BIOSENSORS & BIOELECTRONICS
·
2014
·
IF 6.451
Xi Dai,Qing-Hua Wu,Peng-Chong Wang,Jie Tian,Yu Xu,Sheng-Qing Wang,Jun-Ying Miao,Bao-Xiang Zhao
Acrylic acid 3-acetyl-2-oxo-2 H-chromen-7-yl ester ( ACA ) was rationally designed and synthesized as a simple and effective fluorescent probe for sensing cysteine with high selectivity and naked-eye detection. The probe can detect cysteine by fluorescence spectrometry with a detection limit of 0.657 μM and can be used with calf serum and in live cell imaging . The conjugate addition/cyclization sequence mechanism of the reaction between ACA and cysteine was confirmed by ESI-MS and fluorescence spectra .
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CURRENT ORGANIC SYNTHESIS
·
2021
·Vol. 18
·期 6
·587-591
·
IF 1.975
Song Zurong,Lu Qin,Tao Ali,Wu Tianchen
Background: Paclitaxel, a natural diterpenoid compound, has anti-tumor effect by acting on tubulin, whereas coumarin, another kind of natural product, has anti-tumor effect, along with some other effects, such as anti-bacterial-., Moreover, it also possesses fluorescence. Objective:
Multi targeting is an effective strategy in drug design to combat tumor. Therefore, a combination of paclitaxel with other active molecular drugs for exploring the novel lead with multi-functions is in demand. Materials and Methods: To synthsize paclitaxel-coumarin conjugate via click
chemistry and to investigate anticancer activity by MTT assay and the scratch test. Results and Discussion: The results of MTT assay showed that compared tothe paclitaxel, the anti-tumor activity of the conjugate was significantly improved. The results of flow cytometry showed that the
conjugate had a stronger ability to induce apoptosis. The scratch test results showed that the conjugate had better anti- metastasis ability than paclitaxel. Conclusion: These findings indicated that paclitaxel and coumarin had a synergistic effect, which paved the way for the development
of paclitaxel through fluorescence.
研究领域:
药理学
·
肿瘤学
·
药物化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2024
·
IF 4.3
Jiajun Chen,Yunxi Cui,Peixuan Wu,Rohan Dassanayake,Peng Yu,Kun Fu,Zhicheng Sun,Yuanyuan Liu,Yang Zhou
Nitroxyl (HNO), the single-electron reduction product of nitric oxide (NO), has attracted great interest in the treatment of congestive heart failure in clinical trials. In this paper, we describe the first coumarin-based compound N -hydroxy-2-oxo-2H-chromene-6-sulfonamide (CD1) as a dualfunctional HNO donor, which can release both an HNO signaling molecule and a fluorescent reporter. Under physiological conditions (pH 7.4 and 37 °C), the CD1 HNO donor can readily decompose with a half-life of ∼90 min. The corresponding stoichiometry HNO from the CD1 donor was confirmed using both Vitamin B 12 and phosphine compound traps. In addition to HNO releasing, specifically, the degradation product 2-oxo-2H-chromene-6-sulfinate (CS1) was generated as a fluorescent marker during the decomposition. Therefore, the HNO amount released in situ can be accurately monitored through fluorescence generation. As compared to the CD1 donor, the fluorescence intensity increased by about 4.9-fold. The concentration limit of detection of HNO releasing was determined to be ∼0.13 μM according to the fluorescence generation of CS1 at physiological conditions. Moreover, the bioimaging of the CD1 donor was demonstrated in the cell culture of HeLa cells, where the intracellular fluorescence signals were observed, inferring the site of HNO release. Finally, we anticipate that this novel coumarin-based CD1 donor opens a new platform for exploring the biology of HNO.
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ACS Applied Polymer Materials
·
2026
·
IF 5.2
Xiangzhuo Han,Yingchao Zhang,Jinkai Wang,Na Wang,Zhanchen Cui,Zuosen Shi
Photoinitiators (PIs), as essential components of photosensitive materials, are widely used in photolithography, photocuring, and other photochemical reactions. Coumarin derivatives, known for their excellent optical properties, exhibit significant potential for application in the design and synthesis of photoinitiators. This study focuses on bis-sulfonic acid oxime esters based on coumarin derivatives, aiming to develop green, low-toxicity, and highly efficient PIs. By systematically modifying the molecular structure of coumarin derivatives, the effects of different substituents on photoacid generation efficiency were investigated to provide theoretical and experimental support for optimizing PIs performance. Six PIs were synthesized and their photoinitiating and photoacid generation capabilities were evaluated using ultraviolet–visible (UV–vis) spectroscopy, fluorescence spectroscopy, and real-time infrared spectroscopy (RT-IR); their reaction mechanisms were analyzed. The results demonstrate that these coumarin-based bis-sulfonic acid oxime ester PIs possess excellent photosensitizing properties and efficiently generate sulfonic acid under UV irradiation. This study not only enriches PI synthesis strategies but also provides avenues for their industrial application, holding considerable theoretical and practical significance.
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APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
·
2016
·Vol. 101
·期 8
·3371-3378
·
IF 3.376
Zhang Shanshan,Liu Ningning,Liang Weikang,Han Qingxi,Zhang Weiwei,Li Chenghua
In the present study, the effects of an environmental friendly natural reagent coumarin, on the growth and potential virulence factors, as well as its ability to interfere the infection of Vibrio splendidus (Vs), were determined. Coumarin showed no effects on the maximal growth of Vs, and biofilm formation of Vs, while it significantly decreased protease activity and hemolytic activity by 43 and 80%, respectively. Correspondingly, coumarin exhibited an obviously protective effect, with a relative percent survival of 60% upon Apostichopus japonicus from infection by Vs. To preliminarily investigate the mechanism underlining the inhibitory effects, regulation of genes Vsm and Vsh respectively related to protease activity and hemolytic activity by supernatant and supernatant extract containing acyl-homoserine lactones (AHLs) and coumarin was determined. Cell-free supernatant from higher density and its ethyl acetate extract containing AHL signal molecules could respectively upregulate the mRNA level of Vsm by 17.4- and 2.3-fold and Vsh by 7.2- and 5.0-fold, when Vs was at lower cell density. However, coumarin could reduce the stimulatory effects of both the supernatant and its ethyl acetate extract. Combining all the results in our study, it was suggested that coumarin could be considered as an alternative to be used for controlling infection of Vs, downregulating the expression of potential virulence factors through interfering the AHL-mediated pathways.
研究领域:
微生物学
·
海洋生物学
·
分子生物学
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Open Life Sciences
·
2016
·Vol. 11
·期 1
·542-551
·
IF 0
Huanan Wang,Ming Yao,Wenqing Xu
Cancer is the second leading cause of death worldwide. Traditional antitumor drugs exhibit severe cytotoxic and side effects. Lung cancer needs new and more effective treatment approaches. Coumarin derivatives can act on various tumor cells and show anti-proliferative activity through various mechanisms, including mitochondrial signaling cascades that regulate development and apoptosis of cells. Mitochondria-targeted coumarin derivatives have not been reported yet. Taking advantage of the fact that cancer cells frequently have higher mitochondria membrane potential, we synthesized a mitochondria-targeted 6-(nicotinamide) methyl coumarin by coupling 6-methyl coumarin to nicotinamide. Our results demonstrate that 6-(nicotinamide) methyl coumarin preferentially kills A549 cells through inducing A549 cells apoptosis, mediated by increasing ROS level and causing mitochondrial depolarization. Strikingly, the viability of the A31 cells treated with 6-(nicotinamide) methyl coumarin did not decrease, indicating that 6-(nicotinamide) methyl coumarin preferentially accumulates in A549 cells and A549 cells are much more susceptible to 6-(nicotinamide) methyl coumarin treatment compared with A31 cells.
研究领域:
肿瘤学
·
药理学
·
细胞生物学
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CHEMICAL PAPERS
·
2017
·Vol. 71
·期 9
·1579-1586
·
IF 1.258
Chen Mei-Hang,Lu Dao-Wang,Zhang Xun,Zhou Zeng-Yan,Wang Xiao-Bin,Shu Hua
A series of novel coumarin substituted amide derivatives were synthesized and evaluated for their antibacterial activities. Result indicated that compounds 3f , 3g , 3h , 3i , 3j , 3k , 3l , 3m , 3n , 3o and 3q exhibited excellent antibacterial activities against Xanthomonas oryzae pv. oryzae ( Xoo ) and Xanthomonas citri subsp. Citri ( Xcc ) in vitro, which were better than those of commercial agricultural antibacterial thiodiazole-copper. The title compounds with electron-withdrawing group showed better antibacterial activities than those of compounds with electron-donating group, and the title compounds bearing the same substituent group exhibited better antibacterial activities against Xcc than antibacterial activities against Xoo .
研究领域:
有机化学
·
药物化学
·
植物病理学
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Materials Advances
·
2024
·
IF 5.2
Yanwei Lai,Dashi Deng,Simin Yuan,Xiaocen Liu,Qifang Lei,Guangzhi Li
Albumin proteins have been extensively explored for functionalized delivery of therapeutics. However, their potential in intravesical delivery has not been thoroughly investigated. In this work, we developed a green method for the synthesis of albumin nanocarriers that can efficiently encapsulate the active monoterpene coumarin UM-15 and assemble with fluorinated chitosan (FCS) to form UM-15@BSA/FCS nanoparticles (NPs). Upon intravesical perfusion, BSA/FCS NPs serving as the nano-vehicles of UM-15 demonstrate exceptional transepithelial delivery, efficient intratumoral diffusion, and high tumor-targeting uptake capacities. These remarkable advantages can be attributed to their notable cascade delivery performances, which involve FCS-driven rearrangement of bladder epithelium tight junctions and the charge reversal effect-induced dissociation behavior of FCS-albumin complexes, as well as the high tumor selectivity mediated by albumin-binding protein (SPARC) and disulfide bonds. Additionally, UM-15 loaded in those nanovehicles demonstrates significant induction of apoptosis and stemness suppression of bladder cancer cells. With above effects acting synergistically, remarkably improved intravesical treatment outcomes are achieved in both mouse orthotopic and patient-derived orthotopic xenograft models, with reduced toxic side effects. Thus, our study introduces a novel therapeutic agent for BCa therapy and presents a promising avenue for the tumor targeted delivery of therapeutics through an intravesical cascade delivery mechanism.
研究领域:
药剂学
·
肿瘤学
·
生物医学工程
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POLYMER
·
2026
·
IF 5.1
Xiaoqiang Luo,Zitao Yang,Anjia Zheng,Zhongte Pei,Chuanxi Wang,Jiaming Zhang,Qianyu Wang,Rui Hu,Cancan Zhang,Yaqiong Zhang,Chongxiao Ge,Feng Jiang
Sustainable and functional elastomers derived from renewable resources are highly desirable as alternatives to conventional petroleum-based materials. Herein, a series of chitin-based fluorescent elastomers, Chitin- graft -poly(7-acryloyloxy-4-methyl coumarin- co - n -butyl acrylate) (Chitin-g-P(AMC- co -BA)) copolymers, were successfully synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. In this design, the coumarin derivative AMC was used as the hard and fluorescent segment while BA was selected as the soft segment to graft from the rigid chitin backbone to construct novel bio-based elastomers. By systematically varying the AMC/BA feed ratios and chitin contents, the glass transition temperature ( T g ), mechanical performance, adhesion strength, and fluorescent properties of the Chitin-g-P(AMC- co -BA) could be precisely tailored. The elastomers demonstrated tunable tensile strength (up to 12.2 MPa) and extensibility (up to 1989%). Furthermore, these chitin graft copolymers possess excellent adhesion performance and show strong blue fluorescence under UV irradiation, benefiting from the presence of the coumarin structure. This work provides an effective grafting strategy to develop multifunctional, sustainable elastomers from chitin and bio-based monomers, offering promising potential for applications in adhesives, flexible materials, and fluorescent functional systems.
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CHINESE JOURNAL OF POLYMER SCIENCE
·
2015
·Vol. 33
·期 8
·1086-1095
·
IF 1.835
Chang Huan,Shi Mei,Sun Ya-nan,Jiang Jin-qiang
The photo-dimerization characteristics of coumarin pendants within amphiphilic random copolymer micelles in aqueous solution was comprehensively investigated using various selected wavelength light in the UV-Vis-NIR region. The time-dependent photo-dimerization degree (PD) changes in the photo-dimerization experiments showed saturating behaviors with intensity-independent of PD max values at 28%, 44%, 92%, 85%, 36%, 35%, 32% and 31% for 254, 288, 320, 360, 400, 500, 650 and 900 nm irradiations, respectively. The irradiation experiments at 254 and 288 nm announced the occurring of an asymmetric equilibrium of photo-dimerization and photo-cleavage at the used conditions. Both the alternative irradiation cycles of 360 and 254 nm, 650 and 254 nm showed a partially, but evidently reversible photo-dimerization tendency.
研究领域:
高分子化学
·
光响应材料
·
超分子化学
·
高分子科学
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
·
2025
·
IF 2.2
Xiyan Tang,Jie Pang,Yanmin Huang,Jianguo Cui,Chunfang Gan,Zhiping Liu
This study systematically evaluated the antibacterial activity of three classes of coumarin-fused [3,4]-tetrahydroheterocycles against two animal-derived pathogenic bacteria— Staphylococcus aureus and Escherichia coli —as well as three plant pathogens: Xanthomonas citri , Pseudomonas oryzae , and Fusarium oxysporum . The results demonstrated that coumarin-fused tetrahydrofuran derivatives (e.g., 3aa , 3 ac , and 3ae ; MIC = 2 μg/mL) exhibited pronounced and selective antibacterial activity against Staphylococcus aureus . Meanwhile, coumarin-fused tetrahydropyridazine compounds showed potent efficacy against Pseudomonas oryzae and Fusarium oxysporum , with a minimum inhibitory concentration (MIC) of 2 μg/mL (e.g., 7ae , 7ah , and 7ag ), significantly surpassing the positive control osthole. In contrast, coumarin-fused tetrahydro-1,2-oxazine analogues displayed relatively weak broad-spectrum antibacterial activity. These findings provide a robust theoretical foundation for the design and synthesis of novel coumarin-based heterocyclic antibacterial agents and offer valuable guidance for future research directions.
研究领域:
药物化学
·
抗菌研究
·
杂环化学
·
药用微生物学
·
有机合成
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MACROMOLECULAR RAPID COMMUNICATIONS
·
2012
·Vol. 34
·期 3
·274-279
·
IF 4.596
Jingguo Li,Hao Jiang,Wenlong Hu,Hongyan Xia,Gang Zou,Qijin Zhang
Herein, we synthesize a coumarin-substituted diacetylene monomer (CODA) and report the novel photo-controlled reversible assembly and disassembly behavior of the polymerized CODA (PCODA) vesicles. The photo-triggered dimerization and cleavage reactions of the coumarin groups within the surface of the adjacent PCODA vesicles can be utilized as the driving force to induce assembly and disassembly of PCODA vesicles. Moreover, the boundary of PCODA vesicles in the aggregates becomes more obscure when the irradiation time exceeds 30 min. Fusion occurs upon close docking of target membranes, driven by sufficient dimerization of the coumarin groups within the surface of PCODA vesicles.
研究领域:
材料科学
·
生物化学
·
纳米医学
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