ANALYTICA CHIMICA ACTA
·
2016
·
IF 4.712
Xi Dai,Zhi-Fang Du,Li-Hong Wang,Jun-Ying Miao,Bao-Xiang Zhao
We have designed and synthesized a simple but effective fluorescent probe for sensing glutathione (GSH) by PET process based on coumarin and quinone , which worked as fluorophore and reaction site, respectively. The probe could discriminate GSH from cysteine and homocysteine within 1 min in PBS-buffered solution. The sensing mechanism was confirmed by density functional theory (DFT), viscosity test, fluorescence spectrum analysis and HRMS , respectively. The probe has a low limit of detection (0.1 μM) and finally been used in cell imaging successfully.
研究领域:
生物化学
·
分析化学
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PubMed
高影响因子
Chemosensors
·
2021
·Vol. 9
·期 3
·48
·
IF 3.398
Wei Wang,Hongren Zhao,Bing Zhao,Huimin Liu,Qinglei Liu,Yan Gao
In this paper, a novelNL-Fe3+ensemble was designed as a fluorescent chemosensor for highly selective detection of pyrophosphate (PPi) in DMSO/H2O (2:8/v:v, pH = 7.2) solution and living cells.NLshowed a strong affinity for Fe3+and was accompanied by obvious fluorescence quenching. Upon the addition of PPi to the generatedNL-Fe3+ensemble, the fluorescence and absorption spectra were recovered completely. Spectroscopic investigation showed that the interference provoked by common anions such as adenosine-triphosphate (ATP), adenosine diphosphate (ADP), and phosphates (Pi) can be ignored. The detection limit ofNL-Fe3+to PPi was calculated to be 1.45 × 10−8M. Intracellular imaging showed thatNL-Fe3+has good membrane permeability and could be used for the detection of PPi in living cells. A B3LYP/6-31G(d,p) basis set was used to optimizeNLandNL-Fe3+complex.Keywords:coumarin;Fe(III);pyrophosphate;cells imaging
研究领域:
生物化学
·
分析化学
·
细胞生物学
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DOI
高影响因子
International Journal of Electrochemical Science
·
2023
·
IF 1.5
Muhammad Yasir Nawabi,Waqar Uddin,Gang Hu,Saif Ullah,Zhaohui Fang,Saira Sardar
In this article, we presented an innovative work of distinguishing the two different positional heterosubstituents-aromatic isomers i.e. 4-hydroxycoumarin (4-HC) and 7-hydroxycoumarin (7-HC) on their perturbation effect by a novel analytical Belousov-Zhabotinskii (BZ) oscillator. In such BZ oscillator, the tetra-aza-macrocyclic copper complex ([CuL](ClO4)2) was used in which the ligand L is 5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraeazacyclotetradeca-4,11 diene. Experimental data confirmed that, by discrete injection of these two isomers (4-HC and 7-HC) into the active BZ system with equal concentrations reflected in their inhibition time (t in ), but the tin produced by 4-HC was higher than the tin initiated by 7-HC. The interesting feature is that, with increasing concentrations (9.0 x 10 -5 to 3.6 x 10 4 ) of 4-HC constantly increase the tin and decreased the oscillation number (N) after the regeneration of oscillation. Whereas, the upsurge concentrations of 7-HC didn’t change the tin but reduced the N after regeneration of oscillation. Thus, the two isomers were identified. Based on the mechanistic approach of FKN (Field-Koros-Noyes) model, the reaction perturbation mechanism was discussed. A fleeting description is that both 4-HC and 7-HC isomers were oxidized by BrO 2 intermediate radical (which produce during the course of reaction) into salicylic acid and quinone respectively and the system was temporary freeze (t in ) as well. The products (salicylic acid and quinone) were identified by infra-red and Ultra-Visible spectroscopies.
研究领域:
分析化学
·
物理化学
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POLYMER
·
2026
·
IF 5.1
Yongchao He,Hanzhao Kuang,Xiaoqing Liu,Hai Zheng,Yinhang Zhang,Xuan Wang,Yinghua Huang,Jinjing Tang,Feng Wang,Xudong Cui,Mingbo Yang,Hang Chen,Yanhao Huang
Coumarin oxime esters (COXEs) have received extensive attention for their outstanding photoinitiation performance, but their rational and efficient design is challenged by the vast combinatorial space of possible electron donor/acceptor substituents on the coumarin core. In this work, a two-dimensional quantitative structure-activity relationship (2D-QSAR) analysis of reported COXE structures was performed to examine the relationship between structural descriptors and photo-reactivity. It was revealed that the acceptor and donor of hydrogen bond (HA, DH), total energy ( E ), as well as energy gap ( E g ) strongly influence the absorption wavelength ( λ max ). In particular, the phenyl ring with electron-withdrawing substituents enhances the charge asymmetry of the adjacent N–O bond and induces a red shift in the absorption wavelength. As a result, a novel COXE, namely C-5, was rationally designed and synthesized with a pentafluorophenyl substituent. The λ max of C-5 was predicted by DFT and confirmed by the UV-vis spectrum to be 424 nm in acetonitrile. Meanwhile, C-5 exhibits strong absorption ( ε ) of about 8.66 × 10 3 M −1 cm −1 at 405 nm and shows rapid photobleaching under 405 nm irradiation. In addition, the GelNB system photocured by the C-5 photoinitiator enabled a polymerization conversion of about 25.8%, with an elastic modulus of 2878 MPa. This modulus is significantly higher than that of the samples cured by the LAP and Irgacure 2959. These results demonstrate that the 2D-QSAR-DFT collaborative design can identify and optimize novel COXE photoinitiators, thereby advancing the highly efficient, rational preparation of visible-light-active photoinitiators for visible-light photopolymerization.
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RSC Advances
·
2025
·Vol. 15
·期 36
·29879-29889
·
IF 4.6
Jing Ge,Jing Xiao,Bingqian Xue,Duidui Liu,Bingqi Du,Xilin Bai
Twisted intramolecular charge transfer (TICT) is a critical mechanism influencing the emission efficiency and stability of fluorescent materials, thereby playing a pivotal role in the design of highly fluorescent and stable dyes. Although substantial research has concentrated on the role of intermolecular hydrogen bonding in excited-state dynamics, the impact of intramolecular hydrogen bonding has not been thoroughly investigated. To elucidate the solvent polarity dependence of C7 and C30, we employed the Kamlet–Taft and Catalán 4P models in conjunction with steady-state and transient absorption spectroscopy, complemented by time-dependent density functional theory (TDDFT) calculations. Our findings demonstrate that C30 exhibits a pronounced TICT process in both solvents. Conversely, C7, stabilized by intramolecular hydrogen bonds, retains a planar configuration of its benzimidazole and benzopyrone moieties, effectively preventing the TICT process. Moreover, in MeOH, the intermolecular hydrogen bonding in C30 significantly extends the lifetime of the TICT state compared to ACN. Theoretical analyses of electrostatic potential, molecular geometry, and frontier molecular orbitals further corroborate these observations. This work provides valuable insights into the design of fluorescent dye molecules and the selection of solvents, laying a foundation for advancing the photophysical and photochemical understanding of coumarin dyes.
研究领域:
物理化学
·
光化学
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材料科学
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光谱学
·
理论化学
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PubMed
高影响因子
Analytical Methods
·
2023
·Vol. 15
·期 13
·1639-1648
·
IF 3.1
Jiali Kou,Zhiyuan Meng,Xiaoyuan Wang,Zhonglong Wang,Yiqin Yang
In this work, a novel coumarin derivative-modified cellulose acetate (DCB-CA) was synthesized as a fluorescent probe for highly selective and sensitive determination of CN− in food samples. The DCB-CA was synthesized by using CA as a skeleton, and the coumarin derivative as the fluorophore. The DCB-CA obtained was characterized by different methods including FTIR, SEM, 1H-NMR, TGA and UV-vis spectroscopy. The DCB-CA exhibited a significant “turn-off” fluorescence response to CN−, accompanied by a distinct fluorescence color change from bright yellow to colorless. The detection limit of CN− using DCB-CA was calculated to be 5.8 × 10−7 M, which was much lower than the threshold limit of CN− recommended by the World Health Organization (1.9 × 10−6 M). Because of the favorable solubility and processability of the CA, the DCB-CA was easily processed into different fluorescent materials including fluorescent films and coatings. The fluorescent film obtained was also applied to the selective detection of CN−. Furthermore, the DCB-CA was successfully applied to determine CN− in food samples.
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高影响因子
CHEMISTRY & BIODIVERSITY
·
2022
·Vol. 20
·期 1
·e202200867
·
IF 2.745
Huiyan Wang,Mengyang Su,Xuli Shi,Xiangyu Li,Xinyu Zhang,Aihong Yang,Rui Shen
Coumarins and their derivatives possessed a variety of biological activities and some of coumarin-based drugs have been approved by the US Food and Drug Administration. Alzheimer's disease (AD) has caused great losses to human society. However, due to its complex pathogenesis, the ideal therapeutic approach has not been found yet. Free radical scavenging activity which is one of the main activities of coumarin core structure is closely related to other anti-AD activities. Therefore, in this work coumarins were chosen as privileged lead compounds for the development of anti-AD drugs based on strategy of multi-target directed ligands (MTDLs). Derivatives 1 – 3 which could modulate multiple targets simultaneously, including ROS, cholinesterase, βamyloid (Aβ) aggregation, and metal dyshomeostasis were designed and for the first time synthesized. Their anti-AD activities were studied both in vitro and in silico . Results showed that 1 – 3 possessed potent antioxidant activities and 7-OH group did change the electron distribution of the molecule and enhance the antioxidant activities. They also have good inhibition activities on acetylcholinesterase (AChE) and Aβ aggregation and compound 1 had the strongest AChE inhibitory effect among the three compounds (AChE IC 50 =11.15 μM). Compound 1 – 3 could also selectively chelate with Cu 2+ and Al 3+ to regulate the metal homeostasis. In silico simulations, including molecular docking and prediction of ADMET performance, indicated that 1 – 3 could interact with target proteins and cross the blood brain barrier. In conclusion, 1 – 3 could be promising MTDLs applied as anti-AD candidate drugs. Graphical
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
·
2023
·
IF 4.3
Chunhui Yi,Fanyong Yan,Xin Wei,Yawei Wu,Xueyu Wang,Jinxia Xu
Based on the fluorescence resonance energy transfer (FRET) principle, a yellow-green light fluorescent probe was designed and synthesized for the detection of neutral red using fluorescein monoaldehyde-3-acetylcoumarin as the fluorophore. The fluorescein moiety in the probe structure is readily interchangeable and heterogeneous in the form of an anion, and the neutral red is a quaternary ammonium salt structure with N. Therefore, the two are bound together in the form of ionic bonds through the mutual attraction of anions and cations. At the same time, FRET occurs, resulting in the absorption of the fluorescence emitted by the probe by the neutral red molecule, leading to a significant quenching of its fluorescence. The probe has a high selectivity for neutral red with a linear range of 0–30 μM and a detection limit of 8. 68 μM. Furthermore, the fluorescent probe has been successfully applied to the detection of neutral red content in real water samples with a recovery of 101 %-115 %. The probe has promising potential in the quantitative detection of neutral red.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2026
·
IF 4.8
Chennan Zheng,Jiahao Li,Yijin Chang,Dazhi Zhou,Changchun Hao
Ligand glycosylation is often assumed to enhance protein binding by increasing hydrogen-bonding capacity, but its actual role in coumarin–β-lactoglobulin (β-LG) recognition has not been clearly resolved. Here, fraxin (FXN) and its aglycone fraxetin (FXT) were used as a paired model to examine how a glucose moiety regulates β-LG binding through multispectroscopic analysis and molecular simulations. Both ligands associated with β-LG and quenched its intrinsic fluorescence, but FXT showed stronger quenching, higher apparent affinity, a shorter FRET-derived donor–acceptor distance, and a more pronounced reduction in fluorescence lifetime. Thermodynamic analysis indicated spontaneous, entropy-favored binding for both systems. Synchronous and three-dimensional fluorescence spectra further showed that FXT caused greater perturbation of the aromatic-residue microenvironment, whereas far-UV CD revealed only limited secondary-structure fluctuations without a consistent concentration-dependent trend. Docking, MD simulation, and MM/PBSA calculations indicated that the glucose group in FXN introduced additional polar contacts but also a larger polar-solvation penalty and possible steric constraints. In contrast, FXT achieved closer hydrophobic accommodation near the fluorescence-sensitive region of β-LG. These results suggest that glycosylation does not simply strengthen coumarin–β-LG binding, but reshapes molecular recognition through a trade-off among polar interactions, desolvation, and hydrophobic fitting.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2023
·
IF 4.4
Fang Li,Rong Tang,Yujie Kang,Xiaoyan Cui,Ya Wang,Xiupei Yang
New coccine (NC), as a kind of common colorant, has been frequently used in our daily life. Herein, the fluorescent composite (PNTs@C6) prepared by the hydrophobic non-covalent interaction between peptide nanotubes and coumarin 6 (C6) was designed for the determination of NC. Due to the activation of C6 by peptide nanotubes, the composite exhibits strong green fluorescence emission, which can be selectively quenched by NC through the inner filter effect. Therefore, a new fluorescent method based on the PNTs@C6 composite for NC detection was constructed. Under optimal conditions, the fluorescence quenching of the sensor exhibits a good linear relationship with the concentration of NC in the range of 0.01–10 μM and the limit of detection is 3.6 nM. Furthermore, the strategy shows simplicity, rapid response and high selectivity and has been successfully applied to the detection of NC in food samples.
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PubMed
高影响因子
NANOTECHNOLOGY
·
2021
·Vol. 32
·期 45
·455101
·
IF 3.874
Xiaojing Yang,Di-Feng Chen,Lin-Song Li,Xue-Jie Zhao,Mei-Xia Zhao
In this study, a nanodrug carrier (mesoporous silica nanoparticle (MSN)-SS-cysteamine hydrochloride (CS)-hyaluronic acid (HA)) for targeted drug delivery was prepared using MSNs, in which HA was used as a targeting ligand and blocking agent to control drug release. Coumarin is a fluorescent molecule that targets mitochondria. Two conjugates (XDS-DJ and 5-FUA-4C-XDS) were synthesized by chemically coupling nitrogen mustard and 5-fluorouracil with coumarin, which was further loaded into MSN-SS-CS-HA nanocarriers. MTT analysis demonstrated that the nanocomposite MSN-SS-CS@5-FUA-4C-XDS/HA displayed stronger cytotoxicity toward HCT-116 cells than HeLa or QSG-7701 cells. Furthermore, MSN-SS-CS@5-FUA-4C-XDS/HA was able to target the mitochondria of HCT-116 cells, causing decreased mitochondrial membrane potential and excessive production of reactive oxygen species. These results indicate that MSN-SS-CS@5-FUA-4C-XDS/HA has the potential to be a nanodrug delivery system for the treatment of colon cancer.
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高影响因子
NEW JOURNAL OF CHEMISTRY
·
2019
·Vol. 43
·期 37
·14763-14771
·
IF 3.069
Yu Bai,Ming-Xia Wu,Qiu-Juan Ma,Chun-Yan Wang,Jing-Guo Sun,Mei-Ju Tian,Jian-Sheng Li
Cysteine, as an important amino acid in the human body, plays a vital role in people's normal life activities. In this paper, a ratiometric fluorescent probe for detecting cysteine was designed and synthesized based on the fluorescence resonance energy transfer (FRET) process. In this FRET system, a coumarin derivative was used as the energy donor, a rhodol fluorophore was chosen as the energy receptor, and an acrylate group was utilized as a cysteine recognition unit. In the absence of cysteine, the rhodol receptor was in the non-fluorescent lactone state and the FRET process was inhibited. Upon addition of cysteine, the closed spirolactone form was converted to a conjugated fluorescent xanthene form to induce the occurrence of FRET which resulted in a fluorescent signal decrease at 470 nm and enhancement at 543 nm. The ratiometric fluorescent probe exhibited excellent selectivity to Cys over Hcy and GSH. In addition, I543nm/I470nm of the probe for cysteine displayed a good linear relationship in the range of 5.0 × 10−7–1.0 × 10−4 mol L−1, and the detection limit was 2.0 × 10−7 mol L−1. Furthermore, the probe showed low cell toxicity and was successfully applied to the confocal imaging of cysteine in HepG2 cells using dual emission channels.
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