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BIOORGANIC & MEDICINAL CHEMISTRY · 2022 · IF 3.461

Discovery of honokiol thioethers containing 1,3,4-oxadiazole moieties as potential α-glucosidase and SARS-CoV-2 entry inhibitors

Ting Xu,Jie-Ru Meng,Wanqing Cheng,Jia-Zheng Liu,Junyan Chu,Qian Zhang,Nannan Ma,Li-Ping Bai,Yong Guo

Honokiol, isolated from a traditional Chinese medicine (TCM) Magnolia officinalis , is a biphenolic compound with several biological activities. To improve and broaden its biological activity, herein, two series of honokiol thioethers bearing 1,3,4-oxadiazole moieties were prepared and assessed for their α -glucosidase and SARS-CoV-2 entry inhibitory activities. Among all the honokiol thioethers, compound 7l exhibited the strongest α -glucosidase inhibitory effect with an IC 50 value of 18.9 ± 2.3 µM, which was superior to the reference drug acarbose (IC 50  = 24.4 ± 0.3 µM). Some interesting results of structure–activity relationships (SARs) have also been discussed. Enzyme kinetic study demonstrated that 7l was a noncompetitive α -glucosidase inhibitor, which was further supported by the results of molecular docking. Moreover, honokiol thioethers 7e , 9a , 9e , and 9r exhibited potent antiviral activity against SARS-CoV-2 pseudovirus entering into HEK-293 T-ACE2 h . Especially 9a displayed the strongest inhibitory activity against SARS-CoV-2 pseudovirus entry with an IC 50 value of 16.96 ± 2.45 μM, which was lower than the positive control Evans blue (21.98 ± 1.98 μM). Biolayer interferometry (BLI) binding and docking studies suggested that 9a and 9r may effectively block the binding of SARS-CoV-2 to the host ACE2 receptor through dual recognition of SARS-CoV-2 spike RBD and human ACE2. Additionally, the potent honokiol thioethers 7l , 9a , and 9r displayed relatively no cytotoxicity to normal cells (LO2). These findings will provide a theoretical basis for the discovery of honokiol derivatives as potential both α -glucosidase and SARS-CoV-2 entry inhibitors.

CAS / MDL: 35354-74-6
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Particuology · 2023 · IF 3.5

Cross-linked α-amylase aggregates on Fe3O4 magnetic nanoparticles modified with polydopamine/polyethyleneimine for efficient hydrolysis of starch

Jiandong Cui,Xiuming Tang,Qingqing Ma,Yuyan Chang,Qunli Zhang,Shiru Jia

In this work α-amylase was immobilized on magnetic Fe 3 O 4 nanoparticles with polyethylenimine (PEI)/polydopamine (PDA) coating or 3-aminopropyl triethoxysilane (APTES) for the first time via adsorption–precipitation–cross-linking. Compared with the free α-amylase, the resultant magnetic cross-linked α-amylase aggregates (PEI/PDA-M-CLEAs and N-M-CLEAs) exhibited excellent thermal and storage stability as well as pH stability. After storage at 25 °C for 60 days, free α-amylase only retained 60% of its initial activity, while PEI/PDA-M-CLEAs and N-M-CLEAs retained 80% and 78% of their initial activities, respectively. Furthermore, N-M-CLEAs and PEI/PDA-M-CLEAs showed good reusability. After 6 repeated uses, PEI/PDA-M-CLEAs and N-M-CLEAs still maintained 65% and 62% of their initial activities, respectively. Especially, PEI/PDA-M-CLEAs and N-M-CLEAs exhibited higher starch hydrolysis efficiency than free α-amylase. The maximum dextrose equivalent (DE) values of starch hydrolysis by PEI/PDA-M-CLEAs and N-M-CLEAs reached 29.24% and 28.79% within 90 min, respectively. However, the maximum DE values of starch hydrolysis by the free α-amylase was only 27.89% even in 150 min. The magnetic cross-linked α-amylase aggregates could be introduced as effective biocatalyst for industrial applications in production of maltose syrups.

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Food Frontiers · 2023 · IF 9.9

Preparation and characterization of bioactive binary composite film based on gelatin–dextran incorporated with citronellal and α-tocopherol

Chenlinrui Yue,Fengjiao Fan,Yinji Chen,Yong Fang,Hongkai Xie

Biodegradable active packaging films with antimicrobial and antioxidant functions have received much attention due to the food safety and plastic pollution issues. This study prepared and characterized a novel bioactive binary composite film based on gelatin (Ge) and dextran (Dx) incorporated with various concentrations (0%, 0.3%, 0.6%, 0.9%, 1.2%, w/w) of citronellal (Cit) and α-tocopherol (Toc). The thickness, L *, b *, total color difference, water contact angle, opacity, and crystallinity of film significantly increased, whereas the film solubility, swelling degree, water vapor permeability, tensile strength, elongation at break, and a * of film significantly decreased with the increase of Cit and Toc concentrations. However, the addition of Cit and Toc had no significant effect on the film's moisture content and thermal stability. Fourier transforms infrared spectral pattern indicated that physical interactions (H-bonding) between biopolymer matrix and active fillers were formed. Scanning electron microscope images showed that the film added with active fillers had a rough surface and a spongelike cross-section structure compared to control film. Moreover, the release curves of Cit and Toc showed that the film in 95% ethanol solution had the longest release time. Furthermore, the film added with Cit and Toc effectively inhibited the growth of pathogenic and spoilage bacteria ( Shewanella putrefaciens and Escherichia coli ) and quenched the free radicals (2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)). Overall, it can be inferred that the Ge–Dx-based composite film incorporated with Cit and Toc is a potential antibacterial and antioxidant biodegradable material for food packaging applications to maintain food quality.

CAS / MDL: 1898-66-4 28752-68-3
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Piceid dicarboxylic acid esters as potent α-glucosidase inhibitors and antiglycation agents: Synthesis, spectroscopic and molecular docking studies

Hai-Xia Xu,Hui Chen,Zhong-Ping Yin,Qing-Feng Zhang

s Inhibition of α-glucosidase and non-enzymatic glycation is an effective approach to treat type 2 diabetes. Piceid (PI) is a potential α-glucosidase inhibitor and antiglycation agent found in many plant-based foods and herbs. To enhance the liposolubility and hypoglycemic effects of PI, two PI dicarboxylic acid esters were synthesized via enzymatic acylation in green solvents using dicarboxylic acids with hypoglycemic activity as acyl donors. Their structures were characterized by HPLC, HRMS, and 13 C NMR. Also, the antiglycation and α-glucosidase inhibitory effects of PI derivatives were investigated by enzymatic kinetics, CD, bovine serum albumin (BSA)-fructose model, FTIR, and molecular docking analysis. The results found that the introduction of dicarboxylic acid molecules significantly enhanced liposolubility, antiglycation, and α-glucosidase inhibitory activities of PI. The IC 50 values of two PI derivatives on α-glucosidase were nearly 9.9-fold and 16.2-fold lower than native PI, respectively. Moreover, the dicarboxylic acid moieties in PI derivatives induced the conformational changes of α-glucosidase, which made the secondary structure of α-glucosidase tighter, thus hindering the entry of substrates. Molecular docking results showed that PI derivatives could insert into the active pocket of α-glucosidase and interact with more key amino acid residues than PI. Also, PI derivatives could block the glycation sites of BSA.

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ACS Applied Nano Materials · 2023 · IF 5.9

Lamellar α-Zirconium Phosphate Nanoparticles Supported on N-Doped Graphene Nanosheets as Electrocatalysts for the Detection of Levofloxacin

Guangli Li,Xuan Wan,Yonghui Xia,Du Tuo,Xiaoman Qi,Tianyu Wang,Mohammad Mehmandoust,Nevin Erk,Quanguo He,Qing Li

The excessive use of levofloxacin (LEV) can lead to significant environmental pollution, while also damaging human health. The accurate detection of its concentration is therefore essential to protect both the environment and human health. Herein, we report the simple synthesis of α-zirconium phosphate supported on nitrogen-doped graphene nanosheets (α-ZrP/NG) and its application in the voltammetric determination of trace LEV in real samples. The surface morphology, microstructure, and electrochemical properties of α-ZrP/NG were investigated by microscopic and spectroscopic techniques. The analytical parameters, including the accumulation potential, accumulation time, loading volume, and buffer pH, were optimized to improve the electrocatalytic sensing performance of α-ZrP/NG. Owing to the synergetic interaction between α-ZrP and NG, the proposed sensor exhibited an excellent electrocatalytic activity for the electrical oxidation of LEV. In the range of 0.01–5.0 μM, the anodic peak current of LEV increased linearly with an increase in the LEV concentration, and the limit of detection was 2.6 nmol L–1. Finally, the LEV levels in wastewater, human serum, milk, and eye drop samples were determined by using the α-ZrP/NG system combined with a glassy carbon electrode to give satisfactory recoveries (98.48–103.2%), indicating that the prepared sensor demonstrates promise for use in environmental, food, and drug monitoring applications.

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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Highly efficient photo-degradation for tetracycline elimination in pharmaceutical wastewater by α-Fe2O3/V2O5/BC assisted peroxymonosulfate activation

Junfei Liu,Yue Zhang,Yingbo Dong,Zeyi Jiang,Liping Zhang,Wei Liu,Jing Guan,Hai Lin

In this study, a novel α-Fe 2 O 3 /V 2 O 5 /BC catalyst with high   peroxymonosulfate (PMS)   activation performance was constructed by co-pyrolysis method and 99.58% of tetracycline is degraded within 120 min. The electrons conversion of Fe-V on biochar surface induces the continuous generation of sulfate radical   and singlet oxygen molecules ( 1 O 2 ).   The XPS results show that it is Fe 3+   and Fe 0   rather than Fe 3+   and Fe 2+   in the iron cycle after the introduction of vanadium, indicating a more efficient electron transfer efficiency between interface. The optical properties characterization and density function theory calculation (DFT) of α-Fe 2 O 3 /V 2 O 5 /BC reveal that the electrons of the entire α-Fe 2 O 3   and the vanadium atoms are redistributed to new molecular orbitals due to strong interfacial chemical bonding, inducing a direct transfer of electrons to generate   1 O 2   for tetracycline removal that is the main cause of selective degradation. Besides, the possible degradation mechanism and tetracycline degradation pathways were also proposed. The α-Fe 2 O 3 /V 2 O 5 /BC maintains a high removal efficiency of tetracycline only decrease by 7.09% after six cycles. This study provides a better strategy and recyclable purification material for the efficient treatment of antibiotic pharmaceutical wastewater.

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CHEMOSPHERE · 2023 · IF 8.8

Photocatalytic membrane coated with α-Fe2O3/Fe3O4 for enhanced filtration performance and antifouling property in surface water treatment

Yuanqing Guo,Quan Liu,Xiaobin Tang,Heng Liang,Guibai Li,Liwei Yang,Lu Wang,Xiaoling Li,Yan Sun

A photocatalytic membrane coated with α-Fe 2 O 3 /Fe 3 O 4 nanoparticles has been developed to address the challenges of membrane fouling and organic removal in the treatment of natural surface water. The photocatalytic and filtration properties of the membranes were investigated through a variety of methods. The successful preparation of iron oxide was confirmed by UV–vis diffuse reflectance spectra and X-ray diffractometry, with α-Fe 2 O 3 identified as the primary photocatalytic agent. A commercial ultrafiltration (UF) membrane was employed as a comparison to evaluate the photocatalytic performance and filtration properties of the modified membrane. Results showed that the photocatalytic membrane achieved better removal rates for UV 254 (22.0%) and specific fluorescent organic compounds, such as component 2 (19.38%) and component 3 (16.89%), compared to the control group. Furthermore, both irreversible and reversible fouling resistances of the prepared membranes were significantly lower than that of the control group, with reductions of 39.4% and 50.2%, respectively. The membrane coated with α-Fe 2 O 3 /Fe 3 O 4 nanoparticles exhibited moderate removal of protein-like and terrestrially derived humic-like fluorescent organics while controlling membrane fouling. Although the α-Fe 2 O 3 /Fe 3 O 4 nanoparticles-coated photocatalytic membrane demonstrated good anti-fouling properties, the removals of organic matters were not as effective as anticipated due to the shorter hydraulic retention time. This study provides valuable insights for enhancing pollutant degradation and anti-fouling properties of membranes through the utilization of solar photocatalytic α-Fe 2 O 3 /Fe 3 O 4 surface-modified membranes in the treatment of natural surface water.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Soft Matter · 2021 ·Vol. 17 ·期 17 ·4604-4614 · IF 3.679

Spontaneous vesicle formation and vesicle-to-α-gel transition in aqueous mixtures of sodium monododecylphosphate and guanidinium salts

Meihua Gao,Na Du,Zhiyin Yao,Ying Li,Nan Chen,Wanguo Hou

Monoalkyl phosphates (MAPs) are one kind of important single-chain weak acid/salt type surfactants, but the understanding of their aggregation behavior in water is very limited due to their insolubility at room temperature. In the current work, the effect of guanidinium salts (GuSalts) on the solubility of sodium monododecylphosphate (SDP), a typical MAP, in water was determined at 25.0 °C, and the aggregation behavior of SDP in the GuSalt/water mixtures was investigated. The solubility of SDP is significantly improved by GuSalts including GuCl, GuSO4, GuSO3, GuPO4, and GuCO3 at 25.0 °C, resulting in an isotropic phase. SDP vesicles are spontaneously formed in the isotropic phase, with a critical vesicle concentration of ∼1.0 mM independent of the type of GuSalts. A “bridging dimer” mechanism is proposed to explain the formation of SDP vesicles. The SDP vesicles have a unilamellar structure with a size of ∼80 nm and an alkyl interdigitated degree of ∼25%, and exhibit size-selective permeability. Interestingly, a temperature-induced reversible transition between vesicles and α-gels was observed for the SDP/GuSalt/H2O systems when the SDP content is higher than 20 mM. The α-gels obtained are composed of vesicles and bilayer sheets, showing similar viscoelasticity to conventional gels, although their water content is as high as ∼98 wt%. The microviscosity of SDP vesicle membranes (ca. 35.79–49.34 mPa s at 25.0 °C) and the transition temperature between vesicles and α-gels (ca. 21.0–22.8 °C) are all dependent of the type of GuSalts. This work deepens the understanding of the aggregation behavior of MAPs and also provides valuable information for their practical applications.

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JOURNAL OF FOOD PROCESSING AND PRESERVATION · 2021 ·Vol. 45 ·期 7 ·e15604 · IF 2.19

The effects of α-L-rhamnosidase, β-D-glucosidase, and their combination on the quality of orange juice

Cheng Peng,Rui Li,Hui Ni,Li Jun Li,Qing Biao Li

The naringinase, a desirable candidate for citrus juice debittering, consists of α-L-rhamnosidase and β-D-glucosidase. This study aimed to elucidate the effects of α-L-rhamnosidase, β-D-glucosidase, and their combination on naringin, polyphenols, antioxidant activity, and aroma quality. The α-L-rhamnosidase and the two enzymes combination reduced the naringin concentration from 356.33 to 10.52 and 4.17 mg/L, respectively. The α-L-rhamnosidase, β-D-glucosidase, and their combination significantly increased the antioxidant activity. The unpleasant cooking note was significantly weakened and the floral note was increased after three treatments. The combinational treatment increased the sweet note greatly. The substrate competition between α-L-rhamnosidase and β-D-glucosidase may help to explain the inconsistencies of the polyphenols, antioxidant activity, and aroma quality after single enzyme or combined enzymes treatments. The results indicated that taste, antioxidant activity, and aromatic quality were well improved by the combined treatment than either α-L-rhamnosidase or β-D-glucosidase treatment, providing an attractive reference for debittering orange juice. Practical applications The work showed that the combined treatment of α-L-rhamnosidase and β-D-glucosidase was better to remove the bitter taste of citrus juice than the solo treatment with α-L-rhamnosidase or β-D-glucosidase in regarding with taste, antioxidant activity, and aromatic quality. It helps to better the quality of citrus juice with enzymatic treatment.

CAS / MDL: 196504-57-1 1898-66-4
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JOURNAL OF BIOMATERIALS APPLICATIONS · 2021 · IF 2.646

PEG-α-CD/AM/liposome @amoxicillin double network hydrogel wound dressing—Multiple barriers for long-term drug release

Shan Wang,Zhicun Wang,Cheng Xu,Lin Cui,Guihua Meng,Shengchao Yang,Jianning Wu,Zhiyong Liu,Xuhong Guo

Wound infection and poor wound healing are the major challenges of wound treatment. Antibiotic drug treatment is the effective way to inhibit wound infection. It is necessary to achieve sustained release of antibiotics to get a longer treatment for wound infection. The double network hydrogels based on liposome, polyethylene glycol (PEG), α- cyclodextrin (α-CD) and acrylamide (AM) were developed, in which liposome acts as amoxicillin repository. Because the drug would release from the multiple barriers including two cavities of liposome and α-CD, as well as polyethylene glycol -α- cyclodextrin/acrylamide (PEG-CD/AM) double network, the PEG-α-CD/AM/liposome @amoxicillin double network hydrogels could achieve sustained drug release. The drug release assay showed that the dressing could release amoxicillin continuously until 12 days, than that of 8th day for single-network hydrogel releasing. The antibacterial ratio of the hydrogel could reach above 80%. What’s more, the hydrogels present adjustable mechanical strength by changing the ratio of the components. The swelling ratio proved that the hydrogel had potential ability to absorb wound exudates. The cytotoxicity test of the hydrogels demonstrated excellent biocompatibility. These results indicated that this study can provide a new thought for antibacterial wound dressing and has a broad application prospect.

CAS / MDL: 79-06-1 25322-68-3
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Catalysts · 2021 ·Vol. 11 ·期 4 ·499 · IF 4.146

Rapid Synthesis of Asymmetric Methyl-Alkyl Carbonates Catalyzed by α-KMgPO4 in a Sealed-Vessel Reactor Monowave 50

Tiefeng Wang,Xu Li,Xiaosheng Zhang,Jinxiang Dong

Dimethyl-carbonate (DMC) is a green carboxymethylation agent for synthesis of the versatile long-chain alkyl carbonates through base-catalyzed transesterification with aliphatic alcohols. Herein, we demonstrated the facile preparation of a novel heterogeneous base catalyst α-KMgPO4using commercially cheap metal salts via hydrothermal-calcination procedure. The combination of temperature programmed desorption (TPD) and FTIR measurements with CO2pre-adsorbed revealed the presence of weak and medium base sites on α-KMgPO4. Furthermore, α-KMgPO4catalyzed transesterification of DMC and n-octanol was performed in a sealed-vessel reactor (Monowave 50). The results show that the reaction was completed in only 10 min with the 97.5% conversion of n-octanol and >99% selectivity to asymmetric methyl-octyl carbonate under the optimal conditions. Additionally, the possible catalytic mechanism is proposed. As an extended contribution, the tribology performance of the asymmetric methyl-alkyl carbonates was further evaluated.Keywords:catalyst;α-KMgPO4;transesterification;asymmetric carbonates;Monowave 50 reactor

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COLLOIDS AND SURFACES B-BIOINTERFACES · 2020 · IF 4.389

A colorimetric method for screening α-glucosidase inhibitors from flavonoids using 3,3′,5,5′-tetramethylbenzidine as a chromogenic probe

Dong-Mei Liu,Chen Dong,Run-Tian Ma

A facile and novel colorimetric method for screening of α-glucosidase inhibitors (AGIs) from flavonoids using 3,3’,5,5’-tetramethylbenzidine (TMB) as a chromogenic probe is proposed. This method is based on the colorimetric detection of ascorbic acid (AA) through the TMB oxidation reaction catalyzed by horseradish peroxidase (HRP) in the presence of hydrogen peroxide (H 2 O 2 ). In the TMB/H 2 O 2 /HRP system, HRP catalyzes the oxidation of H 2 O 2 to ‧OH radical which oxidizes TMB to blue-colored oxidized TMB (oxTMB). In the presence of AA, the production of ‧OH radical is suppressed and causes the decrease of oxTMB, resulting in the fading of the blue color and the decrease of absorbance at 652 nm. Based on this, the existence of AA can be facilely identified. In the 2- O -α- d -glucopyranosyl- l -ascorbic acid (AA-2 G)/α-glucosidase (α-Glu) system, the produced AA inhibits the oxidation of TMB to blue-colored oxTMB. In the presence of AGIs, the production of AA is inhibited, which inhibits the reduction of oxTMB, resulting in a blue color recovery and an increase of the absorbance at 652 nm. Based on this, the colorimetric method is developed for screening of AGIs from 7 flavonoids.

CAS / MDL: 56180-94-0
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