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vanillin-based functionalization strategy to construct multifunctional microspheres for treating inflammation and regenerating intervertebral disc

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Bioactive Materials 2023年第10期28卷 167-182页

作者： Zhuang Zhu Qifan Yu Hanwen Li Feng Han Qianping Guo Heng Sun He Zhao Zhengdong Tu Zhuang Liu Caihong Zhu Bin Li Orthopedic Institute Department of Orthopedic SurgeryThe First Affiliated HospitalSchool of Biology&Basic Medical SciencesSuzhou Medical CollegeSoochow UniversitySuzhouJiangsu215007China Institute of Functional Nano&Soft Materials Jiangsu Key Laboratory for Carbon-Based Functional Materials and DevicesSoochow UniversitySuzhouJiangsu215123China Children’s Hospital of Soochow University Pediatric Research Institute of Soochow UniversitySuzhouJiangsu215123China

Intervertebral disc degeneration(IVDD)is one of the main causes of low back *** local delivery strategies using biomaterial carriers have shown potential for IVDD treatment,it remains challenging for intervention against multiple adverse contributors by a single delivery *** the present work,we propose a new functionalization strategy using vanillin,a natural molecule with anti-inflammatory and antioxidant properties,to develop multifunctional gelatin methacrylate(GelMA)microspheres for local delivery of transforming growth factorβ3(TGFβ3)toward IVDD *** vitro,functionalized microspheres not only improved the release kinetics of TGFβ3 but also effectively inhibited inflammatory responses and promoted the secretion of extracellular matrix(ECM)in lipopolysaccharide-induced nucleus pulposus(NP)*** vivo,functionalized platform plays roles in alleviating inflammation and oxidative stress,preserving the water content of NP and disc height,and maintaining intact structure and biomechanical functions,thereby promoting the regeneration of ***-throughput sequencing suggests that inhibition of the phosphatidylinositol 3-kinase(PI3K)-Akt signaling might be associated with their therapeutic *** summary,the vanillin-based functionalization strategy provides a novel and simple way for packaging multiple functions into a single delivery platform and holds promise for tissue regeneration beyond the IVD.

关键词： Intervertebral disc degeneration Microsphere vanillin Transforming growth factorβ3 Regeneration

Effects of solvent,supersaturation ratio and silica template on morphology and polymorph evolution of vanillin during swift cooling crystallization

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Particuology 2022年第6期20卷 93-104页

作者： Jinbo Ouyang Xiaohong Xing Jian Chen Limin Zhou Zhirong Liu Jerry Y.Y.Heng Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices East China University of TechnologyNanchang 330013China Department of Chemical Engineering Imperial College LondonSouth Kensington CampusLondon SW72AZUK

Swift cooling crystallization of vanillin was investigated in water,ethanol,isopropanol and ethyl *** and polymorph evolution of vanillin were discussed in terms of solvent,supersaturation ratio and silica ***,DSC,FTIR and microscope were used to identify polymorphs of *** showed that the nucleated polymorphs of vanillin depended largely on the solvent,supersaturation ratio and silica *** supersaturation ratios favor the nucleation of stable form I in water,and high supersaturation ratio exceeds 7 generating 100%metastable form ***,if the supersaturation ratio is too high(S>8),liquid-liquid phase separation will occur,and no crystals could be *** other solvents such as ethanol,isopropanol and ethyl acetate,only form I was ***,it should be noted that the morphology of form I prepared in ethanol,isopropanol and ethyl acetate is distinct from that obtained in water,the former is flake-like and the latter is *** nucleation of vanillin from different solution was also studied with the presence of SiO_(2),SiO_(2)-NH_(2)and SiO_(2)−COOH templates,which did not change the nucleated polymorph of vanillin,but changed the nucleation and growth rate of stable form I.

关键词： vanillin Supersaturation ratio Nucleation Polymorph Template

A modeling strategy investigation for selective hydrodeoxygenation biomass upgrading of vanillin via metal supported on pyridinic and pyrrolic nitrogen-doped carbon catalysts

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Rare Metals 2024年第12期43卷 6460-6472页

作者： Yi Xiao Li Liu Wei-Bin Zhang Li-Li Han State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of Sciences Laboratory of New Energy and Materials Xinjiang Institute of Engineering Institute of Physics and Electronic Information Yunnan Normal University

To extend the practical application of biomass upgrading conversion to liquid fuel,it is crucial to develop highly catalytic and reversible nonprecious metal ***,we propose a high-throughput density functional theory（DFT） approach to design a high-efficiency catalyst for the selective electrocatalytic upgrading of vanillin via hydrodeoxygenation（HDO）.The optimal pyridinic and pyrrolic nitrogen carbon transition metal（TM）-based monolayers exhibit excellent activity for producing2-methoxy-4-methylphenol（MMP） from *** pyridinic and pyrrolic nitrogen carbon substrates can provide unique sites to support TM atoms,and TM-pyridinic or pyrrolic N moieties serve as catalytic activity sites for the electrocatalytic upgrading of *** DFT calculations suggest that the pyridinic N@TM（TM=Zr,Ru,Rh,Os and Ir） and pyrrolic N@TM（TM=Rh and Os）catalysts possess high activity for MMP synthesized from vanillin,and they have a relatively small limiting potential（UL） of the rate-determining step.A new route reaction path was used to explore the activity of metal nitrogendoped carbon catalysts,finding that a single metal atom through strong electron correlation between metal and N4C8sites can improve the activity of the vanillin HDO *** results show that pyridinic N@Ir and pyrrolic N@Rh with limiting potential（UL） of 0.04 and 0.29 V are the most preferable candidate catalysts for the vanillin HDO *** high stability and relatively low |UL| for vanillin electrocatalytic upgrading are the best candidate *** work proposes new ideas for designing and developing novel catalysts for selective HDO of biomass under real conditions.

关键词： Biomass upgrading Dominant metal environment Pyridinic and pyrrolic nitrogen carbon metal-based catalysts Selective hydrodeoxygenation (HDO) vanillin

Rational design of palladium single-atoms and clusters supported on silicoaluminophosphate-31 by a photochemical route for chemoselective hydrodeoxygenation of vanillin

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Nano Research 2021年第11期14卷 4347-4355页

作者： Xiaowen Lu Chunmu Guo Mingyang Zhang Leipeng Leng J.Hugh Horton Wei Wu Zhijun Li Joint International Research Laboratory of Advanced Chemical Catalytic Materials&Surface Science College of Chemistry and Chemical EngineeringNortheast Petroleum UniversityDaqing163318China National Center for International Research on Catalytic Technology School of Chemistry and Material ScienceHeilongjiang UniversityHarbin150080China Department of Chemistry Queen’s UniversityKingstonK7L 3N6Canada

Chemoselective hydrodeoxygenation of vanillin is of great importance in converting biomass into high value-added ***,we describe a facile photochemical route to access palladium single atoms and clusters supported on silicoaluminophosphate-31(SAPO-31)as a highly active,chemoselective,and reusable catalyst for hydrodeoxygenation of *** by aberration-corrected high-angle annular dark-field scanning transmission electron microscopy,extended X-ray absorption fine structure measurement,and CO-absorbed diffuse reflectance infrared Fourier transform spectroscopy reveal the atomically dispersed palladium single atoms and clusters are loosely bonded and randomly dispersed,without forming strong palladium-palladium metallic bonding,over the SAPO-31 *** catalyst,with a full metal availability to the reactants,exhibits exceptional catalytic activity(TOF:3,000 h^(−1),Yield:>99%)in the hydrodeoxygenation of vanillin toward 2-methoxy-4-methylphenol(MMP)under mild conditions(1 atm,80°C,30 min),along with excellent stability,scalability(up to 100-fold),and wide substrate *** superior catalytic performance can be attributed to the synergistic effect of the positively charged palladium single atoms and fully exposed clusters,as well as the strong metal-support *** work may offer a new avenue for the design and synthesis of fully exposed metal catalysts with targeted functionalities.

关键词： heterogeneous catalysis photochemical reduction palladium single atoms and clusters atomic dispersion hydrodeoxygenation vanillin

Comparative toxicity study of a novel non-ionic surfactant,vanillin ethoxylates, and nonylphenol ethoxylates in Chinese hamster ovary cells in vitro

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Journal of Environmental Sciences 2019年第8期31卷 70-81页

作者： Shengwu Yuan Xiaoya Ji Mei Ma Fengmei Ding Kaifeng Rao Zijian Wang Rong Yang Yihong Liu Key Laboratory of Drinking Water Science and Technology Research Center for Eco-Environmental Sciences Chinese Academy of Sciences College of Resources and Environment University of Chinese Academy of Sciences College of Chemistry Chemical Engineering and Biotechnology Donghua University State Key Laboratory of Environmental Aquatic Chemistry Research Center for Eco-Environmental Sciences Chinese Academy of Sciences Beijing Water Quality Monitoring Center for South-to-North Water Diversion

Surfactants such as alkylphenol polyethoxylates(APEOs) and nonylphenol ethoxylates(NPEOs) are commonly used worldwide, but the majority of these compounds, together with their metabolites, have been reported to induce severe biological toxicity. Here, we evaluated for the first time the cytotoxicity,genotoxicity and mitochondrial damage in Chinese hamster ovary(CHO-K1) cells caused by a novel non-ionic surfactant, vanillin ethoxylates(VAEOs), an alternative to APEOs. In parallel, the same in vitro bioassays were conducted on NPEOs along with their metabolic byproducts 4-nonylphenol(4-NP) and vanillin. The results showed that the cytotoxic potency order was NPEOs > 4-NP > VAEOs>vanillin using CCK-8 assays. Also, 4-NP showed potential direct DNA damage in SOS/umu tests, whereas NPEOs, VAEOs and vanillin showed no positive result with and without S9 addition. In addition, none of the test compounds showed obvious genotoxic effects with low olive tail moment value using comet assays. However, all test compounds were shown to cause mitochondrial impairment by increasing mitochondrial mass and decreasing mitochondrial membrane potential in a concentration-dependent manner. And further analysis of reactive oxygen species(ROS) and mitochondrial superoxide(MNSOD)measurement showed that mitochondrial impairment was induced by oxidative stress with intracellular ROS and MNSOD overproduction. It's worth noting that VAEOs and vanillin cause relative lower cytotoxic, genotoxic and mitochondrial damage effects than NPEOs and 4-NP, indicating that VAEOs have the potential to substitute NPEOs as suitable surfactants. Take together, this study elucidates the toxicity profiles of VAEOs and NPEOs relatively comprehensively, and further toxicity analyses are suggested in the population, community and ecosystem.

关键词： vanillin ethoxylates(VAEOs) Nonylphenol ethoxylates(NPEOs) Cytotoxicity Genotoxicity Mitochondrial impairment

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vanillin and its derivatives,potential promising antifungal agents,inhibit Aspergillus flavus spores via destroying the integrity of cell membrane rather than cell wall

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Grain & Oil Science and Technology 2021年第2期4卷 54-61页

作者： Qian Li Xiaoman Zhu Henan Key Laboratory of Cereal and Oil Food Safety Inspection and Control College of Food Science and EngineeringHenan University of Technology

To study the structure-antifungal activity of vanillin against Aspergillus flavus(***),the susceptibilities of *** to vanillin and its isomers(o-vanillin,2-hydroxy-4-methoxybenzaldehyde(HMB),2-hydroxy-5-methoxybenzaldehyde)and the possible antifungal mechanisms have been *** the four volatile aldehydes could inhibit the germination of spores,and the minimum inhibitory concentrations(MICs)of them were in this order:vanillin(200μg/mL),o-vanillin(100μg/mL),2-hydroxy-5-methoxybenzaldehyde(100μg/mL),HMB(70μg/mL).The minimum fungicidal concentrations(MFCs)of them were in this order:vanillin(240μg/mL),o-vanillin(160μg/mL),HMB(140μg/mL),2-hydroxy-5-methoxybenzaldehyde(140μg/mL).Spore size was arrested at 0 h with the treatment of the four volatile *** of the four volatile aldehydes on the cell wall and cell membrane integrity of A flavus were observed by calcofluor white(CW)staining and propidium iodide(PI)*** results showed that HMB exerted the strongest antifungal and fungicidal effects on the growth of *** four volatile aldehydes had little influence on cell wall integrity after 3-hour treatment,however,they could strongly damage the cell membrane *** the four volatile aldehydes could effectively prevent the growth of *** on peanut *** antifungal mechanisms of the four volatile aldehydes provide theoretical foundations for their development of new antifungal agents.

关键词： Aspergillus flavus vanillin o-vanillin HMB 2-Hydroxy-5-methoxybenzaldehyde Antifungal mechanism

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Bio-Based Waterborne Poly(vanillin-Butyl Acrylate)/MXene Coatings for Leather with Desired Warmth Retention and Antibacterial Properties

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Engineering 2024年第5期36卷 250-263页

作者： Jianzhong Ma Li Ma Lei Zhang Wenbo Zhang Qianqian Fan Buxing Han College of Bioresources Chemical and Materials Engineering Shaanxi University of Science and TechnologyXi’an 710021China Xi’an Key Laboratory of Green Chemicals and Functional Materials Xi’an 710021China College of Chemistry and Chemical Engineering Shaanxi University of Science and TechnologyXi’an 710021China Shaanxi Collaborative Innovation Center of Industrial Auxiliary Chemistry and Technology Shaanxi University of Science and TechnologyXi’an 710021China Institute of Chemistry Chinese Academy of SciencesBeijing 100190China

This study presents a solvent-free,facile synthesis of a bio-based green antibacterial agent and aromatic monomer methacrylated vanillin(MV)using *** resulting MV not only imparted antibacterial properties to coatings layered on leather,but could also be employed as a green alternative to petroleum-based carcinogen styrene(St).Herein,MV was copolymerized with butyl acrylate(BA)to obtain waterborne bio-based P(MV-BA)miniemulsion via miniemulsion ***,MXene nanosheets with excellent photothermal conversion performance and antibacterial properties,were introduced into the P(MV-BA)miniemulsion by ultrasonic *** the gradual solidification of P(MV-BA)/MXene nanocomposite miniemulsion on the leather surface,MXene gradually migrated to the surface of leather coatings due to the cavitation effect of ultrasonication and amphiphilicity of MXene,which prompted its full exposure to light and bacteria,exerting the maximum photothermal conversion efficiency and significant antibacterial *** particular,when the dosage of MXene nanosheets was 1.4 wt%,the surface temperature of P(MV-BA)/MXene nanocomposite miniemulsioncoated leather(PML)increased by about 15℃ in an outdoor environment during winter,and the antibacterial rate against Escherichia coli and Staphylococcus aureus was nearly 100%under the simulated sunlight treatment for 30 ***,the introduction of MXene nanosheets increased the air permeability,water vapor permeability,and thermal stability of these *** study provides a new insight into the preparation of novel,green,and waterborne bio-based nanocomposite coatings for leather,with desired warmth retention and antibacterial *** can not only realize zerocarbon heating based on sunlight in winter,reducing the use of fossil fuels and greenhouse gas emissions,but also improve ability to fight off invasion by harmful bacteria,viruses,and other microorganisms.

关键词： MXene nanosheets vanillin Styrene substitute Leather coating Photothermal conversion Warmth retention Antibacterial properties

Highly dispersed Pd nanoparticles in situ reduced and stabilized by nitrogen-alkali lignin-doped phenolic nanospheres and their application in vanillin hydrodeoxygenation

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Frontiers of Chemical Science and Engineering 2024年第11期18卷 205-216页

作者： Xue Gu Yu Qin Jiahui Wei Bing Yuan Fengli Yu Liantao Xin Congxia Xie Shitao Yu State Key Laboratory Base of Eco-chemical Engineering College of Chemistry and Molecular EngineeringCollege of Chemical EngineeringQingdao University of Science and TechnologyQingdao 266042China

Herein,we introduced a nitrogen-alkali lignin-doped phenolic resin(N@AL_(n)PR)to produce palladium nanoparticles through an in situ reduction of palladium in an aqueous phase,without the need for additional reagents or a reducing *** phenolic resin nanospheres and the resulting palladium nanoparticles were extensively *** lignin created a highly conducive environment for nitrogen incorporation,dispersion,reduction,and stabilization of palladium,leading to a distinct catalytic performance of palladium nanoparticles in vanillin *** specific conditions of 1 mmol of vanillin,40 mg of catalyst,1 MPa H_(2),90°C,and 3 h,the optimized Pd/N@AL_(30)PR catalyst exhibited a nearly complete conversion of vanillin,98.9%selectivity toward p-creosol,and good stability for multiple ***,an environmentally friendly lignin-based catalyst was developed and used for the efficient hydrodeoxygenation conversion of lignin-based platform compounds.

关键词： alkali lignin phenolic nanosphere palladium nanoparticles hydrodeoxygenation vanillin

Phthalonitrile Resins Derived from vanillin: Synthesis, Curing Behavior, and Thermal Properties

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Chinese Journal of Polymer Science 2020年第1期38卷 72-83,I0007页

作者： Yue Han Dong-Hao Tang Guang-Xing Wang Ya-Nan Sun Ying Guo Heng Zhou Wen-Feng Qiu Tong Zhao South China Advanced Institute for Soft Matter Science and Technology South China University of Technology Laboratory of Advanced Polymeric Materials Institute of Chemistry Chinese Academy of Sciences University of Chinese Academy of Sciences Sinosteel Anshan Research Institute of Thermo-Energy Co. LTD

vanillin was used as sustainable source for phthalonitrile monomer synthesis, and allyl/propargyl ether moieties were introduced to improve the processability at the minimal cost of thermal properties. The synthesis route was optimized to minimize side-reactions and simplify post-processing, and the monomers were obtained in high purity and good yields. The curing behavior, mechanism, and processability of the monomers were studied, and the thermal properties of cured polymers were evaluated. Of the two monomers, the allyl ether-containing one exhibited a wide processing window of 185 °C, and was mainly cured into phthalocyanine and linear aliphatic structures through self-catalytic curing process. Also, the glass transition temperature was higher than 500 °C. In contrast, the propargyl ether-containing monomer could only be partially cured, and heat resistance was found to be compromised. Compared with traditional petroleum-based phthalonitrile resins, the biobased monomers could be cured without the addition of catalysts, and improvement in processability was achieved at no cost of thermal performances.

关键词： Allyl ether Curing mechanism Phthalonitrile Thermal properties vanillin

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