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ORGANIC & BIOMOLECULAR CHEMISTRY · 2022 ·Vol. 20 ·期 14 ·2909-2921 · IF 3.89

Asymmetric total synthesis of (+)-(2R,4′R,8′R)-α-tocopherol enabled by enzymatic desymmetrization

Haidi Yang,Jinyao Liu,Pan Hu,Liang Gao,Zedu Huang,Fener Chen

A new and highly stereoselective synthesis of chiral diol (S)-14, the common synthetic intermediate to (+)-(2R,4′R,8′R)-α-tocopherol (1), was accomplished in seven steps with 13.8% overall yield. This developed route featured a lipase-catalyzed desymmetric hydrolysis of prochiral diester 39a, which was prepared through a challenging Heck coupling, to chiral quaternary carbon-containing monoester (R)-37a of the correct configuration in 81% yield and 96.7% ee, to the best of our knowledge, leading to the most efficient enzymatic desymmetric synthesis of the chiral chroman skeleton of vitamin E members reported to date. Coupled with the modified preparation of the phytol-derived side chain, the chemoenzymatic total synthesis of 1 was completed in 15 longest linear steps with 3.1% overall yield.

✓ 已验证 DOI PubMed 高影响因子
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Experimental and Therapeutic Medicine · 2022 ·Vol. 23 ·期 4 ·1-9 · IF 2.751

Pterostilbene attenuates the proliferation and differentiation of TNF‑α‑treated human periodontal ligament stem cells

Min Yi,Guanglei Wang,Jianhua Niu,Minghui Peng,Yi Liu

Periodontitis is a common chronic inflammatory oral disease. The objective of periodontal treatment is to control infection whilst regenerating damaged periodontal tissue. The present study aimed to determine the potential effects of pterostilbene (PTE), a representative stilbene compound, on the proliferation and differentiation of human periodontal ligament stem cells (hPDLSCs). Different concentrations (1, 5, 10 and 20 µM) of PTE were applied to hPDLSCs, after which Cell Counting Kit‑8 and western blotting assays were performed to examine the protein levels of Ki67, PCNA, p‑IκBα, IκBα, Bcl‑2, Bax, cleaved caspase3. The effect of PTE on the release of inflammatory factors, including IL‑1β, IL‑6 and IL‑10 was assessed by RT‑qPCR. The apoptosis of TNF‑α‑induced hPDLSCs was evaluated by TUNEL assay and western blotting. Additionally, the role of PTE in hPDLSC mineralization was evaluated using alizarin red staining. The expression levels of mineralization indices, including RUNX2 and ALP were subsequently determined using western blotting. Subsequently, the target of PTE was predicted using TargetNet database and AutoDock v4.2 software and verified using western blotting. The results of the present study revealed that PTE promoted the proliferation of hPDLSCs in a concentration‑dependent manner. Furthermore, PTE treatment decreased the release of inflammatory factors and alleviated the apoptosis of TNF‑α‑induced hPDLSCs. PTE was also demonstrated to promote the formation of mineral nodules in TNF‑α‑induced hPDLSCs. The Targetnet database, along with molecular docking, indicated that histone deacetylases (HDACs) were the probable targets of PTE upstream of regulating periodontitis. The results of western blotting implied that TNF‑α significantly increased expression levels of HDAC2, 4, 6 and 8, whilst PTE treatment markedly decreased HDAC4, 6 and 8 expression in a concentration‑dependent manner compared with the TNF‑α group, which further confirmed these conclusions. In summary, results of the present study revealed that PTE promoted TNF‑α‑induced hPDLSC proliferation and differentiation, whilst alleviating inflammation and apoptosis. PTE also inhibited the expression of HDACs, which may be involved in the mechanism of periodontitis.

CAS / MDL: 67-68-5
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

High-performance Ti/IrO2-RhOx-TiO2/α-PbO2/β-PbO2 electrodes for scale inhibitors degradation

Huachang Jin,Xuejiao Zhang,Yang Yu,Xueming Chen

The extensive evaporation-induced aggregation of scale inhibitors in the wastewater of recirculating cooling systems causes severe environmental pollution . In this study, Amino Trimethylene Phosphonic Acid (ATMP), an ordinary scale inhibitor, was degraded via electrochemical oxidation using a multi-layered Ti/IrO 2 -RhO x -TiO 2 /α-PbO 2 /β-PbO 2 electrode. The electrochemical oxidation experimental results verified the superior electro-catalytic properties of the β-PbO 2 electrode. Accelerated lifetime tests suggested that Ti/IrO 2 -RhO x -TiO 2 /α-PbO 2 /β-PbO 2 possesses a service lifetime of 201 h under a current density of 40000 A/m 2 , which is 3.4–100.5 times as long as other β-PbO 2 electrodes reported by other researchers. Four major operational parameters, namely electrolyte, current density, initial ATMP concentration, and pH, were discovered to significantly affect the ATMP degradation rate and electrical efficiency. The direct oxidation mechanism predominated in the degradation process of ATMP, achieving a 55.11% and 38.82% removal efficiency in Na 2 SO 4 and NaCl solutions, respectively. In addition, two possible degradation pathways of ATMP were proposed: induced by the breaking of either C-P or C-N bonds.

CAS / MDL: 7647-01-0
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Crystals · 2023 ·Vol. 13 ·期 5 ·810 · IF 2.7

Novel Mixed-Phase α/γ-Fe2O3 Micro-Flower Assembled with Nanosheets for Enhancing Acetone Detection

Ruonan Tian,Huai Tan,Gang Chen,Hongtao Guan,Chengjun Dong,Zongyou Yin

Although individual γ-Fe2O3and α-Fe2O3have been widely fabricated for gas sensors, their mixed phase of α/γ-Fe2O3might deliver excellent sensing properties. In this study, a facile solvothermal method was used to fabricate Fe-alkoxide. After thermal treatment, it was converted into γ-Fe2O3, α-Fe2O3and their mixed-phase α/γ-Fe2O3with a nanosheets-assembled flower-like structure. We studied the influence of calcination temperature on the phase and sensing properties on acetone detection. The α/γ-Fe2O3which annealed at 400 °C included 18% α-Fe2O3and it exhibited excellent sensing performance towards acetone compared to that of γ-Fe2O3and α-Fe2O3. It showed a response of 353 to acetone with a concentration of 200 ppm, and a low limit of detection of 0.5 ppm at 160 °C. In addition, the change in responses with acetone concentration from 50 to 200 ppm shows a good linear relationship. Moreover, this material has good reproducibility and selectivity as well as a fast response time of 22 s and recovery time of 14 s to 200 ppm. Therefore, our mixed phase of α/γ-Fe2O3possesses great prospects for acetone detection.Keywords:Fe2O3;phase;gas sensor;acetone;sensing performance

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ACS Biomaterials Science & Engineering · 2023 · IF 5.8

Silk Fibroin-Based Hydrogel Microneedles Deliver α-MSH to Promote Melanosome Delivery for Vitiligo Treatment

Shubin Chong,Chengxiu Wei,Longbao Feng,Rui Guo

Microneedles have shown great advantages in subcutaneous drug delivery and skin disease treatment. Vitiligo is a difficult-to-cure skin disease characterized by the depigmentation of the epidermis. Melanosomes produced in melanocytes are transported through dendrites to adjacent keratinocytes, where they accumulate, resulting in skin pigmentation. However, melanocytes in vitiligo patients are functionally disrupted. Silk fibroin (SF) methacrylate hydrogel microneedle can deliver α-MSH to the epidermis directly, where α-MSH helps the protection of melanocytes, extension of melanocytic dendrites, and transfer of melanosomes. In addition, the expression of melanogenesis-related melanocyte-inducing transcription factor and tyrosinase-related protein 1 (TRP1) was up-regulated, and the number of hair follicle stem cells increased with good proliferative activity. This slow release α-MSH SF-based hydrogel microneedles provides a new idea for the treatment of vitiligo.

CAS / MDL: 85073-19-4
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MICROCHIMICA ACTA · 2023 ·Vol. 190 ·期 5 ·1-10 · IF 5.7

Electrochemical peptide nucleic acid functionalized α-Fe2O3/Fe3O4 nanosheets for detection of CYP2C19*2 gene

Ni Yun,Chen Xiu,Ling Chen,Zhu Ziye,Yue Yao,Wang Jie,He Aolin,Liu Ruijiang

The CYP2C19*2 gene carriers and non-carriers are closely related to the dosage of clopidogrel. To correctly guide the use of clopidogrel and promote individualized therapy, an ultra-sensitive electrochemical biosensor was developed for the detection of CYP2C19*2 gene. The heterogeneous α-Fe 2 O 3 /Fe 3 O 4 nanosheets were prepared via the hydrothermal-calcination process, and the preparation parameters were optimized. The average diameter and thickness of the nanosheets were approximately 150 nm and 53 nm, respectively; and the saturation magnetization was 80.2 emu/g. The α-Fe 2 O 3 /Fe 3 O 4 @Au nanosheets were prepared by sodium borohydride reduction method, and self-assembled to the electrode surface with magnetic field. Ultra-sensitive detection of CYP2C19*2 gene was realized through the recognition ability of strong single base mismatching of peptide nucleic acid and signal amplification effect of magnetic α-Fe 2 O 3 /Fe 3 O 4 @Au nanosheets. Under optimal detection conditions, the current had a good linear correlation with the negative logarithm of CYP2C19*2 gene concentration in the range 1 pM—1 nM, and the detection limit was 0.64 pM (S/N = 3). Meanwhile, the electrochemical signals of target DNA and incomplete complementary DNA were detected. The constructed biosensor exhibited good selectivity, reproducibility, and stability, providing a promising strategy for the detection of other gene mutations by electrochemical biosensors. Graphical Abstract

CAS / MDL: 9002-98-6 51805-45-9
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ACS Applied Nano Materials · 2023 · IF 5.9

Magnetic Amine-Functionalized ZIF-8 with Hierarchical Pores for Efficient Covalent Immobilization of α-Amylase

Haizhi Zhang,Zhiping Sun,Cunhui Wu,Xinguang Qin,Gang Liu

The immobilization strategy between ZIF-8 and different enzymes has focused on in situ encapsulation and pore infiltration, while the surface attachment has been seldom reported because of less functional groups on the ZIF-8 surface. Here, a magnetic amine-functionalized ZIF-8 with hierarchical pores was designed for efficient covalent immobilization of α-amylase (α-Amy). By using Fe3O4 nanoparticles as the core and ZIF-8 as the shell, followed by Au3+–Zn2+ exchange reaction and β-mercaptoethylamine modification, the magnetic hollow ZIF-8 nanoparticle with amine groups on the surface was synthesized. With the assistance of glutaraldehyde, an α-Amy-magnetic hollow ZIF-8 composite was prepared and fully characterized by scanning electron microscopy, transmission electron microscopy, Fourier transform infrared spectrometry, X-ray photoelectron spectroscopy, energy-dispersive X-ray spectroscopy element mapping analysis, and vibration sample magnetometry. Then, the catalytic activity of immobilized α-Amy was explored with a Km of 2.307 mg/mL and Vmax of 0.506 mg/mL·min, indicating excellent catalytic activity. The study about stability and reusability demonstrated that the catalytic activity of immobilized α-Amy remained above 50% after 10 times of reuse. Thus, the designed magnetic amine-functionalized ZIF-8 was verified to be a nice carrier for covalent enzyme immobilization.

CAS / MDL: 156-57-0 693-98-1
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JOURNAL OF BIOSCIENCE AND BIOENGINEERING · 2021 · IF 2.894

Omeprazole inhibits α-glucosidase activity and the formation of nonenzymatic glycation products: Activity and mechanism

Chen Yu,Zi-Yi Yu,Yi-Ting Wen,Wei-Ming Chai,Lin-Jun Wang,Mei-Zhen Lin

In this study, the inhibitory effect and mechanism of omeprazole on α-glucosidase and nonenzymatic glycation were investigated in vitro by using multi-spectroscopic methods and molecular docking . Enzyme kinetic results showed that omeprazole inhibited α-glucosidase in a reversible and noncompetitive manner (IC 50 = 0.595 ± 0.003 mM). The results from fluorescence quenching and thermomechanical analyses signified that omeprazole reduced the fluorescence intensity of α-glucosidase by forming an omeprazole-α-glucosidase complex primarily driven by hydrogen bonds . Molecular docking further confirmed that hydrogen bonds and hydrophobic forces were the major driving forces for omeprazole binding to α-glucosidase. The nonenzymatic glycation assays revealed that omeprazole had a moderate inhibition against the formation of fructosamine , dicarbonyl compounds, and advanced glycation end products (AGEs). This study provides a new inhibitor of both α-glucosidase and nonenzymatic glycation and provides a practicable candidate for treating diabetes and its complications.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Frontiers in Cell and Developmental Biology · 2021 · IF 6.684

Arbutin Alleviates the Liver Injury of α-Naphthylisothiocyanate-induced Cholestasis Through Farnesoid X Receptor Activation

Peijie Wu,Ling Qiao,Han Yu,Hui Ming,Chao Liu,Wenjun Wu,Baixue Li

Cholestasis is a kind of stressful syndrome along with liver toxicity, which has been demonstrated to be related to fibrosis, cirrhosis, even cholangiocellular or hepatocellular carcinomas. Cholestasis usually caused by the dysregulated metabolism of bile acids that possess high cellular toxicity and synthesized by cholesterol in the liver to undergo enterohepatic circulation. In cholestasis, the accumulation of bile acids in the liver causes biliary and hepatocyte injury, oxidative stress, and inflammation. The farnesoid X receptor (FXR) is regarded as a bile acid–activated receptor that regulates a network of genes involved in bile acid metabolism, providing a new therapeutic target to treat cholestatic diseases. Arbutin is a glycosylated hydroquinone isolated from medicinal plants in the genus Arctostaphylos , which has a variety of potentially pharmacological properties, such as anti-inflammatory, antihyperlipidemic, antiviral, antihyperglycemic, and antioxidant activity. However, the mechanistic contributions of arbutin to alleviate liver injury of cholestasis, especially its role on bile acid homeostasis via nuclear receptors, have not been fully elucidated. In this study, we demonstrate that arbutin has a protective effect on α -naphthylisothiocyanate–induced cholestasis via upregulation of the levels of FXR and downstream enzymes associated with bile acid homeostasis such as Bsep, Ntcp, and Sult2a1, as well as Ugt1a1. Furthermore, the regulation of these functional proteins related to bile acid homeostasis by arbutin could be alleviated by FXR silencing in L-02 cells. In conclusion, a protective effect could be supported by arbutin to alleviate ANIT-induced cholestatic liver toxicity, which was partly through the FXR pathway, suggesting arbutin may be a potential chemical molecule for the cholestatic disease.

CAS / MDL: 497-76-7 128-13-2
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RSC Advances · 2021 ·Vol. 11 ·期 56 ·35280-35286 · IF 3.361

Al-doped α-MnO2 coated by lignin for high-performance rechargeable aqueous zinc-ion batteries

Jingliang Xu,Xinhang Hu,Md Asraful Alam,Gul Muhammad,Yongkun Lv,Minghai Wang,Chenjie Zhu,Wenlong Xiong

Zn/MnO2 batteries, one of the most widely studied rechargeable aqueous zinc-ion batteries, suffer from poor cyclability because the structure of MnO2 is labile with cycling. Herein, the structural stability of α-MnO2 is enhanced by simultaneous Al3+ doping and lignin coating during the formation of α-MnO2 crystals in a hydrothermal process. Al3+ enters the [MnO6] octahedron accompanied by producing oxygen vacancies, and lignin further stabilizes the doped Al3+ via strong interaction in the prepared material, Al-doped α-MnO2 coated by lignin (L + Al@α-MnO2). Meanwhile, the conductivity of L + Al@α-MnO2 improves due to Al3+ doping, and the surface area of L + Al@α-MnO2 increases because of the production of nanorod structures after Al3+ doping and lignin coating. Compared with the reference α-MnO2 cathode, the L + Al@α-MnO2 cathode achieves superior performance with durably high reversible capacity (∼180 mA h g−1 at 1.5 A g−1) and good cycle stability. In addition, ex situ X-ray diffraction characterization of the cathode at different voltages in the first cycle is employed to study the related mechanism on improving battery performance. This study may provide ideas of designing advanced cathode materials for other aqueous metal-ion batteries.

CAS / MDL: 10034-96-5 7446-20-0
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Nanomaterials · 2023 ·Vol. 14 ·期 1 ·76 · IF 5.3

Design Polyaniline/α-Zirconium Phosphate Composites for Achieving Self-Healing Anti-Corrosion of Carbon Steel

Ziqi Lv,Kai Ren,Tao Liu,Yunyan Zhao,Zhonghua Zhang,Guicun Li

The rupture of a micro/nano container can trigger the release of repair agents and provides the coating with a self-healing and anti-corrosion effect. However, the defect and inhomogeneity of the coating, produced by the rupture of the micro/nano container, may weaken its anti-corrosion performance. This study reports a rare protection mechanism, which optimizes the space occupying of zirconium phosphate, and the de-doping peculiarity of polyaniline without the rupture of the micro/nano container. Polyaniline/α-zirconium phosphate composites were constructed through in situ oxidation polymerization. Repair agents were added in the form of doped acids. According to the different repair agents in polyaniline/α-zirconium phosphate composites (citric ion, tartaric ion and phytic ion), the performance and protection mechanism of the composites were researched. Polyaniline/α-zirconium phosphate coating (with phytic ion) shows an excellent self-healing anti-corrosive effect, due to the large spatial structure and abundant chelating groups of the precipitation inhibitor. Considering the anti-corrosive application, the developed polyaniline/α-zirconium phosphate composite has a far-reaching influence on marine development.Keywords:polyaniline;α-zirconium phosphate;phytic acid;anti-corrosion;self-healing

CAS / MDL: 83-86-3
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Scientific Reports · 2026 · IF 4.9

An efficient photo-Favorskii rearrangement of α-chloroketones for the synthesis of 2-arylpropionic acids

Ren Yanrong,Zhu Wenhui,He Yueyue,Ye Songlin,Lv Jie,Liu Jianqiao,Li Anqi,Yuan Ziliang

2-Arylpropionic acids, exemplified by ibuprofen, are important structural motifs widely found in bioactive molecules and pharmaceutical agents, and their industrial synthesis is therefore of considerable significance. Herein, we report a systematic study of the photo-Favorskii rearrangement synthesis of 2-arylpropionic acids using zinc acetate as a cost-effective, readily available, and environmentally benign acid scavenger. Under mild visible-light irradiation conditions, this protocol enables efficient conversion of α-chloroketones into the corresponding 2-arylpropionic acids, delivering moderate to good yields across a broad range of more than 11 substrates. This work demonstrates the potential of zinc acetate for sustainable organic synthesis and provides an environmentally benign, efficient strategy for the preparation of valuable carboxylic acid derivatives.

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