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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 pain.Although 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 platform.In 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 treatment.In 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)cells.In 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 IVD.High-throughput sequencing suggests that inhibition of the phosphatidylinositol 3-kinase(PI3K)-Akt signaling might be associated with their therapeutic effects.In 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

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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 acetate.Morphology and polymorph evolution of Vanillin were discussed in terms of solvent,supersaturation ratio and silica template.PXRD,DSC,FTIR and microscope were used to identify polymorphs of Vanillin.Results showed that the nucleated polymorphs of Vanillin depended largely on the solvent,supersaturation ratio and silica template.Low supersaturation ratios favor the nucleation of stable form I in water,and high supersaturation ratio exceeds 7 generating 100%metastable form II.However,if the supersaturation ratio is too high(S>8),liquid-liquid phase separation will occur,and no crystals could be obtained.In other solvents such as ethanol,isopropanol and ethyl acetate,only form I was obtained.However,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 rod-like.The 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

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A Vanillin-Derived,DOPO-Contained Bisphenol as a Reactive Flame Retardant for High-Performance Epoxy Thermosets

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Journal of Renewable Materials 2022年第5期10卷 1349-1364页

作者： Li Wang Rongbai Tong Juanli Wang Jintao Wan Yuhu Li Pujun Jin Daodao Hu School of Materials Science and Engineering Shaanxi Normal UniversityXi’an710062China Engineering Research Center of Historical and Cultural Heritage Protection Ministry of EducationShaanxi Normal UniversityXi’an710062China Hangzhou First Applied Material Co. Ltd.Hangzhou311300China

Quest for bio-based halogen-free green flame retardant has attracted many concerns in recent years.Herein a reactive functional flame retardant containing phosphorus VDP is synthesized from Vanillin,9,10-dihydro-9-oxa-10-phosphophene-10-oxide(DOPO)and phenol via a facile way.VDP is characterized with^(1)H NMR,^(31)P NMR,FTIR and Time of Flight Mass Spectrometry,and used as a new reactive flame retardant for bisphenol epoxy thermosets.Thermogravimetry analysis shows that when the VDP loading is only 0.5P%(based on phosphorus content),the residue increases from 14.2%to 21.1%at 750℃ in N_(2)compare with neat DGEBA.Correspondingly,the limit oxygen index increased to 29.6%,and flame retardancy reaches UL-94 V0 grade.Micro combustion calorimetry(MCC)and cone calorimetry analyses demonstrate that VDP can significantly lower flammability of the epoxy thermoset.With only 0.5P%of VDP,the heat release rate,total heat release rate and smoke production are reduced markedly.At the same time,the mechanical properties of the modified epoxy thermosets are also improved.The impact strength increases by 34%and the flexural strength increased by 23%,with 1.5P%of VDP.In short,VDP not only improves the flame retardancy,but also improves the mechanical properties of the epoxy thermosets.

关键词： Epoxy resin bio-based flame retardant Vanillin properties of thermosets

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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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Potassium Bromate-induced Changes in the Adult Mouse Cerebellum Are Ameliorated by Vanillin

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Biomedical and Environmental Sciences 2018年第2期31卷 115-125页

作者： Hajer Ben Saad Dorra Driss Imen Jaballi Hanen Ghozzi Ons Boudawara Michael Droguet Christian Magne Monsef Nasri Khaled Mounir Zeghal Ahmed Hakim Ibtissem Ben Amara Laboratory of Pharmacology University of SfaxFaculty of Medicine3029 SfaxTunisia Laboratory of Enzyme engineering and Microbiology National Engineering School in SfaxUniversity of SfaxB.P.11733038 SfaxTunisia Centre of Biotechnology of Sfax P.O.Box 11773018 SfaxTunisia Anatomopathology Laboratory University of SfaxHabib Bourguiba Hospital3029 SfaxTunisia EA 4324 ORPHY Faculty of MedicineUniversity of Brest29238 Brest CedexFrance EA 2219 Geoarchitecture University of BrestUFR Sciences&Techniques29238 Brest Cedex 3France

Objective The current study aimed to elucidate the effect of Vanillin on behavioral changes, oxidative stress, and histopathological changes induced by potassium bromate （KBrO3）, an environmental pollutant, in the cerebellum of adult mice.Methods The animals were divided into four groups： group 1 served as a control, group 2 received KBrO3, group 3 received KBrO3 and Vanillin, and group 4 received only Vanillin. We then measured behavioral changes, oxidative stress, and molecular and histological changes in the cerebellum.Results We observed significant behavioral changes in KBrO3-exposed mice. When investigating redox homeostasis in the cerebellum, we found that mice treated with KBrO3 had increased lipid peroxidation and protein oxidation in the cerebellum. These effects were accompanied by decreased Na＋-K＋ and Mg2＋ ATPase activity and antioxidant enzyme gene expression when compared to the control group. Additionally, there was a significant increase in cytokine gene expression in KBrO3-treated mice. Microscopy revealed that KBrO3 intoxication resulted in numerous degenerative changes in the cerebellum that were substantially ameliorated by Vanillin supplementation. Co-administration of Vanillin blocked the biochemical and molecular anomalies induced by KBrO3.Conclusion Our results demonstrate that Vanillin is a potential therapeutic agent for oxidative stress associated with neurodegenerative diseases.

关键词： Cerebellum Behavior Potassium bromate Vanillin ATPases Genes expression

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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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Isolation and identification of fungi found in contaminated fermented milk and antifungal activity of Vanillin

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Food Science and Human Wellness 2021年第2期10卷 214-220页

作者： Xu Pei Mekonen Tekliye Mingsheng Dong College of Food Science and Technology Nanjing Agricultural University1 Weigang RoadNanjingJiangsu 210095China

Fungi contamination is an important factor affecting the quality and commercial value of fermented milk.Vanillin is known as a safe and efficient natural antimicrobial additive with great potential value as a food bio-preservative.In this study,the microbiological quality of fermented milk of different brands retailed in China and the antimicrobial activity of Vanillin were investigated.A total of 27 fermented milk samples were purchased and evaluated.Fungal isolates obtained were characterized by DNA sequencing of the internal transcribed spacer(ITS)region.The effects of Vanillin on the growth of fungi were studied by plate dilution method,radical colony diameter,and mycelium biomass.The result showed that 14.8%of the samples were contaminated with three different species of fungi with Cladosporium spp.being the most predominant fungal contaminant.The study further showed that Vanillin had significant inhibitory activity against the growth of the fungi species.The cell number,radical colony diameter,and the mycelium biomass of the fungal contaminant were significantly reduced by the inhibitory action of the Vanillin.The study thus provides reliable data evidence that will help relevant stakeholders in the fermented milk industries to improve their quality control strategies and consider Vanillin as a bio-preservative with the potential to increase the shelf-life and safety of fermented milk.

关键词： Fermented milk FungiInternal transcribed spacer Vanillin Antimicrobial activity

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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(A.flavus),the susceptibilities of A.flavus to Vanillin and its isomers(o-Vanillin,2-hydroxy-4-methoxybenzaldehyde(HMB),2-hydroxy-5-methoxybenzaldehyde)and the possible antifungal mechanisms have been investigated.All 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 aldehydes.Effects 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)staining.The results showed that HMB exerted the strongest antifungal and fungicidal effects on the growth of A.flavus.The four volatile aldehydes had little influence on cell wall integrity after 3-hour treatment,however,they could strongly damage the cell membrane integrity.All the four volatile aldehydes could effectively prevent the growth of A.flavus on peanut seeds.The 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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Studies on the Interaction Between Vanillin and β-Amyloid Protein via Fluorescence Spectroscopy and Atomic Force Microscopy

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Chemical Research in Chinese Universities 2016年第2期32卷 172-177页

作者： SONG Shengmei MA Xuewen ZHOU Yehong XU Maotian SHUANG Shaomin DONG Chuan Institute of Environmental Science Shanxi University Taiyuan 030006 P. R. China Key Laboratory of Biomolecular Recognition and Sensing of Shangqiu Normal University Shangqiu 476000 P. R. China

β-Amyloid（Afl） plaques and intracellular neurofibrillary lesions in the brain are markers of Alzheimer＇s disease（AD）. The ability to safely decrease Aft concentrations is potentially important as a preventive strategy for AD. The interactions between Vanillin and Aft polypeptide were investigated via fluorescence spectroscopy and atomic force microscopy（AFM）. The results of fluorescence and synchronous spectroscopies illustrate that the intrinsic fluorescence of tyrosine（Tyr） residues in Aβ1-42 aggregates can be quenched strongly upon the formation of vanil- lin-Aβ-42 complex. Thioflavine T（ThT）-induced fluorescence changes indicated that Aβ1--42 aggregates could be disaggregated by Vanillin, and the AFM images of Aβ1-42 enunciated the depolymerization of Aβ1-42 aggregates by Vanillin in a dose-dependent manner. Vanillin may be a potential pharmacological agent for the treatment of AD.

关键词： β-Amyloid fibril Vanillin Interaction Fluorescence spectroscopy Atomic force microscopy

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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 chemicals.Herein,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 Vanillin.Characterizations 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 support.This 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 scope.The 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 interactions.This 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

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