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coumarin
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.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2019 · IF 4.916

7-(Diethylamino)coumarin-3-carboxylic acid as derivatization reagent for 405 nm laser-induced fluorescence detection: A case study for the analysis of sulfonamides by capillary electrophoresis

Chengxin Wu,Yuanyuan Sun,Yuanhang Wang,Wenzhen Duan,Jiangyue Hu,Lei Zhou,Qiaosheng Pu

Diode lasers, especially 405 nm diode laser, as excitation sources offer new opportunities for laser-induced fluorescence (LIF) detection, but the lack of available derivatization reagents limits their widespread applications. Herein, a commercial fluorescent dye , 7-(diethylamino)coumarin-3-carboxylic acid (DEAC-C) was introduced as derivatization reagent and corresponding derivatization strategy for DEAC-C labeling sulfonamides was developed for 405 nm LIF detection. After systematic optimization, three sulfonamides including hydrochlorothiazide (HCTZ), chlorothiazide (CTZ) and chlortalidone (CTD) could be efficiently labeled by DEAC-C in the presence of cyanuric chloride and triethylamine (1.5%) in acetonitrile at 50 °C for 180 min. Based on the laboratory-built capillary electrophoresis-LIF system, a robust method was then proposed for the separation of DEAC-C labeled sulfonamides by micellar electrokinetic chromatography (MEKC) using the classic borax-SDS system. Under the optimized conditions, a baseline separation of three sulfonamides was achieved within 15 min, and the detection limits were determined to be 0.24, 0.29, and 0.23 nM for HCTZ, CTZ, and CTD, respectively. Furthermore, the developed MEKC-LIF method was validated using sulfonamide standards and spiked human urine sample and successfully applied for the analysis of three sulfonamides in complex pharmaceutical and physiological samples.

研究领域: 分析化学 · 药学
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MOLECULAR PHARMACEUTICS · 2017 · IF 4.44

Ex Vivo and in Vivo Evaluation of the Effect of Coating a Coumarin-6-Labeled Nanostructured Lipid Carrier with Chitosan-N-acetylcysteine on Rabbit Ocular Distribution

Dandan Liu,Jinyu Li,Bingchao Cheng,Qingyin Wu,Hao Pan

This study is focused on further understanding the characteristics of chitosan-N-acetylcysteine surface-modified nanostructured lipid carriers (CS-NAC-NLCs) in their interaction with ocular mucosa. Coumarin-6 (C6)-labeled NLCs, including uncoated NLCs, chitosan hydrochloride (CH)-, and CS-NAC-coated NLCs, were developed using a melt-emulsification technique and subsequently decorated with different types or portions of chitosan derivatives. Mucoadhesion was evaluated ex vivo using a flow-through process with fluorescence detection. The results demonstrated that the presence of CS-NAC on the C6-NLC surface provided the most obvious enhancement in adhesion due to the formation of both noncovalent (ionic) and covalent (disulfide bridges) interactions with mucus chains. Meanwhile, the concentration of CS-NAC in the formulation positively influenced the viscosity of the nanoparticles and hence prolonged their retention in the ocular tissue. Transcorneal penetration studies revealed that CS-NAC-NLC particles were able to penetrate through the entire corneal epithelium primarily via a transcellular route. The transport depth and velocity strongly relied on the modification material and the particle size. Ex vivo fluorescence imaging and in vivo ocular distribution investigations showed that C6 was broadly distributed in rabbit eye tissues and absorbed by aqueous humor after CS-NAC-NLC instillation. In relation to C6 eye drops, CS-NAC-NLCs achieved considerably higher Cmax (4.01-fold), MRT0-∞ (1.87-fold), and AUC0-∞ (16.29-fold) in the aqueous humor. Moreover, the increase in drug absorption was greater in the cornea than in the conjunctiva. Thereby, it is possible to draw a conclusion that CS-NAC-NLCs presented great potential for drug application to the front portion of the eye.

CAS / MDL: 38215-36-0
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MICROCHEMICAL JOURNAL · 2024 · IF 4.9

Enzyme-responsive aptasensing based on the ATP aptamer and benzothiazole-coumarin G-quadruplex fluorescent probe for label-free detection of adenosine deaminase activity and its inhibitor

Yuxiang Xia,Hongyu Li,Yating Lu,Yanfei Zhang,Kaixin Xue,Jiaheng Zhang,Yujie Zhao,Xingyu Luo

Adenosine deaminase (ADA) is a vital enzyme for regulating the biological process in humans and its abnormal expression level is related to various severe diseases. Nevertheless, conventional approaches for detecting ADA activity are hindered by the drawbacks of complexity and limited detection performances. To address these challenges, we here designed an ADA-responsive aptasensing strategy based on a synthesized benzothiazole-coumarin G-quadruplex (G4) fluorescent probe, which can bind to the G-rich ATP aptamer (G-APA) and form the high-contrast fluorescent complex (S1/G-APA). While the fluorescence of S1/G-APA could be quenched by ATP competition due to the allosteric process, the deamination in ATP catalyzed by ADA would recover the fluorescence of S1/G-APA and allow a facile, turn-on, label-free, and selective detection of ADA activity. This proposed method exhibits favorable detection performances for ADA activity analysis with a wide detection linear range varied from 1 to 100 U/L and a detection limit of 0.82 U/L. Meanwhile, it can be applied for ADA inhibitor (DCF) evaluation and provide a turn-off and sensitive detection performances. Inspired by these detection efficacies, the serum samples spiked with ADA and DCF have been investigated to present the satisfied recovery rates and detection reliability. Collectively, this method will provide a promising way for portable and efficient ADA activity quantification and evaluating the inhibition efficiencies of ADA inhibitors, which hold the potential in promoting ADA-related sensing and pharmaceutical research.

CAS / MDL: 70-18-8
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NEW JOURNAL OF CHEMISTRY · 2026 · IF 2.6

Evaluation of anticancer potential of a binuclear copper(II) complex with a 3-(pyridin-3-yl) coumarin ligand: synthesis, crystal structure, magnetism, DNA interaction and molecular dynamics simulations

Wuhan Sang,Miaomiao Liu,Li Xu,Shilong Yang,Yanqin Wang,Caihua Zhang,Wen Lu

A binuclear Cu(II) complex, [Cu2L2(OAc)4]·H2O (Coupy-Cu), with 3-(pyridin-3-yl) coumarin as the ligand, was synthesized by the slow solvent evaporation method. Complex Coupy-Cu was characterized by elemental analysis and infrared spectroscopy, and its crystal structure was determined by X-ray single-crystal diffraction, revealing a distorted octahedral geometry around each copper center. The antiferromagnetically coupled dimeric structure was further confirmed by EPR and VSM, which indicated a diamagnetic singlet ground state (S = 0) with weak paramagnetic susceptibility. Complex Coupy-Cu exhibited favorable cytotoxic activity against a panel of human cancer cell lines (HeLa, A549, MCF-7, and HepG2), with anti-proliferative efficacy against HepG2 cells superior to that of oxaliplatin and induced 43.3% apoptosis at 20 µM in a concentration-dependent manner. It is worth emphasizing that the complex showed significantly lower toxicity toward normal cells compared to cisplatin and oxaliplatin, displaying a safety index 5.2 times that of oxaliplatin and 30.4 times that of cisplatin. Investigations via electronic absorption spectroscopy, fluorescence spectroscopy, viscosity measurements, and molecular docking indicated that the complex binds to calf thymus DNA (CT-DNA) primarily through an intercalative mode. This binding was further validated via molecular dynamics simulations, which demonstrated stable complex formation and a calculated binding free energy of −13.74 kcal mol−1, driven predominantly by van der Waals interactions.

✓ 已验证 DOI 高影响因子
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POSTHARVEST BIOLOGY AND TECHNOLOGY · 2023 · IF 7

Integration of 4-OH-7-C3HO-coumarin and controlled atmosphere storage extends the storage period of peeled water chestnuts (Eleocharis dulcis) by delaying the yellowing and quality deterioration

Jialin Duan,Zhiyan Xu,Yunmin Shi,Lanxiang Jiang,Yali Fan,Yulin Li,Ming Ni,Jianjun Hou

The yellowing and quality deterioration are important factors to shorten the storage period of peeled water chestnuts (PWCs). Integration of 4-OH-7-C 3 HO-coumarin and controlled atmosphere (CA) storage (Ne, O 2 ) to extend the storage period of PWCs has not been studied. The objective of the investigation was to reveal the mechanics with that integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ) extended the storage period of PWCs. PWCs were treated with 4-OH-7-C 3 HO-coumarin (1.2 %), CA storage (81.2 % Ne, 18.8% O 2 ), and integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ). The yellowing degree, weight loss, yellowing substance contents, enzymatic activities, total soluble solids content, titratable acidity content, ascorbic acid content, and microbe of PWCs were detected. 4-OH-7-C 3 HO-coumarin (1.2 %), CA storage (81.2 % Ne, 18.8 % O 2 ), and integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ) extended the storage period by 3, 9 and 12 d. Integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8% O 2 ) was the best. On day 12, integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ) reduced the yellowing degree from 99.5% to 0, the peroxidase activity from 35,603.37 to 28,504.61 U s −1 kg, the eriodictyol content from 3.09 × 10 −4 % to 0, the weight loss from 5.24 % to 0. Integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ) increased the total soluble solids content from 9.37 % to 13.49%, the titratable acidity content from 5.67 × 10 −3 % to 8.62 × 10 −3 % , and the titratable acidity content from 8 × 10 −5 % to 8.55 × 10 −5 %. Integration of 4-OH-7-C 3 HO-coumarin (1.2 %) and CA storage (81.2 % Ne, 18.8 % O 2 ) can be employed to extend the storage period of PWCs. This study provided a theoretical basis for the practical application of integration of 4-OH-7-C 3 HO-coumarin and CA storage (Ne, O 2 ) to extend the storage period of PWCs.

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SENSORS AND ACTUATORS B-CHEMICAL · 2021 · IF 7.46

Dual detection of mercury (II) and lead (II) ions using a facile coumarin-based fluorescent probe via excited state intramolecular proton transfer and photo-induced electron transfer processes

Selvaraj Muthusamy,Kanagaraj Rajalakshmi,Dongwei Zhu,Weihua Zhu,Shengjun Wang,Kang-Bong Lee,Haijun Xu,Long Zhao

A Schiff base fluorophore coumarin incorporated 4-(diethylamino)salicylaldehyde ( Cou-S ) is designed and synthesized to allow an excited state intramolecular proton transfer and photo-induced electron transfer processes for detecting toxic heavy metal ions of Hg 2+ and Pb 2+ in aqueous samples. The solid blue emission of Cou-S was gradually quenched to weak cyan in Hg 2+ detection and to green channels in the presence of Pb 2+ . The coordination behaviours of the probe with Hg 2+ /Pb 2+ are studied using a series of spectroscopic measurements and density functional theory (DFT) calculations. The probe exhibited good water solubility, great selectivity and excellent sensitivity with the LOD values of 8.3 and 10.5 nM for Hg 2+ and Pb 2+ in aqueous medium, respectively. The utility of Cou-S towards dual ions detection was explored in various sources of water samples, Whatmann paper strips, Boolean logic NOR gate operations and PC3 live cells, demonstrating the promising on-site visualization of the probe in controlling the toxicity levels in waste water sources and biosystems.

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