- A highly selective water-soluble optical probe for endogenous peroxynitrite
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A colorimetric and fluorescent probe C-Py-1 for ONOO- was prepared and it could exhibit high sensitivity and excellent selectivity toward ONOO- among reactive oxygen species (ROS) and reactive nitrogen species (RNS) with a rapid response time in 100% water solution. Meanwhile, C-Py-1 was successfully applied in the imaging of endogenous ONOO- in RAW264.7 cells.
- Hou, Ji-Ting,Yang, Jin,Li, Kun,Liao, Ye-Xin,Yu, Kang-Kang,Xie, Yong-Mei,Yu, Xiao-Qi
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- Tyrosine specific sequential labeling of proteins
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We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner.
- Cserép, Gergely B.,Herner, András,Wolfbeis, Otto S.,Kele, Péter
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- Rationally designed fluorescence turn-on sensors: A new design strategy based on orbital control
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Herein, we explore a new strategy in the chemo-sensor field for fluorescence amplification upon binding with metal ions based on controlled participation of the nitrogen lone pair orbital. The basic architecture of the sensor entails a fluorophore, the sp2 hybridized nitrogen lone pair (-C=N-), and a chelator site referred to as the control part. Though nonplanar and nonfluorescent, compound IC1 achieved pseudo planarity from binding with Zn2+ as indicated by the increased fluorescence signal. Its other analogue (IC2) is also planar, and unlike IC1-Zn2+ was fluorescent with a lack of binding affinity to metal ions. The time-dependent density functional theory (TDDFT) calculations revealed that the fluorescence amplification was due to the blocking of the nitrogen lone pair orbital; unlikely geometrical rearrangements were insignificant. This could indicate a breakthrough concept in the future design of fluorescent turn-on sensors.
- Jung, Hyo Sung,Ko, Kyoung Chul,Lee, Jae Hong,Kim, Sang Hoon,Bhuniya, Sankarprasad,Lee, Jin Yong,Kim, Youngmee,Kim, Sung Jin,Kim, Jong Seung
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- A highly sensitive fluorescent probe for the detection of bisulfite ion and its application in living cells
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A novel direct visualisation, fluorescent probe derived from coumarin for bisulfate ion detection has been designed and synthesized. This probe shows a rapid, high selectivity, and sensitivity in the detection of bisulfate ion. In a solution of DMSO:HEPES (1:9, v:v, 10 mM, pH 7.4) buffer containing the probe, the presence of HSO3? made the UV–vis absorption of the probe blue-shift from pink to yellow, and the fluorescence of the probe also changed from red to green. Other investigated analytes and ions did not disturb the determination of HSO3?. The reaction mechanism of the determination was proposed based on the nucleophilic attack toward electron-poor C[dbnd]C bond of the probe. This probe has been successfully applied for determination of HSO3? in living cells.
- Yang, Yutao,Bai, Bozan,Xu, Wenzhi,Xu, Zhidong,Zhang, Jinchao,Li, Wei
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- Live-cell imaging of lipid droplets using solvatochromic coumarin derivatives
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Lipid droplets (LDs), the lipid-rich intracellular organelles, serve to regulate many physiological processes and therefore attention has been attracted towards their selective detection. We report positively solvatochromic lipophilic dyes, based on the push-pull framework containing coumarin-pyridine heterocycles for selective live-cell imaging of lipid droplets (LDs) in Cos-7 and McA-RH7777 cells at ultralow concentrations (200 nM). The fluorescent probes show a remarkable increase in fluorescence intensity with time with the hydrophobic core of the lipid droplets contributing to the observed intensity enhancement. The simple structural framework, red emission, strong Stokes shift (>80 nm), and excellent biocompatibility highlight their significance as a versatile imaging tool for studying lipid droplets (LDs).
- Jana, Palash,Kanvah, Sriram,Siva, Aravintha,Soppina, Virupakshi
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- Development of a coumarin-based fluorescent probe for hydrogen peroxide based on the Payne/Dakin tandem reaction
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Hydrogen peroxide (H2O2) is associated with many physiological and pathological processes in biological systems. Here, we report 7-diethylamino-3-formyl-coumarin (Cou-CHO) as a turn-on fluorescent probe for H2O2. The proposed probe employs a tandem Payne/Dakin reaction to convert the electron-withdrawing aldehyde to the electron-donating hydroxyl group, thus hindering the formation of twisted intramolecular charge transfer (TICT) state of 7-diethylaminocoumarin, and thereby resulting in a fluorescence turn-on response. Cou-CHO features high specificity, excellent sensitivity and fast response toward H2O2. In particular, Cou-CHO enables the direct visualization of basal and endogenously produced H2O2 in living cells. The results demonstrate that the tandem Payne/Dakin reaction can provide a new choice to develop H2O2-selective probes.
- Wu, Fangfang,Yu, Hanjie,Wang, Qin,Zhang, Jianjian,Li, Zheng,Yang, Xiao-Feng
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- KCN sensor: Unique chromogenic and 'turn-on' fluorescent chemodosimeter: Rapid response and high selectivity
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An indole conjugated coumarin 1 for KCN chemodosimeter has been prepared and displayed considerable dual changes in both absorption (blue-shift) and emission (turn-on) bands exclusively for KCN. DFT/TDDFT calculations support that the fluorescence enhancement of 1-KCN is mainly due to blocking of the ICT process. The Royal Society of Chemistry.
- Kim, Hyun Jung,Ko, Kyoung Chul,Lee, Jae Hong,Lee, Jin Yong,Kim, Jong Seung
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- Coumarin-based thiol chemosensor: Synthesis, turn-on mechanism, and its biological application
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A new chemodosimetric probe (1) is reported that selectively detects thiols over other relevant biological species by the turning on of its fluorescence through a Michael type reaction. The fluorogenic process upon its reaction was revealed to be mediated by intramolecular charge transfer, as confirmed by time-dependent density functional theory calculations. The application of probe 1 to cells is also examined by confocal microscopy, and its cysteine preference was observed by an ex vivo LC-MS analysis of the cellular metabolite.
- Jung, Hyo Sung,Ko, Kyoung Chul,Kim, Gun-Hee,Lee, Ah-Rah,Na, Yun-Cheol,Kang, Chulhun,Lee, Jin Yong,Kim, Jong Seung
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- A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation
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Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.
- Zhang, Yanhui,Teng, Hao,Gao, Ying,Afzal, Muhammad Wasim,Tian, Jingye,Chen, Xi,Tang, Haoyang,James, Tony D.,Guo, Yuan
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p. 2917 - 2920
(2020/03/13)
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- Near-infrared fluorescent probe for simultaneously detecting DNA and RNA under double channels as well as preparation method and application of the near-infrared fluorescent probe
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The invention discloses a fluorescent probe for simultaneously detecting DNA and RNA in cells under double channels as well as a preparation method and application of the fluorescent probe. The structure of the fluorescent probe is shown as a formula (I) or (II), wherein the Ar is an aromatic ring or an aromatic heterocyclic ring; the R1 and R2 are respectively and independently hydrogen, N-piperazine, N-methyl piperazine, -NH(CH2)nR3 and -NR3R4; the n is any integer from 1 to 5, and R3 and R4 are respectively and independently hydrogen, C1-C5 alkyl or C1-C5 haloalkyl; the A- is halide ions orp-toluenesulfonic acid ions. The fluorescent probe disclosed by the invention can be used for simultaneously detecting DNA and RNA in vitro and in cells under double channels; meanwhile, the fluorescent probe has the characteristics of rapid synthesis, near-infrared emission wavelength, good light stability, high detection sensitivity and the like, and is convenient to popularize and apply.
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- A method for detecting the viscosity of the fluorescent probe and its preparation method and application (by machine translation)
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The invention provides a method for detecting the viscosity of the fluorescent probe, its chemical formula is: . The present invention provides a different viscosity of the distinction between the fluorescent probe, has higher sensitivity, good optical stability and viscosity specific response. The emission spectrum of the probe in the near-infrared region, is realized in the cell in the detection of mouse viscosity and inflammation, cell and tissue light injury to small, the penetration depth of level. At the same time, the present invention provides a method for synthesis of the probe, the step is simple, convenient purification, high yield. (by machine translation)
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Paragraph 0023
(2019/07/01)
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- Preparation method of large emission wavelength fluorescent dye
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The invention discloses a preparation method of a large emission wavelength fluorescent dye, comprising the following steps: first, modifying a naphthalimide by three-step reaction to obtain naphthalimide with activated methyl; second, carrying out four-step reaction to obtain aldehyde modified coumarin; third, reacting the naphthalimide with the activated methyl with the aldehyde modified coumarin to obtain a target product, the large emission wavelength fluorescent dye. Compared with the existing fluorescent dyes, the fluorescent dye synthesized in the invention has a near-infrared emission spectrum and Stokes shift up to 150 nm and is applicable to the fields such as laser, electroluminescence and fluorescent probes.
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- Ruthenium(II)-polyimine-coumarin light-harvesting molecular arrays: Design rationale and application for triplet-triplet-annihilation-based upconversion
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RuII-bis-pyridine complexes typically absorb below 450 nm in the UV spectrum and their molar extinction coefficients are only moderate (Iμ-1cm-1). Thus, Ru II-polyimine complexes that show intense visible-light absorptions are of great interest. However, no effective light-harvesting ruthenium(II)/organic chromophore arrays have been reported. Herein, we report the first visible-light-harvesting RuII-coumarin arrays, which absorb at 475 nm (Iμ up to 63300M-1cm-1, 4-fold higher than typical RuII-polyimine complexes). The donor excited state in these arrays is efficiently converted into an acceptor excited state (i.e., efficient energy-transfer) without losses in the phosphorescence quantum yield of the acceptor. Based on steady-state and time-resolved spectroscopy and DFT calculations, we proposed a general rule for the design of Ru II-polypyridine-chromophore light-harvesting arrays, which states that the 1IL energy level of the ligand must be close to the respective energy level of the metal-to-ligand charge-transfer (MLCT) states. Lower energy levels of 1IL/3IL than the corresponding 1MLCT/3MLCT states frustrate the cascade energy-transfer process and, as a result, the harvested light energy cannot be efficiently transferred to the acceptor. We have also demonstrated that the light-harvesting effect can be used to improve the upconversion quantum yield to 15.2% (with 9,10-diphenylanthracene as a triplet-acceptor/annihilator), compared to the parent complex without the coumarin subunit, which showed an upconversion quantum yield of only 0.95%. Copyright
- Wu, Wanhua,Ji, Shaomin,Wu, Wenting,Shao, Jingyin,Guo, Huimin,James, Tony D.,Zhao, Jianzhang
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p. 4953 - 4964
(2012/06/04)
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- Development of an ICT-based ratiometric fluorescent hypochlorite probe suitable for living cell imaging
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We have judiciously constructed a novel ICT-based ratiometric OCl - probe capable of ratiometric imaging in the live cells based on the new OCl--promoted de-diaminomaleonitrile reaction. The Royal Society of Chemistry 2011.
- Yuan, Lin,Lin, Weiying,Song, Jizeng,Yang, Yueting
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scheme or table
p. 12691 - 12693
(2012/01/12)
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- Coumarin-Cu(II) ensemble-based cyanide sensing chemodosimeter
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An "ensemble"-based chemodosimeter 1-Cu(II) for cyanide detection is reported. 1-Cu(II) can recognize a cyanide ion over other anionic species to show a marked fluorescence enhancement under aqueous conditions. "Off-on" fluorescence change of 1-Cu(II) is proceeded by addition of cyanide, which induces decomplexation of the Cu(II) ion from nonfluorescent 1 followed by hydrolytic cleavage of the resulted Schiff base to give a strongly fluorescent coumarinaldehyde (2). The selective detection of cyanide with 1-Cu(II) for biological application was also performed in HepG2 cells.
- Jung, Hyo Sung,Han, Ji Hye,Kim, Zee Hwan,Kang, Chulhun,Kim, Jong Seung
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supporting information; scheme or table
p. 5056 - 5059
(2011/12/15)
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