74696-96-1Relevant articles and documents
Detection of SO2 derivatives using a new chalco-coumarin derivative in cationic micellar media: Application to real samples
Gómez, Marisol,Aliaga, Margarita E.,Arancibia, Verónica,Moya, Alexis,Segura, Camilo,Nu?ez, Marco T.,Aguirre, Pabla,Nagles, Edgar,García-Beltrán, Olimpo
, p. 31261 - 31266 (2018)
A new probe (E)-7-(diethylamino)-3-(3-(thiophen-2-yl)acryloyl)-2H-chromen-2-one (ChC16) was synthesized and studied as a turn-on fluorescent probe, based on a Michael addition mechanism for sensing SO2 derivatives, which is favored in the presence of cationic micellar media such as cetylpyridinium bromide (CPB). The probe showed high selectivity and sensitivity toward bisulfite over other anions and biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), with a detection limit of 240 nM. Moreover, the probe showed great potential for its practical application in the detection of bisulfite in real samples, such as dry white wine, and in bioimaging.
A Fluorescent coumarinylalkyne probe for the selective detection of mercury(II) ion in water
Lee, Dong-Nam,Kim, Gun-Joong,Kim, Hae-Jo
, p. 4766 - 4768 (2009)
A coumarin-based alkyne was developed as a fluorescent chemodosimeter for the selective detection of mercuric ion. It showed a high selectivity and sensitivity to mercury(II) ion over other metal ions in water.
Controlled keto-enol tautomerism of coumarin containing β-ketodithioester by its encapsulation in cucurbit[7]uril
Aliaga, Margarita E.,García-Río, Luis,Numi, Ambar,Rodríguez, Alejandra,Arancibia-Opazo, Sandra,Fierro, Angélica,Ca?ete, Alvaro
, p. 15574 - 15580 (2017)
Conventional spectroscopy techniques (UV-Vis, fluorescence and NMR), mass spectrometry and molecular modeling studies are used to assess the inclusion of cucurbit[7]uril (CB7) with coumarin 7-N,N-diethylamino-2H-chromen-2-one derivatives bearing ethyl acetoacetate (CAM1) and methyl β-ketodithioester (CAM2) moieties. For the first time, it has been demonstrated that the macrocycle CB7 is able to stabilize the keto tautomeric form of both coumarin derivatives. More interestingly, it was also seen that for CAM2, the macrocycle CB7 shifts the keto-enol equilibrium from its enol form to the keto tautomer after its inclusion, establishing important differences with inclusion in β-CD, while for CAM1, the macrocycle CB7 maintains the original keto form.
A novel coumarin-based pyrazoline fluorescent probe for detection of Fe3+ and its application in cells
Guo, Hui-Chen,Teng, Qi,Xue, Ji-Jun,Yang, Yun-Shang,Zhang, Ying-Peng
, (2021)
A novel coumarin-based pyrazoline fluorescent probe A was synthesized through a four-step reaction. The structure was characterized by 1H NMR(Nuclear magnetic resonance), 13C NMR and HR-ESI-MS(High resolution electrospray ionization mass spectrometry). The optical properties of the fluorescent probe was investigated by UV–vis absorption and fluorescence emission spectra. The results showed that the addition of Fe3+ makes the fluorescence emission spectra of A quenched and displayed a linear fluorescence response to Fe3+ with a detection limit of 1.01 × 10?7 M. It also shows good reversibility upon addition of EDTA(Ethylene diamine tetraacetic acid). The structure of the fluorescent probe was optimized by DFT(Density functional theory) calculations, and the binding mechanism between the fluorescent probe and the recognition ion was explained. Moreover, the probe also has practical application in cell imaging.
A sensitive and selective fluorescent thiol probe in water based on the conjugate 1,4-addition of thiols to α,β-unsaturated ketones
Lin, Weiying,Yuan, Lin,Cao, Zengmei,Feng, Yanming,Long, Lingliang
, p. 5096 - 5103 (2009)
Compound 1 was designed and synthesized as a new fluorescent thiol probe. Probe 1 was constructed on the basis of the conjugate 1,4-addition of thiols to α,β-unsaturated ketones. Notably, probe 1 has suitable water solubility, which allows the sensing assay to be performed in water. Probe 1 is highly sensitive for thiols with a 211-fold fluorescence dynamic range and a low detection limit of 9.25 × 10-7M. The major features of probe 1 also include a high selectivity for thiols over other relevant biological species, excitation and emission in the visible region, rapid functioning at pH 7.4, and a good linear relationship between the fluorescence signal and the thiol concentration. Accordingly, these desirable characteristics may render probe 1 as potentially useful for biological applications.
Novel coumarin sensitizers based on 2-(thiophen-2-yl)thiazole π-bridge for dye-sensitized solar cells
Han, Liang,Kang, Rui,Zu, Xiaoyan,Cui, Yanhong,Gao, Jianrong
, p. 2046 - 2053 (2015)
2-(Thiophen-2-yl)thiazole was introduced as a π-bridge into diethylamino coumarin and novel coumarin sensitizers were synthesized with cyanoacrylic acid or rhodanine acetic acid as electron acceptor. Their light-harvesting capabilities and photovoltaic performance were investigated and compared with those of a similar sensitizer bearing a phenylthiophene bridge. Replacement of benzene in the π-bridge with a thiazole ring contributes to the improvement of the light-harvesting capability and hence superior JSC. 7-Diethylamino coumarin dye with a 2-(thiophen-2-yl)thiazole bridge and cyanoacrylic acid acceptor shows the most efficient photoelectricity conversion efficiency which has the maximum value of 4.78% (VOC = 690 mV, JSC = 9.79 mA cm-2, and ff = 0.71) under simulated AM 1.5 G irradiation (100 mW cm-2).
Restriction of molecular twisting on a gold nanoparticle surface
Debnath, Tushar,Dana, Jayanta,Maity, Partha,Lobo, Hyacintha,Shankarling, Ganapati S.,Ghosh, Hirendra N.
, p. 5704 - 5708 (2015)
To understand the photophysical properties of intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT) states on a gold nanoparticle (Au NP) surface, we have designed and synthesized a new coumarin molecule (C3) that exists b
A reversible coumarin-based sensor for intracellular monitoring cysteine level changes during Cu2+-induced redox imbalance
Chao, Jianbin,Huo, Fangjun,Jia, Jinping,Yin, Caixia,Zhang, Yongbin,Zhao, Jiamin
, (2021)
Biological thiols are crucial small molecule amino acids widely existing in cells, which play indispensable roles in maintaining redox homeostasis of living systems. Owing to their abnormal levels have close relation with many diseases, thus, developing more convenient, rapid and practical in-vivo detection tools is imminent. Herein, a reversible coumarin-based probe (HNA) was successfully constructed through a simple two-step synthesis. HNA can detect Cys/Hcy with high response speed and desirable selectivity based on Michael addition recognition mechanism. Free HNA has an orange emission at 580 nm, but after addition of Cys/Hcy, the conjugated structure of probe HNA was destroyed by the attack of sulfhydryl, resulting in a new green emission at 507 nm. Further, HNA has been applied to monitor Cys/Hcy in HeLa cells and zebrafish. Notably, HNA has also been successfully applied for real-time tracing Cys levels changes in living cells and zebrafish during the imbalance in redox status caused by copper (II). This provides a new strategy for studying the process of oxidative stress in cells.
A coumarin-based fluorescent and colorimetric chemosensor for rapid detection of fluoride ion
Ma, Liulei,Leng, Taohua,Wang, Kai,Wang, Chengyun,Shen, Yongjia,Zhu, Weihong
, p. 1306 - 1310 (2017)
A novel coumarin-based compound 1 featuring thiosemicarbazone as binding unit, was reported as a colorimetric and fluorescent probe for the detection of fluoride anion. The addition of F?to a solution of probe 1 in tetrahydrofuran resulted in evident naked-eye color change from green-yellow to orange-red under daylight and obvious fluorescence quenching within 3?s. And the detection limit toward F?was calculated to be as low as 2.16?×?10?7?mol/L.1H NMR titrations proved that the interaction between 1 and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Besides, it exhibited highly sensitivity and selectivity for F?over other examined ions (Cl?, Br?, I?, AcO?, NO3?, HSO4?, H2PO4?) in tetrahydrofuran solution.
Tracking mitochondrial viscosity in living systems based on a two-photon and near red probe
Peng, Min,Yin, Junling,Lin, Weiying
, p. 16945 - 16949 (2019)
A two-photon fluorescent probe, Mito-V, was designed and prepared for sensing the viscosity changes of mitochondria. The systematic investigations demonstrated that the fluorescence emission at 634 nm increased about 22-fold from methanol to 99% glycerol, indicating high viscosity dependence. Notably, using the probe, the mitochondrial viscosity fluctuations have been successfully monitored not only in living cells but also in zebrafish and living mice.
A ratiometric fluorescent probe for biological signaling molecule H 2S: Fast response and high selectivity
Liu, Jing,Sun, Yuan-Qiang,Zhang, Jingyu,Yang, Ting,Cao, Jianbin,Zhang, Lishen,Guo, Wei
, p. 4717 - 4722 (2013)
Selective and fast: A flavylium derivative-based ratiometric fluorescent probe (1) for H2S is reported. The reaction mechanism (see scheme) is based on the nucleophilic addition of H2S towards the electrically positive benzopyrylium moiety of 1, which can efficiently differentiate H 2S from other competitive species. The probe exhibits a fast response toward H2S, within 10 s, which is superior to most of the reported H2S probes. Copyright
A colorimetric and fluorogenic probe for bisulfite using benzopyrylium as the recognition unit
Zhang, Yun,Zhang, Xiangwen,Yang, Xiao-Feng,Zhang, Juan
, p. 1233 - 1239 (2017)
A coumarin–benzopyrylium (CB) platform has been developed for the colorimetric and fluorogenic detection of bisulfite. The proposed probe utilizes coumarin as the fluorophore and positively charged benzopyrylium as the reaction site. The method employs the nucleophilic addition of bisulfite to the benzopyrylium moiety of CB to inactivate the electron-deficient oxonium ion. The driving force for photo-induced electron transfer is considerably diminished, thereby promoting the emission intensity of the coumarin fluorophore. The fluorescence intensity at 510?nm is linear with bisulfite concentration over a range of 0.2–7.5?μM with a detection limit of 42?nM (3δ). CB shows a rapid response (within 30?s) and high selectivity and sensitivity for bisulfite. Preliminary studies show that CB has great potential for bisulfite detection in real samples and in living cells.
A new coumarin-based fluorescence “turn-on” sensor for Al(III) ions and its bioimaging in cell
Jin, Lei,Wang, Wenling,Shen, Zheyu,Xu, Jiahao,Wang, Qingming,Zhao, Chengying
, p. 73 - 79 (2019)
A new coumarin-based probe 3-acetyl-7-diethylaminocoumarinthiosemicarbazone (DCT) is synthesized for Al3+ fluorescence detection in CH3CH2OH/H2O (6: 4, v/v). The fluorescence intensity at 428 nm was enhanced about 15-fold with the fluorescence changed from colorless to blue. The binding constantof Al3+ with DCT is 5.04 × 106 M?1. The limit of detection (LOD) of Al3+ is calculated to be 82 nM. Furthermore, the binding details are determined by Job's plot and ESI - MS studies, which indicated that a stoichiometric ratio of 1: 1 complex is formed between Al3+ and DCT. Cell imaging confirmed that DCT could useful for detecting Al3+ in HepG2 cells.
A novel near-infrared turn-on and ratiometric fluorescent probe capable of copper(ii) ion determination in living cells
Aydin, Ziya,Yan, Bing,Wei, Yibin,Guo, Maolin
, p. 6043 - 6046 (2020)
A near-infrared ratiometric fluorescent probe CR-Ac based on a coumarin-benzopyrylium platform has been developed for selective detection of Cu2+. The cell imaging data revealed the capabilities of CR-Ac in monitoring the dynamic changes of sub
Irreversible coumarin based fluorescent probe for selective detection of Cu2+ in living cells
Ahmed, Nadeem,Yang, Xiaopeng,Ye, Yong,Zareen, Wajeeha,Zhang, Di
, (2022)
Copper ion (Cu2+) is an essential part of the living organisms. Cu2+ ions play a vital role in many biotic processes. An abnormal amount of Cu2+ ions may result in serious diseases. Herein, a novel “fluorescent ON” probe NC-Cu to trace minute levels of Cu2+ ions in presence of various biological active species has been developed. Lysosomal cells targeting group (Morpholine) was added to the probe. The spectral properties of probe NC-Cu were recorded in HEPES buffer (0.01 M, pH = 7.4, comprising 50% CH3CN, λex = 430 nm, slit: 5 nm). The synthesized probe NC-Cu work based on copper promoted catalytic hydrolysis of hydrazone and shows remarkable fluorescence enhancement. The reaction of the probe with Cu2+ ions was completed within 20 min. An excellent linear relationship (R2 = 0.9952) was found and the limit of detection (LOD, according to the 3σ/slope) for Cu2+ ions was calculated to be 5.8 μM. Furthermore, NC-Cu was effectively functional in the living cells (KYSE30 cells) to trace Cu2+ ions.
A coumarin based chemodosimetric probe for ratiometric detection of hydrazine
Goswami, Shyamaprosad,Das, Sangita,Aich, Krishnendu,Sarkar, Deblina,Mondal, Tapan Kumar
, p. 2695 - 2699 (2014)
A coumarin-based sensor containing trifluoroacetyl acetonate moiety was designed, synthesized, and applied for hydrazine detection. Hydrazinolysis of the chemodosimeter results in a prominent chromogenic and fluorescence ratiometric response toward hydrazine within 3 min. The probe is highly selective toward hydrazine over other important amines and other biologically and environmentally abundant analytes. The limit of detection (LOD) of the probe is in 10-6 M range. The sensing mechanism was supported by NMR and HRMS analysis. The experimentally observed change in structure and electronic properties of the sensor after reaction with hydrazine was modeled by Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TDDFT) computational calculations, respectively.
Independent bi-reversible reactions and regulable FRET efficiency achieving real-time visualization of Cys metabolizing into SO2
Li, Tao,Huo, Fangjun,Chao, Jianbin,Yin, Caixia
, p. 11453 - 11456 (2020)
In this work, we synthesized an independent bi-reversible reaction sensorBPCfor simultaneously detecting cysteine (Cys) and sulfur dioxide (SO2), showing multi-fluorescence signal modes due to the regulable FRET efficiency, and finally achieving real-time process visualization of Cys metabolizing into SO2in subcellular organelles and tumors.
Ruthenium, rhodium, and iridium complexes featuring coumarin hydrazone derivatives: Synthesis, characterization, and preliminary investigation of their anticancer and antibacterial activity
Dkhar, Lincoln,Verma, Akalesh Kumar,Banothu, Venkanna,Kaminsky, Werner,Kollipara, Mohan Rao
, (2022/01/19)
Coumarin hydrazone derivatives (L1, L2, L3, and L4) have been prepared by Knoevenagel condensation. Half-sandwich ruthenium, rhodium, and iridium complexes containing these coumarin hydrazone derivatives (1–12) have been synthesized. The deprotonation of hydrazinic proton from the ligand leads to the formation of anionic species, thereby forming neutral N?∩?N chelation complexes. These complexes have been confirmed by spectroscopic technique and single-crystal X-ray diffraction studies. Spectroscopic analysis of the ligands and complexes shows that the data are consistent with the formulated data. The stability studies of some of the complexes (1, 5, and 6) were performed by the 1H-NMR technique using deuterated DMSO-d6 solvent. They are found to be stable in solution as well as in the air and are nonhygroscopic. In vitro antibacterial activity against gram-positive Staphylococcus aureus and gram-negative Escherichia coli, Klebsiella pneumoniae strains have been tested. Also, their cytotoxicity study was evaluated against Dalton's ascites lymphoma (DL), Ehrlich ascites carcinoma (EAC), and normal cell lines (peripheral blood mononuclear cells [PBMC]). In both the studies, complexes (5 and 6) are found to be the most active compared to the other complexes.
Coumarin-based red light aggregation-induced emission material and preparation method thereof
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Paragraph 0032-0034, (2021/08/21)
The invention discloses a coumarin-based red light aggregation-induced emission material and a preparation method thereof, and belongs to the technical field of organic chemistry and material chemistry. The structural formula of the luminescent material f
