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JOURNAL OF BIOMATERIALS APPLICATIONS · 2014 · IF 2.764

Using glucosamine to improve the properties of photocrosslinked gelatin scaffolds

Hairui Suo,Kedi Xu,Xiaoxiang Zheng

The use of hydrogel-based cell transport scaffolds holds great promise in regenerative medicine, such as treating osteoarthritis. Gelatin and glucosamine are the ideal materials to be used in the hydrogel scaffolds for cartilage regeneration for they could act as compositions of cartilage. To overcome the weak strength of traditional gelatin hydrogels and down-regulate cell toxicity of glucosamine, gelatin and glucosamine molecules were grafted with acrylate groups and covalently crosslinked under photo-radiation to form hydrogels. Hydrogels with tuning physiochemical properties were produced according to different proportions of methacrylate gelatin (GelMA) and N-acryloyl glucosamine (AGA). The process of photocrosslinking was elaborated, and the hypothesis of increasing AGA concentration leading to higher strength of hydrogels was corroborated by testing rheological property and scanning micro-morphological features. A serial of properties, including smaller swelling ratio, lower gelatin dissolution and slower degradation of GelMA/AGA hydrogels with higher AGA concentration further proved our hypothesis. Moreover, AGA molecules showed less cytotoxicity than unmodified glucosamine molecules and the incorporation of AGA molecules in GelMA/AGA hydrogels upregulated cell adhesion and spreading on the hydrogel surface. All of these results indicated that addition of AGA molecules could significantly alter the physiochemical properties of GelMA/AGA hydrogels, which may have broad application prospects in the future.

研究领域: 生物材料学 · 再生医学
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INTERNATIONAL JOURNAL OF DAIRY TECHNOLOGY · 2015 ·Vol. 69 ·期 2 ·169-176 · IF 0.943

Impacts of glucosamine/oligochitosan glycation and cross-linking by transglutaminase on the structure and in vitro antigenicity of whey proteins

Ying-Hua Zhang,Jia-Qi Liu,Di Xu,Xin-Huai Zhao

With the fixed and selected conditions, whey protein concentrate (WPC) was glucosamine-/oligochitosan-glycated and cross-linked by transglutaminase, resulting in glucosamine conjugation of 4.18–5.88 g/kg. Electrophoretic analysis showed cross-linking and glycation of whey proteins, while circular dichroism analysis indicated that the two reactions contributed less ordered secondary structure to the two products. Enzyme-linked immunosorbent assay results showed that the two products lost 64–95% antigenic responses of WPC, and oligochitosan was more powerful than glucosamine to reduce the responses. Rocket immuno-electrophoretic analysis also evidenced antigenicity loss. This applied treatment is efficient to modify the structure and to decrease the allergenicity of whey proteins.

CAS / MDL: 107-96-0 3416-24-8
研究领域: 食品科学 · 免疫学
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BIOMACROMOLECULES · 2017 · IF 5.246

“Bitter-Sweet” Polymeric Micelles Formed by Block Copolymers from Glucosamine and Cholic Acid

Kun Zhang,Yong-Guang Jia,I-Huang Tsai,Satu Strandman,Li Ren,Liangzhi Hong,Guangzhao Zhang,Ying Guan,Yongjun Zhang,X. X. Zhu

Natural compounds glucosamine and cholic acid have been used to make acrylic monomers which are subsequently used to prepare amphiphilic block copolymers by reversible addition–fragmentation chain transfer (RAFT) polymerization. Despite the striking difference in polarity and solubility, three diblock copolymers consisting of glucosamine and cholic acid pendants with different hydrophilic and hydrophobic chain lengths have been synthesized without the use of protecting groups. They are shown to self-assemble into polymeric micelles with a “bitter” bile acid core and “sweet” sugar shell in aqueous solutions, as evidenced by dynamic light scattering and transmission electron microscopy. The critical micelle concentration varies with the hydrophobic/hydrophilic ratio, ranging from 0.62 to 1.31 mg/L. Longer chains of polymers induced the formation of larger micelles in range of 50–70 nm. These micelles can solubilize hydrophobic compounds such as Nile Red in aqueous solutions. Their loading capacity mainly depends upon the hydrophobic/hydrophilic ratio of the polymers, and may be also related to the length of the hydrophilic block. These polymeric micelles allowed for a 10-fold increase in the aqueous solubility of paclitaxel and showed no cytotoxicity below the concentration of 500 mg/L. Such properties make these polymeric micelles interesting reservoirs for hydrophobic molecules and drugs for biomedical applications.

研究领域: 材料科学 · 药学 · 生物医学工程
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2015 · IF 4.152

N-acetyl-d-glucosamine decorated polymeric nanoparticles for targeted delivery of doxorubicin: Synthesis, characterization and in vitro evaluation

Baocheng Tian,Yuanyuan Ding,Jian Han,Jing Zhang,Yuzhen Han,Jingtian Han

A novel targeting drug delivery system containing poly(styrene-alt-maleic anhydride) 58 -b-polystyrene 130 (P(St-alt-MA) 58 -b-PSt 130 ) as a copolymer backbone, N -acetyl glucosamine (NAG) as a targeting moiety was designed and synthesized. The NAG grafted copolymer (NAG-P(St-alt-MA) 58 -b-PSt 130 ) was characterized by FTIR and 1 H NMR. The NAG-P(St-alt-MA) 58 -b-PSt 130 nanoparticles exhibited spherical shapes with an average diameter about 56.27   ±   0.43   nm, low critical micelle concentration of 0.028   mg/mL, negative zeta potential −41.46   ±   0.99   mV, high drug loading 25.83   ±   1.09% and encapsulation efficiency 69.69   ±   3.98%. In vitro cell cytotoxicity was conducted to confirm the safety of the NAG-P(St-alt-MA) 58 -b-PSt 130 nanoparticles. Confocal laser scanning microscopy (CLSM) and flow cytometry (FCM) results showed that the NAG targeting moiety enhanced the internalization and targeting ability of NAG-P(St-alt-MA) 58 -b-PSt 130 nanoparticles. Anticancer activity toward MCF-7 cells and HT29 cells showed that DOX-loaded NAG-P(St-alt-MA) 58 -b-PSt 130 nanoparticles exhibited a higher antitumor activity compared to DOX-loaded P(St-alt-MA) 58 -b-PSt 130 nanoparticles, which could attribute to NAG receptor-mediated endocytosis. These results suggest that the biocompatible and non-toxic NAG-P(St-alt-MA) 58 -b-PSt 130 nanoparticles may be used as an effective targeting drug delivery system for cancer therapy.

CAS / MDL: 25316-40-9 7512-17-6
研究领域: 药剂学 · 肿瘤学 · 生物材料
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Amino Acid Ionic Liquids Catalyzed d-Glucosamine into Pyrazine Derivatives: Insight from NMR Spectroscopy

Pengfei Liu,Jiaojiao Zhang,Yan Qiao,Xianglin Hou,Yu Liu,Yingxiong Wang

Using environment-friendly catalysts to convert biomass into compounds with high values is one of the central topics of green chemistry. In this work, [Ch][Pro] (cholinium as the cation and l-proline as the anion) ionic liquid was synthesized and applied as a model catalyst in the production of deoxyfructosazine (DOF) and fructosazine (FZ) from d-glucosamine (GlcNH2). The 13C NMR chemical shift titration experiments and the diffusion-ordered NMR spectroscopy (DOSY) measurements showed that, when the [Ch][Pro] interacted with GlcNH2, the l-proline anion ([Pro]−) played a major catalytic role instead of cholinium cation ([Ch]+). The effects of the reaction temperature and the amount of [Ch][Pro] on the product yields were surveyed. The experimental results showed that the highest DOF yield (33.78%) was obtained after 30 min at 100 °C when the molar ratio of [Ch][Pro]/GlcNH2 was 1. Moreover, in situ1H NMR and in situ13C NMR experiments were applied to monitor the reaction process with [Ch][Pro] as the catalyst. The reactive intermediate, dihydrofructosazine, was clearly detected by these in situ techniques. Accordingly, a possible reaction pathway was proposed. By applying other amino acids as the anions, we also prepared five other [Ch][AA] ionic liquids, and they showed different catalytic activities and selectivity in the GlcNH2 self-condensation reaction.

研究领域: 绿色化学 · 催化化学 · 生物质转化
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Efficient separation of boron from salt lake brine using a novel flotation agent synthesized from NMDG and 1-bromooctadecane

Chun Bai,Kexin Li,Dezhen Fang,Xiushen Ye,Huifang Zhang,Quan Li,Jun Li,Haining Liu,Zhijian Wu

A novel flotation agent named N-octadecyl-N-methyl- D -glucamine (NO-NMDG), was designed and prepared using N-methyl- D -glucamine as a polyhydroxy molecule and 1-bromooctadecane as the provider of a long-chain alkyl group . The results of characterization by NMR, MS and FT-IR showed that the target compound was successfully synthesized. NO-NMDG can effectively separate boron from aqueous solutions because of its complexing ability for boron and its foamability. The flotation experiments results showed that the flotation isotherm was in better accordance with the Langmuir model, indicating that the surface reaction in flotation by NO-NMDG belongs to the single molecular layer trapping. The response surface experimental results indicated that under the optimum conditions, the boron recovery rate can reach to 89.12%. The boron recovery rate in Xiao Chaidan brine could reach to 97.26% by NO-NMDG. The mechanism analysis exhibited that the meglumine group in NO-NMDG can complex with boron, and the long-chain alkyl group can attach to the surface of the bubble and enter into the bubble layer to separate boron from the aqueous solution.

CAS / MDL: 112-89-0 6284-40-8
研究领域: 化学工程 · 环境科学
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ACS Sustainable Chemistry & Engineering · 2018 · IF 6.14

Deep Eutectic Solvents: Green Solvents and Catalysts for the Preparation of Pyrazine Derivatives by Self-Condensation of d-Glucosamine

Mengjie Wu,Hui Ma,Zhongyi Ma,Yufang Jin,Chunyan Chen,Xiaoya Guo,Yan Qiao,Christian Marcus Pedersen,Xianglin Hou,Yingxiong Wang

Deep eutectic solvents (DESs) exhibit similar physicochemical properties to the ionic liquids. They are inexpensive, renewable, nontoxic, and environmentally benign solvents and have gradually attracted attention in several fields, for example, biorefinery. Here choline chloride-based DESs have been used as solvents and catalysts for the preparation of deoxyfructosazine (DOF) through a self-condensation reaction of d-glucosamine (GlcNH2). The catalytic performances of a “green cocatalyst”, amino acids, and the reaction mechanism were also studied. The results displayed that choline chloride/urea was capable to convert GlcNH2 efficiently, with a 13.5% yield of DOF at low temperature and with a short reaction time (100 °C, 150 min). Among the screened amino acids, arginine showed the highest activity and gave the highest yield of DOF (30.1%) under the optimized reaction conditions. Nuclear magnetic resonance (NMR) studies revealed a strong hydrogen bond interaction between GlcNH2 and arginine. Moreover, a detectable intermediate, namely dihydrofructosazine, in the condensation of GlcNH2 to DOF/fructosazine (FZ) was captured by in situ NMR technique.

研究领域: 有机化学 · 绿色化学
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JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES · 2025 · IF 2.8

Chiral separation of fluoroquinolones by capillary electrophoresis using glucosamine-functionalized carbon quantum dots as a Pseudostationary phase

Guoli Wu,Chen Li,Yue Zhang,Tingli Qu

Fluoroquinolones are a class of widely used antibiotics, most of which contain chiral centers. Significant differences exist between their enantiomers in terms of antimicrobial activity, pharmacokinetics, and toxicity. In this study, glucosamine chiral-functionalized carbon quantum dots (GA-CQDs) were successfully synthesized and employed as a pseudostationary phase. By optimizing the chromatographic conditions, an efficient and novel chiral separation platform based on capillary electrophoresis (CE) was established for the enantioseparation of six fluoroquinolones. Compared to the CE system using free glucosamine solely as the chiral selector, the CE system employing GA-CQDs as a pseudostationary phase demonstrated a substantial improvement in chiral resolution (Rs) for all six model analytes (Ofloxacin: 1.56 → 9.21; Pazufloxacin: 0 → 8.53; Prulifloxacin: 1.38 → 7.58; Lomefloxacin: 1.01 → 2.84; Gemifloxacin: 0 → 1.25; Balofloxacin: 0 → 0.88). The incorporation of the pseudostationary phase significantly enhanced the chiral separation capability. This proposed strategy is characterized by its operational simplicity and low cost, thereby offering a valuable conceptual framework and a highly promising approach for developing chiral separation methods for fluoroquinolone antibiotics. This study represents the first report on employing GA-CQDs as a chiral selective medium to construct a capillary electrophoresis system, which achieved satisfactory enantioselectivity. Furthermore, the chiral recognition mechanism of glucosamine was preliminarily investigated through molecular modeling simulations, with the binding energy providing insights into the separation process.

CAS / MDL: 2432-99-7 6066-82-6
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JOURNAL OF MEMBRANE SCIENCE · 2024 · IF 8.4

Structure design and performance optimization of PVDF-CTFE nanofibrous composite nanofiltration membrane modified by C–Cl active site grafting

Wanzheng Ren,Jian Pan,Zhuoqun Li,Min Huang,Lilan Huang,Liqiang Gu,Hailin Cong

The substrate membrane plays a crucial role in determining the performance of composite nanofiltration membranes prepared by interfacial polymerization (IP). In this study, persistent hydrophilic modification of polyvinylidene fluoride-co-chlorotrifluoroethylene (PVDF-CTFE) was achieved by incorporating N-methylglucamine (N-MG) without altering the membrane's morphology or pore size. Moreover, thin-film nanofibrous composite (TFNC) nanofiltration membranes were prepared using the surfactant assembly regulated interfacial polymerization (SARIP) method with the modified PVDF-CTFE@N-MG nanofibrous membrane as the substrate. The effect of N-MG addition on the substrate membrane's hydrophilicity and the structure and performance of the polyamide (PA) separation layer was investigated. The results showed that the addition of N-MG significantly improved the hydrophilicity of the PVDF-CTFE nanofibrous membrane. The TFNC-5 membrane, prepared with the modified PVDF-CTFE@N-MG nanofibrous membrane as the substrate, exhibited permeability exceeding 13.5 L m −2  h −1 ·bar −1 for various dye solutions at 3 bar pressure, with rejection rates above 98 %. It also demonstrated excellent selective separation performance (separation factor for NaCl/Orange G reaching 97.38) and long-term operational stability. This work provides a method for the preparation of low-pressure, high-flux nanofiltration membranes, which is applicable to seawater desalination and dye wastewater treatment .

研究领域: 材料科学 · 环境工程
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ADVANCED FUNCTIONAL MATERIALS · 2025 · IF 19

Fe3O4@PDA Nanoparticle-Doped Smart Hydrogel Scaffold for Osteochondral Defect Repair by Synergistical Stimulation

Tiantian Chen,Zhihan Zhang,Xiaohu Zhou,Zhiyue Zhang,Jun Liu,Qirui Gong,Tengda Ma,Abulimiti Dilihumaer,Yuhang Zhan,Zhizhong Xie,Lihong Fan,Yue Zhang,Shengxiang Tao,Yingying Chu

Osteochondral defects are common orthopedic conditions that can lead to osteoarthritis and severe joint pain. Recently, smart biohydrogels have been widely applied in osteochondral repair and regeneration, owing to their 3D structural resemblance to osteochondral tissues and their remarkable responsiveness to external stimuli. Glucosamine hydrochloride (GH) has been proved to stimulate the proliferation and chondrogenic differentiation of bone mesenchymal stem cells (BMSC), thereby accelerating wound healing and tissue regeneration. Herein, double-crosslinked smart hydrogels SPA 5 -Mg/GH/FP are fabricated using sodium alginate, acrylamide and N-Isopropylacrylamide (NIPAM) as the substrates. Simultaneously, the incorporation of Mg 2+ and Polydopamine (PDA)-coated Fe 3 O 4 NPs into the system further enhanced its properties. The results emphasized the favorable microenvironment created by the 3D architecture of the hydrogel, which effectively facilitated tissue repair and regeneration of the defects. Notably, the controlled release of GH aligned with the repair process is achieved through the responsiveness of Fe 3 O 4 @PDA NPs to near-infrared light. Moreover, in vivo assessments have demonstrated the effectiveness of the smart hydrogel in repairing osteochondral defects, highlighting its structural similarities to native tissue. This promising outcome underscores the potential of SPA 5 -Mg/GH/FP as a sophisticated solution for addressing the challenges associated with osteochondral repair.

研究领域: 生物材料学 · 再生医学 · 骨科
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TALANTA · 2015 · IF 3.545

Parallel microscope-based fluorescence, absorbance and time-of-flight mass spectrometry detection for high performance liquid chromatography and determination of glucosamine in urine

Bo Xiong,Ling-Ling Wang,Qiong Li,Yu-Ting Nie,Shuang-Shuang Cheng,Hui Zhang,Ren-Qiang Sun,Yu-Jiao Wang,Hong-Bin Zhou

A parallel microscope-based laser-induced fluorescence (LIF), ultraviolet–visible absorbance (UV) and time-of-flight mass spectrometry (TOF-MS) detection for high performance liquid chromatography (HPLC) was achieved and used to determine glucosamine in urines. First, a reliable and convenient LIF detection was developed based on an inverted microscope and corresponding modulations. Parallel HPLC-LIF/UV/TOF-MS detection was developed by the combination of preceding Microscope-based LIF detection and HPLC coupled with UV and TOF-MS. The proposed setup, due to its parallel scheme, was free of the influence from photo bleaching in LIF detection. Rhodamine B , glutamic acid and glucosamine have been determined to evaluate its performance. Moreover, the proposed strategy was used to determine the glucosamine in urines, and subsequent results suggested that glucosamine, which was widely used in the prevention of the bone arthritis, was metabolized to urines within 4   h. Furthermore, its concentration in urines decreased to 5.4   mM at 12   h. Efficient glucosamine detection was achieved based on a sensitive quantification (LIF), a universal detection (UV) and structural characterizations (TOF-MS). This application indicated that the proposed strategy was sensitive, universal and versatile, and it was capable of improved analysis, especially for analytes with low concentrations in complex samples, compared with conventional HPLC-UV/TOF-MS.

CAS / MDL: 81-88-9
研究领域: 分析化学 · 医学检验 · 生物化学
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NEW JOURNAL OF CHEMISTRY · 2018 ·Vol. 42 ·期 14 ·11334-11340 · IF 3.201

One-dimensional controllable crosslinked polymers grafted with N-methyl-D-glucamine for effective boron adsorption

Jingjing Kang,Yakun Tang,Shasha Gao,Lang Liu

In this research, a series of one-dimensional controllable crosslinked polymers with the different mass ratios of 4-vinylbenzychloride (VBC) and divinyl benzene (DVB) was prepared via cationic polymerization, and the polymers were grafted with the functional group N-methyl-D-glucamine (NMDG) for boron removal. The optimum polymeric mass ratio and a series of boron adsorption performances were studied. The maximum adsorption capacity was 18.15 mg g−1, of which 94% was retained after 4 cycles. Meanwhile, different pH values had negligible effect on the boron adsorption capacity, which was favorable for the removal of boron from its aqueous solution in a wide pH window. In addition, a magnetic adsorbent was prepared by the combination of Fe3O4 nanoparticles and the polymer, which provided an effective way to collect and recover adsorbents from their aqueous solutions.

CAS / MDL: 109-63-7 1321-74-0
研究领域: 材料科学 · 环境科学 · 化学工程
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