CELLULAR SIGNALLING
·
2018
·
IF 3.487
Wei-Chao Chen,Lei Liu,Yu-Feng Shen,Yang Hu,Fei Ling,Gao-Xue Wang,Bin Zhu
Coumarin forms an elite class of naturally occurring compounds that possess promising antiviral therapeutic perspectives. In this study, a coumarin derivative 7-[6-(2-methylimidazole) hexyloxy] coumarin (D5) was designed and synthesized to evaluate antiviral activity on a rhabdovirus , spring viraemia of carp virus (SVCV). Our results demonstrated that D5 had a robust antiviral activity with >90% inhibitory rate of SVCV expression in the host cells. And D5 significantly reduced viral-induced apoptosis and recovered virus-activated caspase-3/8/9 activities. Further data determined that SVCV could alter the cytoskeletal structure of EPC cells, characterized by a circumferential ring of microtubules and a disrupted microfilament organization, whereas cytoskeleton structure in D5-treated cells kept the normal morphology. Mechanistically speaking, D5 could interfere with SVCV replication inside or outside of cells through two different approaches. Before the process of virus entry into EPC cells, D5 had an impact on SVCV glycoprotein structure so as to disrupt viral binding to the cell surface or translocation to the cytosol. Another strategy for D5 to against SVCV was that D5 significantly suppressed SVCV-activated autophagy, which was beneficial for the host cells to restrict SVCV viral replication, accompanied by a higher phosphorylation of Akt-mTOR. In summary, our results revealed that D5 was effective in weakening SVCV infection and regulating SVCV-induced undesirable conditions, and this compound provided new therapeutic implications for the treatment of rhabdoviruses.
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TETRAHEDRON
·
2014
·
IF 2.817
Shouhai Yang,Wenge Yang,Qirun Guo,Tuan Zhang,Keyi Wu,Yonghong Hu
A simple but highly selective coumarin-based fluorescence probe 1 , 8-(1,3-dithiane)-7-hydroxycoumarin was designed and synthesized for both the ratiometric detection of Hg 2+ and the on–off response to pH change in aqueous solution. The sensor detected Hg 2+ selectively via Hg 2+ -promoted thioacetal deprotection reaction within five minutes and reflected pH in the range from 7.8 to 11.9 as a result of the equilibrium between weak-fluorescent acid form and strong-fluorescent base form. In addition, the probe has an excellent selectivity towards Hg 2+ over other competitive metal ions for biomedical and environmental applications. The sensing behavior of our probe was studied by UV–visible absorption spectra and fluorescence spectra .
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ANALYTICAL SCIENCES
·
2015
·Vol. 31
·期 10
·1055-1059
·
IF 1.394
Li-Qiang YAN,Mei-Fang CUI,Yan ZHOU,Yun MA,Zheng-Jian QI
A novel chemosensor L based on coumarin Schiff-base was synthesized and investigated. Sensor L showed remarkable selectivity for Al3+ in Tris–HCl aqueous buffer solution (pH 7.2), and the selectivity was not affected by the presence of a large excess of other competitive ions. The sensor responded rapidly to Al3+ in aqueous solutions with a 2:1 stoichiometry. Meanwhile, it indicated significant improvement of quantum efficiency and ideal fluorescent lifetime.
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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.
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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.
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NEW JOURNAL OF CHEMISTRY
·
2025
·
IF 2.5
Yaqin Nong,Xiaowei Su,Yinyue Xu,Qiujuan Chen,Xiaochen Liu,Xing Xia,Wenya Chen,Peiyuan Li,Rui Chen,Lini Huo
The pollution caused by heavy metals poses a significant threat to both the natural environment and human health. Therefore, developing straightforward and efficient analytical methods for detecting heavy metal ions is crucial. Given that Fe3+ plays an essential role in biological systems, researchers have worked hard to develop tests that specifically identify Fe3+ in clinical, pharmacological, and environmental settings. Seven novel coumarin amino acid-based Fe3+ fluorescent probes were designed and synthesized in this paper, and their structures were confirmed by 1H/13C NMR and high-resolution mass spectrometry. Spectroscopic tests demonstrated that three compounds (TAC-4, TAC-5, and TAC-7) identified Fe3+ specifically and in particular were able to distinguish between Fe3+ and Fe2+. For example, the fluorescent probe TAC-5 is characterized by its strong selectivity and sensitivity to Fe3+, as evidenced by a large change in fluorescence intensity, a rapid response time (30 seconds), a low detection limit (1.1 μM), and good solubility in water (up to 50%). Furthermore, TAC-5 was successfully used to detect changes in Fe3+ in zebrafish and HeLa Cells and to recognize Fe3+ in the presence of a chelating agent (EDTA). These results are expected to improve the development of new sensitive and selective fluorescence sensors for Fe3+.
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Green Chemistry Letters and Reviews
·
2019
·
IF 2.754
Adil Omar,Keyume Ablajan
A simple, efficient, eco-friendly and catalyst-free procedure was developed for the construction of novel coumarin-spiro[indoline-3,4'-pyran] conjugates via three-component reactions of various synthetic beta-ketoesters with isatins and malononitrile in aqueous medium. In addition to operational simplicity and absence of tedious separation procedures, being catalyst–free is the prominent advantage of this method.
研究领域:
有机化学
·
药物化学
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Polymer Chemistry
·
2022
·Vol. 13
·期 22
·3367-3376
·
IF 5.364
Xinyue Guo,Huanv Mao,Chunyan Bao,Decheng Wan,Ming Jin
In this work, three dyes based on fused carbazole–coumarin–ketone structures were designed and synthesized. These dyes were named CCK–Me, CCK–Ph, and CCK–Tol in accordance with their different substituents. Their excellent absorption properties can match the wavelength band of visible light-emitting diodes (LEDs) (i.e., 405–450 nm). Density functional theory calculations, steady-state photolysis, and electron spinning resonance spin trapping experiments were performed to explain the photophysical and photochemical mechanisms of the dyes. These dyes are available as one- or two-component type II photoinitiators (PIs). Both kinds can efficiently initiate the polymerization of acrylate monomers via two different mechanisms under 405–450 nm LED irradiation. Notably, CCK–Tol exhibited excellent photobleaching ability when initiated alone, making it ideal for deep curing. The polymeric samples were up to 57 mm thick. Remarkably, the photolysis product of CCK–Tol showed satisfactorily low cytotoxicity. The above excellent properties showed the great potential application of the dyes in various photocuring materials, especially dental materials and thick three-dimensional structures.
研究领域:
材料科学
·
化学
·
生物医学工程
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MACROMOLECULES
·
2018
·
IF 5.914
Zhukang Du,Xiaolong Yan,Renfeng Dong,Kang Ke,Biye Ren,Zhen Tong
Telechelic associative polymers (TAPs) can form a dynamic transient network in water and have been widely used as rheological modifiers for improving solution rheological properties in many industrial fields. In this work, we designed and prepared a novel photoresponsive coumarin-functionalized telechelic associative model polymer (CouTAP), which was used to investigate the influence of light-induced dimerization of coumarin end groups on the polymer structure and solution rheological properties. The effects of light intensity, irradiation time, polymer concentration, and temperature on the transient network and rheological behavior of the CouTAP aqueous solution were studied in detail. The rheological properties of the dimerized CouTAP aqueous solution show weak temperature dependence, and the dynamics hardly depends on concentration due to the transformation of triblock to multiblock polymers. A novel transient network model composed of train loops and bridges covalently linked to train loops was proposed to describe the unique solution properties. This work will not only provide new insights into the influence of the light-induced dimerization of coumarin end groups on the network structure and rheological properties of CouTAP solution but also opens a new perspective for the controlled self-assembly of amphiphilic polymers and some special applications of TAPs in the manufacturing and transmission of soft materials, waterborne coating, inks, medicines, cosmetics, and so on.
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JOURNAL OF SOLID STATE CHEMISTRY
·
2025
·
IF 3.5
Peng Wang,Hongmei Qu,Xia Li,Ruyu Liu,Ruihan Dai,Yameng Li,Zhihua Zhang
To further enhance the performance of MOFs-based hydrogen sulfide (H 2 S) detection probes, we proposed a novel strategy for constructing for H 2 S detection. We have designed and synthesized a new reactive coumarin-based ligand (NTA) and directly prepared the MOFs-based fluorescent probe UiO-66-NTA using the new ligand. This approach overcame the issues of low grafting rates and uneven reactive sites associated with post synthetic modification (PSM) strategy prepared MOFs-based fluorescent probes. This construction strategy endowed MOFs with a greater number of active sites on their surfaces for H 2 S detection, thereby achieving superior sensing performance for H 2 S, which included an ultra-fast response time (5 s) and a low detection limit (0.063 μM). The rigid topological structure of the MOFs minimizes π-π interactions between fluorophores, conferring aggregation-induced emission (AIE) characteristics to the probe. To enhance the practical utility of the probe, a smartphone-assisted test strip sensing system was developed and successfully applied to the detection of real water samples. Additionally, the probe was integrated into the sodium alginate (SA) hydrogel to create a portable sensor UiO-66-NTA@SA for assessing the freshness of meat by detecting H 2 S.
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EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS
·
2017
·
IF 4.159
Jinyu Li,Guoxin Tan,Bingchao Cheng,Dandan Liu,Weisan Pan
To facilitate the hydrophobic drugs modeled by coumarin-6 (Cou-6) acrossing the cornea to the anterior chamber of the rabbit eye, chitosan (CS) derivatives including chitosan-N-acetyl- l -cysteine (CS-NAC), chitosan oligosaccharides (COS) and carboxymethyl chitosan (CMCS) modified nanostructured lipid carriers (NLCs) were designed and characterized. We found that, with similar size distribution and positive charges, different CS derivatives based on NLCs led to distinctive delivery performance. In vivo precorneal retention study on rabbits revealed that these CS derivatives coating exhibited a stronger resistant effect than Cou-6 eye drops and Cou-6-NLC (P < 0.05), moreover, the AUC (0−∞) , C max and MRT (0−∞) of them followed the sequence of CMCS-Cou-6-NLC < COS-Cou-6-NLC < CS-NAC-Cou-6-NLC. Confocal laser fluorescence microscopy (CLSM) for in vitro corneal penetration study showed that COS-, and CS-NAC-coated NLCs penetrated through the whole corneal epithelium barrier (about 40 μm), while CMCS failed to significantly enhance the intraocular drug penetration as expected, displayed a negligible fluorescence at 30 μm deep. In addition, penetration through the intact cornea was achieved and the penetration levels through the ocular tissues were increased thoroughly for the COS and CS-NAC coating ones compared with CMCS-NLC (P < 0.05), and successfully reduced the conjunctival-to-corneal permeability ratio (ratio (C - S/C) ) thus resulted in a higher bioavailability, which was confirmed by ex vivo fluorescence imaging on ocular tissues. In summary, CS-NAC-NLC and COS-NLC are promising ocular drug delivery systems to achieve prolonged precorneal retention, higher corneal permeability and enhanced ocular bioavailability. And comparatively speaking, CS-NAC-NLC possesses the highest potential for ocular drug delivery.
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Plants-Basel
·
2026
·Vol. 15
·期 11
·1694
·
IF 4.7
Hui Yang,Rong-Rong Xie,Tian-Tian Xia,Liang-Yuan Tong,Ti Wu,Xin Ye,Zeng-Rong Huang,Lin-Tong Yang,Li-Song Chen
No data to date are available on the underlying mechanisms by which coumarin (COU) alleviates plant aluminum (Al) toxicity.Citrus grandis(L.) Osbeck seedlings were submitted to 0 (Al0) or 1.2 (Al1.2 or Al3+toxicity) mM AlCl3·6H2O and 0 (COU0) or 50 (COU50) μM COU for 18 weeks. The results demonstrated that COU50 attenuated Al1.2-induced decreases of seedling growth, chlorophyll (Chl) level, and CO2assimilation (ACO2) and impairment of the photosynthetic electron transport chain (PETC). Further analysis suggested that reduced tissue Al concentration and enhanced capability to maintain nutrient and redox homeostasis played a role in COU-mediated amelioration of seedling growth inhibition, leaf Chl and ACO2decline, and PETC impairment. Notably, seedlings treated with COU0 showed some adaptive responses to Al1.2. For example, Al1.2 decreased the biosynthesis and accumulation of proteins and amino acids to meet the increased need for energy; increased the diphenylpicrylhydrazyl (DPPH) scavenging activity and phenolic compound accumulation to meet the elevated demand for reactive oxygen species (ROS) and Al detoxification; and increased the accumulation of soluble sugars (glucose, fructose, and sucrose) to meet the augmented demand for ROS scavenging and energy. To conclude, the research revealed some mechanisms for COU-mediated amelioration of plant Al3+toxicity.
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