100343-98-4Relevant articles and documents
FRET-based rhodamine-coumarin conjugate as a Fe3+ selective ratiometric fluorescent sensor in aqueous media
Qin, Jing-Can,Yang, Zheng-Yin,Wang, Guan-Qun,Li, Chao-Rui
, p. 5024 - 5029 (2015)
Abstract In this study, a novel ratiometric fluorescent sensor (HL) for Fe3+ based on the conjugation of rhodamine and coumarin has been designed and synthesized. The free sensor displays fluorescence emission at 475 nm, on the addition of Fe3+ to an aqueous solution of HL, the sensor shows significant fluorescence enhancement at 550 nm which should be attributed to an intramolecular fluorescence resonance energy transfer (FRET) mechanism from coumarin to Rhodamine 6G.
Synthesis of a fluorogenic probe for thiols based on a coumarin schiff base copper complex and its use for the detection of glutathione
He, Guangjie,Li, Jing,Wang, Zhongquan,Liu, Chenxi,Liu, Xiangli,Ji, Liguo,Xie, Chenyan,Wang, Qingzhi
, p. 272 - 277 (2017)
Glutathione is the most abundant non-protein thiols compound in cells and plays important metabolic roles. Changes in the amount of glutathione or its metabolic dysregulation can lead to a series of diseases. The determination of glutathione levels is very helpful to the diagnosis and treatment of the related diseases. A coumarin schiff base (compound 1) was synthesized from coumarin hydrazide and 2,6-pyridine dicarboxaldehyde and the fluorogenic probe for thiols (compound 1-Cu2+) was prepared by coordinating compound 1 with copper ions. Compound 1 showed strong fluorescence, while compound 1-Cu2+hardly had fluorescence due to the paramagnetism and/or photoinduced electron transfer of Cu2+. However, after the addition of thiols-containing compounds, the fluorescence of compound 1 was restored. The UV–vis absorption and fluorescence spectra indicated that the fluorogenic probe had good thiols selectivity and sensitivity, particularly for glutathione in CH3CN:HEPES (3:2, v/v) buffer. It was successfully applied to the fluorescence imaging detection of glutathione in human cervical squamous cancer cells (SiHa cells).
Rapid Optical Determination of Enantiomeric Excess, Diastereomeric Excess, and Total Concentration Using Dynamic-Covalent Assemblies: A Demonstration Using 2-Aminocyclohexanol and Chemometrics
Herrera, Brenden T.,Moor, Sarah R.,McVeigh, Matthew,Roesner, Emily K.,Marini, Federico,Anslyn, Eric V.
, p. 11151 - 11160 (2019)
Optical analysis of reaction parameters such as enantiomeric excess (ee), diastereomeric excess (de), and yield are becoming increasingly useful as assays for differing functional groups become available. These assays typically exploit reversible covalent or noncovalent assemblies that impart optical signals, commonly circular dichroism (CD), that are indicative of the stereochemistry and ee at a stereocenter proximal to the functional group of interest. Very few assays have been reported that determine ee and de when two stereocenters are present, and none have targeted two different functional groups that are vicinal and lack chromophores entirely. Using a CD assay that targets chiral secondary alcohols, a separate CD assay for chiral primary amines, a UV-vis assay for de, and a fluorescence assay for concentration, we demonstrate a work-flow for speciation of the enantiomers and diastereomers of 2-Aminocyclohexanol as a test-bed analyte. Because of the fact the functional groups are vicinal, we found that the ee determination at the two stereocenters is influenced by the adjacent center, and this led us to implement a chemometric patterning approach, resulting in a 4% absolute error in full speciation of the four stereoisomers. The procedure presented herein would allow for the total speciation of around 96 reactions in 27 min using a high-Throughput experimentation routine. While 2-Aminocyclohexanol is used to demonstrate the methods, the general workflow should be amenable to analysis of other stereoisomers when two stereocenters are present.
Synthesis and application of a “turn on” fluorescent probe for glutathione based on a copper complex of coumarin hydrazide Schiff base derivative
He, Guangjie,Hua, Xiaobo,Yang, Nan,Li, Linlin,Xu,Yang, Linlin,Wang, Qingzhi,Ji
, (2019)
Discrimination and quantification of intracellular biothiols, such as cysteine (Cys), homocysteine (Hcy), glutathione (GSH) under physiological conditions is significant for academic research and disease diagnosis. A new fluorescent probe (complex 1-Cu2+) for discriminate detection of GSH was prepared by copper ions coordinate with coumarin carbohydrazide Schiff base derivative 1. In suitable buffer solution (CH3CN: HEPES = 3:2, v/v) and under appropriate pH condition (pH = 7.2–7.4), the UV–vis spectroscopy experiments showed that compound 1 and copper ion exhibited a 1:1 ratio binding mode and moderate binding ability. Fluorescence quenching of compound 1 was observed when it complexed with Cu2+ ions. An obviously fluorescence restoration appeared after addition of GSH to the solution of probe, which also exhibited a highly selectivity relative to cysteine (Cys) and homocysteine (Hcy) in the amino acid competitive experiments. The minimum detection limit was calculated to 0.12 μM by fluorescent method, which was distinctly below the physiological concentration of GSH in live cells. Its biological application to detect the endogenous GSH was further proved by the HepG2 cell fluorescence image test.
An acylhydrazone coumarin as chemosensor for the detection of Ni2+ with excellent sensitivity and low LOD: Synthesis, DFT calculations and application in real water and living cells
Chen, Jichao,Gao, Buhong,Jiang, Weina,Li, Zhong,Lu, Wen,Shi, Jiuzhou,Xu, Li,Yang, Shilong
, (2021)
A novel acylhydrazone coumarin fluorescent chemosensor C4 for detection of Ni2+ was designed and synthesized. The experimental results revealed a low detection limit of 2.1 × 10?11 M with high selectivity and excellent sensitivity towards Ni2+. C4 showed a good linear relationship with the concentration of Ni2+ from 1.3 × 10?6 to 1.6 μM. Moreover, a stable complex was formed between C4 and with Ni2+ and the binding ratio was proved to be 2: 1 by Job's plot and mass spectrum. The sensing ability of C4 towards Ni2+ was attributed to parity-forbidden transition according to fluorescence titrations and DFT calculations. The detection of Ni2+ in water samples illustrated C4 could be successfully applied for the detection of Ni2+ in real environmental samples. What's more, the fluorescence microscopy images of Hela cells demonstrated the high potential of the novel biosensor for the investigation of biological processes involving Ni2+, as well.
A novel ratiometric fluorescent probe based on coumarin derivative for the recognition of Al(III) and its application on test strips
Xue, Jia,Tian,Yang, Zheng-yin
, (2019)
A novel ratiometric probe (L) which was composed of chromone and coumarin moieties has been designed and synthesized for sensing Al3+ in EtOH in view of the internal charge transfer (ICT) mechanism. The free probe L exhibited a strong fluorescence emission at 477 nm, and the fluorescence emission here almost disappeared after adding Al3+ (10 equiv.) while a new peak appeared at 524 nm. This may be due to the enhancement of intramolecular electron transfer efficiency from donor to acceptor. In addition, this probe L could be form a 1:1 complex with Al3+, which could be explained by the ESI-MS spectra, and L had a low detection limit for Al3+ with a binding constant of 1.32 × 104 M?1. More importantly, L could be applied to a solid probe for rapid detection of Al3+ with a significant color change.
A turn-on fluorescent probe based on quinoline and coumarin for rapid, selective and sensitive detection of hypochlorite in water samples
Liu, Ruxin,Zhao, Yuqi,Cui, Xiaoqian,Sun, Xiaoxiao,Fei, Qiang,Feng, Guodong,Shan, Hongyan,Huan, Yanfu
, p. 1231 - 1237 (2020)
A fluorescent probe L-Cu2+ based on quinoline, coumarin and Cu2+ has been synthesized and characterized for hypochlorite determination. After copper ion was added to the solution of ligand L, the fluorescence quenching at 490 nm might result from a ligand–metal charge transfer (LMCT) process and its strong coordination ability for Cu2+. In the presence of hypochlorite, the structure of ligand L was destroyed to form 7-(diethylamino)-coumarin-3-carboxylic acid, and the fluorescence was restored at 460 nm. In this case, L-Cu2+ complex could be used as a fluorescent probe to detect hypochlorite, with the advantages of rapid, selective, wide linear range and low detection limit.
Coumarin-based palladium ion fluorescent probe compound and preparation method thereof
-
, (2021/06/09)
The invention discloses a coumarin-based palladium ion fluorescent probe compound and a preparation method thereof, and belongs to the technical field of organic small molecule fluorescent probes. The palladium ion fluorescent probe compound has a structural formula shown in the specification. The preparation method comprises the following steps of: adding diethyl malonate, glacial acetic acid and piperidine into an ethanol solution of a compound 1, namely 4-(diethylamino)-salicylaldehyde, purifying, adding hydrazine hydrate, heating and the like. The prepared palladium ion probe is in a fluorescence enhancement mode and is high in sensitivity, and the detection limit is as low as 4.45*10. The probe shows high selectivity to palladium ions and strong anti-interference performance.
