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.
A novel schiff base fluorescent probe based on coumarin and benzothiazole for sequential detection of Al3+ and PPi and its applicability in live cell imaging
Cao, Duanlin,Han, Xinghua,Hu, Zhiyong,Li, Shengling,Li, Zhichun,Ma, Wenbing,Meng, Xianjiao,Yuan, Changchun,Zhou, Tao
, (2020)
In this study, a novel schiff base fluorescent probe (E)-N'-(3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methylbenzylidene)-7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide (CHS) was synthesized for sequential detection of Al3+ and pyrophosphate ions (PPi) in a DMSO/HEPES (4:1 v/v, pH = 7.4) buffer system and characterized by 1H NMR, 13C NMR, ESI-HR-MS and DFT calculation. Its detection limit was determined to be 0.16 μM for Al3+ and 0.18 μM for PPi in a pH range of 4～8, respectively. The Job’ s plot showed that the stoichiometric ratio to Al3+ was 1:1, and CHS-Al3+ showed highly selective recognition of PPi. The sensor CHS could also recognize Al3+ and PPi and exhibited fluorescence enhancement and quenching properties in HeLa cells.
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).
Synthesis and application of a highly selective copper ions fluorescent probe based on the coumarin group
He, Guangjie,Liu, Xiangli,Xu, Jinhe,Ji, Liguo,Yang, Linlin,Fan, Aiying,Wang, Songjun,Wang, Qingzhi
, p. 116 - 120 (2018)
A highly selective copper ions fluorescent probe based on the coumarin-type Schiff base derivative 1 (probe) was produced by condensation reaction between coumarin carbohydrazide and 1H-indazole-3-carbaldehyde. The UV–vis spectroscopy showed that the maximum absorption peak of compound 1 appeared at 439 nm. In the presence of Cu2 + ions, the maximum peak decreased remarkably compared with other physiological important metal ions and a new absorption peak at 500 nm appeared. The job's plot experiments showed that complexes of 1:2 binding mode were formed in CH3CN:HEPES (3:2, v/v) solution. Compound 1 exhibited a strong blue fluorescence. Upon addition of copper ions, the fluorescence gradually decreased and reached a plateau with the fluorescence quenching rate up to 98.73%. The detection limit for Cu2 + ions was estimated to 0.384 ppm. Fluorescent microscopy experiments demonstrated that probe 1 had potential to be used to investigate biological processes involving Cu2 + ions within living 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.
Fluorescence chemosensor properties of two coumarin-based compounds for environmentally and biologically important Al3+ ion
Li, Chao-rui,Qin, Jing-can,Wang, Bao-dui,Bai, Xue,Yang, Zheng-yin
, p. 141 - 149 (2017)
In this study, two novel coumarin-based compounds called 2-Acetylpyrazine (coumarin-3′-formyl) hydrazone (1) and 2-Acetylpyrazine (7′-diethylaminocoumarin-3′-formyl) hydrazone (2) have been designed, synthesized and characterized. Compound 1 showed higher selectivity and sensitivity for Al3+ over other environmentally and biologically important metal ions than compound 2, and a remarkable enhancement of compound 1 in fluorescence emission intensity at 486?nm with a large red-shift was observed in the presence of Al3+. This phenomenon was attributed to the inhibition of the photoinduced electron-transfer (PET) process upon complexation of 1 with Al3+. Thus, compound 1 could be used as a fluorescent sensor for Al3+.
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.
A diarylethene derived Fe3+ fluorescent chemosensor and its application in wastewater analysis
Li, Yongjie,Pan, Wenhao,Zheng, Chunhong,Pu, Shouzhi
, (2020)
A diarylethylene derivative containing an acylhydrazone Schiff base moiety was designed and synthesized. Upon alternative irradiation with UV and visible lights, the compound showed distinct fluorescence switching properties based on fluorescence resonance energy transfer mechanism. On the other hand, the fluorescence can be efficiently quenched by 69 fold in the presence of Fe3+ ion in methanol. As a Fe3+ fluorescent chemosensor, the sensing mechanism, the influence of pH on sensing properties, and the practical application were also studied. In the complex, the breaking of the intramolecular H-bonding between the –CO [dbnd] NH– proton and the oxygen at the C[dbnd] O of lactone, the weaking of electrons transfer, and the paramagnetic nature of Fe3+ induced a consequent decrease fluorescence. The compound was found to be stable in a wide range of pH and a highly efficient Fe3+ ion quencher with a detection limit of 4.6 × 10?6 mol L?1. Moreover, the fluorescent detection of Fe3+ was demonstrated by filter paper strips. A series of test papers with different Fe3+ concentrations were prepared and used as the standard card. The analytical application of measuring Fe3+ concentration in wastewater samples were evaluated by comparison with the standard card directly and quickly.
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 chromone derivative as a colorimetric and “ON-OFF-ON” fluorescent probe for highly sensitive and selective detection of Cu2+ and S2?
Liu, Cong,Tian, Limei,Liu, Kui,Xue, Jia,Fan, Long,Li, Tianrong,Yang, Zheng-yin
, (2021)
A chromone derivative (L) which could be utilized for reversibly detecting Cu2+ and S2? by means of fluorescence quenching and displacement in aqueous solution was designed and developed. Upon the addition of Cu2+, the strong blue-green fluorescence emission of L was quenched rapidly and then recovered in 1 min by successively adding S2?. Furthermore, with the alternate addition of Cu2+ and S2?, the reversible cycles could be repeated for at least four times, which meant that L could be identified as a renewable dual-functioning probe. What's more, due to its excellent sensing performances, this probe L could also be used to detect Cu2+ and S2? with test strips conveniently.
