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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

Enhancement of Galloylation Efficacy of Stigmasterol and β-Sitosterol Followed by Evaluation of Cholesterol-Reducing Activity

Shanshan Wang,Kai Ye,Tong Shu,Xiuwen Tang,Xiu Jun Wang,Songbai Liu

In this study, incorporation of gallic acid into typical phytosterols (β-sitosterol and stigmasterol) through Steglich esterification was optimized employing the protection and deprotection strategy. A novel mechanism leading to side esterification was discovered. Complication of the phenolic hydroxyl groups and side reactions were successfully reduced under the optimized conditions. The structural identity and purity of galloyl stigmasterol and galloyl β-sitosterol were confirmed by NMR, FT-IR, and HPLC-MS. Evaluation of galloyl β-sitosterol and galloyl stigmasterol revealed their excellent antioxidant and cholesterol-reducing activities. Significant enhancement of cholesterol-reducing activity by galloylation was unveiled especially for β-sitosterol. Galloyl β-sitosterol had slightly better antioxidant activity at ambient temperature and better cholesterol-reducing activity. Molecular modeling suggested that a subtle difference of galloyl β-sitosterol and galloyl stigmasterol in activities could be attributed to variation of molecular rigidity and conformation. The excellent properties of galloyl β-sitosterol and galloyl stigmasterol suggested their great potential application in the food industry.

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Food Analytical Methods · 2018 ·Vol. 12 ·期 3 ·697-704 · IF 2.245

Monolithic Material Prepared with Nanodiamond as Monomer for the Enrichment of β-Sitosterol in Edible Oil

Cui Beijiao,Liu Haiyan,Yu Huan,Pang Xiaoya,Yan Hongyuan,Bai Ligai

In this paper, a hybrid monolithic column with modified nanodiamond and 1-dodecene as co-monomers was prepared and applied to the online enrichment and purification of β-sitosterol in edible oil. The obtained monolithic column was characterized by scanning electron microscopy (SEM) and nitrogen adsorption–desorption isotherm measurement, which indicated that the monolith possessed characteristics of porous structure and high permeability. Under the optimum conditions for extraction and determination, the linear regression coefficient for β-sitosterol was 0.998; the limit of detection (LOD) and the limit of quantitation (LOQ) were 3.0 μg mL −1 and 10.0 μg mL −1 , respectively; the relative standard deviation (RSD) of intra-day and inter-day assays for four edible oils were 2.33–6.58% and 3.24–6.94%, respectively. The recovery was in the range of 89.6–105.5%. The results showed that the hybrid monolithic column with high selectivity and good permeability were successfully used as online solid-phase extraction (SPE) column for determination of β-sitosterol in edible oil.

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CARBOHYDRATE POLYMERS · 2018 · IF 5.158

β-Cyclodextrin modified electrospinning fibers with good regeneration for efficient temperature-enhanced adsorption of crystal violet

Shuyue Jia,Dongyan Tang,Jing Peng,Zhaojie Sun,Xu Yang

Novel β-cyclodextrin modified fibers with highly insoluble infraction and temperature enhanced adsorption performance were fabricated via electrospinning technology and followed thermo-crosslinking. The fabricated fibers were characterized by FT-IR, 1 H NMR, TGA and SEM. In the fibers, β-CD was crosslinked with methacrylic acid (MAA) units to maintain morphologies of fibers and further be utilized for the adsorption of Crystal Violet through complex and electrostatic interaction. In particular, N -isopropyl acrylamide (NIPAM) units were introduced to create thermo-responsively hydrophobic internal cavity within the swelling fibers at high temperatures. Benefiting from that, the maximum adsorption amount could reach to 1253.78 mg g −1 , enhanced by 20% than that at low temperatures. The adsorption data of the fibers fit well the pseudo-second-order model and Langmuir isotherm model. Moreover, the fibers could maintain high regeneration efficiency even after four adsorption-desorption cycles. These results indicated the practical application values of the β-cyclodextrin modified fibers in the dye wastewater treatment field.

CAS / MDL: 7585-39-9 548-62-9
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LIFE SCIENCES · 2019 · IF 3.448

Cancer-associated fibroblast regulate proliferation and migration of prostate cancer cells through TGF-β signaling pathway

Dai-Yu Sun,Jia-Qi Wu,Zhi-Heng He,Ming-Fang He,Hong-Bin Sun

Aims Prostate cancer (PCa) incidence rates are rising in China currently. Cancer-associated fibroblasts (CAFs), as a major component of tumor microenvironment, are crucial for tumor progression. This study was aimed to explore the promotion effect of patient-derived CAFs on the proliferation and migration of prostate cancer cells. Main methods CAFs were isolated from tumor tissues of PCa patients. The promotion effect of CAFs on the proliferation and migration of PC-3 and LNCaP cells were evaluated in vitro and in vivo . The concentration of TGF-β1 was measured by Luminex assay. The blocking activity of LY2109761 on the promotion effect of CAFs was also evaluated. Key findings CAFs could significantly promote the proliferation and migration of PC-3 and LNCaP cells both in vitro and in vivo . TGF-β1 was identified as a highly increased factor in CAFs-CM compared with the normal culture medium of these two cancer cell lines. TGF-β receptor inhibitor LY2109761 could suppress the CAFs-induced cellular proliferation and migration of PC-3 cells but not LNCaP cells. Significance Our study suggested a crucial role for CAFs and TGF-β signaling in the progression of PCa. Zebrafish xenograft model was an ideal animal model for the study of CAFs and cancer cell interaction.

CAS / MDL: 700874-71-1
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ChemNanoMat · 2019 ·Vol. 5 ·期 10 ·1311-1316 · IF 3.431

Luminescent CH3NH3PbBr3/β-Cyclodextrin Core/Shell Nanodots with Controlled Size and Ultrastability through Host-Guest Interactions

Sihui Huang,Ting Zhang,Chunli Jiang,Ruijuan Qi,Chunhua Luo,Ye Chen,Hechun Lin,Jadranka Travas-sejdic,Hui Peng

Graphical Well-defined core/shell structured CH 3 NH 3 PbBr 3 /β-cyclodextrin nanodots are successfully prepared via host-guest interaction between β-cyclodextrin and hexylamine. The nanodots show high luminescence with photoluminescence quantum yields of 89.7% in solution and 38.0% in solid state. They also exhibit superior stability against water, heat and UV light due to the formation of a β-CD shell, which gives them great potential for optoelectrical and biological applications. Luminescent lead halide perovskite nanocrystals (LHP NCs) have attracted great attention. This work reports the synthesis of well-defined core/shell structured CH 3 NH 3 PbBr 3 /β-cyclodextrin (MAPbBr 3 /β-CD) nanodots via host-guest interaction between β-cyclodextrin and hexylamine. The MAPbBr 3 /β-CD nanodots show high luminescence with photoluminescence quantum yields (PLQYs) of 89.7% in solution and 38.0% in solid state. The MAPbBr 3 /β-CD nanodots have superior stability in water, under heat and UV light exposure due to the formation of a β-CD shell, which gives them great potential for optoelectrical and biological applications.

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ANALYTICAL CHEMISTRY · 2019 · IF 6.35

Efficient Modulation of β-Amyloid Peptide Fibrillation with Polymer Nanoparticles Revealed by Super-Resolution Optical Microscopy

Zhongju Ye,Lin Wei,Yiliang Li,Lehui Xiao

β-Amyloid peptide (Aβ) aggregation is the essential hallmark of neurodegenerative disorders such as Alzheimer’s disease. Efficient inhibitors are highly desired for the prevention of Aβ assembly that has been considered as the primary therapeutic strategy for neurodegenerative diseases. Apart from this, visualization of the aggregates and morphology at high spatial resolution is widely considered of crucial significance on biological treatment. In this work, we have developed small-sized (with diameter of ∼4.7 nm) and positively charged fluorescent conjugated polymer nanoparticles (CPNPs) with strong inhibition effect on Aβ1–40 peptides fibrillation. Interestingly, the CPNPs also possess excellent photophysical properties, including high photon counts, robust blinking, and repetitive fluorescence switching, that are especially suitable for localization-based super-resolution imaging. Spatial resolution of ∼20 nm for these blinking CPNPs is readily achieved. According to the optical microscopic results, it was found that binding of CPNPs to the terminal of seed fibrils can effectively inhibit the fibrillation process. Owing to these attractive biological and unique photophysical properties, the small-sized CPNPs show high potential in a variety of super-resolution based biological applications.

CAS / MDL: 81-88-9
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ELECTROCHIMICA ACTA · 2018 · IF 5.116

Voltammetric enantiomeric differentiation of tryptophan by using multiwalled carbon nanotubes functionalized with ferrocene and β-cyclodextrin

Xiaohui Niu,Xing Yang,Zunli Mo,Ruibin Guo,Nijuan Liu,Pan Zhao,Zhenyu Liu,Meixuan Ouyang

Two types of ferrocene-functionalized multiwalled carbon nanotubes (MWCNTs) are described. The first was obtained by adsorption of ferrocene (Fc) on MWCNTs via π-π stacking and is referred to as Fc/MWCNTs. The second was prepared via a conjugation reaction between ferrocenecarboxylic acid and aminated MWCNTs to result on covalently modified MWCNTs referred to as MWCNT-Fc. MWCNT/Fc has a better conductivity than MWCNT-Fc. But electrochemical recognition results clearly showed the MWCNTs-Fc/β-CD/GCE can exhibit better chiral recognition ability to tryptophan enantiomers than β-CD/Fc/MWCNTs/GCE. By combining the merits of β-cyclodextrin (β-CD) and MWCNTs-Fc, an electrochemical sensor for l -tryptophan was obtained. Its characterizations by SEM, TEM , TGA , Raman spectroscopy and XPS showed that the Fc/MWCNTs and MWCNTs-Fc have successfully been synthesized. Enantioselective recognition was accomplished by differential pulse voltammetry . Tryptophan enantiomers can be differentiated with an enantioselectivity coefficient (I D-Trp /I L-Trp ) of 5.78. Moreover, the chiral recognition mechanism of β-CD recognition tryptophan enantiomers was proposed.

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JOURNAL OF CHROMATOGRAPHY A · 2019 · IF 3.858

High uptake carboxyl-functionalized porous β-cyclodextrin polymer for selective extraction of lysozyme from egg white

Hui-Ling Duan,Qi-Le Niu,Jun Wang,Shi-Yao Ma,Jing Zhang,Zhi-Qi Zhang

Lysozyme is widely used in medical, food and industrial fields due to its bacteriolytic effect and thus it is significant to design and develop a specific adsorbent with high adsorption capacity and selectivity for lysozyme. Inspired by the high uptake capacity of tetrafluoroterephthalonitrile-crosslinked porous β-cyclodextrin polymers (P-CDPs) and the noncovalent interaction between lysozyme and carboxyl groups, the carboxyl-functionalized P-CDPs (P-CDP-COO − ) were synthesized by base-catalysed hydrolysis of nitrile group in P-CDPs to carboxyl. Porous structure, large extent of carboxylic functional groups, cyclodextrin's preventing aggregation, and negatively charged make P-CDP-COO − possess an outstanding adsorption capability for lysozyme. The maximum saturated adsorption capacity reaches 1520 mg g −1 , which is much better than the parent polymer and other reported materials. The as-prepared material was successfully utilized for the selective extraction of lysozyme from egg white.

CAS / MDL: 76-05-1
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NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 10 ·4282-4290 · IF 3.069

A new strategy for the construction of β-cyclodextrin-based magnetic nanocarriers: a molecular docking technique

Pengfei Chen,Shun Yao,Xianggui Chen,Yukun Huang,Hang Song

Herein, Fe3O4 magnetic nanoparticles (CD-MNPs, CM-CD-MNPs and MA-CD-MNPs) surface-modified with β-cyclodextrin (β-CD) and its derivatives, carboxymethyl-β-CD (CM-β-CD) and maleated-β-CD (MA-β-CD), respectively, were successfully synthesized via a layer-by-layer method, and the resulting nanocarriers possessed good magnetic character and biocompatibility. Using carmofur as a model drug, the results of loading and release experiments indicate that these magnetic nanocarriers can serve as targeted drug delivery systems in the future, and the loading capacity and release behaviour are highly dependent on the surface properties of the nanocarriers. Based on the molecular docking technique, for the first time, the correlation between the lowest binding energy (ΔGbinding) of the inclusion complex and the loading and release performances of the corresponding magnetic nanocarriers was investigated to establish a method to fast select an effective β-CD-based surface coating for the construction of high-performance magnetic nanocarriers. The results revealed a ΔGbinding-dependent manner demonstrating that the magnetic nanocarriers surface modified with the cyclodextrin unit with a larger absolute value of ΔGbinding would possess better loading and release performances. This encouraging result suggested that the ΔGbinding obtained from molecular docking could provide a significant reference for the fast selection of an effective surface coating during the construction of high-performance β-CD-based magnetic nanocarriers. Although it is clear that the present study should be considered only as a preliminary study, the good results obtained herein demonstrate the feasibility of this new type of approach.

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INTERNATIONAL JOURNAL OF HYDROGEN ENERGY · 2019 · IF 4.084

One-pot production of γ-valerolactone from furfural using Zr-graphitic carbon nitride/H-β composite

Tingwei Zhang,Yijuan Lu,Wenzhi Li,Mingxue Su,Tao Yang,Ajibola Ogunbiyi,Yongcan Jin

In order to efficiently produce γ-valerolactone (GVL) from furfural , a Zr-graphitic carbon nitride/H-β composite (Zr CN/H-β) had been simply prepared via an impregnation-calcination protocol. The morphology and structure, elemental information, and total acid and base properties of the Zr CN/H-β and related catalysts (H-β, CN/H-β, and Zr/H-β) were determined by SEM, TEM , X-ray photoelectron spectroscopy (XPS), and temperature-programmed desorption (TPD-NH 3 , CO 2 ) characterizations. The effects of reaction temperature and time, and the furfural dosage on GVL production as well as the recyclability of Zr CN/H-β were investigated. With a catalyst/furfural dosage of 0.1/0.22 g, the Zr CN/H-β produced a remarkable 76.5% of GVL yield at 160 °C in 18 h using isopropanol as the solvent. The results of NH 3 , CO 2 -TPD experiments indicated that the simultaneous introduction of Zr species and carbon nitride onto H-β formed new types of acid and base, which should be responsible for the high efficient conversion of furfural to GVL. Additionally, the recyclability of Zr CN/H-β was reasonable.

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DRUG DELIVERY · 2019 · IF 3.829

SYL3C aptamer-anchored microemulsion co-loading β-elemene and PTX enhances the treatment of colorectal cancer

Xiaorong Zhou,Chuanpei Cao,Nan Li,Shaofei Yuan

The aim of this study is to construct a SYL3C aptamer-anchored microemulsion based on β-elemene and PTX (SYL3C/EP-MEs) for enhancement on colorectal cancer therapy. Such microemulsion is consist of encapsulated drugs (β-elemene and PTX), tumor targeting ligand (3’-end thiolated SYL3C aptamer), thiol conjugated site (maleimide-modified PEGylated 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine, mal-DOPE-PEG), pH-sensitive component (DOPE) and other necessary excipients. SYL3C/EP-MEs showed a spherical particle with an average particle size around 30 nm and a high encapsulation efficiency (>80%) for both drugs. β-elemene and PTX could be released controllably from SYL3C/EP-MEs as pH values changed. SYL3C/EP-MEs displayed a selective affinity to HT-29 cells, leading to an obvious increase in cellular uptake, cell apoptosis and cytotoxicity. In the HT-29 tumor xenograft-bearing nude mice model studies, SYL3C/EP-MEs showed an overwhelming tumor growth inhibition, the longest survival time and the lowest systemic toxicity among all the treatments. The potential mechanism of enhanced anti-cancer ability was probably associated with the induction of M1 macrophage polarization, the downregulation of mutant p53 protein and the reduction of bcl-2 protein expression. Collectively, the microemulsion codelivery of β-elemene and PTX using functionalization with SYL3C aptamer provides a novel approach for combinational colorectal cancer-targeted treatment.

CAS / MDL: 3326-32-7 4792-15-8
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Polymers · 2019 ·Vol. 11 ·期 9 ·1417 · IF 3.164

Preparation of Modified Chitosan Microsphere-Supported Copper Catalysts for the Borylation of α,β-Unsaturated Compounds

Wei Wang,Zufeng Xiao,Chaofan Huang,Kewang Zheng,Yin Luo,Yumin Dong,Zitong Shen,Wei Li,Caiqin Qin

Chitosan microspheres modified by 2-pyridinecarboxaldehyde were prepared and used in the construction of a heterogeneous catalyst loaded with nano-Cu prepared by a reduction reaction. The chemical structure of the catalyst was investigated by Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), and X-ray Photoelectron Spectroscopy (XPS). Under mild conditions, such as no ligand at room temperature, the catalyst was successfully applied to catalyze the borylation of α,β-unsaturated receptors in a water-methanol medium, yielding 17%–100% of the corresponding β-hydroxy product. Even after repeated use five times, the catalyst still exhibited excellent catalytic activity.Keywords:chitosan microspheres;copper;organoboron compounds

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