17754-90-4Relevant academic research and scientific papers
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.
Colorimetric "Naked-eye" highly selective detection of Cu(II) ion by a simple chemosensor: An experimental and theoretical modeling
Dalapati, Sasanka,Jana, Sankar,Guchhait, Nikhil
, p. 279 - 281 (2011)
The selectivity and sensitivity of N,N'-bis(4-diethylaminosalicylidene) hydrazine (sensor 1) toward Cu2+ ion have been established both by distinct "naked-eye" color change as well as UVvis spectrophotometry. Sensor 1 formed 1:1 complex with Cu2+ ion where the most stable s-trans form of the sensor is trapped in the high energy conformer. Single-crystal X-ray structure of sensor 1 supports its s-trans conformation. Theoretical calculations support well the experimental result.
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).
ESIPT-active multi-color aggregation-induced emission features of triphenylamine-salicylaldehyde-based unsymmetrical azine family
Mathivanan, Moorthy,Tharmalingam, Balamurugan,Lin, Chia-Her,Pandiyan, Baskaran Vijaya,Thiagarajan, Viruthachalam,Murugesapandian, Balasubramanian
, p. 213 - 228 (2019)
The development of multi-color aggregation-induced emission (AIE)-featured azine molecules with excited-state intramolecular proton transfer (ESIPT) characteristics has drawn significant interest in recent years. In this study, we report the construction of donor-acceptor-structured triphenylamine-functionalized unsymmetrical azine molecules (L1-L4) prepared from 4-(hydrazonomethyl)-N,N-diphenylaniline with different salicylaldehyde derivatives. By changing the electron donating ability at the ESIPT moiety, we could tune the optical properties of the newly synthesized molecules. All the compounds exhibited the AIE behavior in a THF/water mixture and the excited-state intramolecular proton transfer phenomenon. Further, the tuning of a peripheral substituent in the salicylaldehyde moiety resulted in different emission colors in the aggregated state. The crystal structure of all the compounds (L1-L4) revealed that the multiple weak interactions present in the solid-state structure lead to various supramolecular networks. In addition, these molecules showed a prominent positive solvatochromic effect, which was confirmed by their solvent polarity-dependent emission behavior. The appearance of dual emission bands in the solid as well as in the solution state, lifetime values and HOMO, LUMO energy gap of the keto and enol forms strongly support the occurrence of ESIPT in all the compounds (L1-L4). Furthermore, the presence of two different electron donating groups in L3 (triphenylamine and diethylamino) induced pH-dependent emissive features in solution.
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.
PH-dependent fluorescent probe that can be tuned for cysteine or homocysteine
Yue, Yongkang,Huo, Fangjun,Li, Xiaoqi,Wen, Ying,Yi, Tao,Salamanca, James,Escobedo, Jorge O.,Strongin, Robert M.,Yin, Caixia
, p. 82 - 85 (2017)
The very close structural similarities between cysteine and homocysteine present a great challenge to achieve their selective detection using regular fluorescent probes, limiting the biological and pathological studies of these two amino thiols. A coumarin-based fluorescent probe was designed featuring pH-promoted distinct turn-on followed by ratiometric fluorescence responses for Cys and turn-on fluorescence response for Hcy through two different reaction paths. These specific responses demonstrate the activity differences between Cys and Hcy qualitatively for the first time. The probe could also be used for Cys and Hcy imaging in living cells.
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.
Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
Huang, You,Li, Xiaohu
supporting information, p. 9934 - 9937 (2021/10/12)
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
Near-infrared fluorescent probe for detecting hydrogen sulfide, and preparation method and application thereof
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Page/Page column 6-10, (2019/02/13)
The invention discloses a near-infrared fluorescent probe for detecting hydrogen sulfide, and a preparation method and an application thereof. The structural formula of the probe is shown in the description. The preparation method comprises the following steps: 1) reacting isophorone with malononitrile in ethanol, and purifying the obtained reaction product to obtain a compound 1; 2) heating, stirring and refluxing POCl3 and 3-N,N-diethylamino phenol in DMF under an ice-water bath condition, adjusting the pH value of a solution obtained after the above reaction is finished to 7, and purifyingthe obtained reaction product to obtain a compound 2; 3) reacting the compound 1 with the compound 2 in ethanol, and purifying the obtained reaction product to obtain HZ-1; and 4) reacting the HZ-1 with NBD-Cl to obtain HZ-NBD. The fluorescent probe is used for detecting H2S in a tetrahydrofuran-phosphate buffer solution or detecting H2S in HepG2 cells and zebra fish. The fluorescent probe has a good selectivity and a high detection sensitivity in H2S identification, and can reach the naked eye identification effect.
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.
