JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY
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2020
·
IF 2.734
Longgui Zhang,Yuji Pu,Junhua Li,Jianqin Yan,Zhongwei Gu,Wenxia Gao,Bin He
Polymer-small molecule conjugates could act as drug carriers to load hydrophobic antineoplastics by π-π interactions. However, weak hydrophobicity would lead to limited drug loading capacity and stability in blood circulation. Herein, we used the graft strategy to significantly increase the hydrophobicity for improving drug loading capacity and microenvironment stimuli characteristics. Coumarin and imidazole were grafted to biodegradable and biocompatible poly(ethylene glycol)- b -poly( l -lysine) (PEG-PLL), respectively, endowing strong hydrophobicity for efficient drug loading and pH-responsiveness for controlled drug release . The critical micelle concentration of mPEG-PLL- g -COU/IMZ could be as low as 9.49 × 10 −6 mol/L. Anticancer drug doxorubicin (DOX) was used as a model drug and COU-grafted polymers showed high drug loading contents of ~17%. The π-π interactions between DOX and COU were established by UV and fluorescence spectroscopy. The pH-sensitive and COU-grafted polymeric micelles showed enhanced in vitro anticancer efficacy, due to the high drug loading capacity, faster cellular uptake, and pH-responsive drug release. This study indicated that stimuli-responsive, aromatic small molecule-grafted polymeric micelles could be a promising platform for efficient drug delivery and cancer therapy, due to their high drug loading capacity and controlled drug release.
研究领域:
药剂学
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材料科学
·
肿瘤学
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DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2019
·
IF 3.375
Qiang Chen,Qian Yang,Pei Gao,Baihong Chi,Jun Nie,Yong He
The photoresponse of the coumarin derivative based on reversible photodimerization and photocleavage has been studied for a long time. This paper reports a novel approach of preparing photoresponsive polymer materials containing coumarin structure by photopolymerization based on the wavelength selectivity. A photopolymerizable and photoresponsive monomer, 7-(hydroxyethoxy)-4-methyl-coumarin (AECM), was synthesized, and photopolymerization was performed on it using UV light irradiation (λ = 405 nm). After polymerization the polymer with coumarin pendant groups can achieve reversible photo-induced [2 + 2] dimerization under UV light (λ > 300 nm) and photocleavage of the cross-link to recovery back to the original structure through further irradiation with UV light (λ = 254 nm). What’s more, this monomer could be used to produce a high-resolution pattern and photo-responsive pressure sensitive adhesive through photopolymerization. The demonstrated approach opens new perspectives for the design of photoresponse materials.
研究领域:
材料科学
·
光化学
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产品关联
DOI
高影响因子
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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产品关联
DOI
PubMed
高影响因子
JOURNAL OF COLLOID AND INTERFACE SCIENCE
·
2013
·
IF 3.172
Yangyang Xu,Jingguo Li,Wenlong Hu,Gang Zou,Qijin Zhang
Herein, a novel single-chain coumarin-substituted diacetylene monomer (CODA) was synthesized. CODA LB films exhibited obvious chirality although CODA monomer was achiral. Upon UV irradiation , CODA LB films could be polymerized into blue form and exhibit reversible thermochromism and chiroptical properties. Strong intermolecular interaction among the coumarin chromophores was assumed to be responsible for the complete reversibility of absorption and chiroptical changes for PCODA films upon thermal stimulus. And the helical packing of the coumarin chromophores seemed to play a dominating role in the subsequent formation of the helical PDA backbone. Moreover, the single-chain CODA monomer could be further photo-dimerized, and a novel gemini-type diacetylene monomer (DCODA) could be prepared. The effects of the photo-dimerization reaction of the coumarin moieties on the thermochromism and chiroptical properties of the resulting PDCODA films had been evaluated. The dimerization of head groups would enhance the thermal stability of PDCODA films but inhibit the chirality formation for PDA backbone.
研究领域:
材料化学
·
高分子科学
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产品关联
DOI
PubMed
高影响因子
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
·
2014
·Vol. 30
·期 3
·362-367
·
IF 1.119
Cao Li,Jia Chunman,Zhang Qi,Chen Da,Zhang Chunyan,Qian Yaao
A fluorescent probe with a coumarin moiety bound to rhodamine 6G hydrazide( 1 ) was synthesized. Its sensing behavior toward various metal ions was investigated with fluorescence methods. Compound 1 displays different fluorescence emission responses to Al 3+ and Ca 2+ at the same excitation wavelength in the visible light region, while no changes occur after the addition of other metal ions. The binding ratios of the complexs of 1 -Al 3+ and 1 -Ca 2+ are both 2:1 according to the Job plot and high resolution mass spectrometer(HRMS) experiments. Moreover, emission spectrum of 1 -Ca 2+ complex and absorption spectrum of the rhodamine dyes overlap largely. When Al 3+ was added to the 1 -Ca 2+ system, calcium in complex 1 -Ca 2+ can be displaced by Al 3+ , resulting in the output of another ratiometric sensing signal, which demonstrates that the 1 -Ca 2+ complex can be served as a new and effective fluorescence resonance energy transfer(FRET) donor for rhodamine derivatives.
研究领域:
化学传感器
·
荧光共振能量转移
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产品关联
DOI
高影响因子
DYES AND PIGMENTS
·
2015
·
IF 3.966
Kangnan Wang,Lin Ma,Guoqun Liu,Duxia Cao,Ruifang Guan,Zhiqiang Liu
Two novel diethylaminecoumarin Schiff's base chemosensors for cyanide with pyridine or thiophene as terminal group have been synthesized. Their photophysical properties as well as recognition properties for cyanide anions have also been examined. Both the compounds exhibit strong green fluorescence in all the solvents. Density functional theory calculation indicates that both the compounds exhibit intramolecular charge transfer from diethylaminecoumarin group to terminal pyridine or thiophene group. The compounds can recognize cyanide anions with fluorescence turn-on response based on copper ion complex displacement mechanism and obvious color change from red to yellow-green can be observed by naked eyes. The chemosensors exhibit a degree of repeatability and can be used repeatedly to recognize cyanide anions for several times.
研究领域:
分析化学
·
生物化学
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产品关联
DOI
高影响因子
Frontiers in Chemistry
·
2022
·
IF 5.545
Hu Chun-Mei,Luo Yong-Xin,Wang Wen-Jing,Li Jian-Ping,Li Meng-Yue,Zhang Yu-Fei,Xiao Di,Lu Li,Xiong Zhuang,Feng Na,Li Chen
Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 (a∼v) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC50: 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α-glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC50: 1.5 × 105 μM) and the positive control acarbose (IC50: 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α-glucosidase inhibitory activity (IC50: 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t (KI = 18.82 μM, KIS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t.
研究领域:
药理学
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有机化学
·
生物化学
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产品关联
DOI
PubMed
高影响因子
DYES AND PIGMENTS
·
2022
·
IF 5.122
Rumeng Tian,Xiaojie Ren,Peixin Niu,Lei Yang,Ailing Sun,Yuhan Li,Xingjiang Liu,Liuhe Wei
In this work, a series of new dyes, CQ-Cou , with a newly prepared chromophore acquired by hybridizing classic coumarin with chromenoquinoline, are designed and synthesized for the first time. We systematically investigated the photophysical properties of these chromenoquinoline-fused coumarin dyes and found they have the properties of relatively high fluorescence quantum yield , high photostability and molar absorption coefficient. Furthermore, the mechanisms of intramolecular charge transfer (ICT) related to donor and acceptor in these chromophores were researched by the theoretical calculations using density functional theory (DFT) and time-dependent density functional theory (TD-DFT). Importantly, the successful application of these new dyes in biological imaging for living cells and zebrafish is demonstrated.
研究领域:
化学
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生物学
·
医学影像学
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DOI
高影响因子
MOLECULES
·
2022
·Vol. 27
·期 9
·2738
·
IF 4.927
Lu Xu,Jinmeng Yu,Lu Jin,Le Pan
A series of 30 succinate dehydrogenase inhibitors (SDHIs) of 4-amino coumarin-based derivatives were designed and synthesized. According to the analysis of fungicidal activity in vitro, most of the compounds expressed broad-spectrum antifungal activity against four plant pathogenic fungi (Alternaria alternata, Alternaria solani, Fusarium oxysporum,andBotrytis cinerea) using the mycelium growth inhibition method. The results showed that compounds3nwith the group of 2-ene-3-methyl-butyl and4ewith the group of 2-bromo-1-oxo-hexyl displayed excellent activity againstAlternaria alternataandAlternaria solani, with EC50values of 92~145 μg/mL. Molecular docking showed that the inhibitor3nwas completely locked into the cavity of SDH, forming a conventional hydrogen bond interacting with the amino acid residue TYR58. The present work indicates that these derivatives would serve as novel potential fungicides targeting SDH.Keywords:succinate dehydrogenase;inhibitor;4-amino coumarin;fungicide;antifungal activity;molecular docking
研究领域:
植物保护学
·
药物化学
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生物化学
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产品关联
DOI
PubMed
高影响因子
PROGRESS IN ORGANIC COATINGS
·
2024
·
IF 6.5
Jianwei Hou,Xinghai Hao,Jiali Xu,Geoffrey I.N. Waterhouse,Chunhua Ni,Zhiming Zhang,Liangmin Yu
The demand for non-toxic antifouling coatings has led to the development of multifunctional antifouling coatings. In this work, a series of coumarin acids with fluorescence were first prepared via the Knoevenagel condensation reaction . Then, multifunctional zinc acrylate resins were produced successfully by employing an acrylic acid monomer , ZnO, and coumarin acids by free radical polymerization and polycondensation processes. The self-polishing and antifouling properties of the resins were investigated by dynamic simulation experiments, E. coli growth inhibition experiments, algae adhesion inhibition experiments, and marine environment antifouling experiments. The results show that the zinc acrylate resins containing the coumarin structures not only have good self-polishing performance but also have better antifouling performances than the zinc acrylate resin containing benzoic acid . This work not only reveals the antifouling mechanism of the multifunctional resins, but also provides a new strategy for the development of environmentally friendly antifouling coatings.
研究领域:
材料科学
·
海洋生物学
·
环境科学
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产品关联
DOI
高影响因子
RSC Advances
·
2018
·Vol. 8
·期 59
·33947-33951
·
IF 2.936
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.
研究领域:
分析化学
·
环境科学
✓ 已验证
DOI
PubMed
高影响因子
CHINESE JOURNAL OF POLYMER SCIENCE
·
2025
·
IF 4
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.
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产品关联
DOI
高影响因子
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