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JOURNAL OF APPLIED POLYMER SCIENCE · 2023 ·Vol. 140 ·期 43 ·e54594 · IF 3

Dihydromyricetin encapsulated gelatin-dialdehyde-β-cyclodextrin hydrogels for antibacterial application

Aomei Zhang,Tingting Wang,Feng Huang,Minghui Yang,Xingxing Jiang,Xiang Chen

Dihydromyricetin (DMY), a natural flavonoid compound, has garnered extensive research interests owing to its high pharmaceutical value with antioxidant, anticancer and antimicrobial properties. However, its intrinsic limitation of low water-solubility and poor stability severely obstructs its biomedical applications. Herein, a dynamic imine cross-linking strategy to assemble DMY/DA-β-CD/gelatin hydrogel (DDG) is reported, with the aim of enhancing DMY bio-efficacy and achieve a synergistic antibacterial effect. DMY can be wrapped by the amphiphilic dialdehyde-β-cyclodextrin (DA-β-CD) to form an inclusion compound (DMY/DA-β-CD), significantly increasing its water-solubility without compromising its sustainable release. Furthermore, the Schiff base reaction between DA-β-CD and gelatin drive the formation of DDG hydrogel featuring viscoelastic, self-healing and injectability properties, serving as a DMY delivery platform. DMY and DA-β-CD synergistically inhibited bacterial proliferation, enabling a broad-spectrum antibacterial effect against Escherichia coli and Staphylococcus aureus with over 90% inhibition and good biocompatibility. Our work provides a paradigm for self-assembling DMY inclusion compound into a hydrogel to improve the bio-efficacy of DMY, so that the hydrogel can be used as a carrier for hydrophobic drug delivery with promising applications in the biomedical field.

CAS / MDL: 7585-39-9 9000-70-8
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BIOORGANIC CHEMISTRY · 2023 · IF 5.1

Discovery of small molecule β-catenin suppressors that enhance immunotherapy

Xuchen Feng,Jun Ge,Hui Fu,Lin Miao,Feng Zhao,Jingyu Wang,Yujiao Sun,Yingpeng Li,Yunfei Li

Small molecules directly downregulating β-catenin could potentially offer a more effective therapeutic approach for combating against cancer stem cells, as compared to targeting the downstream components of the Wnt/β-catenin pathway. The challenge, however, lies in the fact that very few β-catenin suppressors have proven clinically effective, leaving a significant gap in medical solutions. Given that E-cadherin has a natural affinity for β-catenin, it stands to reason that agents designed to increase E-cadherin expression might provide an alternative method of regulating β-catenin levels. In this study, we report our discovery of DSS-C12 and DSS-B8, specific ester-based drugs derived from Dan-Shen-Su (DSS) extracted from the herb Salvia miltiorrhiza . Remarkably, these compounds display a potent ability to downregulate β-catenin, while also improving overall survival in post-surgery mice. Additionally, when these drugs are used in combination with PD-L1 checkpoint blockade, they stimulate enhanced systemic immune responses leading to significant suppression of primary tumor growth. In-depth mechanistic studies revealed that DSS-B8 functions as a vitamin D receptor agonist without inducing hypercalcemic effects. Collectively, our findings indicate that DSS-derived small molecules have considerable potential as clinically viable therapeutic strategies for β-catenin deactivation.

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COLLOIDS AND SURFACES B-BIOINTERFACES · 2017 · IF 3.887

Evaluation of molecular chaperone drug function: Regorafenib and β-cyclodextrins

Xiurong Hu,Mengying Sun,Yang Li,Guping Tang

Regorafenib (RG) was an oral multi-kinase inhibitor with poor water solubility. In order to enhance the drug’s solubility, dissolution and bioavailability, the binary molecular chaperone drug between RG and β-cyclodetrin (β-CD) had prepared by co-crystallization. The structure of RG-β-CD was characterized by thermal analysis, powder X-ray diffraction, infrared spectroscopy and nuclear magnetic resonance. Phase-solubility study revealed the higher solubility and complexing ability of β-CDwith RG.The solubility and dissolution of RG-β-CD was significantly enhanced in pH 1.2 medium, pH 6.8 PBS buffer solution and distilled water compared to RG. In vivo distribution and antitumor studies revealed that the bioavailability of RG-β-CD was increased when β-CD mated with RG. Therefore, these findings could provide a suitable pharmaceutical dosage to enhanced therapeutic activity.

CAS / MDL: 7585-39-9
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ACS Applied Bio Materials · 2021 · IF 0

Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging

Huan Xu,Fang Xie,Yiwen Lu,Pingdong Wei,Jie Cai

Fluorescent materials span multiple applications from biological probes and chemical sensing to optoelectronic systems. Although great efforts have been made toward developing classes of fluorescent materials, 100,000+ traditional fluorescent dyes still suffer from the obstacle of aggregation-caused quenching (ACQ). Thus, designing fluorescent materials with excellent optical performance from ACQ luminogens remains challenging. In this work, we prepared fluorescent amphiphilic quaternized β-chitin (QC-F) via nucleophilic addition between the amino groups of QC and isothiocyanate groups of fluorescein isothiocyanate (FITC). Due to the covalent anchoring of the QC backbone, steric hindrance of the bulky acetamido groups, electrostatic repulsion of the quaternary ammonium groups, and homogeneous distribution of FITC units, the FITC units were spatially and electronically isolated, and the QC-F series exhibited unique fluorescent behaviors. The QC-F series could be used to observe their interactions with microbial cells through fluorescence imaging to gain insights into the QC antibacterial mechanism. Moreover, with their favorable cytocompatibility, the QC-F series are also suitable for cell imaging. Thus, the present work will broaden the applications of chitin and conventional ACQ luminogens.

CAS / MDL: 3326-32-7
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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY · 2019 · IF 4.833

Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives

Liyu Zhao,Nannan Sun,Linfeng Tian,Yin Sun,Yixuan Chen,Xinran Wang,Shizhen Zhao,Xin Su,Dongmei Zhao,Maosheng Cheng

A series of β-azole-phenylacetone derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible fungal infections and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against five susceptible strains and five fluconazole-resistant strains. Antifungal activity tests showed that most of the compounds exhibited excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03–1  μ g/mL. Compounds with R 1  = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1–8  μ g/mL. Compounds with R 1  = H or 2-F (such as 15a , 15o , 15p ) displayed moderate to good antifungal activity against fluconazole-resistant strains 632 , 901 and 904 with MIC values in the range of 0.125–4  μ g/mL. Notably, 15o and 15ae exhibited antifungal activity against five susceptible strains and five fluconazole-resistant strains. Preliminary mechanistic studies showed that the potent antifungal activity of compound 15ae stemmed from inhibition of C. albicans CYP51 . Compounds 15o , 15z and 15ae were nearly nontoxic to mammalian A549 cells.

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Biochemistry and Biophysics Reports · 2021 · IF 0

β-elemene combined with temozolomide in treatment of brain glioma

Xiaomin Zhang,Yidan Chen,Ju Yao,Yingxin Zhang,Mengying Li,Bo Yu,Kaifeng Wang

Temozolomide (TMZ) is a widely used chemotherapeutic agent for malignant glioma. β-Elemene has been reported to have the ability of passing through the blood-brain barrier and reverse multidrug resistance. In the present study, transport of drugs through the in vitro blood-brain barrier (BBB) model also suggested that β-elemene can assist in TMZ transport to the brain. Plasma and brain pharmacokinetics demonstrated that when β-elemene is used in combination with TMZ, the metabolic rate of TMZ in plasma is slowed, and mean residence time (MRT) in brain is prolonged. The brain tissue distribution at 1 h indicated that the combination of TMZ and β-elemene promotes the distribution of β-elemene in the brain but slightly reduces the distribution of TMZ in the brain. Furthermore the antitumor effect and toxicity in vivo were also investigated. The combination of β-elemene and TMZ was well tolerated and significantly inhibited tumor growth in glioma xenografts. In summary, the present study indicates a synergistic antitumor effect of β-elemene and TMZ in glioma.

CAS / MDL: 54-21-7
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Materials Science & Engineering C-Materials for Biological Applications · 2020 · IF 5.88

Nanosized-Ag-doped porous β-tricalcium phosphate for biological applications

Junjie Yuan,Baoxin Wang,Chen Han,Xiaoyan Huang,Haijun Xiao,Xiao Lu,Jianxi Lu,Dong Zhang,Feng Xue,Youzhuan Xie

The treatment of infectious or potentially infective bone defects remains a major problem in clinical practice. Silver has the ability to potentiate antibiotics against resistant bacterial strains. In order to reduce the risk of long-term infections, it is necessary for the biomaterial scaffold to release Ag + in a controlled manner during the entire healing process. In this study, given the antimicrobial characteristics of nanosized Ag (NSAg), we synthesized β-tricalcium phosphate (β-TCP) doped with 5 and 10 wt% NSAg (5 wt% NSAgTCP and 10 wt% NSAgTCP, respectively). The NSAgTCP composites exhibited similar macroporous structures to pure β-TCP. The NSAgTCP samples were examined by scanning electron microscopy at 10,000-times magnification, which revealed that silver was still present at the nanometer scale. X-ray diffraction revealed that silver does not change the crystalline properties of β-TCP. In addition, we observed that the mechanical strength of NSAgTCP increased with increasing amounts of added Ag. The antibacterial, physical, and chemical properties of NSAgTCP were investigated in vitro. We found that NSAgTCP is effective at inhibiting the growth of Staphylococcus aureus and Escherichia coli and is not cytotoxic to human bone marrow mesenchymal stem cells. Moreover, it does not hinder liver or kidney function when tested in vivo. As the bioceramic degrades, Ag ions are slowly released and new bone is formed. No significant cytotoxic effects were observed even when 10 wt% NSAgTCP was used. NSAgTCP has the ability to simultaneously repair bone defects and act as an anti-infective agent; hence, we expect that this material, with its good bone-repairing and anti-infective properties, will find wide spread use as a novel bone substitute.

CAS / MDL: 9011-14-7 67-64-1
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POLYMER BULLETIN · 2020 ·Vol. 78 ·期 6 ·2993-3008 · IF 2.014

Synthesis and characterization of β-cyclodextrin centered polysiloxane star polymers

Chen Yuying,Chen Juan,Li Jianping,Jiang Jingzhe,Fang Ziang,Lin Xing,Jiang Yan,Zhang Hongwen,Liu Hongbo

In this study, a macroinitiator of β-CD-ONa was prepared by a substitution reaction of β-cyclodextrin (β-CD) with sodium (Na). The macroinitiator was then used in the ring-opening polymerization of octamethylcyclotetrasiloxane (D 4 ) to obtain a star polymer, in which β-CD is the core and polysiloxane is the arm. FTIR, NMR, TGA, CA, etc., were used to characterize the structure and properties of star polymers. The results indicated that there were four polysiloxane arms attached to each β-CD core, and the star polymer had good thermal stability. With the increase in D 4 monomer dosage, the hydrophobicity of the star polymer slightly improved, but the reaction time had no significant effect on hydrophobicity. When the star polymer was coated onto polyethylene terephthalate membrane, the transmittance increased from 87.6% to 92.8%, and the haze did not change significantly. Furthermore, the surface of star polymer porous membranes was prepared by the static breath-figure method using n -hexane as solvent at 30 °C. The results showed uniform pore distribution and increased hydrophobicity.

CAS / MDL: 7440-23-5
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JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY · 2021 ·Vol. 102 ·期 1 ·109-116 · IF 1.633

A β-cyclodextrin/graphene oxide hybrid gel with smart responsiveness

Ma Mingfang,He Zirui,Zhou Shumin,Liu Xuyan,Zhao Min,Wang Xinyan,Liu Huan,Hao Aiyou

Abstract Even through gels based on the polymer modified with β-cyclodextrin have been researched widely, there are only few studies focus on gels based on β-cyclodextrin directly. In this study, we report a novel smart responsive β-cyclodextrin/graphene oxide hybrid gel. Graphene oxide can be loaded into the network of β-cyclodextrin gel successfully by co-assembly method, which can be supported by transmission electron microscope and scanning electron microscope. Hydrogen bonding is the main driving force in gel formation from fourier transform infrared spectroscopy and X-ray diffraction analysis. More interesting is that β-cyclodextrin/graphene oxide hybrid gel can respond to multiple stimuli sensitively. The change of temperature can induce the formation and deformation of gel reversibly. Besides, gel will collapse with the addition of different metal ions including Na + , K + , Zn 2+ , Ba 2+ and Fe 3+ . Hence, this composite gel is a smart responsive material, may have great potential applications in intelligent material fields. Graphic Abstract In this study, we report a novel smart responsive β-cyclodextrin/graphene oxide hybrid gel. Graphene oxide can be loaded into the network of β-cyclodextrin gel successfully by co-assembly method, which can be supported by transmission electron microscope and scanning electron microscope. Hydrogen bonding is the main driving force in gel formation from fourier transform infrared spectroscopy and X-ray diffraction analysis. More interesting is that β-cyclodextrin/graphene oxide hybrid gel can respond to multiple stimuli sensitively. The change of temperature can induce the formation and deformation of gel reversibly. Besides, gel will collapse with the addition of different metal ions including Na + , K + , Zn 2+ , Ba 2+ and Fe 3+ . Hence, this composite gel is a smart responsive material, may have great potential applications in intelligent material fields.

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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2019 ·Vol. 55 ·期 5 ·1900-1908 · IF 2.281

Structure and thermal properties of β-sitosterol-beeswax-sunflower oleogels

Min Pang,Xiuxiu Wang,Lili Cao,Zhaojuan Shi,Zheng Lei,Shaotong Jiang

Summary Oleogels of β-sitosterol (Sit) and beeswax (BW) were combined at varying ratios (w/w) and added to sunflower oil (SFO) at concentrations of 10 g per 100 g and 20 g per 100 g oil to prepare oleogels (Sit/BW/SFO). Structural and thermal properties were characterised and results showed that the hardness and enthalpy of oleogels were affected by the amount of β-sitosterol and beeswax in the oleogelator combination (Sit/BW, w/w). Oleogels with beeswax as the only oleogelator (Sit0/BW10) had the highest hardness and maximum enthalpy change. Gel network form was influenced by the crystalline behaviour of the oleogelator, and Sit0/BW10-oleogel was densely packed, spherical and white while Sit10/BW0-oleogel displayed a needle shape. X-ray diffraction patterns showed that the oleogel width of the crystals and D- spacing increased with increasing amounts of β-sitosterol and the FTIR spectra revealed that oleogels formed via non-covalent bonding and may be stabilised with physical entanglements.

CAS / MDL: 83-46-5
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FOOD HYDROCOLLOIDS · 2019 · IF 5.839

Hericium Erinaceus β-glucan modulates in vitro wheat starch digestibility

Tao Feng,Mengzhu Shui,Zhongqiu Chen,Haining Zhuang,Wenxin Wang,Yan Yang,Jingsong Zhang,Ran Ye

The mechanism of Hericium Erinaceus β-glucan inhibiting starch digestion has been seldom studied. In this study, the mechanism of inhibited starch digestion was explored in the context of interaction between β-glucans of different molecular weights (Mw) and starch. The rates of starch digestion and glucose release decreased with increased Hericium erinaceus β-glucan ( HEBG ) Mw. HEBG reduced leached amylose but increased peak, minimum and final viscosity. In laser confocal scanning microscopy experiments, HEBG was observed to coat the starch. The mechanisms of HEBG modulating glucose release and starch digestion might be due to increase system viscosity and coat starch. We address the specific mechanisms by which starch granules interact with β-glucan molecules and thus contribute to further applications to develop starchy foods with low predicted Glycemic Index (pGI).

CAS / MDL: 9000-90-2
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RSC Advances · 2015 ·Vol. 5 ·期 63 ·51364-51370 · IF 3.84

Preparation of a novel anti-fouling β-cyclodextrin–PVDF membrane

Zongxue Yu,Yang Pan,Yi He,Guangyong Zeng,Heng Shi,Haihui Di

As part of this work, polyvinylidene fluoride (PVDF) membranes were prepared via a phase inversion method. A novel β-cyclodextrin (β-CD)–PVDF membrane was prepared via an interfacial reaction, using Trimesoyl Chloride (TMC) and β-CD as cross-linking and modification agents, respectively. The membranes were modified by a simple dip-coating method. The results of comparison between the modified and unmodified membranes by attenuated total reflectance Fourier transform infrared spectroscopy (FTIR-ATR) and X-ray photoelectron spectroscopy (XPS) methods confirmed successful grafting of β-CD on the membrane surfaces. The morphology of the membrane was investigated by scanning electron microscopy (SEM) and atomic-force microscopy (AFM). The roughness of PVDF membranes increased after their surfaces were grafted with β-CD. It was also found that β-CD–PVDF membranes had higher permeate flux and hydrophilicity than those of the pristine PVDF membranes. Furthermore, in protein fouling experiments, bovine serum albumin (BSA) was used as a protein model solution. Modified membranes exhibited a higher flux recovery ratio. The experiment showed that the anti-fouling performance of β-CD–PVDF membranes was more effective in reducing the irreversible membrane fouling. The results of this study hold promise for useful applications of β-CD–PVDF membranes in membrane separation areas.

CAS / MDL: 4422-95-1
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