MOLECULES
·
2026
·Vol. 31
·期 4
·595
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IF 5.1
Xiaohua Wang,Xueliang Lu,Wanwan Jin,Xiaoyan Tan,Gang Wang
A new series of tacrine–coumarin hybrids (compounds15a–18b) linked by 1,2,3-triazole had been designed and synthesized as multifunctional ligands for the treatment of Alzheimer’s disease (AD). The inhibitory effects of the synthesized compounds on AChE and BuChE, their ability to inhibit Aβ aggregation, and their MAO inhibitory activities were evaluated. In vitro studies showed that some of the hybrids (compounds17a–18b) exhibited significant abilities to inhibit both AChE and BuChE, self-induced Aβ aggregation, and MAO-B. In particular, compound17dshowed a well-balanced inhibitory profile against AChE and BuChE (IC50= 0.080 ± 0.007 μM for AChE, IC50= 0.044 ± 0.004 μM for BuChE), self-induced Aβ aggregation (58.4% ± 2.1% at 20 μM), and MAO-B (IC50= 0.18 ± 0.01 μM), suggesting that17dmight be an excellent multifunctional agent for AD treatment. In addition, compounds15aand15bwere identified as selective inhibitors of BuChE at micromolar concentrations.
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ACS Applied Polymer Materials
·
2026
·
IF 5.2
Ziyan Li,Xiaoxiao Xing,Ke Wang
Abstract In this study, coumarin-functionalized homopolymer P(Cou-N-AM), spiropyran-functionalized homopolymer P(SP-N-AM), and dual-functional block copolymer P(Cou-N-AM)-b-P(SP-N-AM) were synthesized via reversible addition–fragmentation chain-transfer (RAFT) polymerization. These polymers exhibited quadruple-responsive characteristics. The experimental results demonstrated that they displayed typical lower critical solution temperature (LCST) behavior in a buffer solution at pH = 4, which can be precisely tuned by adjusting the polymerization degree and solution concentration. Moreover, these polymers possessed a definite critical pH in water. Alternate bubbling of CO2 and N2 achieved reversible cyclic variations in solution pH and transmittance, indicating excellent gas-responsive cycling stability. Upon UV irradiation, P(Cou-N-AM) showed gradual decay in characteristic UV absorption, while P(SP-N-AM) and the block copolymer exhibited reversible photoisomerization with good cycling stability. Fluorescence measurements confirmed that all the polymers exhibited fluorescence properties and could be regulated by temperature, pH, and CO2. With the increase of temperature, fluorescence underwent thermal quenching. P(Cou-N-AM) produced stable blue fluorescence under alkaline conditions, while P(SP-N-AM) realized reversible red fluorescence emission under acidic environments. The block copolymer achieved mutually exclusive reversible switching between blue and red fluorescence through acid–base regulation or CO2/N2 gas alternation. Based on the superior multistimuli responsiveness and tunable dual-color luminescence performance of the block copolymer, a multilevel and reversible intelligent anti-counterfeiting system was successfully constructed. This work provides insight for the rational design and fabrication of multistimuli-responsive fluorescent polymers, showing promising applications in multilevel anti-counterfeiting and intelligent gas sensing.
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INDUSTRIAL CROPS AND PRODUCTS
·
2023
·
IF 5.9
Minglei Tao,Shengzhi Liu,Yaohan Li,Amin Liu,Zijian Sun,Vinesh Maharaj,Shouxin Li,Jingkui Tian,Wei Zhu
Coumarin synthase (COSY) is the key enzyme involved in the coumarin biosynthesis. Although it has been identified firstly in Arabidopisis thaliana , there is little known about the COSY gene function in Clematis terniflora DC. Our previous study indicated that the contents of coumarins in C. terniflora leaf were increased under ultraviolet-B radiation and dark treatments (UV-D). To reveal the function of COSY in C. terniflora and its role in response to UV-D stress, the functional characterization of CtCOSY which was identified as a BADH acyltransferase was performed. The results showed that coupled reaction of CtCOSY with 4-coumarinyl CoA-ligase in vitro to produce umbelliferone . Moreover, the functions of CtCOSY in response to UV-D stress was studied using proteomic and metabolomic techniques. Multi-omics analyses of CtCOSY -silenced C. terniflora indicated that as well as a limitation of coumarin synthesis, aspects of the energy metabolism, such as the TCA cycle, were disturbed in these plants. Under UV-D stress, CtCOSY affected the biosynthesis of phenylpropanoids in C. terniflora , resulting in the improvement of coumarin biosynthesis and affecting purine metabolism. This study provides the evidences of CtCOSY responsible for the biosynthesis of coumarin in C. terniflora and the resistance to UV-D stress.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2018
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IF 2.88
Xu Tang,Zhi Zhu,Renjie Liu,Liang Ni,Yue Qiu,Juan Han,Yun Wang
A novel fluorescence probe L2 based on coumarin has been designed and synthesized. The probe L2 can be used for relay recognition of metal ions Al 3+ and anion F − in the aqueous HEPES buffer (0.05 M, pH = 7.4), and build a OFF-ON-OFF detection system. The probe showed high selectivity and sensitivity to target ions in the process of relay recognition, and the corresponding detection limit could be as low as 0.014 μM (Al 3+ ) and 0.03 μM (F − ). Besides, the geometry optimizations of probe L2 and [L2 + Al 3+ ] complex were carried out using the Gaussian 16 program based on DFT, and the identification mechanism of the probe was also discussed by the mass spectrometry and theoretical calculations. Moreover, the probe has also been successfully applied to detection of target ions in living cells.
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Frontiers in Bioengineering and Biotechnology
·
2022
·
IF 6.064
Liu Xina,Zhu Meiqing,Xu Chenyang,Fan Fugang,Chen Panpan,Wang Yi,Li Dongyang
As an inorganic small molecule pollutant, the toxicity and potential carcinogenicity of hydrazine (N2H4) are of increasing concern. In this work, A water-soluble fluorescent probe (OCYB) based on the intramolecular charge transfer (ICT) mechanism for the detection of hydrazine was designed and synthesized. Taking the advantage of 4-bromobutyryl as the recognition group, the high selectivity of OCYB to N2H4 was confirmed by steady-state fluorescence spectroscopy. The limit of detection (LOD) was calculated to be 78 nM in the DMSO-HEPES (pH 7.4) system. The detection mechanism was verified by NMR, HRMS and density functional theory (DFT) calculations. In addition, OCYB exhibits strong anti-interference ability and an “Off-On” fluorescence enhancement effect. Importantly, OCYB can be used to effectively monitor the fluorescence distribution of N2H4 in environmental water samples and organisms.
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FOOD CHEMISTRY
·
2021
·
IF 7.514
Wei Yang,Chenyuan Weng,Xiaoyun Li,Wei Xu,Jianwen Fei,Junli Hong,Jun Zhang,Wanying Zhu,Xuemin Zhou
Herein, using Fe 3 O 4 nanoparticles (Fe 3 O 4 NPs) as a magnetic artificial peroxidase, an “on–off” ratiometric photoluminescence sensor with high-sensitivity and high-selectivity for coumarin was constructed based on photoinduced electron transfer (PET) between 7-hydroxycoumarin and rhodamine B (RB). The results showed that Fe 3 O 4 NPs catalyzed H 2 O 2 to generate nucleophilic group ·OH, which attacked the active site of coumarin and produced strong fluorescent 7-hydroxycoumarin molecules. Then, the fluorescence of RB was quenched with 7-hydroxycoumarin through the PET effect. The ratio signal generated in the above process was used for the quantitative detection of coumarin. Under optimized conditions, the linear range 0.5–25 mg/L was acquired for coumarin with the detection limit of 0.016 mg/L. This method had excellent selectivity and the recovery rate was 81.8%−106.8% with the relative standard deviation less than 5.6%, so it can be used for the quantitative analysis of coumarin in complex matrix samples.
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SENSORS AND ACTUATORS B-CHEMICAL
·
2021
·
IF 7.46
Dongxia Nie,Dakai Guo,Qingwen Huang,Wenbo Guo,Jianhua Wang,Zhihui Zhao,Zheng Han
Nanocomposites of thiol-terminated liposomes encapsulating with coumarin-6 ( [email protected] ) were successfully prepared via a simple thin-film dispersion method to construct a novel fluorescent sensor for selectively detecting trace amounts of patulin. Thiol group ( SH) was designed not only as a specific recognition element to capture patulin, but also as a convenient linker for the further separation of patulin-derivatized and un-derivatized [email protected] by combination with magnetic NH 2 [email protected] 3 O 4 nanoparticles. Liposomes primarily provided an effective platform with a large surface area for facilitated accommodation of large amounts of recognition element ( SH group) and fluorophore (coumarin-6). In such an assay protocol, a reliable link was established between the changes in fluorescent intensity (ΔF) from the nanocomposites of [email protected] /NH 2 [email protected] 3 O 4 and the concentrations of patulin in the range of 0.05–20 ng mL −1 , with the correlation coefficient of 0.996. This approach also effectively eliminated the background interference from other mycotoxins and metal ions. Under the optimal conditions, the designed sensor displayed excellent performance for patulin analysis, with an extremely low detection limit (0.033 ng mL −1 ), high recovery (96.2–107.6 %) and excellent selectivity. Furthermore, the feasibility of its applications has also been demonstrated in the analysis of real juice samples, providing a novel tactics for rational design of a fluorescence assay, for point-of-care diagnostics of patulin, with great potential to be extended to other hazardous compounds by substitution of the recognition elements.
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JOURNAL OF MOLECULAR STRUCTURE
·
2020
·
IF 2.463
Da-Hua Shi,Wei Min,Meng-qiu Song,Xin-Xin Si,Ming-Cheng Li,Zhao-yuan Zhang,Yu-Wei Liu,Wei-Wei Liu
Coupling of two distinct pharmacophores , carbazole and coumarin , endowed with different biological properties, afforded four hybrid compounds. The structures of the carbazole-coumarin hybrids were characterized by FT-IR, NMR, HRMS and single-crystal X-ray diffraction studies. All of these compounds exhibited significant acetylcholinesterase inhibitory activities. Among them, compound 4-((5-(9H-carbazol-9-yl)pentyl)oxy)-2H-chromen-2-one ( 3d ) exhibited the best inhibition activity with IC 50 of 3.75 μ M for acetylcholinesterase from electric eel and 70.51 μ M for human recombinant acetylcholinesterase. Moreover, the compound 7-(3-(9H-carbazol-9-yl propoxy)-4-methyl-2H-chromen-2-one ( 3a ) had the best antioxidant activity . The docking studies demonstrated that compound 3d could interact with both the catalytic active site and the peripheral anionic site of acetylcholinesterase. These attributes imply carbazole-coumarin hybrids as multifunctional agents for the Alzheimer’s disease treatment.
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CHEMICO-BIOLOGICAL INTERACTIONS
·
2022
·
IF 5.168
Moath Refat,Guoqiang Zhang,Abdulaziz Ahmed A.Saad,Salem Baldi,Fang Zheng,Xin'an Wu
Cholestasis is primarily caused by bile acid homeostasis dysregulation, resulting in retention, aggregation, and accumulation of the toxic cholate in the hepatocytes. Existing therapies for cholestasis are limited, demanding the urgent development of novel drugs. As a result, targeting FXR specifically promises a unique treatment strategy for cholestasis. The current study aims to evaluate the influence of 7, 8-dihydroxy-4-methyl coumarin (DMC) against alpha-naphthyl isothiocyanate (ANIT)-induced liver injury in mice. The “Computer-Aided Drug Design” (CADD) and molecular docking study anticipated that DMC would proficiently bind and activate the FXR. Accordingly, the hepatoprotective activity of DMC against ANIT-induced hepatotoxicity and cholestasis was investigated in ANIT-treated HepaRG cells and the ANIT-induced cholestatic mouse model. Outcomes indicated the protective effects of DMC against ANIT toxicity in HepaRG cells after 24 h of intervention and animals after seven days of treatment. DMC partially blocks ANIT-induced increases in serum markers of hepatocellular injury , liver and gall bladder enlargement , and hepatic necrosis . Western blotting revealed that DMC alleviates ANIT-induced hepatotoxicity and cholestasis via activating the FXR receptor and regulating CYP7A1 , the enzyme responsible for bile acid synthesis. DMC exhibited protective activity against cholestasis through activating FXR, suggesting it might be a promising strategy for preventing and treating cholestatic liver disease.
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MICROCHEMICAL JOURNAL
·
2024
·
IF 4.9
Wenqing Zhang,Hao Zhu,Wenjie Xie,Chuanyuan Du,Xiuqiang Fang,Ruiming Zhang,Xiaosong Hu,Yawei Lin
A novel fluorescent probe , 3-(4-((hydroxylamino)methyl)-1H-pyrazol-1-yl)-7-methoxyl coumarin (HAPMC), has been designed and synthesized. The compound exhibits exceptional fluorescence properties due to a coumarin-pyrazolyl fluorophore. Moreover, it incorporates an N -hydroxylamine functional group capable of reacting with aldehydes to yield nitrone derivatives under mild conditions. This unique combination renders it an ideal derivatization reagent for aldehyde analysis. A standard method was established for the quantitative analysis of eight fatty aldehydes by utilizing high-performance liquid chromatography with fluorescence detection (HPLC-FLD) and a pre-column derivatization process, which has low detection limits (0.3–1.2 nM), satisfactory reproducibility (intraday and interday relative standard deviations in the range of 1.29 %-2.92 % and 1.73 %-3.45 %), and an extensive linear range (25–5000 nM) with excellent linearity (R 2 ≥ 0.9989). The spiked recoveries of the fatty aldehydes range from 89.6 % to 106.0 %. The greenness and sustainability of our approach are reinforced by evaluations conducted with the AGREE and RGB 12 algorithms. The established method was successfully applied to the qualitative and quantitative detection of fatty aldehydes in nine real vegetable oil samples, including peanut, canola, rice, soybean, olive, rapeseed, corn, sunflower, and blended oils. The fatty aldehydes are known to have adverse effects on human health due to their carcinogenic and mutagenic properties. The findings revealed that hexanal and nonanal were the most prevalent saturated fatty aldehydes, with a notable increase in the total aldehyde concentration observed as the temperature and duration of heating increased. Compared to alternative analytical techniques, this pre-column derivatization method utilizing HAPMC displayed simplicity, reliability, and sensitivity. The results demonstrate the potential for broad application of this approach in various important research domains, including food quality control, environmental monitoring, and medical research.
研究领域:
食品科学
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分析化学
·
医学研究
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY
·
2022
·
IF 7.129
He Mei,Jianping Wang,Xiaolei Zhu,Juan Sun,Wei Shi,Huili Wang,Shugen Qu,Xuedong Wang
A novel ratiometric fluorescent probe was constructed for sensitive assay of hydrogen peroxide (H 2 O 2 ) and glucose, which utilized the synergistically enhanced effects of Ce 3+ and Fe 2+ on copper nanoclusters (CuNCs) and coumarin. In the CuNCs-Ce 3+ /Fe 2+ -coumarin system, Ce 3+ triggered the aggregation-induced emission phenomenon of CuNCs, and Fe 2+ catalyzed the Fenton reaction to efficiently yield hydroxyl radical (•OH). In the presence of H 2 O 2 , the 625-nm red fluorescence of CuNCs was sharply quenched owing to the oxidation of CuNCs to Cu(II) by •OH, but the 460-nm blue fluorescence of 7-hydroxycoumarin from the oxidation of coumarin by •OH dramatically increased. Based on the reversible changes in two fluorescence signals, a satisfactorily ratiometric probe was constructed for H 2 O 2 assay with a detection limit (LOD) of 0.6 μM accompanied by a visual color variation from red to blue. For glucose assay, this ratiometric probe gave a linear range of 3.2–160 μM and LOD of 0.96 μM owing to the oxidization of glucose to yield H 2 O 2 in the presence of glucose oxidase and O 2 . Overall, the newly developed ratiometric probe shows a great prospect in real applications for visual assay of H 2 O 2 and glucose by our naked eyes.
研究领域:
分析化学
·
生物医学
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MOLECULES
·
2024
·Vol. 29
·期 3
·618
·
IF 4.2
Dongmei Li,Senlin Peng,Xu Zhou,Lingyi Shen,Xianjiong Yang,Hong Xu,Carl Redshaw,Chunlin Zhang,Qilong Zhang
In this study, we synthesized a coumarin–hemicyanine-based deep red fluorescent dye that exhibits an intramolecular charge transfer (ICT). The probe had a large Stokes shift of 287 nm and a large molar absorption coefficient (ε = 7.5 × 105L·mol−1·cm−1) and is best described as a deep red luminescent fluorescent probe withλem= 667 nm. The color of probe W changed significantly when it encountered cyanide ions (CN−). The absorption peak (585 nm) decreased gradually, and the absorption peak (428 nm) increased gradually, so that cyanide (CN−) could be identified by the naked eye. Moreover, an obvious fluorescence change was evident before and after the reaction under irradiation using 365 nm UV light. The maximum emission peak (667 nm) decreased gradually, whilst the emission peak (495 nm) increased gradually, which allowed for the proportional fluorescence detection of cyanide (CN−). Using fluorescence spectrometry, the fluorescent probe W could linearly detect CN−over the concentration range of 1–9 μM (R2= 9913, RSD = 0.534) with a detection limit of 0.24 μM. Using UV-Vis spectrophotometry, the linear detection range for CN−was found to be 1–27 μM (R2= 0.99583, RSD = 0.675) with a detection limit of 0.13 μM. The sensing mechanism was confirmed by1H NMR spectroscopic titrations,13C NMR spectroscopy, X-ray crystallographic analysis and HRMS. The recognition and detection of CN−by probe W was characterized by a rapid response, high selectivity, and high sensitivity. Therefore, this probe provides a convenient, effective and economical method for synthesizing and detecting cyanide efficiently and sensitively.
研究领域:
化学
·
分析化学
·
环境科学
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