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coumarin
MACROMOLECULES · 2018 · IF 5.914

Unusual Transient Network and Rheology of a Photoresponsive Telechelic Associative Model Polymer in Aqueous Solution Induced by Dimerization of Coumarin End Groups

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.

✓ 已验证 产品关联 DOI 高影响因子
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Plants-Basel · 2026 ·Vol. 15 ·期 11 ·1694 · IF 4.7

Coumarin Reduces Aluminum-Induced Inhibition of Growth and Photosynthesis in Citrus grandis by Reducing Tissue Al Concentration and Maintaining Nutrient and Redox Homeostasis

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.

✓ 已验证 DOI PubMed 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

A H2O2-free electrochemiluminescence immunosensor constructed on all-in-one bioprobe comprised of TiO2-B supported fluoro-coumarin silicon phthalocyanine for deoxynivalenol sensing

Dandan Fang,Xiangqin Zheng,Huan Yi,Hong Dai,Zhensheng Hong,Yiru Peng,Yanyu Lin

A highly sensitive electrochemiluminescence (ECL) immunosensor was fabricated for the quantitative analysis of deoxynivalenol (DON) based on an effective all-in-one bioprobe that composed of TiO 2 -B with Fluoro-coumarin silicon phthalocyanine (F-couSiPc) and luminol. Herein, TiO 2 -B with large specific area was served as a favorable carrier, greatly increased the loading of enhancer F-couSiPc and luminophore luminol, resulting in the tremendous enhancement of ECL signal. Specifically, F-couSiPc as coreaction accelerator could facilitate the decomposition of dissolved O 2 to generate substantial reactive oxygen species (ROS) to participate in the ECL reaction of luminol. Additionally, the prepared PEDOT/HA@mp MnO 2 was employed as the sensing platform of biosensor, which can not only capture substantial antibody to improve the sensitivity, but also could expedite the electronic transmission rate to make the ECL intensity further amplified. Ultimately, the proposed immunosensor presented favorable performance for the determination of DON, such as high sensitivity, good stability, wide liner range (from 1.0*10 −6 ng/mL to 10 ng/mL) and a low detection limit of 3.3*10 -7 ng/mL.

研究领域: 分析化学 · 食品安全检测
✓ 已验证 DOI 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2018 ·Vol. 42 ·期 11 ·8805-8814 · IF 3.201

Delivery of coumarin-containing all-trans retinoic acid derivatives via targeted nanoparticles encapsulating indocyanine green for chemo/photothermal/photodynamic therapy of breast cancer

Jia Jiao,Hongshuai Wu,Fanghui Chen,Renjie Chen,Baiwang Sun,Mingliang Wang

Development of chemo/photothermal/photodynamic therapy with nanoplatforms offers a promising strategy for effective cancer treatment. Recently, all-trans retinoic acid (ATRA), as a potential antitumor drug, has attracted great attention due to its antitumor activity. In this study, a novel coumarin-containing ATRA (AC) and indocyanine green (ICG) dye-loaded nanoparticles with the targeted ligand cyclic (Arg-Gly-Asp-D-Phe-Lys) (cRGD) peptide were fabricated by self-assembly and used as a new theranostic nanoplatform for chemo/photothermal/photodynamic therapy. The as-formed nanoparticles (AC/ICG-TNPs) had a diameter of around 133 nm with uniform monodispersity. Additionally, AC/ICG-TNPs showed marked stability under normal physiological conditions. However, it could rapidly release drugs in a mild acidic microenvironment. Moreover, confocal microscopic observations confirmed that the uptake of AC/ICG-TNPs increased in the breast cancer cells, particularly in MDA-MB-231 cells, probably mediated by cRGD via specific recognition of the overexpressed integrin αvβ3. Moreover, free AC exhibited stronger cytotoxic effects than free ATRA in the MTT assay, and AC/ICG-TNPs were demonstrated to possess excellent antitumor efficacy when exposed to NIR irradiation through the combination therapy. Hence, the therapeutic method designed in this study is a good candidate for improved bioactivity of ATRA and site-specific combinational therapy against breast cancer.

✓ 已验证 产品关联 DOI 高影响因子
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ACS Applied Materials & Interfaces · 2018 · IF 8.097

Coumarin-Based Oxime Esters: Photobleachable and Versatile Unimolecular Initiators for Acrylate and Thiol-Based Click Photopolymerization under Visible Light-Emitting Diode Light Irradiation

Zhiquan Li,Xiucheng Zou,Guigang Zhu,Xiaoya Liu,Ren Liu

Developing efficient unimolecular visible light-emitting diode (LED) light photoinitiators (PIs) with photobleaching capability, which are essential for various biomedical applications and photopolymerization of thick materials, remains a great challenge. Herein, we demonstrate the synthesis of a series of novel PIs, containing coumarin moieties as chromophores and oxime ester groups as initiation functionalities and explore their structure–activity relationship. The investigated oxime esters can effectively induce acrylates and thiol-based click photopolymerization under 450 nm visible LED light irradiation. The initiator O-3 exhibited excellent photobleaching capability and enabled photopolymerization of thick materials (∼4.8 mm). The efficient unimolecular photobleachable initiators show great potential in dental materials and 3D printings.

CAS / MDL: 68-12-2 7446-08-4
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF MEDICINAL CHEMISTRY · 2026 · IF 7.3

Novel Hybrids of 3-Substituted Coumarin and Phenylsulfonylfuroxan as Potent Antitumor Agents against Wild-Type and Drug-Resistant Nonsmall Cell Lung Cancer Cell Lines

Weijie Wang,Xiufan Wu,Fan Cao,La Li,Xuqin Guo,Hongyang Zhao,Mengru Li,Hongrui Liu,Ying Chen

Lung cancer represents a major global health challenge, and the development of new therapeutic agents remains a serious task. This study designed and synthesized 27 novel coumarin-furoxan hybrids. Among them, compound 6o exhibited potent nanomolar-level antiproliferative activity against six nonsmall cell lung cancer (NSCLC) cell lines, including both wild-type and drug-resistant models. Mechanistic investigations revealed that 6o downregulates the expression of ferroptosis-related factors SLC7A11 and GPX4, thereby disrupting redox homeostasis, depleting glutathione, and accumulating lipid peroxides, which collectively trigger ferroptosis. Furthermore, 6o elevated mitochondrial nitric oxide (NO) and reactive oxygen species (ROS) levels, exacerbating cellular damage. 6o also displayed low hERG channel toxicity, favorable in vivo safety, and acceptable solubility. In summary, 6o demonstrates high efficacy against both wild-type and drug-resistant NSCLC cells via a ferroptosis-mediated mechanism, along with a promising safety profile, supporting its potential as a candidate for further development.

✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF ETHNOPHARMACOLOGY · 2023 · IF 5.4

Unveiling hepatotoxicity distinction of coumarin-related compounds from glycosides to aglycones in Fructus Psoraleae by integrating UPLC-Q-TOF-MS and high content analysis

Benyu Liu,Shiming Fang,Kun Zhou,Lulu Ma,Yaling Shi,Yuefei Wang,Xiumei Gao

Ethnopharmacological relevance Fructus Psoraleae (FP), the dried and ripe fruit of Cullen corylifolium (L.) Medik., is widely used due to its various clinical pharmacological effects, but its hepatotoxicity restricts its clinical application. So far, its hepatotoxic components and their underlying mechanism have not been systematically elucidated. Aim of the study This study was undertaken to reveal the hepatotoxicity distinction of coumarin-related compounds from glycosides to aglycones in FP and elucidate their potential mechanism. Methods Rats were administrated with the aqueous extract of Fructus Psoraleae (AEFP), in which eight coumarin-related compounds were focused. Subsequently, compounds exposed in rats' livers were detected by UPLC-Q-TOF-MS, and the identified hepatotoxic compounds were evaluated to elaborate their possible mechanism by the aid of high content analysis (HCA). Results Eight coumarin-related compounds were identified, among which psoralenoside (PO), isopsoralenoside (IPO), psoralen (P), and isopsoralen (IP) were the principally exposed compounds in rats' livers. Furocoumarinic acid glucoside (FAG), ( E )-3-(4-(((2 S , 3 R , 4 S , 5 S , 6 R )-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2 H -pyran-2-yl) oxy) benzofuran-5-yl) acrylic acid (isofurocoumarinic acid glucoside, IFAG), furocoumarinic acid (FA), and ( E )-3-(4-hydroxybenzofuran-5-yl) acrylic acid (isofurocoumarinic acid, IFA) were also detected in low abundance. P, IP, FA, and IFA were identified as the hepatotoxic compounds, while their glycosides were almost non-hepatotoxic. The HCA's results showed that hepatotoxic compounds disrupted the balance in reactive oxygen species (ROS), nuclear area, and mitochondrial membrane potential of HepG2 cells, leading to the occurrence of hepatotoxicity. Conclusions P, IP, FA, and IFA were identified as hepatotoxic compounds, from which P and IP were proposed as the important risk components for hepatotoxicity. The conversion from glycosides to aglycones played an essential role in FP-induced hepatotoxicity.

CAS / MDL: 64-18-6
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ANALYTICAL CHEMISTRY · 2022 · IF 8.008

Two Ratiometric Fluorescent Probes Based on the Hydroxyl Coumarin Chalcone Unit with Large Fluorescent Peak Shift for the Detection of Hydrazine in Living Cells

Miaomiao Xing,Yanyan Han,Yilin Zhu,Yatong Sun,Yanyan Shan,Kang-Nan Wang,Qiuxin Liu,Baoli Dong,Duxia Cao,Weiying Lin

Hydrazine is widely used in industrial and agricultural production, but excessive hydrazine possesses a serious threat to human health and environment. Here two new ratiometric fluorescence probes, DDP and DDC, with the hydroxyl coumarin chalcone unit as the sensing site are developed, which can achieve colorimetric and ratiometric recognition for hydrazine with good sensitivity, excellent selectivity, and anti-interference. The calculated fluorescence limits of detections are 0.26 μM (DDC) and 0.14 μM (DDP). The ratiometric fluorescence response to hydrazine is realized through the adjustment of donor and receptor units in coumarin conjugate structure terminals, accompanied by fluorescence peak shift about 200 nm (DDC, 188 nm; DDP, 229 nm). Stronger electropositivity in the carbon–carbon double bond is helpful to the first phase addition reaction between the probe and hydrazine. Higher phenol activity in the hydroxyl coumarin moiety will facilitate the following dihydro-pyrazole cyclization reaction. In addition, both of these probes realized the convenient detection of hydrazine vapor. The probes were also successfully applied to detect hydrazine in actual water samples, different soils, and living cells.

CAS / MDL: 112726-66-6 120-21-8
✓ 已验证 产品关联 DOI PubMed 高影响因子
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EUROPEAN POLYMER JOURNAL · 2022 · IF 5.546

Photo-healable ion gel with high mechanical property, fatigue resistance and shear resistance using a coumarin group containing diblock copolymer in an ionic liquid

Lei Wang,Jing Chen,Ye Sha,Imtiaz Hussain,Bo Yu,Linlin Wu,Yijun Shi,Qun Gu,Zhenyang Luo,Xiaofeng Ma

Ion gels, polymer networks swollen with ionic liquid (IL), are ideal materials for application in flexible electronic devices. It remains a challenge to fabricate an ion gel with photo-healing, high mechanical properties, fatigue resistance and shear resistance. Herein, a well-defined diblock copolymer polystyrene- b -poly(methyl acrylate- r -7-(2′-methacryloyloyloxyethoxy)-4-methylcoumarin) (PS- b -P(DMA- r -MAOEMC), brief name: SMM, PS: IL-phobic segment and P(DMA- r -MAOEMC): IL-philic segment) was synthesized by reversible addition fragmentation chain transfer (RAFT) polymerization. For comparison, a random copolymer P(DMA- r -MAOEMC) (MM) also be prepared. In dilute solution, the SMM can form spherical micelles with PS-core surrounded by P(DMA- r -MAOEMC) corona chains in an IL, 1-ethyl-3-methylimidazolium bis(trifluoromethane sulfone)amide ([C 2 mim][NTf 2 ]). In a suitable polymer concentration, the SMM and MM can form ion gels in [C 2 mim][NTf 2 ] under 365 nm UV light irradiation through photo-dimerization of coumarin groups in corona MM polymer chains of spherical micelles and photo-dimerization of coumarin groups in MM random polymer chains, respectively. Compared with the MM ion gel, the SMM ion gel has high mechanical properties, shear resistance and relatively high fatigue resistance. Under 254 nm UV light irradiation, photo-induced gel to jammed micelles transition for the SMM ion gel and photo-induced gel to sol transition for the MM ion gel occur due to photo-cleavage of dimer in polymer chains. Photo-induced jammed micelles - gel transition for the SMM ion gel and photo-induced sol - gel transition for the MM ion gel are reversible by alternating 365 nm and 254 nm UV light irradiation, whereby photo-healable materials can be fabricated. Compared to the MM ion gel, the SMM ion gel has high photo-healing efficiency. The electrochemical property of the SMM ion gel can be recovered completely after photo-healing.

✓ 已验证 产品关联 DOI 高影响因子
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2020 · IF 3.232

A novel fluorescent chemosensor based on coumarin and quinolinyl-benzothiazole for sequential recognition of Cu2+ and PPi and its applicability in live cell imaging

Shengling Li,Duanlin Cao,Xianjiao Meng,Zhiyong Hu,Zhichun Li,Changchun Yuan,Tao Zhou,Xinghua Han,Wenbing Ma

In this study, a highly selective fluorescent sensor ( E )-2-((2-(benzo[ d ]thiazol-2-yl)quinolin-8-yl)oxy)- N ′ -((7-(diethylamino)-2-oxo-2 H -chromen-3-yl)methylene)acetohydrazide ( TQC ) was synthesized from 2-methylquinolin-8-ol and 4-(diethylamino)-2-hydroxybenzaldehyde and its structure was characterized by 1 H NMR, 13 C NMR, ESI-HR-MS and density functional theory (DFT) calculation. Sensor TQC showed an obvious “on-off-on” fluorescence response to Cu 2+ and PPi in a DMSO/HEPES (3:2 v/v, pH = 7.4) buffer system. The detection limits of sensor TQC were 0.06 μM to Cu 2+ and 0.01 μM to PPi. In addition, sensor TQC showed a 1:1 binding stoichiometry to Cu 2+ and TQC- Cu 2+ complex showed a 2:1 binding stoichiometry to PPi. The optimum pH range of sensor TQC and TQC- Cu 2+ was 3–8. Further studies demonstrated that sensor TQC could be made into test paper strips for the qualitative of Cu 2+ and PPi and showed sequentially “on-off-on” fluorescent bio-imaging of Cu 2+ and PPi in HeLa cells.

✓ 已验证 DOI PubMed 高影响因子
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Materials Science & Engineering C-Materials for Biological Applications · 2019 · IF 4.959

UV-light cross-linked and pH de-cross-linked coumarin-decorated cationic copolymer grafted mesoporous silica nanoparticles for drug and gene co-delivery in vitro

Shuai Zhou,Chendi Ding,Cheng Wang,Jiajun Fu

The chemotherapy combined with gene therapy has emerged as a promising strategy for cancer therapy because of enhanced anticancer efficacy. To this end, we constructed a novel UV-light cross-linked and pH de-cross-linked coumarin-decorated cationic copolymer functionalized mesoporous silica nanoparticles (MSN) for co-delivery of chemotherapeutic agent 5-FU and tumor suppresser p53 gene. The multifunctional MSN were modified with poly(glycidyl methacrylate)-b-poly(2-(dimethylamino)ethyl methacrylate) (PGMA-b-PDMAEMA) via two sequential surface-initiated atom transfer radical polymerization (ATRP), followed by ring-opening of epoxy groups with ethanediamine and covalent conjugation with coumarin moieties via acid-liable cis-aconityl bonds. The in vitro drug release results indicated that the premature release was negligible at physiological pH when coumarin moieties on the MSN-g-PCAAMC-b-PDMAEMA surface underwent UV-light induced photo-dimerization (cross-linking), while the release of embedded drugs was accelerated under acidic conditions, which was attributed to the hydrolytic cleavage of cis-aconityl bonds (de-crosslinking). In addition to small-molecule drug, the established MSN-g-PCAAMC-b-PDMAEMA also could carry p53 gene in outer cationic copolymers, and the formed complex exhibited good gene transfection activity. Interestingly, coumarin moieties themselves could emit blue fluorescence, which was used to track the cellular uptake of the nanocarriers without the need of additional fluorescence probes. Importantly, the cytotoxicity and cell apoptosis assays confirmed that co-delivery of 5-FU and p53 gene by the cross-linked [email protected] /p53 induced enhanced chemotherapeutic efficacy as compared to 5-FU delivery alone. In conclusion, these results suggested that the constructed stimuli-responsive co-delivery system may hold the promise for cancer therapeutic application.

研究领域: 纳米技术 · 药学 · 生物医学工程 · 癌症研究 · 材料科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2020 · IF 3.306

A novel schiff base fluorescent probe based on coumarin and benzothiazole for sequential detection of Al3+ and PPi and its applicability in live cell imaging

Shengling Li,Duanlin Cao,Xianjiao Meng,Zhiyong Hu,Zhichun Li,Changchun Yuan,Tao Zhou,Xinghua Han,Wenbing Ma

In this study, a novel schiff base fluorescent probe (E)- N' -(3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methylbenzylidene)-7-(diethylamino)-2-oxo-2 H -chromene-3-carbohydrazide ( CHS ) was synthesized for sequential detection of Al 3+ and pyrophosphate ions (PPi) in a DMSO/HEPES (4:1 v/v, pH = 7.4) buffer system and characterized by 1 H NMR, 13 C NMR, ESI-HR-MS and DFT calculation. Its detection limit was determined to be 0.16 μM for Al 3+ and 0.18 μM for PPi in a pH range of 4∼8, respectively. The Job’ s plot showed that the stoichiometric ratio to Al 3+ was 1:1, and CHS -Al 3+ showed highly selective recognition of PPi. The sensor CHS could also recognize Al 3+ and PPi and exhibited fluorescence enhancement and quenching properties in HeLa cells.

研究领域: 分析化学 · 生物分析 · 分子探针 · 细胞成像 · 金属离子检测
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