17754-90-4Relevant articles and documents
Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies
Chemate, Santosh B.,Sekar, Nagaiyan
, p. 1615 - 1628 (2015)
Three novel iminocoumarin derivatives with high quantum yield are synthesized from 3-benzimidazole substituted coumarin and different aromatic aldehydes. The photophysical behavior of the synthesized compounds was studied using UV-visible and fluorescence spectroscopy in polar and non-polar solvents. The compounds show absorption maxima at around 450 nm and emission maxima at around 500 nm. The quantum yields of compounds in dichloromethane and chloroform are more than 0.90. The absorption, emission and quantum yield of compounds are dependent on the polarity of solvents. Along with an intense absorption, these compounds show shoulder absorption peak in the studied solvents. The solvent polarity plots revealed the charge transfer process in the synthesized molecules from donor to acceptor. Density Functional Theory and Time Dependent Density Functional Theory computations have been used to have more understanding of the structural, molecular, electronic and photophysical parameters of the dyes. The dyes were characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis.
Novel Potent Orthosteric Antagonist of ASIC1a Prevents NMDAR-Dependent LTP Induction
Buta, Andriy,Maximyuk, Oleksandr,Kovalskyy, Dmytro,Sukach, Volodymyr,Vovk, Mykhailo,Ievglevskyi, Oleksandr,Isaeva, Elena,Isaev, Dmytro,Savotchenko, Alina,Krishtal, Oleg
, p. 4449 - 4461 (2015)
Acid sensing ion channels 1a (ASIC1a) are of crucial importance in numerous physiological and pathological processes in the brain. Here we demonstrate that novel 2-oxo-2H-chromene-3-carboxamidine derivative 5b, designed with molecular modeling approach, inhibits ASIC1a currents with an apparent IC50 of 27 nM when measured at pH 6.7. Acidification to 5.0 decreases the inhibition efficacy by up to 3 orders of magnitude. The 5b molecule not only shifts pH dependence of ASIC1a activation but also inhibits its maximal evoked response. These findings suggest that compound 5b binds to pH sensor of ASIC1a acting as orthosteric noncompetitive antagonist. At 100 nM, compound 5b completely inhibits induction of long-term potentiation (LTP) in CA3-CA1 but not in MF-CA3 synapses. These findings support the knockout data indicating the crucial modulatory role of ASIC1a channels in the NMDAR-dependent LTP and introduce a novel type of ASIC1a antagonists (Chemical Equation).
In situ formation of pyronin dyes for fluorescence protease sensing
Debieu, Sylvain,Romieu, Anthony
, p. 2575 - 2584 (2017)
We report a reaction-based strategy for the fluorogenic detection of protease activity. Based on the “covalent-assembly” probe design principle recently put forward by the Yang group for detection of Sarin related threats (J. Am. Chem. Soc., 2014, 136, 6594-6597), we have designed two unusual non-fluorescent caged precursors (mixed bis-aryl ethers) which are readily converted into a fluorescent unsymmetrical pyronin dye through a domino cyclisation-aromatisation reaction triggered by penicillin G acylase (PGA) or leucine aminopeptidase (LAP). Fluorescence-based in vitro assays and HPLC-fluorescence/-MS analyses support the claimed activation mechanism whose the further implementation to “smart” imaging agents for the study of protease function in vivo is expected.
Dual-Site Fluorescent Probe for Visualizing the Metabolism of Cys in Living Cells
Yue, Yongkang,Huo, Fangjun,Ning, Peng,Zhang, Yongbin,Chao, Jianbin,Meng, Xiangming,Yin, Caixia
, p. 3181 - 3185 (2017)
Fluorescent probes, as noninvasive tools for visualizing the metabolism of biomolecules, hold great potential to explore their physiological and pathological processes. For cysteine (Cys), however, none of the reported fluorescent probes could image the metabolic processes in living cells. To achieve this goal, we developed a coumarin derivative based on rational design of the dual recognition sites for Cys and its metabolite, SO2. The probe displayed distinct two channels with turn-on fluorescent emission toward Cys and SO2, which were successfully applied for imaging both A549 cells and zebrafish. Further, with reversible fluorescent responses toward Cys, the probe could image the enzymatic conversion of Cys to SO2 in living A549 cells in a ratiometric manner. The present work reports the first probe to image the endogenous generated SO2 without incubation of the SO2 donors.
An imine-based colorimetric chemodosimeter for the detection of hypochlorite (ClO -) in aqueous media: its application in test strips and real water samples
Yun, Dongju,Chae, Ju Byeong,Kim, Cheal
, (2019/05/10)
Abstract: A highly selective colorimetric chemodosimeter ASAD, (E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid, was readily synthesized and characterized. The probe ASAD could selectively recognize hypochlorite (ClO -) through an oxidative cleavage of C=N bond with a color change from yellow to colorless and detected it down to a low concentration of 0.95 μ M. Importantly, ASAD could be employed as a practical and efficient optical sensor for ClO - in test strips and water samples. Moreover, the detection process of ASAD to hypochlorite was demonstrated by UV-vis spectroscopy, NMR titration and theoretical calculations. Graphical abstract: A highly selective colorimetric chemodosimeter ASAD was developed to selectively recognize hypochlorite (ClO -) through an oxidative cleavage of C=N bond with color change from yellow to colorless and could detect it down to a low concentration of 0.95 μ M.
A near-infrared fluorescent probe based on SNAr reaction for H2S/GSH detection in living cells and zebrafish
Zhang, Han,Xia, Xiang,Zhao, Hong,Zhang, Guo-Ning,Jiang, Dao-Yong,Xue, Xing-Ying,Zhang, Jiao
, p. 183 - 189 (2018/12/11)
Hydrogen sulfide (H2S) and biothiols such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play critical roles in physiological and pathological processes. However, due to the challenge in sensing H2S and biothiols simultaneously, it is of great importance to solve this problem in biological processes. Herein, a near-infrared fluorescent probe (HZ-NBD) based on SNAr reactions was exploited to achieve the sensitive and selective detection of H2S and glutathione (GSH) simultaneously in the same conditions. The design strategy was employing dicyanoisophorone based fluorescent dye as the fluorophore, the NBD moiety as a response unit and a quencher of fluorophore. The probe exhibited a low limit of detection to H2S (13.2 nM) and GSH (112 nM) as well as a favourable large stokes shift (112 nm). The reaction mechanism was investigated via mass spectra. What's more, owing to the advantages of low cytotoxicity, fast response and strong anti-interference ability, the probe HZ-NBD was successfully applied to bioimage H2S and GSH in HepG2 cells and zebrafish.
