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BIOPROCESS AND BIOSYSTEMS ENGINEERING · 2022 ·Vol. 45 ·期 5 ·891-900 · IF 3.434

One-pot synthesis of dihydro-β-ionone from carotenoids using carotenoid cleavage dioxygenase and enoate reductase

Qi Zhipeng,Tong Xinyi,Zhang Xiaomeng,Lin Haifeng,Bu Su,Zhao Linguo

Dihydro-β-ionone is a characteristic aroma compound of Osmanthus fragrans and is widely applied in the flavor & fragrance industry. However, the main focus is on chemical synthesis due to the metabolic pathways of dihydro-β-ionone is still unclear. Here, we explored the one-pot synthesis system for dihydro-β-ionone production using carotenoid cleavage dioxygenase (CCD) and enoate reductase. After screening the CCD enzyme, PhCCD1 from the Petunia hybrid was identified as the suitable enzyme for the first step of dihydro-β-ionone synthesis due to the high enzyme activity for carotenoid. The PhCCD1 was expressed in Escherichia coli and further characterized. The optimal activity of PhCCD1 was observed at pH 6.8 and 45 °C. The enzyme was stable over the pH range of 6.0–8.0 and had good thermal stability below 40 °C. Then, we optimized the coupled reaction conditions for dihydro-β-ionone production by PhCCD1 and enoate reductase AaDBR1 from Artemisia annua . Furthermore, we introduced the NADPH regeneration system with a 1.5-fold enhancement for dihydro-β-ionone production. Collectively, approximately 13.34 mg/L dihydro-β-ionone was obtained by the one-pot biosystem with a corresponding molar conversion of 85.8%. For the first time, we successfully designed and constructed a new synthesis pathway for dihydro-β-ionone production in vitro. The coupled catalysis reported herein illustrates the feasibility of producing dihydro-β-ionone from carotenoids and guides further engineering in the food industry.

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JOURNAL OF MOLECULAR LIQUIDS · 2022 · IF 6.633

Surface charge engineering of β-glucosidase using rational design improves catalytic capacity and ionic liquid tolerance

Yinghui Mu,Xin Ju,Jiaolong Fu,Fanjin Meng,Lishi Yan,Liangzhi Li

β-Glucosidases are susceptible to external factors affecting catalytic efficiency in biomass resource utilization. In this study, a total of 14 positively-oriented and negatively-oriented surface-charged β-glucosidase mutants were constructed by rational design and surface charge engineering, having a gradient in ζ-potential from −4.6 mV to −12.7 mV. The negatively-oriented charged mutant BGL-14 (K283E/K332E) with the lowest ζ-potential (-12.7 mV) exhibited a 14 % increased substrate conversion after 2 h in 6 % (v/v) 1-ethyl-3-ethyl-imidazolium diethylphosphate ([EEIM]DEP) compared to wild-type. The inactivation kinetics indicate that the final plateau activity of positively-oriented charged BGL-1 (D9K/D239N/D273N/E291R) with the highest surface ζ-potential (-4.6 mV) was 75.29 % in 6 % (v/v) [EEIM]DEP, which was 5.23-fold higher than that of the wild-type. Furthermore, the presence of [EEIM]DEP considerably promoted the solubility and enzymatic activity of β-glucosidase, such that the catalytic capacity of BGL-14 was increased by 42 % in 6 % (v/v) [EEIM]DEP compared to 1-ethyl-3-methyl-imidazolium diethylphosphate ([EMIM]DEP). Changes in β-glucosidase charge, as well as structure caused by mutations, have a crucial role in IL tolerance, and the effect of charged residue substitution on IL appears to be complex, enzyme-specific, and highly dependent on the IL ion assemblies. In addition to the electrostatic repulsion of IL ions, other factors may be an extra molecular basis for enhancing tolerance/resistance to charge engineering in the IL environment.

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SOFT MATERIALS · 2019 · IF 0.973

Folic acid-modified β-cyclodextrin nanoparticles as drug delivery to load DOX for liver cancer therapeutics

Wenbo Fan,Yuedi Xu,Zheng Li,Qiang Li

To get the safe and effective therapy for liver cancer, multifunctional nanoparticulate systems with therapeutic efficacy for biomedical application are progressing quite rapidly. The aim of the present research is to determine the potential of doxorubicin (DOX)-loaded folic acid–polyethylene glycol–β-cyclodextrin (FA–PEG–β-CD) nanoparticles (NPs) as drug-delivery system for liver cancer therapy. The targeting delivery of FA–PEG–β-CD was synthesized from FA and β-CD with PEG as a linker, which then loaded antitumor drug DOX to get the FA–PEG–β-CD/DOX NPs. The physicochemical characterizations including flourier transform infrared, 1H nuclear magnetic resonance, transmission electron microscope and dynamic light scattering, drug-loading content, drug encapsulation efficiency, blood compatibility, and in-vitro drug release were investigated. Finally, the in-vitro antitumor activity was estimated by HepG2 cells. The size of FA–PEG–β-CD NPs was about 20–80 nm, while FA–PEG–β-CD/DOX NPs was 30–60 nm. And the FA–PEG–β-CD/DOX NPs have drug-loading efficiency (11.9%) and encapsulation efficiency (95.2%). The in-vitro drug release results showed that the FA–PEG–β-CD NPs could not merely improve the solubility of hydrophobic drugs but also control the drug release. Blood compatibility assays revealed that DOX-loaded NPs did not induce blood hemolysis. In summary, the drug delivery of FA–PEG–β-CD NPs is suitable to carry the drug to the tumor tissues and release the drug effectively, and FA–PEG–β-CD/DOX NPs may be a potential platform for improving the treatment of liver cancer.

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JOURNAL OF BIOMATERIALS APPLICATIONS · 2018 · IF 2.082

Preparation and characterization of porous hydroxyapatite/β-cyclodextrin-based polyurethane composite scaffolds for bone tissue engineering

Jingjing Du,Shuchun Gan,Qihao Bian,Duhan Fu,Yan Wei,Kaiqun Wang,Qiaoxia Lin,Weiyi Chen,Di Huang

In this study, novel porous scaffolds containing hydroxyapatite and β-cyclodextrin-based polyurethane were first successfully fabricated by polymerizing β-cyclodextrin with hexamethylene diisocyanate and hydroxyapatite in situ for bone tissue engineering. The physicochemical and mechanical properties as well as cytocompatibility of porous scaffolds were investigated. The results showed that polyurethane reinforced with hydroxyapatite composites had cancellous bone-like porous structure. The mechanical strength of the scaffolds increased with increasing the hydroxyapatite content in scaffolds. Synthesized scaffolds (PU1, PUHA1, PU2, and PUHA2) presented compressive strength values of 0.87 ± 0.24 MPa, 1.81 ± 0.10 MPa, 6.16 ± 0.89 MPa, and 12.95 ± 2.05 MPa, respectively. The pore size and porosity of these scaffolds were suitable for bone regeneration. Cytocompatibility of composite scaffolds was proven via favorable interactions with MC3T3-E1 cells. The addition of hydroxyapatite into CD-based polyurethane scaffolds improved cell attachment, well-spread morphology, and higher proliferation. The hydroxyapatite-polyurethane scaffolds have the potential to be applied in bone repair and regeneration.

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FOOD CHEMISTRY · 2023 · IF 8.8

Ultrasensitive two-photon probes for rapid detection of β-galactosidase during fruit softening and cellular senescence

Yi-Min Shan,Kang-Kang Yu,Fan-Yuan Yu,Yan-Hong Liu,Xiao-Qi Yu,Kun Li

Senescence is happening in every corner of the living organisms. β -galactosidase ( β -gal) is one of the most important biomarkers during senescence in both plant and mammalian cells. Most β -gal fluorescent probes were focused on bio-imaging, only a few probes were developed for the detection of β -gal in fruit, and the probes that could detect β -gal in both fruits and living cells were even less. Here, two β -gal probes ( TNap-βGal and TBNap-βGal ) were synthesized, which can not only image the increase of β -gal during both fruits softening and cellular senescence, but also prove that bananas are not suitable for storage in refrigerator and the subsequent accumulation of β -gal still in lysosome of mammalian cells. In addition, TNap-βGal was successfully applied to two-photon imaging of endogenous β -gal in both hDPMSCs and tissues of human dental pulp for the first time.

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MOLECULAR AND CELLULAR BIOCHEMISTRY · 2026 · IF 4.7

Luteolin inhibits prostate cancer stem cells through disrupting the lactate/H3K18la/β-catenin/LDHA feedback loop

Zhang Qi,Ren Xinxiang,Cao Wanshuang,Shi Hongfei,Zhu Mingming

Prostate cancer is one of the most common malignant tumors in men, with prostate cancer stem cells (PCSCs) playing an important role in its initiation and progression. Accumulating evidence has demonstrated that lactate and lactate-mediated histone lactylation are crucial regulators of proliferation, metastasis, immune escape and drug resistance in various cancer. However, their functional roles and underlying mechanisms in PCSCs remain largely elusive. In the present study, we found that lactate levels were significantly elevated in PCSC microenvironment, which effectively induced H3K18 lactylation (H3K18la). The increased-lactate enhanced the stemness of PCSCs. ChIP analysis revealed that H3K18la positively regulated the transcription of the β-catenin gene. Furthermore, β-catenin transcriptionally activated lactate dehydrogenase A (LDHA) to promote lactate production, thereby forming a lactate/H3K18la/β-catenin/LDHA positive feedback loop. Notably, luteolin, a natural flavone, disrupted this feedback loop and exerted potent inhibitory effects on PCSCs. Collectively, our findings uncover a novel lactate-driven regulatory axis in PCSCs and provide new insights into the development of intervention strategies in prostate cancer. Graphical abstract

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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2021 ·Vol. 413 ·期 15 ·3933-3944 · IF 4.157

Enantioseparation on a new synthetic β-cyclodextrin chemically bonded chiral stationary phase and molecular docking study

Li Meng,Guo Xingjie,Di Xin,Jiang Zhen

A novel β-cyclodextrin derivative chemically bonded chiral stationary phase (EDACD) was synthesized by the reaction of mono-6-ethylenediamine-β-cyclodextrin with the active alkyl isocyanate, anchoring to silica gel. After the successful analysis and characterization using scanning electron microscopy, Fourier transform infrared spectra, solid-state nuclear magnetic resonance spectra, elemental analysis, and thermogravimetric analysis techniques, the enantioselective performance of the as-prepared EDACD column was evaluated by non-steroidal antiinflammatory drugs and flavonoids under the reversed-phase HPLC condition. The factors that affected enantioseparation including mobile phase compositions and buffers were investigated in more detail. As a result, EDACD showed a satisfactory enantioselectivity for the tested drugs. With the mobile phase of acetonitrile and 20-mM ammonium formate adjusted to pH 4.0 using formic acid (85:15, v/v) at the flow rate of 0.6 mL min −1 , the enantiomers of ibuprofen, carprofen, naproxen, indoprofen, ketoprofen, eriocitrin, naringin, and narirutin were separated with the best resolutions of 1.53, 1.64, 3.72, 2.40, 0.50, 0.61, 0.58, and 0.52. To adjust the proportion of acetonitrile to 80% (by volume), the enantiomers of pranoprofen and flurbiprofen were completely resolved with the best resolutions of 1.60 and 1.59. Additionally, by the study of the molecular docking, hydrogen bonding and inclusion complexation were believed to play an important role in chiral recognition. As a new material, EDACD will have a wider application in the analysis of chiral compounds.

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CHEMICAL & PHARMACEUTICAL BULLETIN · 2021 ·Vol. 69 ·期 12 ·1179-1183 · IF 1.645

Identification of the Inhibitory Compounds for Metallo-β-lactamases and Structural Analysis of the Binding Modes

Taichi Kamo,Keiichi Kuroda,Shota Kondo,Usaki Hayashi,Satoshi Fudo,Tomoki Yoneda,Akiko Takaya,Michiyoshi Nukaga,Tyuji Hoshino

Metallo-β-lactamases (MBLs) are significant threats to humans because they deteriorate many kinds of β-lactam antibiotics and are key enzymes responsible for multi-drug resistance of bacterial pathogens. As a result of in vitro screening, two compounds were identified as potent inhibitors of two kinds of MBLs: imipenemase (IMP-1) and New Delhi metallo-β-lactamase (NDM-1). The binding structure of one of the identified compounds was clarified by an X-ray crystal analysis in complex with IMP-1, in which two possible binding poses were observed. Molecular dynamics (MD) simulations were performed by building two calculation models from the respective binding poses. The compound was stably bound to the catalytic site during the simulation in one pose. The binding model between NDM-1 and the compound was constructed for MD simulation. Calculation results for NDM-1 were similar to those of IMP-1. The simulation suggested that the binding of the identified inhibitory compound was also durable in the catalytic site of NDM-1. The compound will be a sound basis for the development of the inhibitors for MBLs.

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JOURNAL OF CHROMATOGRAPHY A · 2021 · IF 4.759

Facile preparation of ethanediamine-β-cyclodextrin modified capillary column for electrochromatographic enantioseparation of Dansyl amino acids

Zhentao Li,Changjun Hu,Yikun Liu,Qiaoyan Li,Yuanyuan Fu,Zilin Chen

Herein, the fabrication of a fascinating multifunctional cyclodextrin (CD) chiral stationary phase and its chiral separation performance in capillary electrochromatography are proposed. A facile interfacial polymerization was used to anchor ethanediamine-β-cyclodextrin (EDA-β-CD) polymerized with trimesoyl chloride (TMC) and to form the chiral stationary phase (CSP) composite onto the surface wall of the capillary. The characters of prepared columns were confirmed by Fourier transform infrared spectroscopy (FT-IR), X-ray Photoelectron Spectrometer (XPS), scanning electron microscopy (SEM) and energy dispersive X-ray spectrometry (EDS). This novel CSP offers multi-typical interactions including hydrogen bonding, π-interaction, hydrophobic and electrostatic interaction as well as steric effects which contribute to prominent chiral recognition for Dansyl-DL-amino acids in CEC modes. The EDA-β-CD modified column showed eminent enantioseparation performance towards five Dansyl-DL-amino acids (the DL-forms of valine, threonine, leucine, phenylalanine, serine). Besides, the prepared columns were perfectly reproducible and stable. The relative standard deviations of the enantiomer retention times for intra-day (n = 5), inter-day (n = 3) runs and column-to-columns (n = 3) are below 0.54%, 1.35% and 4.89%, individually. This innovative chiral stationary phase shows a broader application view and scope in chiral recognition domain.

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Analytical Methods · 2012 ·Vol. 4 ·期 11 ·3785-3791 · IF 1.547

Cu@Ag/β-AgVO3 as a SERS substrate for the trace level detection of carbamate pesticides

Essy K. Fodjo,Sara Riaz,Da-Wei Li,Lu-Lu Qu,Niamien P. Marius,Trokourey Albert,Yi-Tao Long

A Surface Enhanced Raman Scattering (SERS) substrate based on Ag/β-AgVO3 nanobelts deposited on copper foil (Cu@Ag/β-AgVO3) was used for the detection of carbamate pesticides: carbofuran, carbaryl, isoprocarb and propoxur. Cu@Ag/β-AgVO3 has shown an excellent SERS activity for carbamate pesticides compared to silver nanoparticles (AgNPs). Under optimized conditions, detection limits of 2.5 pM, 10 pM, 50 pM and 75 pM were obtained for carbaryl, carbofuran, isoprocarb and propoxur respectively, suggesting that Cu@Ag/β-AgVO3 is a good candidate for use as a SERS substrate for the trace level detection of these pesticides.

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Crystals · 2021 ·Vol. 11 ·期 9 ·1049 · IF 2.589

Tailoring α/β Ratio of Pollen-Like Anhydrous Lactose as Ingredient Carriers for Controlled Dissolution Rate

Jia Xiang,Bo Wang,Le Fu,Chuanpin Chen,Wenjie Liu,Songwen Tan

Lactose is a commonly used excipient with two isomers. Different isomers have different properties, especially in terms of solubility. This work is mainly to explore the influence of different a/β ratio lactose on drug dissolution. This work has developed novel mesoporous pollen-like lactose anhydrous with tailored α/β ratios as ingredient carriers for controlled dissolution rate. The produced lactose carriers are pollen-like with a particle size of ~15 μm and a mean pore width of ~30 nm. β-lactose anhydrous has a unique FTIR-peak at 948 cm−1, whereas α-lactose anhydrous shows a unique FTIR-peak at 855 cm−1. DSC analysis suggests that the pollen-like α/β-lactose crystals are polymorphs with unique peaks of melting points. XRD analysis suggests that (5:5)α/β-lactose polymorph has high crystalline purity. The loading efficiency (30.6–33.4%w/w) of acetamidophenol within the nanoporous lactose particles is dependent on the surface structure and pore volumes—the pore volumes were found to be 0.0209–0.0380 cm3/g. The release rates of acetamidophenol are lower for lactose with high α/β ratios. The lactose solubility and the first-order release constant can be tailored by changing the proportion of β-lactose in the pollen-like lactose carriers.Keywords:pollen-like anhydrous lactose;α/β ratio;solubility;controlled release

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NEW JOURNAL OF CHEMISTRY · 2021 ·Vol. 46 ·期 5 ·2360-2367 · IF 3.591

Preparation of antibacterial nanofibers by electrospinning polyvinyl alcohol containing a luteolin hydroxypropyl-β-cyclodextrin inclusion complex

Xiaoyan Wang,Xiaona Hu,Shiqing Li,Wenhui Shi,Shujing Li,Yuxi Zhang

Sustained-release antimicrobial nanofibers (PVA-Lut-IC-NF) were prepared by incorporating a luteolin-hydroxypropyl-β-cyclodextrin inclusion complex (Lut-IC) into polyvinyl alcohol (PVA) via the electrospinning technique. PVA-Lut-IC-NF exhibits excellent water solubility and thermal stability. The results also showed significant antibacterial effects of PVA-Lut-IC-NF against Staphylococcus aureus, Candida albicans and Escherichia coli. Moreover, because of the sensitivities of different cytoderms to Lut, PVA-Lut-IC-NF was more effective against Staphylococcus aureus than Candida albicans and Escherichia coli. Additionally, PVA-Lut-IC-NF showed an appropriate slow release and maintained effective concentration in vitro release. PVA-Lut-IC-NF could have potential applications in food, pharmaceuticals, and healthcare due to its efficient antibacterial activity along with enhanced water solubility and thermal stability.

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