INORGANICA CHIMICA ACTA
·
2025
·
IF 3.2
Qian Sun,Lu Ren,Jing Wang,Kun Bai,Chang Liu,Yanqi Liu,Dawei Zhang
Coumarin-structured ( E )-7-(diethylamino)-3-(1-(2-(4-methylbenzo[ d ]thiazol-2- yl)hydrazono)ethyl)-2 H -chromen-2-one (HTM) was synthesized in two steps using N , N -diethylsalicylaldehyde, ethyl acetoacetate and 4-methyl-2-hydrazine-benzothiazole as raw materials. The HTM was characterized by FT-IR, 1 H NMR, 13 C NMR and HR-MS. It was found that the probe HTM has rapid and highly selective recognition ability for Cu 2+ in EtOH/H 2 O (1:1, v /v). The spectral characteristics of the probe HTM were investigated using fluorescence spectroscopy and ultraviolet-visible spectroscopy. The results showed that the binding of probe HTM to Cu 2+ produced a significant fluorescence quenching effect, and the influence of other metal ions was negligible. In visible light, when HTM interacts with Cu 2+ , the solution changes from yellow to orange as observed by the naked eye. Subsequently, the binding mechanism of the probe HTM to Cu 2+ was explored by Job's plot, 1 H NMR titration and DFT calculations, and it was found that they cooperated in a 1:1 manner. Linear equations for ultraviolet-visible and fluorescence intensities at different Cu concentrations were fitted, and the detection limits (LOD) were calculated to be 5.22 nM and 3.70 nM, respectively. Experimental studies on the recovery rates of standard additions indicated that the probe HTM could be used for the quantitative detection of Cu 2+ in actual water samples. The potential application of this probe in fingerprint detection was also investigated. In addition, the probe has been successfully applied to Cu 2+ monitoring in living cells.
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SENSORS AND ACTUATORS B-CHEMICAL
·
2017
·
IF 5.401
Lei Wang,Wenxuan Li,Wenjing Zhi,Dandan Ye,Wenli Zhang,Liang Ni
By employing the oxidation property of hypochlorite (OCl − ), a new probe based on coumarin dye and an OCl − -specific reactive moiety of hydrazide group was designed and synthesized. The probe rendered turn-on type fluorogenic response toward OCl − via hypochlorite-triggered oxidative hydrolysis of hydrazide to release strongly fluorescent coumarin. Most notably, the probe showed sufficiently satisfactory selectivity to OCl − over other oxidants, and high sensitivity with approximate 18-fold fluorescence enhancement at nanomolar level. Moreover, the fast detection of OCl − could be realized by the probe with only 30 s. The interaction mechanism has been proposed and further confirmed by the changes in electrospray ionization (ESI) mass spectra. The probe was also successfully applied to fluorescence imaging of OCl − in its vitro macrophage cells.
研究领域:
分析化学
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生物化学
·
细胞生物学
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NEW JOURNAL OF CHEMISTRY
·
2021
·Vol. 45
·期 27
·11983-11991
·
IF 3.591
Wen Lu,Jiuzhou Shi,Jichao Chen,Lu Sun,Lingcen Shao,Hongyu Ren,Mengmeng Huang,Yanqin Wang,Shilong Yang,Xu Li
This study describes the synthesis of a coumarin-based reversible fluorescent probe BuCAC for the detection of Cu2+ and S2− in CH3CN : PBS (v/v = 8 : 2, pH = 7.4) solution. The resulting BuCAC exhibited high sensitivity (detection limit = 3.03 × 10−7 M) and selectivity towards Cu2+ through a 2 : 1 binding mode. In the presence of S2−, the BuCAC–Cu2+ recovered to BuCAC and CuS, which in turn perform the function of a sensitive probe with a lower detection limit of about 1.7 × 10−7 M. This “on–off–on” process can easily occur in 1 min with a repetition of at least 5 times. The sensing mechanism was confirmed by Job's plot analysis, MS, and density theory calculation. Besides, fluorescence imaging in zebrafish, HeLa cells, and soybean root tissue revealed that the probe BuCAC could serve as a valuable tool for monitoring and tracking intracellular Cu2+ and S2− while benefiting from its excellent fluorescence performance and lower cytotoxicity.
研究领域:
分析化学
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生物化学
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生物医学工程
·
细胞生物学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Mengmeng Li,Canping Pan,Zhijia Zhang,Jialing Wang,Shuai Wang,Wenzhuo Li,Tianbing Zhou,Xiaoyi Wang,Ziyi Liu,Zhan Hu,Ranfeng Sun,Dong Li
Imidacloprid (IMI) stress positively correlates with the potential of coumarins to alleviate abiotic stress. However, little is known about the pathways and mechanisms by which coumarin reduces the IMI residue by regulating plant secondary metabolism and plant–microbe interactions. This study examined the impact of coumarin on the uptake, translocation, and metabolism of IMI in pepper plants by modulating the signal molecule levels and microbial communities in the rhizosphere and phyllosphere. Analysis of 2 h─28 d pesticide residue dynamics revealed that coumarin dramatically reduced IMI concentration in pepper fruits. Coumarin upregulated the phenylpropane pathway genes, which increased the levels of flavonoids, phenolic acids, phytohormones, and capsaicinoids. Importantly, phyllosphere and rhizosphere microbial diversity results showed that coumarin improved the abundance of beneficial microorganisms and positively correlated with secondary metabolite secretion. Therefore, coumarin exploited the interaction between the phenylpropane and coumarin synthesis pathways and beneficial microbes to enhance the nutritional quality and IMI degradation.
研究领域:
植物学
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环境科学
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农业科学
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高影响因子
MOLECULES
·
2019
·Vol. 24
·期 14
·2569
·
IF 3.06
Feifei Yang,Na Zhao,Jiali Song,Kongkai Zhu,Cheng-shi Jiang,Peipei Shan,Hua Zhang
A series of novel coumarin-based hydroxamate derivatives were designed and synthesized as histone deacetylase inhibitors (HDACis). Selective compounds showed a potent HDAC inhibition with nM IC50values, with the best compound (10e) being nearly 90 times more active than vorinostat (SAHA) against HDAC1. Compounds10eand11dalso increased the levels of acetylated histone H3 and H4, which is consistent with their strong HDAC inhibition. In addition,10eand11ddisplayed a higher potency toward human A549 and Hela cancer cell lines compared with SAHA. Moreover,10eand11dsignificantly arrested A549 cells at the G2/M phase and enhanced apoptosis. Molecular docking studies revealed the possible mode of interaction of compounds10eand12awith HDAC1. Our findings suggest that these novel coumarin-based HDAC inhibitors provide a promising scaffold for the development of new potential cancer chemotherapies.Keywords:coumarin;hydroxamate;HDAC inhibitors;antitumor growth;structure–activity relationship
研究领域:
药理学
·
肿瘤学
·
药物化学
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JOURNAL OF INORGANIC BIOCHEMISTRY
·
2022
·
IF 4.336
Wen Lu,Jiongya Tang,Zhenzhen Gu,Lu Sun,Haimeng Wei,Yanqin Wang,Shilong Yang,Xingwei Chi,Li Xu
This work describes the synthesis, anticancer activity and electron structure study of two Cu (II) complexes with coumarin-3-formyl-(3-(aminomethyl) pyridine) ligand ( L ) - C1 (Cu 2 L 2 (OAc) 4 ) and C2 (CuL 2 (NO 3 ) 2 ). The structure of C1 and C2 was confirmed by elemental analysis , FTIR, and single-crystal X-ray analysis. Complex C1 crystallizes as binuclear where two Cu (II) ions are bridged by four acetate ligands while C2 is a mononuclear complex with twisted octahedral geometry. Density functional theory (DFT) calculations revealed that electronic transitions originate from metal-ligand charge transfer and d - d transitions of metal ions . According to the results of UV–Vis and fluorescence titrations, C1 and C2 intercalate with DNA with the binding constants of 6.9 × 10 5 M −1 and 5.9 × 10 5 M −1 , respectively. The in vitro cytotoxicity assays on four cancer cell lines (HeLa, HepG2, MCF-7 and A549) and a normal HUVEC cell line indicated higher anti-MCF-7 activity of C2 compared with cisplatin (IC 50 = 2.86 ± 0.08 μM vs. 9.07 ± 0.10 μM). Moreover, C2 had superior selectivity since IC 50 toward HUVEC cells was over 150 μM compared with 0.58 ± 0.05 μM for cisplatin. We concluded that the anti-MCF activity of mononuclear C2 complex is better than that of binuclear C1 and cisplatin. Therefore, C2 has been selected as a hit compound to develop novel non‑platinum anticancer agents through modification of coumarin-amide structure and variation of copper (II) salts.
研究领域:
无机化学
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药物化学
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生物物理化学
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癌症研究
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EUROPEAN JOURNAL OF PHARMACOLOGY
·
2023
·
IF 5
Xueli Xu,Yangyang Shi,Qingwen Yu,Yajie Peng,Fei Zhao,Jing Cui,Yajing Chen,Lingxu Liu,Yiran Zhang,Ji Zhang,Bo Wei
Myocardial infarction (MI) is irreversible damage caused by ischemia and hypoxia in coronary arteries accompanied by elevated catecholamine levels, leading to the accumulation of free radicals. Our previous study discovered coumarin-derived imino sulfonates as a novel class of potential cardioprotective agents possessing strong anti-oxidative effects in cardiomyocytes. Therefore, identifying the compound with the highest cardioprotective activity, 5h, and the mechanism involved was necessary. As a kind of catecholamine, isoproterenol can clinically induce myocardial infarction injury similar to the symptoms of myocardial infarction patients. Our experiments explored the underlying mechanism of this effect of compound 5h by assessing cardiac function, infarct size, histopathological changes, and downregulation of Sirt1 by transfection of adenovirus in vitro and by administering Ex527 , a specific inhibitor of Sirt1, in vivo . Compound 5h exhibited strong cardioprotective actions in vivo and in vitro via improving cell survival and cardiac function and decreasing the cellular oxidative stress and cardiac infarct size against MI. Furthermore, compound 5h significantly enhanced cardiac expression of Sirt1, subsequently activating the Nrf2/NQO1 signaling pathway. However, adenovirus-induced Sirt1 downregulation or Sirt1-specific inhibitor largely blocked such beneficial effects of 5h in vitro and in vivo , respectively. Taken together, our results demonstrated, for the first time, that the cardioprotective action of 5h against MI was mediated by reducing oxidative stress and apoptosis through the Sirt1/Nrf2 signaling pathway. Our findings proposed novel insights in developing and evaluating coumarin-derived imino sulfonate compounds as epigenetics-targeted drug therapy for MI.
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高影响因子
LUMINESCENCE
·
2023
·Vol. 38
·期 2
·159-165
·
IF 2.9
Linlin Lv,Weiwei Luo,Yixiao Zhou,Tiechun Li,Quanping Diao,Pinyi Ma,Daqian Song
Hydrazine (N 2 H 4 ) is a highly toxic and harmful chemical reagent. Fluorescent probes are simple and efficient tools for sensitive monitoring of N 2 H 4 enrichment in the environment, humans, animals, and plants. In this work, a ratiometric fluorescent probe (FP-1) containing coumarin was used for hydrazine detection. The proposed FP-1 probe had a linear detection range of 0–250 μM and a limit of detection (LOD) of 0.059 μM (1.89 ppb). A large red Stokes shift was observed in fluorescence and UV–vis absorption spectra due to the hydrolysis of ester bonds between FP-1 and hydrazine. The hydrazine detection mechanism of FP-1 was also investigated using density functional theory (DFT) calculations. Finally, FP-1 could sensitively and selectively monitor hydrazine in actual water samples and BEAS-2B cells. Therefore, it has great application potential in environmental monitoring and disease diagnosis.
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BIOORGANIC CHEMISTRY
·
2018
·
IF 3.929
Qi He,Jing Liu,Jin-Shuai Lan,Jiaoli Ding,Yongbing Sun,Yuanying Fang,Neng Jiang,Zunhua Yang,Liyuan Sun,Yi Jin,Sai-Sai Xie
A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer’s disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC 50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 µM for hAChE; 0.101 µM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2022
·
IF 4.831
Rongsheng Gao,Xueyan Liu,Jianyan Feng,Lu Han,Jianhong Xu,Chengyou Kan
A novel polyurethane ( PU- co -HCCA ) nanoemulsion bearing coumarin derivative ( HCCA ) was synthesized as a “turn-on” fluorescent probe and used to modify filter paper, and its sensing properties were investigated. Results showed that PU- co -HCCA nanoemulsion exhibited high selectivity and excellent sensitivity toward Hg 2+ over other metal ions, and possessed excellent fluorescence quantum yields of 0.976, ppb-levels detection limits of 1.61 ppb and large Stokes shifts of 101 nm. Meanwhile, as an application example of as-prepared PU- co -HCCA nanoemulsion, a Hg 2+ test paper was prepared by modifying filter paper with PU- co -HCCA nanoemulsion, and results indicated that the test paper is portable and convenient and has a wide working pH range. We believe that the PU- co -HCCA nanoemulsion and the modified filter paper can provide a new design principle for the application of fluorescence sensors for metal ions including Hg 2+ .
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高影响因子
MOLECULES
·
2021
·Vol. 26
·期 8
·2115
·
IF 4.412
Jiayong Huang,Zhenshuo Yan,Peiling Qiu,Yufeng Mo,Qizhen Cao,Qiuhong Li,Lini Huo,Lichun Zhao
A new coumarin-acridone fluorescent probe S was designed and synthesized, and the structure was confirmed with1H/13C NMR spectrometry, single-crystal X-ray diffraction, and high-resolution mass spectrometry. This probe has high sensitivity and selectivity for Fe3+over other testing metal ions at 420 or 436 nm in acetonitrile–MOPS (3-Morpholinopropanesulfonic Acid) buffer solution (20.0 μM, pH = 6.9, 8:2 (v/v)). Under physiological conditions, the probe displayed satisfying time stability with a detection limit of 1.77 µM. In addition, probe S was successfully used to detect intracellular iron changes through a fluorescence-off mode, and the imaging results of cells and zebrafish confirmed their low cytotoxicity and satisfactory cell membrane permeability, as well as their potential biological applications.Keywords:Fe3+detection;bioimaging;coumarin-acridone compound
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2020
·
IF 3.232
Selvaraj Muthusamy,Kanagaraj Rajalakshmi,Qingxiang Xu,Yan Chen,Long Zhao,Weihua Zhu
Detection of H 2 S to analyze some diseases in living lives demands fast response, high selectivity and biocompatibility. Here we designed an azide containing coumarin attached with 8-aminoquinoline via amide backbone (ACAQ) fluorophore as the H 2 S sensing probe. Excellent response time of 6 min, high sensitivity with the limit of detection (LOD) of 14.6 nM and high selectivity with other possible interferences are revealed for ACAQ after characterized by spectroscopy, 1 H NMR titration and LC–MS measurements. The sensing strategy is explained by amide-iminol tautomerism and azide reduction. In addition, the successful visualization measurement suggests the practicability of the probe ACAQ for H 2 S detection in live samples.
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