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glycolide
MOLECULES · 2024 ·Vol. 29 ·期 16 ·3759 · IF 4.2

Compositional Characterization of Syngas-Based Glycolide Using Gas Chromatogram-Mass Spectrometry and Electrospray Ionization High-Resolution Mass Spectrometry

Yachun Zhang,Junyang Chen,Jianhua He,Shuofan Li,Yuanfeng Wang,Yahe Zhang,Quan Shi

Polyglycolic acid (PGA) is a biologically friendly material with a wide range of applications. The production of dimethyl oxalate using coal-based syngas and the hydrogenation of dimethyl oxalate can produce the polymerization raw material of PGA, glycolide, which requires a methyl glycolate polymerization and depolymerization process. The intermediate products of the production process were analyzed using gas chromatogram-mass spectrometry (GC-MS) and Orbitrap mass spectrometry (Orbitrap MS), which revealed the presence of cyclic and linear PGAs with different capped ends. The impurities present in the oligomer were mostly methyl-capped PGA and were retained in the subsequent depolymerization process to glycolide, solvent washing can be used to remove this part of the impurity and ultimately obtain a refined glycolide product. Furthermore, it is proposed that the use of the specialized Kendrick Mass Defect (KMD) to plot and analyze PGA compounds obtained using mass spectrometry can enable the direct classification of PGAs without the need for exact molecular formula assignment.

CAS / MDL: 920-66-1
研究领域: 化学工程 · 材料科学 · 分析化学
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EUROPEAN POLYMER JOURNAL · 2018 · IF 3.741

Totally biodegradable poly(trimethylene carbonate/glycolide-block-L-lactide/glycolide) copolymers: synthesis, characterization and enzyme-catalyzed degradation behavior

Wu Xiaomeng,Chen Xiaoyu,Fan Zhongyong

The macroinitiator of poly(1,3-trimethylene carbonate- ran -glycolide) (P(TMC- ran -GA)) copolymers terminated with hydroxyl groups were synthesized by ring-opening polymerization (ROP) at 120 °C for 12 h. Then, the novel block copolymers consisting of P(TMC- ran -GA) segments bonding with L -lactide ( L LA) and glycolide (GA) random copolymerization segments were prepared. The poly(TMC/GA- block - L LA/GA)) block copolymers were synthesized by ROP in bulk at 130 °C with high M n ¯ (above 2.0 × 10 5  Da). Such kind of block copolymers composed of P(TMC- ran -GA) and P( L LA- ran -GA) segments show good mechanical properties and adjustable degradation rate. The molecular structures of block copolymers were characterized by GPC, FTIR, and 1 H NMR. Chain microstructure analysis was performed in detail with 13 C NMR spectroscopy. The effect of GA units content on thermal behaviors, mechanical properties as well as biodegradability of copolymers was investigated by DSC, XRD, stress-strain measurements and enzymatic degradation tested in comparison with corresponding block copolymers P(TMC- block - L LA/GA). The results shown that amorphous P(TMC- ran -GA) segments significantly improve the flexibility of block copolymers. The incorporation of GA units strongly decreases the crystallization ability of L LA segment within copolymers due to more random L LA-GA sequence and shorter average L LA block length. Meanwhile, the tensile strength of material and flexibility are significantly improved with the raising GA units content. The enzymatic degradation rate is also accelerated with the increase GA unit content. Thus, the biodegradable block copolymers with unique molecular structure and modifiable properties are promising new materials for biomedical applications.

研究领域: 生物材料学 · 高分子化学 · 生物医学工程
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Materials Science & Engineering C-Materials for Biological Applications · 2017 · IF 4.164

An injectable hydroxyapatite/poly(lactide-co-glycolide) composite reinforced by micro/nano-hybrid poly(glycolide) fibers for bone repair

Yuhang Zhu,Zongliang Wang,Hongli Zhou,Linlong Li,Qingsan Zhu,Peibiao Zhang

Porous nanocomposite of hydroxyapatite/poly(lactide- co -glycolide) (HA/PLGA) is conventionally used in bone tissue engineering but seldom in load-bearing orthopedic applications due to poor mechanical property. This study aimed to fabricate an injectable ternary composite by incorporating different contents of poly(glycolide) (PGA) fibers (0, 30, 50 and 70   wt%) into the nanocomposite HA/PLGA matrix as reinforcing fillers for bone tissue repair. The fibers were obtained from melt-spinning and fiber diameter ranged from 70   nm to 191   μm. The injectability, mechanical strength, solidification rate and cytotoxicity of injectable composites were characterized. All composites achieved the acceptable injectability under an injection force of 100   N. The mechanical properties of composites were gradually enhanced by increasing PGA fiber contents. The compression strength of composite with 70   wt% content of PGA fibers was up to 31.1   MPa, which was four times stronger than that of composite without PGA fibers. In the solidification rate analysis, the compression strength of composites with 50 or 70   wt% PGA fibers in immersion time of only 45   min was similar to that of composite without fibers in immersion time of 4–5   h. The MTT test showed that exceeding 70% cells could survive in the fourfold dilution of extract, and its cytotoxicity focused on the first 4   h after immersing. This study have revealed that the PGA fiber-reinforced HA/PLGA composite is a promising candidate for orthopedic applications.

CAS / MDL: 872-50-4
研究领域: 生物材料学 · 骨组织工程 · 医学材料
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2017 · IF 2.726

Thermodynamic properties of enantiotropic polymorphs of glycolide

Qiaoyin Huang,Yang Li,Fuhong Yuan,Liping Xiao,Hongxun Hao,Yongli Wang

In this work, two different polymorphs (form 1 and form 2) of glycolide were successfully prepared and characterized. The solubility of these two polymorphs in ethyl acetate, 1-propanol, ethanol, 2-propanol and 1-butanol at temperatures from 278.15   K to 328.15   K under atmospheric pressure (0.1   MPa) was experimentally measured by using the isothermal gravimetrical method and correlated by the modified Apelblat model and the van’t Hoff equation. For all the selected solvents, the solubility curve of form 1 crossed the solubility curve of form 2 at a transition temperature in the above temperature range. Combining the results of DSC, solubility curves and dissolution data of these two polymorphs, it was confirmed that form 1 and form 2 were enantiotropic. The dissolution thermodynamic properties of glycolide form 1 and form 2 were also calculated.

CAS / MDL: 134-85-0
研究领域: 物理化学 · 药学
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International Journal of Bioprinting · 2021 · IF 6.638

A Dual-sensitive Hydrogel Based on Poly(Lactide-co-Glycolide)-Polyethylene Glycol-Poly(Lactide-co-Glycolide) Block Copolymers for 3D Printing

Yang Zhou,Yuecheng Cui,Li-Qun Wang

The thermo-sensitive hydrogel formed by triblock copolymers of polyethylene glycols and aliphatic polyesters serves as a promising candidate for bioink due to its excellent biodegradability and biocompatibility. However, the thermo-crosslinking alone cannot achieve a robust hydrogel to support the 3D printed constructs without collapse. Herein, a photo-crosslinkable group was introduced into the triblock copolymers to achieve a dual-sensitive hydrogel. A triblock copolymer poly(lactide-co-glycolide)-polyethylene glycol-poly(lactide-co-glycolide) decorated with acrylate group in the chain end was prepared. The obtained aqueous solutions of the copolymers could transform into hydrogels with excellent shear thinning properties and rapid elastic recovery properties spontaneously on the increase of temperature. The resulted thermogels also allowed for photo-crosslinking by exposure to ultraviolet radiation, with storage modulus dramatically increased to stable the printed constructs. Through a two-step crosslinking strategy, complicated tissue-like constructs with high shape fidelity can be printed using the dual-sensitive inks. Moreover, the mechanical strength, swelling ratio, and printability of the hydrogels can be tuned by varying the substitution rate of the acrylate group without compromising the inks’ extrudability. We expect that the dual-sensitive hydrogels may be used as bioinks to print large constructs for applications in tissue engineering.

研究领域: 材料科学 · 生物医学工程 · 3D打印 · 组织工程
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Acta of Bioengineering and Biomechanics · 2023 ·Vol. 25 ·期 4 ·111-120 · IF 1

Poly(lactide-co-glycolide) microspheres with good biocompatibility

Runze An,Wenmin Tang,Zhanpeng Zhao,Wentao Liu,Liang Kan

Purpose: Curcumin and icariin have multiple pharmacological effects and are widely used in various fields, but their short half-life, poor bioavailability and low water solubility greatly limit their application in clinical medicine. Poly(lactide-co-glycolide) (PLGA) loaded microspheres not only solve these problems, but also have no toxicity in degradation. Methods: To verify whether PLGA drugloaded microspheres have good biocompatibility, the present experiments used the emulsification-solvent evaporation method to prepare PLGA drug-loaded microspheres and successfully performed the loading of curcumin and icariin. Results: The scanning electron microscopy showed that the particle sizes of the PLGA microspheres were 2–15 μm, icariin/PLGA microspheres were 3–22 μm and curcumin/PLGA microspheres were 5–30 μm. Moreover, the surface of the microspheres was smooth and spherical. Furthermore, the drug loading and encapsulation rate were good. In vitro experiments revealed that the prepared PLGA microspheres were safe and nontoxic, and that they could release drugs stably and slowly. Moreover, their proliferation ability was unaffected after inoculation into bone marrow mesenchymal stem cells (BMSCs), and Alcian blue Staining was performed at last, demonstrating their biocompatibility and important applications in tissue engineering.

研究领域: 药剂学 · 组织工程学 · 生物医学
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Journal of Macromolecular Science Part B-Physics · 2022 · IF 1.366

In-Vitro Degradation and Biological Properties of Poly(Lactide-co-Glycolide-co-ε-Caprolactone)/Ethanediamine Modified Poly(Lactide-co-Glycolide) Blend Scaffolds

Zemei Fang,Zhihua Zhou,Wei Wu,Wenjuan Liu,Hailin Xie,Hongbo Hu,Yan Gan,Jianjun Fang

A degradable blend scaffold composed of poly(D,L-lactide-co-glycolide-co-ε-caprolactone) (PLLGC) and ethanediamine modified poly(lactide-co-glycolide) (EMPLGA) was prepared by using a thermally induced phase separation technique. The morphologies of the PLLGC/EMPLGA blend scaffolds were characterized by using scanning electron microscopy (SEM). The in-vitro degradation behaviors and biocompatibility of the individual components and the blend were investigated by using rat L929 cells. The blend scaffolds showed a porous and well interconnected pore structure. The degradation rate sequence of the three scaffolds, the individual components and the blend, was EMPLGA > PLLGC/EMPLGA > PLLGC. The PLLGC/EMPLGA blend scaffold was non-cytotoxic and showed high cell proliferation.

研究领域: 生物材料 · 组织工程 · 高分子科学 · 生物医学工程 · 体外降解
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JOURNAL OF POLYMER RESEARCH · 2012 ·Vol. 19 ·期 12 ·1-8 · IF 1.733

Dimensional stability of electrospun membranes of poly(l-lactide-co-glycolide)/poly(l-lactide-co-glycolide)-b-polyethylene glycol blends under stretch

Ma Chi,Wang Bing,Xiong Cheng-Dong,Chen Dong-Liang,Xiong Zuo-Chun

Control of dimensional stability is crucial for using electrospun membranes in biomedical and tissue engineering applications. In this study, the contraction of electrospun membranes of poly( l -lactide-co-glycolide) (PLLGA) after stretch was investigated. Then, by adding PLLGA-b-polyethylene glycol (PLLGA-PEG), the contraction of the membranes was controlled. In addition, the mechanical properties of the membranes were investigated. On the basis of the strain–stress behavior of the membranes, an elongation of 50 % was used to investigate the orientation degrees of the membrane fibers. On the basis of the morphology of the stretched membranes, the contraction was found to depend on the orientation degree of fibers after stretch. A linear relationship between the contraction and degree of orientation after stretch was confirmed. Two-dimensional fast Fourier transform (2D FFT) analysis of the scanning electron microscopy (SEM) images of the membranes was used to quantify the orientation degree. It was surmised that the different orientation degrees were responsible for the different morphologies and thermal behaviors of the membranes.

CAS / MDL: 9004-74-4 2258654-78-1
研究领域: 生物医学工程 · 组织工程 · 材料科学
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Journal of Macromolecular Science Part B-Physics · 2022 · IF 1.366

Preparation and Properties of Poly(D,L-lactide-co-glycolide-co-ε-caprolactone)/1,4-Butanediamine Modified Poly(lactide-co-glycolide) Blend Porous Microspheres

Jiaming Gu,Zhihua Zhou,Tianlong Huang,Wei Wu,Wenjuan Liu,Yanmin Zhao,Ping Chen,Ziwei Zhou,Dan Wang,Chao Zhang,Meilin Yi,Xiao He,Jianjun Fang

Composite porous microspheres based on blends of poly(D,L-lactide-co-glycolide-co-ε-caprolactone) (PLGCL) and 1,4-butanediamine modified poly(D,L-lactide-co-glycolide) (BMPLGA) were prepared by using a combined solvent evaporation and particle leaching technique. The morphologies and porous structure of the PLGCL/BMPLGA microspheres were observed by using scanning electron microscopy (SEM). The in-vitro degradation behaviors and cytocompatibility were studied. The resultant microspheres showed a porous surface and a three-dimensional network structure with interconnecting pores. The changes of morphologies, pH value and mass loss during in-vitro degradation in phosphate buffered solution (PBS) at 37°C indicated that the degradation rate of the BMPLGA was faster than that of the PLGCL in the PLGCL/BMPLGA blends. We suggest the PLGCL/BMPLGA porous microspheres were non-cytotoxic and showed excellent cytocompatibility. We suggest the PLGCL/BMPLGA porous polymeric microspheres have great potential for application for drugs delivery and tissue regeneration.

研究领域: 生物材料 · 高分子科学 · 药物递送 · 组织工程 · 生物医学工程
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POLYMER · 2021 · IF 4.43

Synthesis and crystallization behavior of poly (lactide-co-glycolide)

Jidong Dai,Min Liang,Zhigang Zhang,Katrien V. Bernaerts,Tianzhu Zhang

Poly (lactide- co -glycolide) (PLGA) has emerged as an important material in tissue engineering. However, lactic acid (LA) produced during PLGA degradation is prone to inflammation, which is a shortcoming that must be avoided. To this end, a method for preparing crystalline PLGA is described here by using cross-linking nucleation. The pentaerythritol (PET), L-lactide and glycolide were first used to prepare the four-armed PLGA (4arm-PLGA) via the ring-opening polymerization (ROP) method. Such symmetrical four-armed PLGA was then grafted and crosslinked with N’N-methylenebisacrylamide (MBAM) simultaneously, and finally obtained the crystalline 4arm-PLGA (C4-PLGA-M). The C4-PLGA-M has controllable crystallinity , which could effectively control the degradation rate of PLGA. The C4-PLGA-M were characterized by POM and WAXS , and the accelerated degradation tests of C4-PLGA-M showed a sixfold increase at most in the degradation time compared to alone four-armed PLGA. The results of cell culture confirmed that the reduction of LA from hydrolysis process could be beneficial to the cell growth. Such crystalline C4-PLGA-M is expected to have ideal performance in tissue engineering.

研究领域: 材料科学 · 生物材料 · 组织工程 · 高分子化学
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Journal of Macromolecular Science Part B-Physics · 2020 · IF 0.911

Preparation and Characterization of Poly(L-lactide-co-glycolide-co-ε-caprolactone)/1,4-Butanediamine Modified Maleated Poly(D,L-lactide-co-glycolide) Blend Porous Films

Dan Wang,Jianjun Fang,Wenjuan Liu,Tianlong Huang,Yanmin Zhao,Jianglong Duan,Hailin Xie,Ping Chen,Ziwei Zhou,Zhihua Zhou

Poly(L-lactide-co-glycolide-co-ε-caprolactone) (PLLGC) and 1,4-butanediamine modified maleated poly(D,L-lactide-co-glycolide) (BMPLGA) were both synthesized by ring-opening polymerization with stannous octoate as catalyst. Then PLLGC/BMPLGA blend porous films were prepared by using NaCl particles as a porogen through a solvent casting/particle leaching method. The PLLGC/BMPLGA blend porous films were characterized by Fourier transform infrared spectroscopy, gel permeation chromatography and scanning electron microscopy. The tensile properties of the PLLGC/BMPLGA porous films were also studied. The results showed that the content and size of the NaCl porogens had significant effects on the porosity of the PLLGC/BMPLGA porous films. The tensile strength and elongation percentage of the porous films decreased with increasing porogen content. Thus, both the pore structure and mechanical properties of the porous PLLGC/BMPLGA blend films can be controlled by changing the amount and size of the porogen.

研究领域: 高分子科学 · 生物材料 · 组织工程 · 材料表征 · 聚合物共混
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Journal of Macromolecular Science Part B-Physics · 2022 · IF 1.366

In-Vitro Degradation Behaviors of Composite Scaffolds Based on Poly(Lactide-co-Glycolide-co-ε-Caprolactone), 1,4-Butanediamine Modified Poly(Lactide-co-Glycolide) and Bioceramics

Yun Ou,Wei Wu,Zhihua Zhou

In this work a novel type of composite scaffolds based on poly(lactide-co-glycolide-co-ε-caprolactone) (PLLGC), 1,4-butanediamine modified poly(lactide-co-glycolide) (BMPLGA), nanobioactive glass (NBAG) and β-tricalcium phosphate (β-TCP) were fabricated by using a thermally induced phase separation (TIPS) method. The in-vitro degradation behaviors were investigated by immersing the scaffolds in phosphate buffered saline (PBS, pH = 7.27) solution at 37 °C for 40 days. The properties, including the PBS pH value change and the water uptake, mass loss and morphology changes of the composite scaffolds, were investigated by comparing with pure PLLGC/BMPLGA scaffolds. The introduction of NBAG and β-TCP nanoparticles decreased the degradation rate of the PLLGC/BMPLGA matrix and improved the wetting behavior. The decrease in the degradation rate of the composite scaffolds correlated well with the results obtained from mass loss, water uptake and pH measurements. The degradation rate of the PLLGC/BMPLGA polymer in the composite scaffolds decreased as a result of the alkaline effect of the NBAG and β-TCP particles, with the OH- ions formed neutralizing acidic polymeric degradation products and binding the H+ ions from the tissue fluids.

研究领域: 生物材料 · 组织工程 · 高分子科学 · 生物医学工程 · 体外降解
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