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iScience · 2025 · IF 4.1

Molecule Engineering of Coumarin to Reverse Aggregation-Caused Quenching: Facile Access to BioAIEgens

Shouji Li,Xiaobin Li,Junyu Liu,Yuting Lin,Xuedan Zhang,Weiren Zhong,Juan Li,Caifa You,Dong Wang,Jisong zhang,Xu Xu,Xu-Min Cai,Can Yang Zhang

Aggregation-induced emission luminogens (AIEgens) have been extensively investigated and widely used in biomedical fields. However, AIEgens are mostly derived from petrochemicals, leading to challenges of renewability, sustainability and biocompatibility. Therefore, it’s of striking prospect to construct bioproduct-based AIEgens (BioAIEgens) based on the natural profits. Herein, we proposed a straight forward method named “Rotor-Alicyclic” strategy to prepare BioAIEgens with high fluorescence and produce reactive oxygen species (ROS) activities as well as high biosafety. We prepared four BioAIEgens by introducing two rotors and a naturally rigid alicyclic moiety into coumarin molecule. The AIE performances were evaluated, especially the fluorescence and production of ROS activities. Mechanistic study proved the two rotors introduction can destroy the planar structure, and the rigid alicyclic moiety can limit the molecular motion. Furthermore, the biosafety was carefully investigated in vitro and in vivo , demonstrating the high biocompatibility. Summarily, we developed a facial engineering method to prepare BioAIEgens.

研究领域: 化学 · 生物医学 · 材料科学
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2017 · IF 2.714

Self-assembling behavior and stimuli-responsive emulsifying performance of coumarin-containing amphiphilic terpolymer

Feng Wang,Yishan Ouyang,Hu Zou,Zhouxiaoshuang Yang,Hui Liu

To explore the self-assembling behavior and oil-water interfacial property of the micelle emulsifiers, a kind of coumarin-containing amphiphilic terpolymer , poly (2-(dimethylamino)ethyl methacrylate-co-methyl methacrylate-co-7-(4-vinyl benzyloxyl)-4-methylcoumarin) (PDMV), was prepared. The self-assembly polymeric micelles were used as particulate emulsifiers to stabilize stimuli-responsive emulsions. The micelle size, morphology, self-assembling behavior and photo-cross-linking were investigated with a combination of techniques. The critical water content (CWC) of terpolymers decreased with the increasing hydrophobic segments and initial concentrations. The larger degree of photo-cross-linking the micelles, the lower emulsifying efficiency the micelles. The tertiary amine groups of terpolymers underwent the inversion from protonation to deprotonation with the increasing pH, causing the observed o/w to w/o phase inversion, and there was coverage of spherical nanoparticle on the surface of polymerized styrene beads. Notably, macrophase separation and demulsification were observed under strong alkaline conditions, and some “reef-like” protuberances arose from a smooth surface of solidified polymerized beads. Thus the findings are not only of theoretical interest but also of great practical application in the polymeric surfactants and cosmetics area.

研究领域: 高分子科学 · 胶体与界面化学 · 材料科学 · 软物质物理 · 化学工程
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Journal of Saudi Chemical Society · 2022 · IF 4.712

Synthesis and antifungal activities of novel trifluoroethane derivatives with coumarin, indole and thiophene

Bingyi Zhou,Xinxin Yuan,Liangxin Fan,Zhenliang Pan,Xiaodan Chang,Shengfei Jiang,Lulu Wu,Caixia Wang,Guoyu Yang,Xiaoming Ji,Lijun Shi,Cuilian Xu

A series of novel 1-(β-coumarinyl)-1-(β-indolyl)-1-(α-thiophenyl)trifluoroethane derivatives 5aaa - 5hdb were prepared by one-pot reaction from 3-(trifluoroacetyl)coumarin with indole and α-substituted thiophene. Their structures were confirmed by 1 H NMR, 13 C NMR, 19 F NMR, HRMS and X-ray single crystal diffraction, and their antifungal activities against F. moniliforme , F. graminearum , F. oxysporum , R. solani and P. nicotianae were evaluated. The title compounds displayed significant to moderate in vitro antifungal activity when compared to the standard drug triadimefon. Among the synthesized compounds, compound 5bfa showed the highest inhibitor rate of 83.5 % at 0.500 mg/mL against R. solani , while compound 5ada displayed the highest inhibitor rate of 73.3 % at 0.500 mg/mL against F. graminearum .

研究领域: 有机化学 · 药物化学 · 植物病理学
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Russian Journal of Physical Chemistry A · 2019 ·Vol. 93 ·期 12 ·2542-2549 · IF 0.581

Intermolecular Interactions of Hybrid Organic Dyes Based on Coumarin 343 for Optoelectronic Applications

Shuai Lin,Zhang Lei,Wu Bo,Li Jingfa

Abstract Understanding the intermolecular interactions in the organic dye mixtures could be critical for the design of high-performance optoelectronic devices. In the present study, we investigate the intermolecular interactions in dye systems combining two kinds of organic dyes, using the coumarin 343 (C343) as an example. The study employs the first principles calculations and the spectroscopic/electrochemical experiments to explore the intermolecular interactions (either synergistic or antagonistic) and their effects on the electronic and optical properties of the hybrid dye systems. The interactions between the coumarin dye and four other dyes, either as free dyes or as self-assembled monolayers that are adsorbed onto semiconductor substrate, are analyzed via the UV–Vis absorption, the emission and the photocurrent measurements. The four dyes include 4-(4-diethylaminophenylazo)pyridine, chlorophosphonazo III, methyl red, and catechol, which have been applied to optoelectronic devices. In particular, the interaction between C343 and 4‑(4‑diethylaminophenylazo)pyridine is found to be synergistic for the photocurrent generation using the aqueous electrolyte, which is not observed in other systems. The study suggests importance of the intermolecular interactions in the hybrid-dye systems, and might provide fundamental insights on the intermolecular interactions that could be leveraged to design optoelectronic devices.

研究领域: 材料科学 · 光学
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INORGANIC CHEMISTRY COMMUNICATIONS · 2011 · IF 1.974

A novel highly selective colorimetric sensor for Ni(II) ion using coumarin derivatives

Jinqiang Jiang,Chao Gou,Jing Luo,Chenglin Yi,Xiaoya Liu

A new coumarin based colorimetric nickel sensor 1 with high selectivity and sensitivity toward Ni 2+ ion was reported. The absorption maximum of 1 shows a large red shift from 341   nm to 540   nm (Δ   =   200   nm) in the presence of Ni 2+ ion, and the resulted color change from colorless to pink upon addition of Ni 2+ is very easily observed by the naked eye, while other metal ions , such as Zn 2+ , Cd 2+ , Cu 2+ , Fe 3+ , Ag + , Pb 2+ , alkali metal and alkaline earth metal cations do not induce such a change. By the “naked eye”, the detection limit of Ni 2+ is as low as 0.5   μM in solution, which is lower than the current American Environmental Protection Agency (EPA) standard for drinking water . As far as we are aware of, this is the first reported colorimetric chemosensor capable of detecting Ni 2+ ion.

研究领域: 分析化学 · 环境科学
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Analytical Methods · 2015 ·Vol. 7 ·期 18 ·7646-7652 · IF 1.821

Highly sensitive and selective coumarin probe for hydrogen sulfide imaging in living cells

Sheng Chen,Chao Ma,Dong-En Wang,Xiang Han,Longlong Zhang,Jinyi Wang

Hydrogen sulfide (H2S) is the third endogenous gasotransmitter, following nitric oxide (NO) and carbon monoxide (CO). Efficient methods for selective monitoring H2S in biological systems are significant. In this study, we designed and synthesized a new coumarin-based probe DNPOCA for H2S with colorimetric and fluorescent dual signaling. In this probe, 7-hydroxycoumarin-4-acetic acid methyl ester was employed as a fluorophore and a dinitrophenyl (DNP) ether moiety was used as the recognition unit. The H2S probe exhibited excellent selectivity and high sensitivity with a detection limit as low as 49.7 nM. The cytotoxicity assay showed that DNPOCA possessed a low effect on cell viability. Furthermore, DNPOCA could be successfully applied for H2S imaging in living cells.

CAS / MDL: 108-46-3
研究领域: 生物化学 · 医学
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CHEMICAL ENGINEERING JOURNAL · 2023 · IF 15.1

Photo-assisted ultrasonic curing for ultrafast and deep prototyping based on coumarin derivatives

Qingze Pan,Siqi Wang,Xiaozhen Ren,Wenkai Liu,Runfeng Xu,Qichao Yao,Yang Zou,Changyu Zhang,Jiangli Fan,Pengzhong Chen,Dongping Wang,Xiaojun Peng

Although photocuring is currently the most commonly used method in 3D additive manufacturing, it still faces significant challenges in rapid prototyping of thick materials due to the limited penetration of light. Ultrasonic technology has the advantages of high penetration depth and unparalleled cavitation, offering opportunities for enabling additive manufacturing of thick materials. In this study, a coumarin-based two-component system composed of Coum-Ph-OC 12 H 25 and N-phenylglycine as initiator and hydrogen supplier, respectively, was developed to achieve ultrasonic curing of tripropylene glycol diacrylate (TPGDA). The ideal curing efficiency of this two-component system was optimized to 90 %, and ultrasonic curing of thick materials was achieved with a penetration depth of up to 15 cm. Moreover, electron spin resonance (ESR) spectroscopic measurements demonstrated the free-radical reaction mechanism. It is believed that this research has the potential to expand the 3D additive manufacturing technology and pave the way for future developments in this field.

CAS / MDL: 42978-66-5
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SENSORS AND ACTUATORS B-CHEMICAL · 2023 · IF 8.4

Donor-acceptor based enhanced electrochemiluminescence of coumarin microcrystals: Mechanism study and sensing application

Qian Han,Na Wang,Mengfan Wang,Jing Wang

Simple and efficient strategy to obtain ideal organic electrochemiluminescence (ECL) luminophores still is a central challenge. Here a series of coumarin microcrystals (C545 MCs) as new generation of ECL luminophores were facilely synthesized by a solvent exchange process. Among them, leaf-like C545 MCs with donor-acceptor system display a stable and robust anodic ECL response with triethanolamine (TEOA) as coreactant, which is 9.28 times higher than that of C545 monomer . Combined with its predecessors (coumarin and coumarin 6 H), the effects of donor and acceptor on the ECL properties of C545 were investigated with the help of experiments and theoretical calculation. On the basis of the quenching effect of dopamine (DA) toward the C545 MCs-TEOA ECL system, it was employed to construct a sensitive sensing platform for DA detection. A low limit of detection (0.38 nmol·L −1 , S/N = 3) is obtained in a wide linear range (1 nmol·L −1 – 1 mmol·L −1 ). This work forcefully enriches the design and application of donor-acceptor based coumarin materials in ECL sensing.

研究领域: 分析化学 · 材料科学 · 生物传感
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2023 ·Vol. 24 ·期 17 ·13177 · IF 5.6

Natural Coumarin Shows Toxicity to Spodoptera litura by Inhibiting Detoxification Enzymes and Glycometabolism

Tao Xia,Yan Liu,Zhanjun Lu,Haizhong Yu

Coumarin and its derivatives are plant-derived compounds that exhibit potent insecticidal properties. In this study, we found that natural coumarin significantly inhibited the growth and development ofSpodoptera lituralarvae through toxicological assay. By transcriptomic sequencing, 80 and 45 differentially expressed genes (DEGs) related to detoxification were identified from 0 to 24 h and 24 to 48 h inS. lituraafter coumarin treatment, respectively. Enzyme activity analysis showed that CYP450 and acetylcholinesterase (AChE) activities significantly decreased at 48 h after coumarin treatment, while glutathioneS-transferases (GST) activity increased at 24 h. Silencing ofSlCYP324A16gene by RNA interference significantly increasedS. lituralarval mortality and decreased individual weight after treatment with coumarin. Additionally, the expression levels of DEGs involved in glycolysis and tricarboxylic acid (TCA) cycle were inhibited at 24 h after coumarin treatment, while their expression levels were upregulated at 48 h. Furthermore, metabonomics analysis identified 391 differential metabolites involved in purine metabolism, amino acid metabolism, and TCA cycle from 0 to 24 h after treated with coumarin and 352 differential metabolites associated with ATP-binding cassette (ABC) transporters and amino acid metabolism. These results provide an in-depth understanding of the toxicological mechanism of coumarin onS. litura.Keywords:Spodoptera litura;coumarin;transcriptome sequencing;metabolome sequencing;RNA interference

CAS / MDL: 91-64-5
研究领域: 昆虫学 · 毒理学 · 分子生物学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

7-(Diethylamino) coumarin-3-carboxylic acid as a novel antibrowning agent: Activity and mechanism

Weiming Chai,Xia Yu,Yan Lin,Qiu-Han Bai,Yi-Feng Wu,Wen-Jing Wu,Hui-Ying Ou-Yang,Qiu-Xia Pan,Hui-Lin Shu

Browning caused by polyphenol oxidase (PPO) and microorganisms significantly impacts the nutritional quality of fruits and vegetables. This study identified 7-(Diethylamino) coumarin-3-carboxylic acid (7-DCCA) as an effective inhibitor of both PPO and bacteria. Enzyme assays revealed that 7-DCCA competitively inhibits PPO activity with an IC 50 value of 0.275 ± 0.002 mM. Fluorescence and molecular simulation methods demonstrated that 7-DCCA forms a complex with PPO through hydrogen bonding and hydrophobic interactions, altering the enzyme's structure and reducing its activity. Thermogravimetric and differential scanning calorimetry (DSC) assays showed that 7-DCCA stabilizes PPO, delaying its thermal decomposition. Antibacterial tests proved that 7-DCCA inhibits Staphylococcus aureus and Escherichia coli by disrupting cell membranes. Additionally, 7-DCCA suppressed PPO and peroxidase activities, delaying phenolic oxidation and preventing browning in fruits and vegetables. Cytotoxicity assays confirmed its safety, with over 85 % cell viability at concentrations up to 0.1 mM. Stability experiments verified that 7-DCCA had greatly light and thermal stability. This study highlighted 7-DCCA as a promising antibrowning agent with potential application in food preservation.

研究领域: 食品科学 · 生物化学 · 微生物学
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TETRAHEDRON LETTERS · 2018 · IF 2.125

A coumarin based highly selective fluorescent chemosensor for sequential recognition of Cu2+ and PPi

Xianjiao Meng,Duanlin Cao,Zhiyong Hu,Xinghua Han,Zhichun Li,Dong Liang,Wenbing Ma

In this study, we have successfully synthesized a new coumarin based fluorescent chemosensor 1 , in which tren and quinolone are introduced as receptors for sequential recognition of Cu 2+ and PPi. The structure of chemosensor 1 was characterized by 1 H NMR, 13 C NMR and ESI-HR-MS. Sensor 1 showed an obvious “on-off” fluorescence quenching response toward Cu 2+ , and the quenching efficiency reached a maximum of 99.6% with the addition of 20 equiv. of Cu 2+ . The 1 -Cu 2+ complex showed an “off-on” fluorescence enhancement response toward PPi over many competitive anions, especially HPO 4 2− and H 2 PO 4 − . The detection limit of sensor 1 was 1.9 × 10 −6  M to Cu 2+ and 5.96 × 10 −8  M to PPi. In addition, sensor 1 showed a 1:1 binding stoichiometry to Cu 2+ and sensor 1 -Cu 2+ showed a 2: 1 binding stoichiometry to PPi in CH 3 CN/HEPES buffer medium (9:1 v/v, pH = 7.4). The stable pH range of sensor 1 to Cu 2+ and 1 -Cu 2+ to PPi was from 4 to 8.

研究领域: 分析化学 · 生物化学
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Synthesis and antitumor study of novel porphyrin–coumarin derivatives for chemotherapy and photodynamic therapy

Zejie Tian,Lei Shi,Zhenhua Liu,Hui Li,Lingyan Yang,Yunmei Liu

Photodynamic therapy (PDT) is attractive in cancer treatment because of its non-invasive and low side effects. In this study, we synthesized 20 porphyrin–coumarin compounds via condensation reactions of porphyrins with coumarin derivatives. In the singlet oxygen ( 1 O 2 ) assay, DPBF fluorescence was quenched by 85% after 10 s of light irradiation; the fluorescence of DPBF almost disappeared at 30 s by light irradiation. This indicates that the porphyrin–coumarin compounds have excellent 1 O 2 generation efficiency. Moreover, porphyrin–coumarin compounds showed different inhibitory effects on A549 and HepG2 cells under light irradiation. Whereas in dark conditions, compounds with shorter alkyl chains showed antitumor activity, the extension of branched and alkyl chains decreased the activity of the compounds. Therefore, accessing coumarin derivatives with shorter alkyl chains to porphyrins achieves PDT and chemotherapy. Additionally, the insertion of metal Zn into porphyrins also enhances the PDT effect of the compounds.

研究领域: 药理学 · 肿瘤学 · 有机化学
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