41175-50-2Relevant academic research and scientific papers
Reaction-based fluorescent turn-on probe for selective detection of thiophenols in aqueous solution and living cells
Wang, Xiao-Bo,Hao, Xue,Zhang, Datong,Jiang, Yan
, p. 167 - 174 (2017)
A novel turn-on florescent probe based on a nucleophilic substitution reaction was developed for the detection of thiophenols in aqueous solution and in living cells. In this probe, 10-hydroxyl derivative of coumarin 6H was selected as fluorophore, 2, 4-dinitrophenlate moiety acted simultaneously as recognition unit and fluorophore quencher. This probe features a remarkable large Stokes shift (128?nm) and shows a highly selective detection process for thiophenols with significant fluorescence turn-on response. Notably, biothiols, aliphatic thiols, amino acids and reducing anions do not interfere with the sensing of thiophenols. The probe shows good linearity ranges with low detection limit of 36?nM for thiophenols. More importantly, it was successfully applied for practical detection of thiophenols in real water samples with a good recovery and imaging of thiophenols in living cells, demonstrating its practical application in environmental samples and biological systems.
Simultaneous Visualization of Endogenous Homocysteine, Cysteine, Glutathione, and their Transformation through Different Fluorescence Channels
Yin, Guoxing,Niu, Tingting,Yu, Ting,Gan, Yabing,Sun, Xinyu,Yin, Peng,Chen, Haimin,Zhang, Youyu,Li, Haitao,Yao, Shouzhuo
, p. 4557 - 4561 (2019)
Studying numerous biologically important species simultaneously is crucial to understanding cellular functions and the root causes of related diseases. Direct visualization of endogenous biothiols in biological systems is of great value to understanding their biological roles. Herein, a novel multi-signal fluorescent probe was rationally designed and exploited for the simultaneous sensing of homocysteine (Hcy), cysteine (Cys), and glutathione (GSH) using different emission channels. This probe was successfully applied to the simultaneous discrimination between and visualization of endogenous Hcy, Cys, GSH, and their transformation in living cells.
Synthesis of a NIR fluorescent dye and its application for rapid detection of HSO3? in living cells
Bu, Dandan,Li, Zhanxian,Ren, Haohui,Yu, Mingming,Zhang, Hongyan,Zhang, Qiang
, (2021)
SO2 and its derivatives (HSO3?, SO32?) play a significant important role in many industries and organisms. Based on coumarin and benzopyranose, a promising NIR ratiometric fluorescent probe BAOA (11-oxo-2,2′,3,3′,6,7,7′,8′-octahydro -1H,1′H,5H,6′H,11H- [10,12′-bipyrano [2,3-f] pyrido [3,2,1-ij] quinolin]-13′-ium perchlorate) was designed and developed to detect HSO3? rapidly and sensitively. The sensing mechanism was Michael addition reaction, in which, strongly nucleophilic HSO3? attacked carbon-carbon double bonds and BAOA-HSO3 was formed. A superior linear calibration curve between the fluorescence ratio I490/I722 and concentrations of HSO3? was obtained in the range of 1.25–8.75 μmol/L and the LOD was figured out as 63.0 nmol/L. Cell experiments showed that BAOA could not only locate mitochondria, lysosomes, ER and Golgi but also detect exogenous HSO3? in living cells.
A novel colorimetric and ratiometric fluorescent probe for selective detection of bisulfite in real samples and living cells
Li, Jin,Gao, Ying,Guo, Haoran,Li, Xiaokang,Tang, Haoyang,Li, Jian,Guo, Yuan
, p. 285 - 290 (2019)
An abnormal level of bisulfite can induce toxicological effects associated with lung cancer, cardiovascular and neurological disorders. Therefore, it is of significance to develop an effective fluorescent probe to detect bisulfite in living cells. Herein, a novel fluorescent probe QPCT, based on a 1,4-addition mechanism, was constructed for the colorimetric and ratiometric detection of bisulfite. QPCT displayed high selectivity and anti-interference ability to bisulfite over other anions and biothiols. The probe renders a sensitive ratiometric response to bisulfite with a remarkable fluorescence blue shift from 590 to 537 nm and the fluorescence ratio was linear with bisulfite concentration over the range of 0–120 μM. More importantly, QPCT has been successfully applied to detect bisulfite in sugars and living A549 cells, which indicated that QPCT had a great capability for monitoring bisulfite in complex systems.
Extensive reduction in back electron transfer in twisted intramolecular charge-transfer (TICT) coumarin-dye-sensitized TiO2 nanoparticles/film: A femtosecond transient absorption study
Debnath, Tushar,Maity, Partha,Lobo, Hyacintha,Singh, Balvant,Shankarling, Ganapati S.,Ghosh, Hirendra N.
, p. 3510 - 3519 (2014)
We report the synthesis, characterization, and optical and electrochemical properties of two structurally similar coumarin dyes (C1 and C2). These dyes have been deployed as sensitizers in TiO2 nanoparticles and thin films, and the effect of molecular structure on interfacial electron-transfer dynamics has been studied. Steady-state optical absorption, emission, and time-resolved emission studies on both C1 and C2, varying the polarity of the solvent and the solution pH, suggest that both photoexcited dyes exist in a locally excited (LE) state in solvents of low polarity. In highly polar solvents, however, C1 exists in an intramolecular charge-transfer (ICT) state, whereas C2 exists in both ICT and twisted intramolecular charge-transfer (TICT) states, their populations depending on the degree of polarity of the solvent and the pH of the solution. We have employed femtosecond transient absorption spectroscopy to monitor the charge-transfer dynamics in C1- and C2-sensitized TiO2 nanoparticles and thin films. Electron injection has been confirmed by direct detection of electrons in the conduction band of TiO 2 nanoparticles and of radical cations of the dyes in the visible and near-IR regions of the transient absorption spectra. Electron injection in both the C1/TiO2 and C2/TiO2 systems has been found to be pulse-width limited (2 system than in the C1/TiO2 system. The involvement of TICT states in C2 is solely responsible for the higher electron injection yield as well as the slower BET process compared to those in the C1/TiO2 system. Further pH-dependent experiments on C1- and C2-sensitized TiO2 thin films have corroborated the participation of the TICT state in the slower BET process in the C2/TiO2 system.
(7-Dialkylamino-3-coumarinyl)pyrazolines – new effective push-pull photogenerators of acidity
Traven,Cheptsov,Vershinina,Solovjeva,Chibisova,Dolotov,Ivanov
, p. 8 - 15 (2018)
(7-Dialkylamino-3-coumarinyl)pyrazolines and their julolidine analog have been synthesized and proved as new effective photogenerators of acidity. Having D-π-linker ?A conjugated system of push-pull type these compounds possess intensive absorption in visible region of electronic spectra, high photosensitivity and undergo photodehydrogenation with proton elimination in the presence of CCl4 or C2Cl6 with a high speed.
Synthesis method of long-wavelength asymmetric rhodamine dye
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Paragraph 0010, (2021/07/08)
The invention discloses a synthesis method of long-wavelength asymmetric rhodamine. The preparation method of the fluorescent dye comprises the following steps of: firstly, carrying out two-step reaction on 3-aminophenol to obtain a dye intermediate, then carrying out reaction on the obtained intermediate and 1, 6-naphthalene diphenol, and finally carrying out esterification to obtain a target product, namely the long-wavelength asymmetric rhodamine fluorescent dye. Compared with the existing fluorescent dye, the synthesized fluorescent dye has the characteristics of near-infrared emission spectrum, laser wavelength of more than 650 nm, good laser conversion efficiency and the like, the synthesis method is simple to operate and high in yield, and the synthesized fluorescent dye can be applied to the fields of laser, electroluminescence, fluorescent probes and the like.
Near-infrared fluorescent probe for detecting hydrogen sulfide as well as preparation method and application of near-infrared fluorescent probe
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Paragraph 0041-0046, (2021/06/12)
The invention belongs to the technical field of organic synthesis, and particularly relates to a near-infrared fluorescent probe for detecting hydrogen sulfide as well as a preparation method and an application of the near-infrared fluorescent probe. The molecular formula of the fluorescent probe is C42H30N2O5S2, and the structural formula of the fluorescent probe is shown in the specification. The disulfide bond of the fluorescent probe reacts with H2S to break the bond, the sulfydryl of the broken disulfide bond attacks carbonyl in a nucleophilic manner, a rhodamine dye molecular monomer is released, and the fluorescence intensity is enhanced by nearly 10 times and is accompanied by obvious color change, so that the fluorescent probe is relatively rapid in H2S atopic recognition reaction, good in selectivity and relatively high in sensitivity, and the detection limit reaches 7.161*10 M.
Stress response decay with aging visualized using a dual-channel logic-based fluorescent probe
Guo, Yuan,James, Tony D.,Li, Jian,Li, Xiaokang,Li, Xinming,Shi, Donglei,Teng, Hao,Tian, Jingye,Zhang, Yanhui
, p. 13483 - 13491 (2021/11/01)
Diagnosing aging for preventative intervention generally relies on the tracking of aging biomarkers in the resting state. However, the static marker levels are insufficient to fully evaluate aging, particularly given that the stress response capacity (SRC) decay is currently viewed as a critical feature of aging. Therefore, we have developed a dual-channel fluorescent probe ROKS capable of the logic-based visualization of thiophenol (stressor) and HOCl (thiophenol-activated stress response product) in vivo, which provides a new strategy from the time dimension to precisely assess the SRC of individuals under stress using the dual-channel fluorescence ratio. Using ROKS we observed that the SRC of live cells decayed with senescence, and that a higher SRC was found for young vs. aged Caenorhabditis elegans. As such, our study offers a promising strategy for the fluorescence-guided diagnosis of aging and paves the way for accurate evaluation of the efficacy of anti-aging drugs.
A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation
Zhang, Yanhui,Teng, Hao,Gao, Ying,Afzal, Muhammad Wasim,Tian, Jingye,Chen, Xi,Tang, Haoyang,James, Tony D.,Guo, Yuan
supporting information, p. 2917 - 2920 (2020/03/13)
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.
