查找使用阿拉丁产品的科研文献

A highly sensitive and selective chemosensor for Pb2+ based on quinoline–coumarin

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

In this study, a highly sensitive and selective fluorescent chemosensor, ethyl(E)-2-((2-((2-(7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)hydrazono)methyl)quinolin-8-yl)oxy)acetate (1), was synthesized and characterized by 1H NMR, 13C NMR and ESI-MS. Sensor 1 showed an “on–off” fluorescence response to Pb2+ with a 1 : 1 binding stoichiometry in CH3CN/HEPES buffer medium (9 : 1 v/v). The detection limit of sensor 1 to Pb2+ was determined to be 0.5 μM, and the stable pH range for Pb2+ detection was from 4 to 8.

Ultrasound-induced Activation of Tetravalent Platinum Polyglutamate Nanoprodrug Accelerated by Coumarin Derivatives

Kong Chao-Ying,Luo Chu-Wen,Xu Ya-Jun,Shen Na,Tang Zhao-Hui

Given that platinum-based drugs are widely used clinically as chemotherapeutic agents, their severe toxic side effects have attracted significant attention. Consequently, the development of novel nanoprodrugs based on low-toxicity tetravalent platinum (Pt(IV)) complexes holds substantial research value. Herein, we discovered that coumarin derivatives exhibit inherent antitumor efficacy and significantly enhance superoxide anion radicals (•O 2 − ) generation in aqueous solutions under ultrasound (US) irradiation. Given that •O 2 − is known to mediate the reduction of Pt(IV) to divalent platinum (Pt(II)), we engineered an US-responsive dual-drug nanoprodrug (P-cisPt(IV)@5-MOP). This nanoprodrug was prepared by covalently conjugating Pt(IV) and methoxy polyethylene glycol hydroxyl (mPEG-OH) to a poly( l -glutamic acid) (PLG) carrier, followed by encapsulating coumarin derivatives. Under low-intensity US irradiation (1.5 W/cm 2 , 1 MHz, 10 min), P-cisPt(IV)@5-MOP achieved a Pt(IV) reduction rate of 91.4%. Furthermore, upon US exposure, its half-maximal inhibitory concentration (IC 50 ) against 4T1 breast cancer cells decreased dramatically from 25.7 µmol/L to 0.1 µmol/L. Remarkably, this system combined with US therapy yielded a tumor inhibition rate of 90.9%, with 40% of tumor-bearing mice achieving complete eradication of tumors, while exhibiting low systemic toxicity. Collectively, this work not only identifies a novel sonosensitizer capable of generating •O 2 − but also develops a new class of ultrasound-activatable Pt(IV) nanoprodrug.

Development of Coumarin-Based Hydroxamates as Histone Deacetylase Inhibitors with Antitumor Activities

Na Zhao,Feifei Yang,Lina Han,Yuhua Qu,Di Ge,Hua Zhang

Histone deacetylases (HDACs) have been proved to be promising targets for the treatment of cancer, and five histone deacetylase inhibitors (HDACis) have been approved on the market for the treatment of different lymphomas. In our previous work, we designed a series of novel coumarin-containing hydroxamate HDACis, among which compounds6and7displayed promising activities against tumor growth. Based on a molecular docking study, we further developed 26 additional analogues with the aim to improve activity of designed compounds. Several of these new derivatives not only showed excellent HDAC1 inhibitory effects, but also displayed significant growth inhibitory activities against four human cancer cell lines. Representative compounds,13aand13c, showed potent anti-proliferative activities against solid tumor cell lines with IC50values of 0.36–2.91 µM and low cytotoxicity against Beas-2B and L-02 normal cells. Immunoblot analysis revealed that13aand13cdose-dependently increased the acetylation of histone H3 and H4. Importantly, the two compounds displayed much better anti-metastatic effects than SAHA against the MDA-MB-231 cell line. Moreover,13aand13carrested MDA-MB-231 cells at G2/M phase and induced MDA-MB-231 cell apoptosis. Finally, the molecular docking study rationalized the high potency of compound13c.Keywords:coumarin;anti-tumor;HDAC inhibitors;structural modification;anti-proliferative

Coumarin Analogues from the Citrus grandis (L.) Osbeck and Their Hepatoprotective Activity

Danmei Tian,Fangfang Wang,Menglong Duan,Lingyun Cao,Youwei Zhang,Xinsheng Yao,Jinshan Tang

Seven new coumarin analogues (1, 2, and 4–8), together with ten known analogues (3, 9–17), were isolated from the air-dried pericarp of Citrus grandis. The structures of these compounds were determined by HR-ESI-MS, UV/vis, and 1D- and 2D-NMR spectra. Meanwhile, the hepatoprotective activities of all these coumarins were evaluated by MTT assays using the d-galactosamine-induced LO2 cell injury model. The results show that compounds 3 and 4 exhibited the strongest hepatoprotective activities. Moreover, compounds 3 and 4 suppressed increases in the levels of alanine transaminase (ALT) and aspartate transaminase (AST) in d-galactosamine-treated LO2 cells, further confirming the hepatoprotective effects of these compounds. Mechanistically, compounds 3 and 4 increased the activities of antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) and decreased the level of malondialdehyde (MDA) in injured LO2 cells induced by d-galactosamine. These findings shed light on a better understanding of the hepatoprotective effect of Citrus grandis, providing novel insights into the development of coumarin-based hepatoprotective drugs in the future.

Ordered co-assembly based on chiral phenylalanine derivatives and achiral coumarin derivatives

Yun-song Zhou,Yang Sheng,Peng Zhang,Rong Zhang,Mark Bradley,Yi-xin Sun

The self-assembly of small molecules into supramolecular hydrogels is of great significance in mimicking biological systems. In this study, we investigated the formation and structure change of supramolecular hydrogels based on the self-assembly behavior of an achiral coumarin derivative (G1) and a chiral phenylalanine derivative (ALP). It was observed that G1 and ALP can self-assemble at various molar ratios, resulting in distinct nanostructured morphologies. Specifically, at a molar ratio of G1/ALP (4 : 1), the achiral G1 molecules initially bifurcate and diverge, ultimately forming a dendritic microstructure at the G1 termini. When the G1/ALP ratio was adjusted to 2 : 1, a chrysanthemum-like microstructure emerged. UV-light can destroy the self-assembled gel structure of different G1/ALP ratios, changing it from gel to sol. The emergence of these higher-order chiral structures during self-assembly was attributed to hydrogen bonding and π–π stacking interactions between the molecules. This research offers valuable insights into the understanding of biological self-assembly processes and the design of artificial biomedical materials.

Circularly polarized yellow luminescence using novel chiral binary coumarin-based Dy3+ complexes

Jiaxiang Liu,Yanan Guo,Qian Zhang,Huizhe Niu,Da Li,Zhenhao Xu,Wentao Li,Yuzhen Zhao,Zongcheng Miao

Circularly polarized luminescence (CPL) in weakly emissive organo-Dy 3+ complexes has been largely unexplored. The energy gap between the Dy 3+ excited 4 F 9/2 -emitting state and adjacent 6 F 1/2 state is extremely narrow. In order to address this challenge, we have adopted a heteroleptic molecular strategy to construct a pair of novel chiral binary coumarin-based Dy 3+ enantiomers: [Dy(Coum) 3 ( R , R - i pr-PyBox)] ( 2 ) and [Dy(Coum) 3 ( S , S - i pr-PyBox)] ( 5 ), where Coum  = 3-acetyl-4-hydroxy-coumarin and R , R / S , S - i pr-PyBox  = 2,6-bis(( R / S )-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine. A synergistic integration of the coumarin-derived Coum ligand with high-efficiency sensitization and light-harvesting capabilities and the CPL-induced bis(oxazoline) Chiral- i pr-PyBox derivatives resulted in complexes 2 and 5 exhibiting intense high-purity yellow light ( Φ PL  = 18–19 %) with intense CPL signals (| g lum | = 0.017–0.090). This approach has enabled an effective trade-off with respect to quantum efficiency and degree of polarization. An integrated superior CPL brightness ( B CPL ; 22.2–46.9 M −1  cm −1 ) has been established for the two Dy 3+ enantiomers across multiple 4 F 9/2 → 6 H J/2 transitions (J = 15, 13 and 11). The findings of this study have demonstrated the viability of the binary molecular design strategy in developing high-performance chiroptical organo-Dy 3+ luminophores.

A highly sensitive fluorescent probe for ozone based on coumarin-benzothiazole derivative

Chen Kangni,Li Yanbo,Shang Jinyan,Zhao Chao,Li Heping

Ozone is widely used in daily life, but studies have shown that O 3 can damage human trachea and lungs, leading to diseases such as asthma, emphysema, and bronchitis. Therefore, it is of great significance to develop a simple and efficient detection method for monitoring O 3 in living cells. In this study, 3-(but-3-en-1-yl)-2-(7-(but-3-en-1-yloxy)-2-oxo-2H-chromen-3-yl)benzo[d]thiazol-3-ium (BCT) as a new type of water-soluble fluorescent probe was synthesized by substitution reaction of 4-bromo-1-butene and hydroxycoumarin-benzothiazole derivatives, which can specifically detect ozone in aqueous solution. The interaction of ozone on the probe can be completed within 20 min, the fluorescence intensity is significantly enhanced, and it has the advantages of high sensitivity (detection limit LOD = 43 nM). The influence of pH on the fluorescent performance of BCT shows that the probe with super stability under weak alkali and acidic environment, which provides the necessary conditions for its detection of ozone in physiological system detection. Therefore, BCT is expected to become an effective tool for detecting ozone in cellular organisms.

An Efficient Synthesis of 1,2,3-Triazole Bridge-Connected Phosphonate Derivatives of Coumarin

Xu Li,Xiaolan Chen,Jinwei Yuan,Yang Liu,Peipei Li,Lingbo Qu,Yufen Zhao

Photo-induced dynamic association of coumarin pendants within amphiphilic random copolymer micelles

Chang Huan,Liu Yan,Shi Mei,Liu Zhaotie,Liu Zhongwen,Jiang Jinqiang

The water-soluble amphiphilic random copolymer of P(DMA- co -VBC) with coumarin pendants has been designed to investigate the photo-induced dynamic association of coumarin pendants within polymer micelles in aqueous solution. Methods of absorption and emission spectra, solution transmittance, dynamic light scattering (DLS), and atomic force microscope (AFM) were applied. It was found that P(DMA- co -VBC) can form polymer micelles in aqueous solution. The time-dependent photo-dimerization degree (PD) of polymer micelles upon different intensity irradiations of 320 nm light showed saturating behaviors with an intensity-independent value of the maximum photo-dimerization extent, while the maximum photo-cleavage extent of coumarin dimers declined with the increasing intensity of 254 nm irradiation at used conditions. Furthermore, a significant emission band at 445 nm ( I 2 ) evidently emerged as against the disappearance of emission band at 385 nm ( I 1 ) during the photo-dimerization, and the time-dependent I 2 /I 1 ratios of polymer aqueous solution upon alternative irradiations of 320 and 254 nm light showed a wave-like increase as a function of irradiation cycles, indicating a wavy closeness of coumarin pendants within polymer micelles during the reversible photo-dimerization cycles.

Selective Zn2+ Recognition of Novel Triazole Schiff-Base Derivatives Bearing the Coumarin Group

Wei Wang,Shuai Qi,Qing-Lei Liu,Ya-Nan Lei,Wen-Jing Yuan,Yan Gao

Three novel triazole Schiff-bases derivatives bearing coumarin units have been synthesised from 3,5-diaryl-4-amino-1,2,4-triazole with three kinds of coumarin aldehydes. The UV-Vis absorption and fluorescence emission spectra of (E)-4-((3,5-diphenyl-4H-1,2,4-triazol-4-ylimino)methyl)-7-methoxy-2H-chromen-2-one exhibited blue-shifted absorption and fluorescent enhancement upon chelation to zinc ion as a 2: 1 ligand-to-metal complex with a binding constant of 3.29 × 106 M−1.

A novel coumarin-based red fluorogen with AIE, self-assembly, and TADF properties

Li Qiang Yan,Zhi Neng Kong,Yong Xia,Zheng Jian Qi

Luminescent materials with aggregation-induced emission (AIE) properties have attracted considerable interest for their promising applications in light-emitting and display devices and fluorescent chemosensors. Coumarin and its derivatives are one of the most attractive chromophores due to their excellent properties, such as high fluorescence quantum yield, large Stokes shift, less toxicity, ease of modification and visible wavelength emission. A coumarin-based AIE-active red fluorogen was designed and synthesised. It was found that CDPA exhibits AIE property, red emission, self-assembly and thermally activated delayed fluorescence (TADF) in the solid state.

Enhanced removal of coumarin by a novel O3/SPC system: Kinetic and mechanism

Chaoqun Tan,Qinglong Xu,Haochen Zhang,Zheming Liu,Shuxin Ren,He Li

A high-efficient, eco-friendly and applicable oxidant of percarbonate (SPC, Na 2 CO 3 ·1.5H 2 O 2 ) is applied as oxidant in ozonation (O 3 ) process. In this work, coumarin (COU) decomposition by O 3 and O 3 /SPC was proposed in terms of diverse parameters, including ozone concentration, SPC dosage and pH, with regard to the pseudo-first-order kinetic model. About 96.5% of 25 mg L −1 COU was removed by 209.3 mg L −1 SPC and 2.08 mg L −1 O 3 within 30 min, whereas 49.8% of COU was exhausted in O 3 system alone. High ozone concentration and pH could enhance COU removal, and overdose SPC has an inhibition effect as CO 3 2− could react with ·OH. Furtherly, the generation of hydroxyl radicals ( OH) via a chain reaction in O 3 was ascertained based on indirect alcohols quenching tests and direct electron spin resonance (ESR) spin-trapping tests, though high initial SPC concentration led to no trapping of OH by 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) in O 3 /SPC. According to the concentration of dissolved ozone and prior study, a fast reaction kinetic model was estimated firstly for O 3 /SPC system and well fitted with different condition. The hydroxylated intermediates of 7-hydroxylcoumarin and 6,7-hydroxylcoumarin were recognized and the degradation pathways were proposed. The findings of the study can broaden the research direction of SPC and provide a new application information for SPC in environmental pollution control .