Journal of Materials Chemistry B
·
2019
·Vol. 7
·期 14
·2261-2276
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IF 5.047
Yufei Bian,Zhiyong Wei,Zefeng Wang,Zhu Tu,Liuchun Zheng,Wenhuan Wang,Xuefei Leng,Yang Li
In this work, we developed a facile end-functionalization method using hydroxylated coumarin to initiate the ring-opening polymerization of cyclic esters to synthesize a series of fluorescent biodegradable aliphatic polyesters with tailorable properties. The resulting fluorescent functionalized poly(L-lactide) (PLLA-COU), poly(ε-caprolactone) (PCL-COU) poly(δ-valerolactone) (PVL-COU) and poly(trimethylene carbonate) (PTMC-COU) were investigated to evaluate the dependence of fluorescence on the chemical structure and molecular weight of the materials. The differences in the electron withdrawing ability and the density of ester groups are responsible for the changes in the fluorescence quantum yield. Then, two representative biodegradable materials, namely, PLLA-COU and PCL-COU, were used to prepare fluorescent paclitaxel-loaded microspheres. During in vitro drug release, the release rate of the PCL-COU microspheres is dramatically faster than that of the PLLA-COU microspheres due to the difference in the material nature and their surface morphologies, possibly achieving a tunable degradation and release rate for the drug carriers. Fluorescent functionalized polyester microspheres can retain their fluorescence properties and emit bright blue light for fluorescence tracing during the degradation process. Biological evaluations showed that both fluorescent polyesters are devoid of any significant toxicity and have good biocompatibility. The results demonstrated that the obtained fluorescent polyesters are promising for use in traceable and controlled drug delivery with tunable drug release.
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PLANT PHYSIOLOGY AND BIOCHEMISTRY
·
2023
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IF 6.5
Minglei Tao,Shengzhi Liu,Yaohan Li,Amin Liu,Jingkui Tian,Yuchang Liu,Hongwei Fu,Wei Zhu
Coumarin is an important secondary metabolite that affects plant physiology. It is a lactone of cis- o -hydroxycinnamic acid and widely exists in medicinal plants . Clematis terniflora DC. is a plant belonging to Ranunculaceae and is rich in variety of coumarins. Feruloyl-CoA 6′-hydroxylase has been reported as a key enzyme in the formation of coumarin basic skeleton only in some common plants, however, its evidence in other species is still lacking especially for the biosynthesis of coumarins in C . terniflora . In the present study, we identified a feruloyl-CoA 6′-hydroxylase CtF6′H in C . terniflora , and functional characterization indicated that CtF6′H could hydroxylate feruloyl-CoA to 6-hydroxyferuloyl-CoA. Furthermore, the expression level of CtF6′H was differed among different tissues in C. terniflora , while under UV-B radiation, the level of CtF6′H was increased in the leaves. Biochemical characteristics and subcellular location showed that CtF6′H was mainly present in the cytosol. The crystal structure of CtF6′H was simulated by homology modeling to predict the potential residues affecting enzyme activity . This study provides the additional evidence of feruloyl-CoA 6′-hydroxylase in different plant species and enriches our understanding of biosynthetic mechanism of coumarin in C . terniflora .
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REACTIVE & FUNCTIONAL POLYMERS
·
2022
·
IF 4.966
Jiali Kou,Zhiyuan Meng,Xiaoyuan Wang,Zhonglong Wang,Yiqin Yang
Hydrazine is a kind of widely used chemical reagent , which has the harmfulness to human health and ecosystem. Therefore, it is necessary to develop a rapid and sensitive method for the detection of hydrazine. In this work, a novel cellulose-based fluorescent probe ( ACBC-CA ) was rationally developed for the selective and sensitive detection of hydrazine. ACBC-CA was synthesized by using cellulose acetate as skeleton and coumarin-based derivative as the fluorophore. ACBC-CA exhibited a significant “turn-on” fluorescence response to hydrazine, accompanied by a distinct fluorescence color change from colorless to bright yellow. The detection limit of ACBC-CA for hydrazine was calculated to be 1.2 × 10 −7 M. Furthermore, ACBC-CA was successfully applied to determine hydrazine in real environmental water and soil samples.
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ACS Sustainable Chemistry & Engineering
·
2019
·
IF 6.97
Junfan Niu,Jingyue Tang,Gang Tang,Zhiyuan Zhou,Rong Tang,Jiale Yang,Na Jiang,Jianqiang Li,Yongsong Cao
Photosensitizers need to be activated by external light to achieve phototherapy. However, unsatisfactory tissue penetration of light and uncontrollable light intensity limit their application. To overcome the limitations, a novel fluorescent conjugate was developed by conjugating coumarin-functionalized nanosilica with acifluorfen to emit fluorescence as the supplementary light to activate protoporphyrin IX (PpIX, a photosensitizer in plant cell that can be induced by acifluorfen) for enhancing phototherapy activity. The results showed that the obtained conjugate could obviously increase the singlet oxygen yield of PpIX and exhibited remarkable photodynamic herbicidal activity against Amaranthus retroflexus. Under low light intensity, its photodynamic herbicidal activity was five to six times higher than that of acifluorfen sodium salt. The conjugate could move upward and downward freely in vascular system of Brassica juncea seedlings and significantly reduced the cytotoxicity of acifluorfen. Moreover, the conjugate was proved to be safe to soybean at concentrations of 200–800 mg/L of acifluorfen. This study gives a novel drug delivery system with the potential of reducing light-dependent drug dosage and harm to nontarget organisms and offers a way to use fluorescent emission as the supplementary light to enhance the phototherapy activity of photosensitizers.
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JOURNAL OF LUMINESCENCE
·
2017
·
IF 2.686
Yanhua Yu,Tingting Shu,Cheng Fu,Bingjie Yu,Dongdong Zhang,Huixiu Luo,Junjie Chen,Changzhi Dong
A novel colorimetric and fluorescent sensor 6 for fluoride and cyanide was developed based on BODIPY-coumarin platform and its anions sensing properties were investigated in the mixture of acetonitrile and Tris–HCl buffer (v/v = 95:5, pH = 7.5). Probe 6 could simultaneously detect F – and CN – through colorimetric method over the other competitive anions, such as Cl – , Br – , I – , NO 3 – , ClO 4 – , HSO 4 – , S 2– and H 2 PO 4 – . It exhibited a distinct color change from red to green upon addition of F – through deprotection of tert -butyldiphenylsilyl group of coumarin . Moreover, it displayed an obvious color change from red to yellow through deprotection process firstly, then with a nucleophilic displacement mechanism. Therefore, the sensor 6 provides a novel method to simultaneously detect F − and CN − with different color change in the same solvent environment. The detection limit of sensor 6 toward F – and CN – ion was determined to be 0.43 μM and 1.9 μM respectively,
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JOURNAL OF MOLECULAR STRUCTURE
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2020
·
IF 2.463
Meng-qiu Song,Wei Min,Jing Wang,Xin-Xin Si,Xiu-Jun Wang,Yu-Wei Liu,Da-Hua Shi
Twelve carbazole-coumarin hybrids were synthesized and biologically evaluated as dual binding site acetylcholinesterase inhibitors. The structures of the carbazole-coumarin hybrids were confirmed by IR, NMR, HRMS and single-crystal X-ray diffraction studies. The compound 3j had the crystal system of triclinic and the space group of P-1. The cholinesterase inhibitory activity of synthesized compounds was measured using colorimetric Ellman's method. Compound 3h exhibited good acetylcholinesterase (AChE) inhibitory activity (IC 50 value of 6.72 μ M) and a high selectivity over butyrylcholinesterase (BuChE). Compound 3k showed the best BuChE inhibitory activity with the IC 50 of 0.50 μM. The SAR studies revealed that the linker length played a crucial role in determining AChE inhibitory activity and the structure of the coumarin moieties affected the BuChE-inhibition activities of the hybrids. Molecular docking study of compound 3h indicated that it interacts with the crucial amino acids present at the catalytic active site and peripheral anionic site of AChE. Compound 3h would be a promising drug candidate to treat AD as a selective and dual binding site inhibitor of AChE.
研究领域:
药物化学
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神经科学
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有机化学
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NEW JOURNAL OF CHEMISTRY
·
2022
·Vol. 46
·期 11
·5034-5042
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IF 3.925
Fubin Fu,Xueyan Zhang,Shengquan Zhou,Wei Shi,Jiangmin Li,Jiajia Yu,Yanzhao Rao,Lei Wu,Jing Cao
In this work, we designed two non-salen coumarin Schiff base chiral fluorescent probes 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(7-methoxy-2H-chromen-2-one) (L1) and 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis-(methaneylylidene))bis(2H-chromen-2-one) (L2), which have outstanding circular dichroic CD signals but almost show no circularly polarized luminescence (CPL) signals. By adding metal ions that can effectively inhibit photo-induced electron transfer (PET), it was observed that L1 can be used as a highly sensitive dual detection ion probe for Mg2+ and Zn2+ as Mg2+ and Zn2+ can turn on the CPL emission of L1. Moreover, (S,S)-L1 has exquisite recognition ability for the enantiomer of the chiral drug D/L-camphorsulfonate and showed reversible fluorescence “on/off” response with Zn2+ and EDTA. It was also found that L2 manifested selective recognition ability for Zn2+.
研究领域:
化学
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分析化学
·
光学
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
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2013
·Vol. 51
·期 18
·3791-3799
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IF 3.543
Jing Yang,Wei-Dong He,Chen He,Jing Tao,Sheng-Qi Chen,Shao-Min Niu,Shao-Lin Zhu
Hollow mesoporous silica nanoparticles (HMSNs) grafted with a photo-responsive copolymer containing coumarin groups were successfully prepared. With uniform polystyrene nanoparticles and cetyltrimethylammonium bromide correspondingly as the template of core and channel, HMSNs were made from tetraethyloxysilane in alkalic condition. Epoxy groups were introduced onto the outer surface of HMSNs with γ-(2,3-epoxypropoxy)propyltrimethoxysilane and converted into azido groups with sodium azide, resulting in azido-functionalized HMSNs (azido-HMSNs). Meanwhile, single-electron transfer-living radical copolymerization of methyl methacrylate (MMA) and 7-(2-methacryloyloxy)-4-methylcoumarin (CMA) with propargyl 2-bromoisobutyrate as the initiator produced alkynyl-capped P(MMA- co -CMA) [alkynyl-P(MMA- co -CMA)]. Finally, photo-responsive HMSNs grafted with P(MMA- co -CMA) [HMSN- g -P(MMA- co -CMA)] was achieved through the click reaction between azido-HMSNs and alkynyl-P(MMA- co -CMA). Different techniques such as transmission electron microscopy, Fourier transform infrared spectroscopy, and thermal gravimetric analysis confirmed the successful preparation of the resultant hybrid nanoparticles and their intermediates. Because of its hollow core, mesoporous shell channels and light responsiveness, the coumarin-modified HMSNs would be an interesting nano-vehicle for guest molecules. Thus, the loading and release of pyrene with HMSN- g -P(MMA- co -CMA) was studied. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51 , 3791–3799
研究领域:
材料科学
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化学
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RSC Advances
·
2025
·Vol. 15
·期 36
·29989-29994
·
IF 4.6
Xin-Yu Liu,Shu-Jing Zhou(Co-author),Fang Luan,Yu-Hang Wang,Xiu-Juan Ma,Li-Yuan Sui,Yan-Ru Feng
Metal-organic frameworks (MOFs), characterized by their high porosity, large specific surface area, and tunable pore structures, have emerged as promising host materials for advanced functional applications. In this study, two organic dyes, fluorescent bleacher (CBS) and coumarin (C6), exhibiting blue and green fluorescence, respectively, were co-encapsulated into europium (Eu)-based MOFs, where Eu3+ served as the central metal to introduce red emission. The ligand employed was 9-butylcarbazole-2-carboxylhydrazide thiophene (Cz). A white fluorescent powder, coumarin/fluorescent bleacher/carbazole derivatives@Eu (C6/CBS/Cz@Eu), was synthesized using an in situ encapsulation method. The C6/CBS/Cz@Eu was incorporated into PVA to prepare a film. The resulting C6/CBS/Cz@Eu film demonstrated a high-quality white light emission under excitation by commercial 400 nm light-emitting diode (LED) chips, achieving ideal Commission Internationale de l'Éclairage (CIE) chromaticity coordinates of (0.34, 0.35) and a correlated color temperature (CCT) of 5267 K. This strategy offers a versatile and scalable method for the design and fabrication of white light-emitting materials, beneficial for the development of next-generation white light-emitting diode (WLED) technologies.
研究领域:
材料科学
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光电子学
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无机化学
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纳米技术
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固态照明
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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
·
2024
·
IF 6
Xuzi Zhao,Ting Wang,Fucheng Shang,Jiangyu Yan,Mingyan Jiang,Xiaoyan Zou,Guorui Li,Zhibin Song,Jing Huang
ABSTRACT Organelle-targeted photosensitizers (PSs) offer valuable tools for improving photodynamic therapy (PDT), yet systematic studies on how different organelles influence phototherapeutic outcomes are limited. In particular, the connection between organelle targeting and various modes of programmed cell death remains unclear. In this study, we developed a series of PSs using the Coumarin-Quinazolinone ( CQ ) scaffold, each designed to target different organelles, including the mitochondria, endoplasmic reticulum (ER), lysosome, and nucleolus. Our results show that their PDT performance is highly dependent on their localization, with phototoxic index (PI) ranging from 2 to 245. Notably, the mitochondria-targeted CQ-Mito and ER-targeted CQ-ER exhibited profound phototherapeutic performances, with PI of 167 and 245 respectively. Our further study reveals that CQ-Mito causes cell death by both apoptosis and ferroptosis, while CQ-ER primarily triggers ferroptosis. This study not only provides new agents for PDT but also offers insights into how organelle targeting influences cell death mechanisms, which can shed light on the design of PSs for controlled cell death.
研究领域:
药理学
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肿瘤学
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细胞生物学
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光化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2024
·
IF 7.7
Jianhua Zhou,Teng Huang,Yan Li,Jing Yuan
In this work, self-healing cellulose nanocrystals/fluorinated polyacrylate with dual dynamic networks of photoreversible crosslinking network and high-density hydrogen bonds was prepared by Pickering emulsion polymerization. The main work was to study the effects of 7-(2-methacryloyloxy)-4-methylcoumarin (CMA) and 2-ureido-4[1H]-pyrimidinone methyl methacrylate (UPyMA) monomer dosage on emulsion polymerization and latex film properties. The monomer conversion increased first and then decreased as the CMA and UPyMA monomer dosage increased, while a reverse trend was noted for the particle size and particle size distribution. Incorporating UPyMA allowed the rapid formation of hydrogen bonds at the crosslinking sites, which increased the interaction force between the healing surfaces. Besides, reversible photocrosslinking reaction of coumarin groups provided another support for self-healing performance. Moreover, the influence of self-healing temperature, self-healing time and UV irradiation on the self-healing ability was also systematically investigated The tensile strength of the prepared cellulose nanocrystals/fluorinated polyacrylate latex film exhibited a self-healing efficiency of 91.4 % under 365 nm UV irradiation and 80 °C for 12 h. The latex film had excellent thermal stability as was shown by TG and DTG analyses. The outstanding self-healing capability of latex film was attributed to the reversible photodimerization of coumarin groups and multiple hydrogen bonds. In addition, the water-oil repellent and mechanical properties of the latex films were improved as the CMA and UPyMA monomer dosage increased.
研究领域:
材料科学
·
高分子化学
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PeerJ
·
2020
·
IF 2.379
Yuanyuan Shi,Shengxiang Zhang,Daiyin Peng,Chunmiao Shan,Liqiang Zhao,Bin Wang,Jiawen Wu
Cnidium monnieri (L.) Cuss ( C. monnieri ) is one of the most widely used traditional herbal medicines, exhibiting a wide range of pharmacological functions for treating asynodia, trichomonas vaginitis, and osphyalgia. Its important medicinal value comes from its abundance of coumarins. To identify genes involved in coumarin biosynthesis and accumulation, we analyzed transcriptome data from flower, leaf, root and stem tissues of C. monnieri . A total of 173,938 unigenes with a mean length of 1,272 bp, GC content of 38.79%, and N50 length of 2,121 bp were assembled using the Trinity program. Of these, 119,177 unigenes were annotated in public databases. We identified differentially expressed genes (DEGs) based on expression profile analysis. These DEGs exhibited higher expression levels in flower tissue than in leaf, stem or root tissues. We identified and analyzed numerous genes encoding enzymes involved in coumarin biosynthesis, and verified genes encoding key enzymes using quantitative real-time PCR. Our transcriptome data will make great contributions to research on C. monnieri and provide clues for identifying candidate genes involved in coumarin metabolic pathways.
研究领域:
植物学
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药理学
·
分子生物学
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