalization. The hydrodynamic size of the AuNPs increased from 17.26 nm to 2167 nm, and the zeta potential shifted from −48.86 mV to −35.59 mV. The platform takes advantage of the selective interaction between spermine and NHS-ester-functionalized AuNPs, inducing nanoparticle aggregation, as shown by a red shift in surface plasmon resonance (SPR). UV-vis spectroscopy demonstrated a robust linear correlation (R2 = 0.958) between spermine concentration (1.0–4.0 μM) and nanoparticle aggregation index, with a limit of detection (LOD) of 0.77 μM. The sensor also exhibited high reproducibility in pork extract matrices (coefficient of variation <5%) and selectivity for spermine amid various interfering analytes. Its eco-friendly design and rapid response time position it as a viable tool for real-time spermine monitoring in food spoilage, offering comparable performance metrics to traditional chromatographic techniques while addressing sustainability concerns.
研究领域:
生物化学
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食品安全
·
分析化学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2017
·
IF 3.671
Junhui Yang,Cuicui Ding,Liulian Huang,Min Zhang,Lihui Chen
γ-PGA-NHS ester, which was prepared using poly(γ-glutamic acid) (γ-PGA) and N-hydroxysuccinimide (NHS) as the raw materials, was synthesized to be a novel cross-linker of collagen. Fourier transform infrared spectra analysis suggested that the products displayed the characteristic absorption peak of ester. Results from nuclear magnetic resonance analysis indicated that the esterification degree of γ-PGA-NHS ester was increased with the increase of NHS. Modified collagen was prepared and characterized. The results of circular dichroism analysis indicated modified collagen retained the triple helix structure of natural collagen. Sodium dodecyl sulphate polyacrylamide gel electrophoresis revealed that the molecular weight of collagen was increased after cross-linking. Peptide mapping of collagen suggested that cross-linked collagen possessed an enhanced resistance to trypsin degradation. Differential scanning calorimeter results showed that the denaturation temperature of collagen was improved from 68.1 ± 0.4 to 91.2 ± 0.5 °C (p < 0.05). Dynamic viscoelastic measurements demonstrated the improvement of thermal stability and reflected the exponential increase in η*. The cross-linked collagen retained porous structure and the pore size became larger as observed by scanning electron microscopy. The investigation results provided useful information to produce collagen with improved physicochemical properties, particularly the thermal stability via the use of γ-PGA-NHS ester as a biomacromolecule-based cross-linker.
研究领域:
生物化学
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材料科学
·
医学工程
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DOI
PubMed
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
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化学工程
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DOI
PubMed
高影响因子
Sustainable Chemistry and Pharmacy
·
2025
·
IF 5.8
Lili Long,Zhenkun Wang,Yuelong Liu,Wei Liu
Biobased cyclic carbonates can be produced by renewable bio-epoxides with CO 2 through a cycloaddition reaction. The reaction has gradually gained attention due to its green, sustainable, and widespread application of cyclic carbonates. However, the primary challenge in synthesizing bio-cyclic carbonates is the recovery and effective utilization of catalysts. In this work, the recovery and reuse of homogeneous catalysts have been achieved successfully. Cetyltrimethylammonium bromide (CTAB) combined with N-hydroxysuccinimide (NHS) (1:1) were used as co-catalyst to synthesize bio-cyclic carbonates from epoxidized soybean oil fatty acid methyl esters. 93.7% yield for cyclic carbonates product was achieved at 120 °C with 15 bar CO 2 pressure for 14 h without any solvents. The most importance is that the homogeneous catalyst can be successfully reused for consecutive four times. Through kinetic experiments, it was found that the addition of NHS reduced the activation energy of the reaction by 12.94 kJ/mol. In addition, a reasonable reaction mechanism was proposed. This work paves the way about a recyclable catalyst system for synthesis of bio-cyclic carbonates.
研究领域:
化学工程
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绿色化学
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催化化学
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DOI
高影响因子
ACS Biomaterials Science & Engineering
·
2023
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IF 5.8
Jun Ma,Cuixia Wen,Meng Chen,Wei Zhang,Lifeng Wang,Haitao Yin
This study fabricates a nanoparticle delivery system of gold nanoparticles–dextran nanoparticles loaded with hypoxia-activated paclitaxel dimeric prodrug nanoparticles (PTX2-NP) and photosensitizer chlorin e6/paclitaxel-nanoparticle/gold@N-(2-hydroxypropyl) (Ce6/PTX2-NP/G@NHs) and analyzed the possible molecular mechanism for enhancing the radiosensitivity of non-small cell lung cancer (NSCLC). Ce6/PTX2-NP/G@NHs were prepared by a coupling reaction and dextran inclusion, followed by characterization using spectroscopy techniques. The cellular uptake and cytotoxicity of Ce6/PTX2-NP/G@NHs were analyzed. Radiosensitizing effects of the nanoparticles were evaluated by determining the malignant phenotypes and reactive oxygen species production of A549 cells and PI3K/AKT pathway-related proteins under 685 nm laser irradiation. A549 tumor-bearing nude mice were modeled to further confirm the radiosensitizing effect. Ce6/PTX2-NP/G@NHs were effectively internalized by A549 cells, producing cytotoxicity under laser irradiation. Ce6/PTX2-NP/G@NHs reduced cell viability, clonogenic potential, migration, and invasion along with reactive oxygen species (ROS) production while promoting apoptosis in A549 cells under laser irradiation. By inhibiting the PI3K/AKT pathway, Ce6/PTX2-NP/G@NHs increased the sensitivity of A549 cells to radiotherapy where apoptotic body (ApoBD)-mediated neighboring effects also played a key role. Ce6/PTX2-NP/G@NHs accumulated in tumor sites of nude mice and enhanced the radiosensitivity of NSCLC. Ce6/PTX2-NP/G@NHs showed no obvious toxicity or side effects in vivo. Collectively, the new Ce6/PTX2-NP/G@NHs nanoparticle delivery system can enhance the radiosensitivity of NSCLC via the promotion of ApoBD-mediated neighboring effects and inactivation of the PI3K/AKT pathway.
研究领域:
肿瘤学
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药学
·
纳米技术
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分子生物学
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放射生物学
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DOI
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
CHINESE JOURNAL OF ANALYTICAL CHEMISTRY
·
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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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
·
生物传感器
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DOI
高影响因子
Materials Today Bio
·
2024
·
IF 8.7
Hanjie Shao,Junjie Deng,Zeping Xu,Jiujun Zhu,Wei Jian,Peiru Zhang,Xinhua Zhou,Xie Zhang,Hao She,Jingyun Ma,Xiang Wu,Hong Li
Hydrogels have indeed achieved significant advancements, yet their clinical translation has been hampered by their inherent limitations in wet adhesion properties. Furthermore, the design of adhesive hydrogels that can resist postoperative adhesions remains an intricate challenge. In this study, we introduce a Janus hydrogel (JGP) that offers a novel approach to address these challenges. The JGP hydrogel has two asymmetrical sides, consisting of an adhesion layer (AL) and an anti-adhesion layer (AAL). Specifically, the AL incorporates three key components: N-[tris(hydroxymethyl)methyl]acrylamide (THMA), acrylic acid (AAc), and the acrylic acid N-hydroxysuccinimide ester (AAc-NHS). By drying the AL, it has a rapid water absorption capability. The abundance of hydroxyl and carboxyl groups in the AL enables the formation of robust hydrogen bonds with tissues, thereby achieving superior adhesive properties. Additionally, the synergistic effect of THMA's tridentate hydrogen bonding and the covalent bonding formed by AAc-NHS with tissue ensures long-lasting wet adhesion. To realize the anti-adhesion function, one side of the AL was immersed in a solution of [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide (SBMA), which undergoes crosslinking to form the AAL. A comprehensive series of tests have confirmed that the JGP hydrogel exhibits exceptional mechanical properties, efficient and enduring adhesion, excellent biocompatibility, and degradability. Moreover, it possesses remarkable hemostatic properties and robust anti-abdominal adhesion characteristics.
研究领域:
生物材料学
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医学工程
·
组织工程
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DOI
PubMed
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
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