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SENSORS AND ACTUATORS B-CHEMICAL · 2020 · IF 7.1

Water-soluble coumarin oligomer based ultra-sensitive iron ion probe and applications

Jingshi Liu,Yuan Guo,Biao Dong,Jiao Sun,Jiekai Lyu,Liheng Sun,Songtao Hu,Lin Xu,Xue Bai,Wen Xu,Svetlana Mintova,Hongwei Song

Organic molecular probes are the main method for metal ion detection because of their excellent selectivity, while the approach remains limited due to the hydrophobic properties of highly efficient fluorescent molecules. Herein, the internal hydrophobic-external hydrophilic molecule design strategy was proposed to improve the water solubility and the sensing performance. Based on a coumarin-molecule-based iron ion probe, we further introduced a central hydrophobic molecule tribromophenol to connect the hydrophobic part of coumarin molecules. By investigating the experimental conditions and molecular structure, the trimeric phenolic coumarin (TPC) molecules with the largest hydrophilic/hydrophobic ratio exhibited excellent water solubility, fluorescent property and ultra-sensitive iron ion detection performance. Greatly enhanced iron ions binding ability lead to ultralow detection limit of 9.6 pM which is much lower than that of coumarin molecule probes and other reported iron ion probes (nM level). And more, this molecular design also enabled sun-excited naked eye Fe 3+ detection. Due to the remarkable biocompatibility of the probe, the sensitive intracellular iron ions are achieved with a very low detection limit of 0.2 mM. This molecule design provides a promising and powerful method for enhanced water soluble and effective metal ion detection.

研究领域: 化学 · 生物分析 · 材料科学
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SUPRAMOLECULAR CHEMISTRY · 2012 · IF 2.145

Fluorescence sensing and intracellular imaging for hydroxyl radical using coumarin-modified cyclodextrin derivatives

Miao Yu,Guo Zhang,Wenhao Wang,Jianbin Niu,Ning Zhang

A coumarin-methyl-β-cyclodextrin (CCA-MCD) was synthesised. Fluorescence studies showed that CCA-MCD could successfully sense hydroxyl radicals (√OH) in water and it had a specific fluorescence response to √OH over other free radicals. Further study showed that it could monitor intracellular √OH as well. These findings suggest that CCA-MCD can be used as a cell-permeable fluorescence sensor to study the function of √OH in biological processes.

研究领域: 生物化学 · 分析化学 · 细胞生物学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2018 · IF 2.88

A novel OFF-ON-OFF fluorescence probe based on coumarin for Al3+ and F− detection and bioimaging in living cells

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.

研究领域: 分析化学 · 生物医学 · 材料科学
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CHINESE CHEMICAL LETTERS · 2016 · IF 1.947

Cetyltrimethylammonium chloride (CTAC) catalyzed one-pot synthesis of novel coumarin-4H-pyran conjugates in aqueous media

Adil Omar,Keyume Ablajan,Mawjvda Hamdulla

Novel fluorescent coumarin-4 H -pyran conjugates were achieved by three-component reactions of various synthetic β -ketoesters with aldehydes and malononitrile in aqueous media. Besides mild reaction conditions, operational simplicity, absence of tedious separation procedures, using of inexpensive and nontoxic commercially available cationic surfactant cetyltrimethylammonium chloride (CTAC) as a catalyst are the prominent advantage of this method.

研究领域: 有机化学 · 药物化学
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NEW JOURNAL OF CHEMISTRY · 2025 · IF 2.5

A new water-soluble coumarin-based fluorescent probe for the detection of Fe3+ and its application in living cells and zebrafish

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+.

CAS / MDL: 10026-22-9
研究领域: 分析化学 · 生物医学 · 环境科学
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TETRAHEDRON · 2014 · IF 2.817

A highly selective and ratiometric fluorescence probe for the detection of Hg2+ and pH change based on coumarin in aqueous solution

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 .

CAS / MDL: 93-35-6
研究领域: 分析化学 · 环境科学 · 生物医学工程
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY · 2012 ·Vol. 50 ·期 19 ·4037-4045 · IF 3.919

Photoresponsive water-dispersible polyaniline nanoparticles through template synthesis with copolymer micelle containing coumarin groups

Jing Luo,Qun Zhou,Jun Sun,Jinqiang Jiang,Xin Zhou,Hongwu Zhang,Xiaoya Liu

A novel kind of photosensitive water-dispersible polyaniline (PANI) nanoparticles was designed and prepared by template synthesis using a photo-responsive vinyl-coumarin (VM)/2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) copolymer micelle containing coumarin moieties. The resulting PANI nanoparticles exhibited reversible photo-crosslinking and photo-decrosslinking behavior similar to coumarin moiety upon irradiation with different UV light as verified by UV–vis absorption. In addition, photoinduced size change of the PANI nanoparticles after 365 nm UV light irradiation was successfully monitored by dynamic light scattering and transmission electron microscopy measurements, further confirming the photosensitivity of the obtained PANI nanoparticles by the incorporation of VM/AMPS copolymer. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

研究领域: 材料科学 · 高分子化学
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JOURNAL OF COORDINATION CHEMISTRY · 2018 · IF 1.703

Highly selective probe of a copper(II) complex based on a coumarin derivative for hydrogen sulfide detection

Yanmei Chen,Xuefang Shang,Weitong Pan,Congshu Li,Tianyun Wang

A fluorescent probe 1 containing copper(II) had been designed and synthesized based on a coumarin derivative. The molecular structure of probe 1 was characterized by 1H NMR, HRMS, IR, and elemental analysis. The interactions of 1 with biologically important anions and amino acid were determined by UV–Vis, fluorescence, and HRMS titration experiments. Results indicated that probe 1 showed the highest binding ability for HS− among studied anions (AcO−, H2PO4 −, F−, Cl−, Br−, and I−) and cysteine in pure dimethyl sulfoxide (DMSO) and HEPES buffer solution. As we expected, the response of UV–Vis spectra in aqueous solution was stronger than that of pure DMSO solvent. In addition, the binding ability for HS− was not hindered by the existence of other anions. HRMS titration experiment showed that the interacted mechanism was that the copper(II) ion in 1 was captured by HS− and then free ligand released. Furthermore, the detection limit of probe 1 with HS− was carried out through UV–Vis titration showing 1 to be highly sensitive for HS−.

研究领域: 分析化学 · 生物化学
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ANALYST · 2020 ·Vol. 146 ·期 4 ·1289-1294 · IF 3.978

A metal-free coumarin-based fluorescent probe for the turn-on monitoring of carbon monoxide in an aqueous solution and living cells

Shiqing Zhang,Xinyue Mu,Jinbiao Zhu,Liqiang Yan

Endogenous carbon monoxide (CO) is an essential cell signaling molecule, which is closely related to numerous physiological and pathological processes. Therefore, it is of great significance to monitor CO in living samples. Fluorescent probe technique provides an effective and convenient method for monitoring CO. Although many fluorescent probes of CO have been reported, most of them require the introduction of heavy metal ions (Pd2+), which is not conducive to the practical application of these probes. Herein, a metal-free coumarin-based fluorescent probe was developed for monitoring CO. For this probe, coumarin was selected as the fluorophore, the aromatic nitro group was used as the reactive site, and the carboxyl moiety acted as the water-soluble unit. As a result, this probe has been proved to be able to monitor CO with good specificity and excellent sensitivity in water medium. After interacting with CO, the aromatic group was reduced to an aryl amino group; accordingly, the emission intensity of the peak corresponding to the probe at 450 nm significantly increased. Moreover, it successfully realized the detection of CO in living cells by a fluorescence signal.

研究领域: 生物化学 · 医学检测 · 分子生物学
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Journal of Materials Chemistry C · 2020 ·Vol. 8 ·期 38 ·13328-13335 · IF 7.059

Coumarin 7 functionalized europium-based metal–organic-framework luminescent composites for dual-mode optical thermometry

Jiaqiang Liu,Xizhuang Yue,Zhuopeng Wang,Xia Zhang,Yan Xu

Developing a highly reliable non-contact optical thermometer probe with excellent sensitivity and multi-mode temperature sensing behaviours is always a great challenge. Here, dual-emitting luminescent composites fabricated using a europium-based metal–organic framework (Eu-MOF) and surface-immobilized molecular dye (Coumarin 7) were successfully prepared by a simple solvothermal method, followed by a post-modification strategy. Benefiting from the linear response in fluorescence intensity ratios (FIRs) of Eu3+ to Coumarin 7 dye molecules in the temperature range from 10 °C to 90 °C, the composite demonstrated the maximum relative temperature sensitivity (Sr) of 0.50% °C−1 at 90 °C. Moreover, the observed red-shift of Coumarin 7 emission with the temperature readout suggests a dual-mode optical thermal sensing mechanism in the dye-immobilized MOF composite. Their excellent reusability and temperature sensing mechanisms have been also investigated. These results demonstrate the potential of the Coumarin 7 functionalized Eu-MOF composite as a dual-mode optical thermometer for temperature sensing applications.

研究领域: 材料科学 · 光学 · 化学
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ACS Applied Materials & Interfaces · 2017 · IF 7.504

Aggregation-Induced Enhanced Electrochemiluminescence from Organic Nanoparticles of Donor–Acceptor Based Coumarin Derivatives

Huiwen Liu,Lifen Wang,Hongfang Gao,Honglan Qi,Qiang Gao,Chengxiao Zhang

Organic nanoparticles (NPs) from donor–acceptor based coumarin derivatives, 6-[4-(N,N-diphenylamino)phenyl]-3-ethoxycarbonyl coumarin (DPA-CM), with an average size of 5.82 nm, were synthesized by a facile reprecipitation method using water as a poor solvent and tetrahydrofuran as a good solvent. Red-shifted absorption, blue-shifted photoluminescence emission, and aggregation-induced enhanced electrochemiluminescence (ECL) emission were observed for the DPA-CM NPs in aqueous solution compared with the original DPA-CM in organic solution. The aggregation-induced enhanced ECL emission is ascribed to the combined effects of the small size of the DPA-CM NPs, the restricted conformational relaxation in the NPs, and the good stability of the cationic radical of DPA-CM. A strong and stable ECL emission is obtained at the DPA-CM NPs modified glassy carbon electrode in the presence of tri-n-propylamine, and the ECL intensity of the DPA-CM NPs modified electrode is quenched linearly in the range of 0.05–50 μM with detection limit of 0.04, 0.2, and 0.4 μM for ascorbic acid, uric acid, and dopamine, respectively. This work shows an example of donor–acceptor based organic NPs as ECL emitters and their analytical applications to monitor biomolecules.

CAS / MDL: 50-81-7
研究领域: 化学 · 分析化学 · 材料科学 · 生物医学
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SENSORS AND ACTUATORS B-CHEMICAL · 2022 · IF 9.221

High-performance fluorescent and colorimetric dual-mode nitrite sensor boosted by a versatile coumarin probe equipped with diazotization-coupling reaction-sites

Tianshi Zhang,Yuan Liu,Jiguang Li,Wenfei Ren,Xincun Dou

Nitrite has posed ubiquitous threats to the environment, human health, and public security because of its crucial role in food processing, construction, farming, and explosive manufacturing industries. To achieve accurate, sensitive, and on-site detection of trace nitrite, a colorimetric-fluorescent dual-mode sensing probe with unique photophysical process was designed for ultrasensitive determination of nitrite by precisely adjusting the amino site and significantly influencing the coupling reaction activity. This modulating strategy breaks through the dilemma of azo-product with only colorimetric phenomenon, facilitating the probe, 7-amino-4-methylcoumarin, to maintain a desirable sensitivity with detection limits of 98 nM and 629 nM in fluorescent and colorimetric modes, respectively, as well as an outstanding specificity even in the presence of 15 common anions and interfering substances. The probe was further integrated into a portable sensor by applying a polyvinyl alcohol hydrogel as a loading substrate, which showed superior sensing performances in analyzing nitrite in various real samples with visualized, anti-interferent, and dual-mode responses. Consequently, the present reaction-site modulation strategy would provide a general reference for ultrasensitive, on-site, and visual detection of nitrite, and it can be broadly applied in environmental monitoring and food safety assessment.

研究领域: 分析化学 · 环境科学 · 食品安全
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