- Silver-catalyzed facile decarboxylation of coumarin-3-carboxylic acids
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A simple and highly efficient protocol with mild reaction conditions has been developed that allows the smooth protiodecarboxylation of diversely functionalized coumarin-3-carboxylic acids. In the presence of catalytic amounts of Ag2CO3 and acetic acid, even un-activated coumarin-3-carboxylic acids were converted in good to excellent yields and with great preparative ease to the corresponding coumarin derivatives.
- Jafarpour, Farnaz,Jalalimanesh, Nafiseh,Olia, Mina Barzegar Amiri,Kashani, Asieh Otaredi
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- Structure-efficiency relationship of newly synthesized 4-substituted donor-π-acceptor coumarins for dye-sensitized solar cells
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Four (MC1-MC4) 4-substituted coumarin dyes having N,N-diethyl aniline as donor and rhodanine-3-acetic acid as acceptor have been synthesized for use in nano-crystalline TiO2-based dye-sensitized solar cells (DSSCs). The alteration at the 4-position of coumarin was carried out by substituting H atom by chlorine (-Cl), piperidine (-NC5H10), and cyano group (-CN) to study the effect of substitution on the efficiency of the DSSCs. All the dyes were characterised by 1H-NMR and 13C-NMR spectroscopy and CHN analysis. The absorption and emission spectra of these coumarin dyes were recorded in eight different solvents and show positive solvatochromism. The TiO2-based DSSCs were fabricated using the four dyes and their photovoltaic properties were estimated. A maximum efficiency of 4.60% was obtained for the MC4 device, which has an electron-withdrawing cyano group at the 4-position of coumarin, while 2.64% efficiency was obtained for the MC1 device, which has only hydrogen at the 4-position. The efficiencies of the MC2 and MC3 devices lie between those of MC1 and MC4, suggesting the significance of substitution at the 4-position. The introduction of a cyano group, which acts as an electron trap, increases the electron-withdrawing capacity of the dye; thus, more electron density is withdrawn from the donor, resulting in enhanced efficiency. These dyes were studied by using density functional theory (DFT) and time dependent density functional theory (TD-DFT) to obtain the vertical excitation, HOMO-LUMO energy levels, band gap and electron distribution in the ground and excited state. The calculated values showed good correlation with the experimental values. Our results suggest that substitution at the 4-position is essential for enhancing the efficiency of coumarin-based DSSCs.
- Jadhav, Manoj M.,Vaghasiya, Jayraj V.,Patil, Dinesh S.,Soni, Saurabh S.,Sekar, Nagaiyan
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- A novel hydrazide Schiff base self-assembled nanoprobe for selective detection of human serum albumin and its applications in renal disease surveillance
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Human serum albumin (HSA) is considered as a biomarker for the early diagnosis of renal disease, therefore identifying and detecting HSA in biological fluids (especially urine) with an easy method is of great importance. Herein, we report a novel hydrazide Schiff base fluorescent probe N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)pyrazine-2-carbohydrazide (NPC), which self-assembled into nanoparticles in aqueous solution. Based on disassembly-induced emission and the site-specific recognition mechanism, the binding of NPC with HSA resulted in a fluorescence "turn-on"response. Probe NPC exhibited superior selectivity and sensitivity toward HSA with a detection limit of 0.59 mg L-1 in PBS and 0.56 mg L-1 in the urine sample. The site-binding mechanism of NPC with HSA was explored by fluorescence quenching study, Job's plot analysis, HSA destruction, site marker displacement and molecular docking. Fluorescence imaging of HSA in MCF-7 cells was achieved by using a non-toxic NPC probe, suggesting that NPC could be applied to visualize the level of HSA in vivo. More importantly, further practical applications of probe NPC in human urine samples were achieved with satisfactory results by using a fluorometer or test paper, which could provide extensive application in clinical diagnosis.
- Li, Qing-Zhong,Liu, Hai-Bo,Liu, Wei,Wang, Zhi-Gang,Xie, Cheng-Zhi,Xu, Jing-Yuan,Yan, Xiao-Jing,Zhang, De-Long
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- Comparative study of two near-infrared coumarin-BODIPY dyes for bioimaging and photothermal therapy of cancer
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Near-infrared (NIR) responsive agents for cancer bioimaging and photothermal therapy are available and significant. Herein, we employed two easily available dyes, boron-dipyrromethane and coumarin, to synthesize a pair of coumarin-borondipyrromethane dyes with different conjugate degrees (BDC and BSC). The difference in conjugate degree made their photophysical properties poles apart. After the self-assembling of BDC and BSC, the newly constructed nanoparticles (BDC NPs and BSC NPs) demonstrated good biocompatibility. Moreover, BDC NPs exhibited a good photothermal effect under irradiation of 808 nm laser, which could effectively inhibit the growth of HeLa cells, and BSC NPs could quickly show a conspicuous fluorescence in the HeLa cells. The exploration demonstrates that the two organic dyes prepared with different conjugation degrees could provide new options for photothermal therapy of cancer and rapid bioimaging.
- Zhang, Yuandong,Song, Nan,Li, Yuanyuan,Yang, Zhiyu,Chen, Li,Sun, Tingting,Xie, Zhigang
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- A colorimetric and ratiometric fluorescence probe for rapid detection of SO2 derivatives bisulfite and sulfite
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As one of the main atmospheric pollutants, sulfur dioxide (SO2) can be easily inhaled and turned into sulfite and bisulfite, which is harmful to both human health and ecological environment. Therefore, it is of significance to develop an effective method to detect the trace SO2 derivatives—SO32? and HSO3?. Herein, we synthesized a semi-cyanine-coumarin hybrid dye for detection of SO32? and HSO3?. Based on the nucleophilic addition of HSO3?/SO32? to the vinyl group, Probe 1 showed high response speed, selectivity, and sensitivity towards SO32? and HSO3?. Upon addition of HSO3?/SO32?, color obviously changes from blue to yellow which can be differentiated by naked eyes. Probe 1 displays colorimetric and ratiometric response toward HSO3? and SO32?. The detection limit is as low as 27.6?nM and the signal-to-background ratio in fluorescence intensity can reach 35-folds. Moreover, Probe 1 showed high selectivity and anti-interference ability in the co-existence of the environmental and biologic species.
- Xiang, Kaiqiang,Chang, Shunzhou,Feng, Jingjing,Li, Changjiang,Ming, Wei,Liu, Ziyan,Liu, Yunchang,Tian, Baozhu,Zhang, Jinlong
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- A new fluorescence "turn-on" type chemosensor for Fe3+ based on naphthalimide and coumarin
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A new Fe3+-selective "turn-on" chemosensor 1 based on coumarin and naphthalimide was designed and synthesized. The chemosensor exhibits high selectivity for Fe3+ over other ions (Mn2+, Co2+, Ni2+, Cu2+, Ag+, Cd 2+, Pb2+, Ca2+, Al3+, Ba 2+, Hg2+, Li+, Mg2+, Sr 2+, Zn2+ and K+) with fluorescence-enhancement in THF-H2O solution. The binding ratio of 1-Fe3+ complex was determined to be 1:1 according to the Job plot. The association constant Ka of Fe3+ binding with sensor 1 was (2.589 ± 0.206) × 103 M-1. The detection limit was calculated to be 0.388 μM.
- Li, Zhengqian,Zhou, Ying,Yin, Kai,Yu, Zhu,Li, Yan,Ren, Jun
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- A coumarin-fused ‘off-on’ fluorescent probe for highly selective detection of hydrazine
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Hydrazine is a kind of widely used industrial raw material and a toxic biochemical reagent. Due to its toxic to organisms, hydrazine has been classified to be a hazardous environmental pollutant. It is urgent to develop fluorescent probe tools for selective sensitivity detection of hydrazine in the environment and the body. We developed here a new coumarin-based fluorescent probe for hydrazine detection. The probe can selectively detect hydrazine over other environmental and endogenous interfering analytes with a large off-on fluorescence response. The detection limit is 8.55 ppb, which is well below the allowed threshold limit value. The sensing mechanism is hydrazine-induced pyrazole ring formation, which is confirmed by HRMS and DFT calculation methods. Additionally, the probe could also be applied for hydrazine imaging in living HeLa cells.
- Wang, Mei,Wang, Xiaoli,Li, Xueyan,Yang, Ziqi,Guo, Zhenbo,Zhang, Jiangyan,Ma, Jingjun,Wei, Chao
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- A "turn-off" red-emitting fluorophore for nanomolar detection of heparin
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A simple fluorophore bearing a diethylaminocoumarin donor and a pyridinium acceptor was synthesized and utilized for the ultra-sensitive detection of heparin. The synthesized dicationic push-pull coumarin derivative emits strongly in the red-region (665 nm) and detects nanomolar concentrations (14.8 nM to 148 nM) of heparin in HEPES buffer and FBS serum solutions. The dication exhibits excellent fluorescence selectivity and sensitivity towards heparin over its analogues such as chondroitin 4-sulfate (CS), hyaluronic acid (HA) and dextran. This fluorescence assay is a convenient, sensitive method for monitoring heparin levels in biological samples. These findings were confirmed using coarse-grained Monte Carlo simulations, which provide us with a rationale for the selective binding of heparin.
- Jana, Palash,Radhakrishna, Mithun,Kanvah, Sriram,Khatua, Saumyakanti
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- A selective thioxothiazolidin-coumarin probe for Hg2+ based on its desulfurization reaction. Exploring its potential for live cell imaging
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Sensing the most toxic heavy metal (mercury) has attracted a lot of attention in recent years due to its extreme harmfulness to both human health and the environment. Thus, we reported herein the synthesis, spectroscopic and kinetic characterization, and biological evaluation of a new thioxothiazolidin coumarin derivative (ILA92), which undergoes a desulfurization reaction induced by mercuric ions (Hg2+). This process is the origin of a selective sensing of Hg2+ ions in aqueous solution by colorimetric and fluorescent methods. Furthermore, the probe showed great potential for imaging Hg2+ in living cells.
- Aliaga, Margarita E.,Gazitua, Marcela,Rojas-Bola?os, Andrea,Fuentes-Estrada, Marcial,Durango, Diego,García-Beltrán, Olimpo
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- Design, synthesis and bioactivity evaluation of coumarin-chalcone hybrids as potential anticancer agents
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The selenoprotein thioredoxin reductases (TrxRs) have been extensively studied as a potential target for the development of anticancer drugs. Herein, we designed, synthesized, and evaluated a series of coumarin-chalcone hybrids as TrxR inhibitors. Most of them exhibited enhancing anticancer activity than Xanthohumol (Xn). The representative Xn-2 (IC50 = 3.6 μM) was a fluorescence agent, wherein drug uptake can be readily monitored in living cells by red fluorescence imaging. Xn-2 down-regulated the expression of TrxR, remarkedly induced ROS accumulation to activate mitochondrial apoptosis pathway. Furthermore, Xn-2 inhibited cancer cell metastasis and abolished the colony formation ability of cancer cells. Taken together, these results highlight that compound Xn-2 may be a promising theranostic TrxR inhibitor for human cancer therapy.
- Dong, Junqiang,Gao, Jianbo,Wang, Yu,Zhang, Wenda
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- Synthesis and combined experimental and computational investigations on spectroscopic and photophysical properties of red emitting 3-styryl coumarins
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The coumarin derivatives are though highly fluorescent, lack in the absorption and emission in the red region. Modifying them to red emission included the strategy of formylation of 7-(N,N-diethyl amino) coumarin by Vilsmeier-Haak reaction followed by oxidative cyanation. The aldehyde synthesized was reacted with cyanomethyl benzoxazole/benzothiazole to give target compounds. All the compounds were characterised by spectral analysis. The cyanated molecules are found to be red shifted in absorption and emission by 90-100 nm. There was an increase in the quantum yield by about 10 times. The solvent polarity plots revealed the charge transfer process in the synthesized molecules and higher excited state to ground state dipole moment ratio. Density functional theory computations were performed to understand the nature of transitions involved in absorption and emission process.
- Tathe, Abhinav B.,Gupta, Vinod D.,Sekar, Nagaiyan
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- Single-atom switching as a general approach to designing colorimetric and fluorogenic probes for mercury ions
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By performing a single-atom replacement within common fluorophores, we have developed a facile and general strategy to prepare a broad-spectrum class of colorimetric and fluorogenic probes for the selective detection of mercury ions in aqueous environments. Thionation of carbonyl groups from existing fluorophore cores results in a great reduction of fluorescence. In the presence of mercury ions, the resulting thiocaged probes are efficiently desulfurized to their oxo derivatives, leading to pronounced changes in chromogenic and fluorogenic signals. Because these probes exhibit high selectivity, excellent sensitivity, good membrane-permeability, and rapid responses towards mercury ions, they are suitable for visualization of mercury in both aqueous and intracellular environments.
- Loredo, Axel,Wang, Lushun,Wang, Shichao,Xiao, Han
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- Bifunctional Fluorescent Probe for Sequential Sensing of Thiols and Primary Aliphatic Amines in Distinct Fluorescence Channels
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Thiols and primary aliphatic amines (PAA) are ubiquitous and extremely important species in biological systems. They perform significant interplaying roles in complex biological events. A single fluorescent probe differentiating both thiols and PAA can contribute to understanding the intrinsic inter-relationship of thiols and PAA in biological processes. Herein, we rationally constructed the first fluorescent probe that can respond to thiols and PAA in different fluorescence channels. The probe exhibited a high selectivity and sensitivity to thiols and PAA. In addition, it displayed sequential sensing ability when the thiols and PAA coexisted. The application experiments indicated that the probe can be used for sensing thiols and PAA in human blood serum. Moreover, the fluorescence imaging of endogenous thiols and PAA as well as antihypertensive drugs captopril and amlodipine in living cells were successfully conducted.
- Huang, Meiyu,Long, Lingliang,Wang, Ning,Yuan, Xiangqi,Cao, Siyu,Gong, Aihua,Wang, Kun
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- A coumarinylaldoxime as a specific sensor for Cu2+ and its biological application
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In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H- chromene-3-carbaldehyde oxime (JB), which can detect Cu2+ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu2+ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed that JB interacts with the lipid bilayer at the level of the glycerol moieties.
- García-Beltrán, Olimpo,Cassels, Bruce K.,Mena, Natalia,Nu?ez, Marco T.,Ya?ez, Osvaldo,Caballero, Julio
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- A thiocoumarin-based colorimetric and ratiometric fluorescent probe for Hg2+ in aqueous solution and its application in live-cell imaging
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A new intramolecular charge transfer (ICT) based colorimetric and ratiometric fluorescent chemodosimeter for the detection of Hg2+ has been rationally designed and developed. The probe operates via the specific mercury-promoted desulfurization reaction of thiocoumarin to coumarin and exhibits high selectivity and sensitivity in almost pure aqueous solution (containing only 1% DMSO) with a low detection limit of 1.85 ppb. Furthermore, the probe was successfully used for the fluorescence imaging of Hg2+ in live cells.
- Qin, Siyao,Chen, Bo,Huang, Jing,Han, Yifeng
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- Oligo(ethylene glycol)-Functionalized Ratiometric Fluorescent Probe for the Detection of Hydrazine in Vitro and in Vivo
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Hydrazine induced toxicity causes serious harm to the health of humans. The detection of N2H4 in vitro and in vivo has attracted a great deal of attention, especially in the context of fluorescent probes. Although some fluorescent N2H4 probes have been reported, only a few operate in purely aqueous media and, as a result, require the use of organic cosolvents which hinders their use in analysis of real samples. In addition, most of the current N2H4 probes are either "off-on" or "on-off" types, in which it is difficult to eliminate interference from background fluorescence commonly occurring in in vitro and in vivo systems. Furthermore, some probes are unable to differentiate hydrazine from other organic amines. To address the above problems, we developed a novel oligo(ethylene glycol)-functionalized fluorescent probe for the detection of N2H4. The probe, which has a donor-π-acceptor (D-π-A)-type structure, is water-soluble, and it can be utilized to selectively detect N2H4 in both colorimetric and ratiometric mode. Furthermore, the probe is able to differentiate hydrazine from other organic amines and can be used to detect hydrazine vapor and for imaging A549 cells and zebrafish.
- Li, Jun,Cui, Yuanchao,Bi, Chenxi,Feng, Shaoqiong,Yu, Fengzhen,Yuan, En,Xu, Shengzhen,Hu, Zhe,Sun, Qi,Wei, Dengguo,Yoon, Juyoung
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- A novel coumarin Schiff-base as a Ni(II) ion colorimetric sensor
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A novel coumarin Schiff base compound (L) prepared from 7-diethylaminocoumarin-3-aldehyde and 3-amino-7-hydroxycoumarin was synthesized and evaluated as a chemoselective Ni2+ sensor. Addition of Ni 2+ to CH3CN solution of L resulted in a rapid color change from yellow to red together with a large red shift from 465 to 516 nm. Moreover, other common alkali-, alkaline earth-, transition- and rare earth metal ions induced no or minimal spectral changes. Experimental results indicated that L could be used as a potential Ni2+ colorimetric and naked-eye chemosensor in CH3CN solution.
- Wang, Lingyun,Ye, Decheng,Cao, Derong
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- Fluorescent coumarinyldithiane as a selective chemodosimeter for mercury(II) ion in aqueous solution
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A coumarin-based dithiane (1) was synthesized for the selective detection of Hg2+ with respect to dual chromo- and fluorogenic changing events in an aqueous solution by the mercury-promoted transformation of a dithiane group into an aldehyde functional unit. The Hg2+-selective response of the chemodosimeter was clearly observed in aqueous buffer as well as in human blood plasma medium.
- Kim, Ja Hyung,Kim, Hyun Jung,Kim, Sang Hoon,Lee, Jae Hong,Do, Jung Ho,Kim, Hae-Jo,Lee, Joung Hae,Kim, Jong Seung
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- A new coumarin based chromo-fluorogenic probe for selective recognition of cyanide ions in an aqueous medium
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The optical behavior of a simple intramolecular charge transfer (ICT) fluorescent probe, a coumarin-nitrobenzene conjugate (CNB), has been described to detect cyanide (CN-) selectively in buffered aqueous media. The cyanide addition on the electron-deficient alkene bridge interrupts the π-conjugation in CNB, which obstructs the ICT process and results in a color change from yellow to colorless and a significant fluorescence enhancement at 410 nm. Job's plot analysis revealed a 1: 1 stoichiometry for the interaction between the probe and cyanide anion with a detection limit of 0.14 μM. The probe was also used for fabrication of test strips that could be used in practical and efficient CN- test kits.
- Sun, Xueyi,Wang, Yu,Zhang, Xiaofeng,Zhang, Shihong,Zhang, Zhao
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- A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase
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A coumarin based compound, 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (DCCO), has been developed as a visual fluorescent chemodosimeter for selective detection of highly toxic phosgene gas. DCCO exhibits absorption bands at 330 nm and 425 nm. In the presence of phosgene, the absorbance at 330 nm increases and the peak at 425 nm is shifted to 420 nm with decreasing absorbance accompanying a color change from yellow to colorless. The fluorescence intensity of the probe at 483 nm is enhanced in the presence of phosgene (λex = 425 nm) but nerve agents and other acid chlorides including trisphosgene could not induce any significant enhancement of the fluorescence. DCCO on interaction with phosgene is converted to the corresponding nitrile derivative, 7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile (DCC). The quantum yield has been increased 13 fold on conversion from DCCO to DCC. The fluorescence enhancement has been explained by the ICT mechanism, which has been supported by theoretical calculations. It exhibits a rapid response for naked eye detection of phosgene. DCCO has been used for the detection of phosgene in solution and the gas phase.
- Paul, Sima,Ghosh, Pritam,Roy, Partha
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- A mitochondria-specific fluorescent probe for visualizing endogenous hydrogen cyanide fluctuations in neurons
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An ability to visualize HCN in mitochondria in real time may permit additional insights into the critical toxicological and physiological roles this classic toxin plays in living organisms. Herein, we report a mitochondria-specific coumarin pyrrolidinium-derived fluorescence probe (MRP1) that permits the real-time ratiometric imaging of HCN in living cells. The response is specific, sensitive (detection limit is ca. 65.6 nM), rapid (within 1 s), and reversible. Probe MRP1 contains a benzyl chloride subunit designed to enhance retention within the mitochondria under conditions where the mitochondria membrane potential is eliminated. It has proved effective in visualizing different concentrations of exogenous HCN in the mitochondria of HepG2 cells, as well as the imaging of endogenous HCN in the mitochondria of PC12 cells and within neurons. Fluctuations in HCN levels arising from the intracellular generation of HCN could be readily detected.
- Long, Lingliang,Huang, Meiyu,Wang, Ning,Wu, Yanjun,Wang, Kun,Gong, Aihua,Zhang, Zhijian,Sessler, Jonathan L.
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- A "naked eye" and ratiometric chemosensor for cobalt(II) based on coumarin platform in aqueous solution
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A novelcolorimetric cobalt(II) chemosensor ratiometric and (HL) based on coumarin platform has been synthesized. It displayed a remarkable (44 nm) red-shift in the absorption spectra upon reaction with Co2+, which is easily observed from yellow to red by the naked-eye. Co2+ could be quantitatively detected in the range of 0-10 μM by both normal and ratiometric absorption spectrometry methods. The detection limit of HL for Co2+ detection was as low as 0.31 μM.
- Liu, Zhaodi,Wang, Wenlong,Xu, Huajie,Sheng, Liangquan,Chen, Shuisheng,Huang, Deqian,Sun, Fei
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- A new ratiometric and colorimetric chemosensor for cyanide anion based on Coumarin-hemicyanine hybrid
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A hybrid coumarin-hemicyanine dye, Cou-BT, was developed as a new ratiometric and colorimetric sensor for cyanide with a sensing mechanism via nucleophilic addition of cyanide anion to the benzothiolium group. Cou-BT shows high sensitivity and selectivity for cyanide detection over other common anion species in aqueous acetonitrile solution. The calculated pseudo-first-order rate constant for cyanide anion addition was (2.13 ± 0.08) × 10 -2 s-1 at 298 K, and the detection limit was estimated to be 0.64 μM. The DFT and TDDFT calculation results suggest that the ratiometric and colorimetric sensing behavior of Cou-BT upon its reaction with cyanide was due to the interrupted π-conjugation and blocked ICT progress.
- Yang, Zhenghao,Liu, Zhipeng,Chen, Yuncong,Wang, Xiaoqing,He, Weijiang,Lu, Yi
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- A dual-functional fluorescent probe for sequential determination of Cu2+/S2? and its applications in biological systems
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A new acylhydrazine-derived Schiff base fluorescence probe DMI based on “ON-OFF-ON” fluorescence strategy was presented in this paper. Probe DMI could detect Cu2+ selectively and sensitively with dramatic fluorescence quenching in CH3OH-PBS (v/v = 3:7) mixed solution. Once the complex DMI-Cu2+ interacted with S2?, 10.67-folds fluorescence increase was induced via a displacement mechanism under the same experimental conditions. The corresponding detection limits for Cu2+ and S2? were calculated to be 1.52 × 10?8 M and 1.79 × 10?8 M, respectively. The structures of DMI and DMI-Cu2+ were systematically characterized by Job's plot analysis, ESI-MS, IR, X-ray diffraction and density functional theory calculations. Furthermore, fluorescence imaging in MCF-7 cells and zebrafish demonstrated the probe DMI could act as a useful tool to monitor and track intracellular Cu2+ and S2?, which was encouraged by remarkable fluorescence performance and low cytotoxicity. Importantly, the complex DMI-Cu2+ could be applied to detect corrupt blood samples, which could estimate the time of death.
- Huang, Yu-Ying,Li, Qing-Zhong,Liu, Hai-Bo,Wang, Yang,Wang, Zhi-Gang,Xie, Cheng-Zhi,Xu, Jing-Yuan,Yan, Xiao-Jing
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- A novel coumarin-based colorimetric and fluorescent probe for detecting increasing concentrations of Hg2+in vitroandin vivo
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Mercury has complex biological toxicity and can cause a variety of physiological diseases and even death, so it is of great importance to develop novel strategies for detecting trace mercury in environmental and biological samples. In this work, we designed a new coumarin-based colorimetric and fluorescent probeCNS, which could be obtained from inexpensive starting materials with high overall yield in three steps. ProbeCNScould selectively respond to Hg2+with obvious color and fluorescence changes, and the presence of other metal ions had no effect on the fluorescence changes. ProbeCNSalso exhibited high sensitivity against Hg2+, with a detection limit as low as 2.78 × 10?8M. More importantly, the behavioral tracks of zebrafish had no obvious changes upon treatment with 10 μM probeCNS, thus indicating its low toxicity. The probe showed potential application value and was successfully used for detecting Hg2+in a test strip, HeLa cells and living zebrafish larvae.
- Chi, Liqun,Duan, Hongdong,Huang, Li,Meng, Xia,Sheng, Wenlong,Wang, Lizhen
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- A coumarin derivative-Cu2+complex-based fluorescent chemosensor for detection of biothiols
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Herein, a novel fluorescent sensor has been developed for the detection of biothiols based on theoretical calculations of the stability constant of the complex between a Cu2+ ion and (E)-3-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)-7-(diethylamino) coumarin (BDC) as a fluorescent ligand. In this study, on the basis of density functional theory method, the Gibbs free energy of ligand-exchange reaction and the solvation model were carried out using thermodynamic cycles. The obtained results are in good agreement with the experimental data. The BDC-Cu2+ complex can be used as a fluorescent sensor for the detection of biothiols in the presence of non-thiol containing amino acids, with a detection limit for cysteine at 0.3 μM. Moreover, theoretical calculations of excited states were used to elucidate variations in the fluorescence properties. The computed results show that the excited doublet states D2 and D1 are dark doublet states, which quench the fluorescence of the complex.
- Hien, Nguyen Khoa,Khanh, Nguyen Tan,Luyen, Nguyen Dinh,Nam, Pham Cam,Quang, Duong Tuan,Tran, Phan Diem,Van Bay, Mai,Van, Dang Ung,Vo, Quan V.
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- Synthesis and fluorescent properties of coumarin-benzimidazole and coumarin–phenanthroimidazole hybrids
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Two coumarin-benzimidazole hybrids and two coumarin-phenanthroimidazole conjugates were conveniently synthesized and characterized. The UV–vis absorption, emission spectra, absolute quantum yields, and fluorescence lifetimes of these compounds in diluted dichloromethane solutions were measured.
- Fan, Hongli,Wang, Lingqiang,Wang, Xiaolong
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- Coumarin-based benzilmonohydrazone as a new proton-sensitive fluorescence dye: Synthesis and investigation of photophysical and acidochromic properties
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Coumarin-based chromogenic and fluorogenic dye 4 was designed and synthesized. The photophysical properties of 4 were determined in solvents with different polarities. Protonation affinity was determined by adding trifluoroacetic acid (TFA) to a dichloromethane solution of dye 4 utilizing the UV-Vis and fluorescence titration methods. The protonation region was investigated by using the 1 H NMR method. Additionally, DFT and TDDFT studies were performed to support the structural and absorption spectral properties of 4.
- Aydiner, Burcu
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- Turn on fluorescent detection of hydrazine with a 1,8-naphthalimde derivative
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It is crucial to develop highly sensitive and selective probes toward hydrazine because it is a class of highly toxic and pollutant compound. Herein, using fracture of carbon carbon double bond and dissociation of amide by hydrazine, a novel off-on fluorescent probe was developed for hydrazine. The probe can quantitatively detect hydrazine in concentration range from 0 to 20 μM with the LOD of 140 nM. Further, it displayed excellent selectivity and anti-interference ability over many neutral molecules, metal ions, anions, and biological species. The ability to target lysosome and the response of hydrazine to this probe in a living cell was successfully tracked via fluorescence imaging.
- Shi, Bingjie,He, Yangyang,Zhang, Panpan,Wang, Yulong,Yu, Mingming,Zhang, Hongyan,Wei, Liuhe,Li, Zhanxian
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- Coumarin-naphthol conjugated Schiff base as a “turn-on” fluorescent probe for Cu2+ via selective hydrolysis of imine and its application in live cell imaging
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An off-on fluorescent probe (CuCIN), coumarin-naphthol linked by an imine group, for detecting Cu2+ in DMSO-HEPES buffer (1:99, v/v) solution was successfully developed. Mechanism studies suggested that CuCIN firstly formed a complex with Cu2+ in a 1:2 metal-to-ligand ratio, and then 60-fold fluorescence enhancement was observed when Cu2+ promoted the imine hydrolysis to release the fluorescence compound 7-diethylaminocoumarin-3-aldehyde. This probe displayed desired properties such as high selectivity toward other metal ions, low detection limit (12.7 nM) and low cytotoxicity. Bio-imaging study revealed that the new probe CuCIN could be applied for imaging living cells with good cell permeability. We hope to apply this probe in the biomedical research field for the imaging of disease-relevant Cu2+.
- Wang, Sisi,Wang, Zhen,Yin, Yong,Luo, Jianguang,Kong, Lingyi
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- Ratiometric fluorescence imaging of cellular polarity: Decrease in mitochondrial polarity in cancer cells
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Mitochondrial polarity strongly influences the intracellular transportation of proteins and interactions between biomacromolecules. The first fluorescent probe capable of the ratiometric imaging of mitochondrial polarity is reported. The probe, termed BOB, has two absorption maxima (λabs = 426 and 561 nm) and two emission maxima - a strong green emission (λem = 467 nm) and a weak red emission (642 nm in methanol) - when excited at 405 nm. However, only the green emission is markedly sensitive to polarity changes, thus providing a ratiometric fluorescence response with a good linear relationship in both extensive and narrow ranges of solution polarity. BOB possesses high specificity to mitochondria (Rr = 0.96) that is independent of the mitochondrial membrane potential. The mitochondrial polarity in cancer cells was found to be lower than that of normal cells by ratiometric fluorescence imaging with BOB. The difference in mitochondrial polarity might be used to distinguish cancer cells from normal cells.
- Jiang, Na,Fan, Jiangli,Xu, Feng,Peng, Xiaojun,Mu, Huiying,Wang, Jingyun,Xiong, Xiaoqing
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- Heavy metal analysis using a Heck-catalyzed cyclization to create coumarin
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This paper describes a new method for heavy metal analysis via catalytic signal amplification. This signal amplification protocol relies upon an exogenous inhibitor for deliberate deactivation of an organometallic reaction that catalytically creates a fluorophore. When the deactivation process is performed in the presence of the analyte, competitive binding of the inhibitor with the analyte and the catalyst occurs. A Heck reaction creating a coumarin fluorophore with a high quantum yield was studied. 1,4,7,10,13-Pentaaza- cyclopentadecane was chosen as the inhibiting ligand to selectively coordinate pre-catalyst Pd(II) and analytes Cd(II), Ni(II), Co(II). Monitoring product fluorescent intensity in real time revealed the concentration of analyte. The Royal Society of Chemistry 2005.
- Wu, Qiaoyin,Anslyn, Eric V.
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- Functionalized coumarin derivatives containing aromatic-imidazole unit as organic luminescent materials
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Three new coumarin derivatives containing aromatic-imidazole unit (i.e., benzo[d]imidazole, phenanthro[9,10-d]imidazole and pyreno[4,5-d]imidazole), 3-(1-phenyl-1H-benzo[d]imidazole-2-yl)-7-(diethylamino)coumarin (BI–C), 3-(1-(4-(tert-butyl)phenyl)-1H-phenanthro[9,10-d]imidazole-2-yl)-7-(diethylamino)coumarin (PI–C) and 3-(9-(4-(tert-butyl)phenyl)-9H-pyreno[4,5-d]imidazole-10-yl)-7-(diethylamino)coumarin (PyI-C), were successfully prepared for organic light-emitting devices. These compounds show good thermal properties and strong emissions from greenish-blue to green lights owing to the extended π-conjugation of the rigid polyaromatic imidazole skeleton, and have high photoluminescence quantum efficiency of 94%, 97% and 98% in chloroform solutions. Among these compounds, the doped organic light-emitting device fabricated from the compound PI-C exhibited the maximum luminous efficiency of 6.07 cd/A and maximum EQE of 2.78%.
- Wang, Youjia,Li, Yanmei,Yu, Tianzhi,Su, Wenming,Ma, Hailin,Zhao, Yuling,Li, Xinyu,Zhang, Hui
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- AIE Based Coumarin Chromophore-Evaluation and Correlation between Solvatochromism and Solvent Polarity Parameters
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A new class of red emitting extensively conjugated donor-π-acceptor type dyes bearing coumarin units have been synthesized by condensation of 7-(diethylamino)-2-oxo-2 H-chromene-3-carbaldehyde with different active methylenes. All the dyes are characterized by 1H NMR, 13C NMR and HRMS spectroscopy. The photophysical behaviour and the relation between structure and properties of the coumarin "push-pull" derivatives were investigated experimentally. The dyes exhibited positive solvatochromism and solvatofluorism in solution of varying polarity. These coumarin dyes show aggregation induced emission properties with red emitting fluorescence. They show absorption in the range of 501-528 and emission in the range of 547-630 nm. We evaluated photophysical properties of coumarin dyes using solvotochromism and solvent dependent shift in the emission wavelength. All the synthesized coumarin dyes COS1-COS4 are showing very good solvatochromic properties.
- Lanke, Sandip K.,Sekar, Nagaiyan
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- Synthesis of Functionalized Benzopyran/Coumarin-Derived Aryne Precursors and Their Applications
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An efficient synthetic method of benzopyran derivatives involving coumarins is disclosed. Gold-catalyzed benzopyran formation and subsequent aryne reactions enabled us to prepare a wide range of benzopyran derivatives by virtue of their good functional group tolerance and versatile transformability of aryne intermediates. The synthetic utility was showcased by a diarylnaphthopyran synthesis through this method and consecutive cross-coupling reactions.
- Nakamura, Yu,Sakata, Yuki,Hosoya, Takamitsu,Yoshida, Suguru
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- A Carborane-Containing Fluorophore as a Stain of Cellular Lipid Droplets
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The use of fluorescent markers and probes greatly enhances biological investigations but relies on the provision of an array of fluorophores with diverse properties. Herein we report a novel carborane-containing coumarin, 5, which is sufficiently lipophilic to localise in cellular lipid droplets. In non-polar solvents which show comparable polarities to those of a lipid environment, compound 5 exhibits a fluorescence quantum yield two orders of magnitude greater than found in aqueous solvents, adding a further degree of selectivity to lipid droplet imaging. Compound 5 can stain lipid droplets in ex vivo adipocytes as well as in cultured cells, and can be utilised in flow cytometry as well as confocal microscopy.
- Wu, Andrew,Kolanowski, Jacek L.,Boumelhem, Badwi B.,Yang, Kylie,Lee, Rebecca,Kaur, Amandeep,Fraser, Stuart T.,New, Elizabeth J.,Rendina, Louis M.
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- Spectral Properties of Highly Emissive Derivative of Coumarin with N,N-Diethylamino, Nitrile and Tiophenecarbonyl Moieties in Water-Methanol Mixture
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The new derivative of coumarin (E)-3-[7-(diethyloamino)-2-oxo-chromen-3yl]-2-(tiophene-2-carbonyl)prop-2-enenitrile (NOSQ) was easy synthesized with commercial substrates as a result of the search of new Michael type addition sensors based on coumarins. Spectral properties of highly emissive NOSQ were investigated by steady state analysis (absorption and fluorescence measurements) and time-resolved analysis (fluorescence lifetime measurements). The effect of water-methanol mixture on the photophysical properties of the NOSQ molecule was analyzed. With increasing of volumetric fraction of water the intensity of absorbance and fluorescence was strongly reduced. The NOSQ quantum yield in methanol was quite high and the first portions of water caused a significant increase in this value. Water, which is usually a quencher, in this case caused the increase in the quantum yield. The fluorescence lifetimes had second-order decay and the values of fluorescence lifetime increased with increasing alcohol content. Density functional theory (DFT) calculations and experimental data remained in agreement and showed that the interaction between the NOSQ molecule and the solvent affects the appearance of the new conformer.
- Kolbus, Anna,Danel, Andrzej,Grabka, Danuta,Kucharek, Mateusz,Szary, Karol
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- Highly effective discrimination of catecholamine derivatives via FRET-on/off processes induced by the intermolecular assembly with two fluorescence sensors
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We proudly presented the novel sensor system based on intermolecular assembled complexes of two fluorescence sensors and a suitable catecholamine acting as a guest linker by the reaction between boronic acid and aldehyde moieties of the sensors with the diol and amine units of catecholamines, respectively. The FRET-on/off induced by the assembly could discriminate structural similarity of catecholamines.
- Chaicham, Anusak,Sahasithiwat, Somboon,Tuntulani, Thawatchai,Tomapatanaget, Boosayarat
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- Di–thioether amide–Pd2+ complex based-methionine fluorescent chemosensor with selectivity over cysteine and histidine
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Determination of methionine (Met) has garnered increasing attention in various fields because methionine is a biomarker for various diseases. However, chemosensors for Met are very limited compared to those for other amino acids, and many Met chemosensors show low selectivity towards Met over cysteine (Cys) and histidine (His). In this study, a di–thioether amide–Pd2+ complex, 1-Pd2+, based on a 7-diethylaminocoumarin scaffold, was prepared as a sensitive and selective fluorescent chemosensor for Met. The limit of detection (LOD) for Met of 1-Pd2+ was determined to be 1.0?μM and the chemosensor exhibited a high selectivity towards Met over various amino acids including Cys and His. 1-Pd2+ worked well in a broad pH range of 4.0–8.0 and was applied to determine the concentration of Met in tap water samples. In addition, ligand 1 was demonstrated to be a selective and sensitive fluorescent chemosensor for Pd2+. The LOD for Pd2+ of 1 was determined to be 1.7?μM and it exhibited a high selectivity for Pd2+ over various other metal ions.
- Lee, Minah,Lim, Taeho,Lee, Youngkeun,Kang, Seungyoon,Han, Min Su
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- A fluorescent probe for hypochlorite with colorimetric and fluorometric characteristics and imaging in living cells
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An excellent fluorescent probe with “turn on” phenomenon for sensitive monitoring hypochlorite (ClO?) was prepared using the mild condensation reaction between coumarin and hydroxylamine (NH2OH). The probe possessed potent selectivity to ClO? with obvious color changes from yellow to light yellow and green to blue fluorescence emission, which could be noticed by the naked eye. Moreover, the probe has been succeeded in imaging ClO? in living A549 cells and thus has the potential prospect in the visual detection of intracellular ClO?.
- Hu, Cunjie,Li, Jianping,Yan, Liqiang
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- A novel ratiometric near-infrared fluorescent probe for monitoring cyanide in food samples
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Cyanide is a highly toxic anion. Nonetheless, many food plants could produce endogenous cyanide, which causes great danger to human health. Thus, monitoring cyanide in food samples is critically significant. Herein, we rationally developed the first ratiometric near-infrared fluorescent probe for sensing cyanide in food samples. The probe displayed noticeable fluorescence in near-infrared region. Moreover, upon treatment with cyanide, the probe exhibited highly selective and sensitive ratiometric fluorescence response, with limit of detection determined to be 0.075 μM and limit of quantification determined to be 0.25 μM. The ratios of fluorescent intensities at 519 and 688 nm (I519/I688) was linear with added cyanide concentrations from 0 to 80 μM. The relative standard deviations for repeatability and reproducibility varied from 0.55 to 8.94 and from 1.17 to 9.46, respectively. Significantly, probe Hy has been successfully applied for monitoring cyanide in various food samples, such as almonds, sprouting potatoes, and bamboo shoots.
- Long, Lingliang,Han, Yuanyuan,Yuan, Xiangqi,Cao, Siyu,Liu, Weiguo,Chen, Qian,Wang, Kun,Han, Zhixiang
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- Concise synthesis and fluorescent properties of coumarin-30 and its isomer 7-(diethylamino)-4-(1-methyl-1H-benzimidazol-2-yl)coumarin
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Coumarin-30 and its regioisomer 7-(diethylamino)-4-(1-methyl-1H-benzimidazol-2-yl)coumarin were synthesised utilising condensation of the corresponding formylcoumarin with N-methylphenylene-1,2-diamine as the key step. Furthermore, absorption and fluorescence emission spectra of the two coumarins were recorded.
- Wang, Xiaolong,Zhou, Jingjing,Yang, Fang,Xue, Ziyan,Xu, Niansheng
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- A highly selective colorimetric and fluorescent probe for quantitative detection of Cu2+/Co2+: The unique ON-OFF-ON fluorimetric detection strategy and applications in living cells/zebrafish
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Identifying and detecting similar target cations through combining “turn on” and “turn off” fluorescence mechanism is effective and challenging. Now a new colorimetric and ON-OFF-ON fluorescent probe N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-3-hydroxy-2-naphthohydrazide (L) was reported, which could detect Cu2+ and Co2+ in phosphate buffered CH3CH2OH-H2O solvent system. With the assistance of glutathione and pH adjustment, a unique ON-OFF-ON fluorescence detection strategy could be achieved for distinguishing Cu2+ and Co2+. The emission of probe could recover from the L-Cu2+ and L-Co2+ system by addition of GSH or adjusting pH value to 4, respectively, which is due to the abolishment of paramagnetic Cu2+/Co2+. Based on fluorescence titration experiments, the limit of detection was determined as 3.84 × 10?9 M and 4.55 × 10?9 M for Cu2+ and Co2+, respectively. Meanwhile, the detection limit reached 6.21 × 10?8 M for Cu2+ and 6.96 × 10?8 M for Co2+ according to absorbance signal output. Fast recognition of Cu2+/Co2+ can be achieved by obvious color changes from green to colorless under UV light, as well as from yellow to orange-red in room light. The binding mode of L toward Cu2+ and Co2+ have been systematically studied by Job's plot analysis, ESI-MS, IR and density functional theory calculations. Most strikingly, further practical applications of the probe L in fluorescence imaging were investigated in MCF-7 cells and zebrafish due to its low cytotoxicity and good optical properties, suggesting that L could serve as a fluorescent sensor for tracking Cu2+ and Co2+ in vivo.
- Wang, Zhi-Gang,Wang, Yang,Ding, Xiao-Jing,Sun, Yu-Xuan,Liu, Hai-Bo,Xie, Cheng-Zhi,Qian, Jing,Li, Qing-Zhong,Xu, Jing-Yuan
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- A highly selective fluorescent probe based on coumarin and pyrimidine hydrazide for Cu2+ ion detection
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A novel diethylamino coumarin Schiff base modified with a pyrimidine-hydrazide (EDMP) was synthesized as Cu2+ fluorescent probe. Its photophysical properties and recognition ability to Cu2+ were studied by UV–Vis, fluorescence, IR and mass spectrum. Under UV light, EDMP probe showed a strong bright green fluorescence. After introducing Cu2+, the probe solution was changed from light green to orange and the maximum absorption wavelength bathochromically shifted from 445 nm to 475 nm. Meanwhile, fluorescence quenching phenomenon was observed. Fluorescence titration experiment showed that EDMP exclusively reacted with Cu2+ and the stoichiometric ratio was 1:1. The lowest detection limit was calculated to be 1.153 μM by fitting the titration curve. Additionally, DFT calculation method was utilized to analyze the action mechanism of EDMP toward Cu2+.
- Zhu, Lin,Yang, Xiqiang,Luo, Xubiao,Hu, Bin,Huang, Wei
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- A coumarin-derived Cu2?+-fluorescent chemosensor and its direct application in aqueous media
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A novel coumarin-based receptor bearing a benzohydrazide (FCBH) was developed as a fluorescent chemosensor with high selectivity toward Cu2?+. The sensor was successfully applied to the monitoring of Cu2?+ in aqueous solution. After the addition of Cu2?+ to FCBH, the color of the solution changed from greenish-yellow to red, and the absorption band at 457?nm red-shifted to 517?nm. The fluorescent green color of FCBH disappeared and the fluorescence emission was completely quenched in the presence of Cu2?+. Upon the addition of Cu2?+, deprotonation of FCBH occurred, and a 1:1 metal-ligand complex formed. DFT theoretical investigation was carried out to understand the behavior of the sensing probe toward Cu2?+. Additionally, the quenched fluorescence of the FCBH-Cu2?+ complex was restored upon the addition of CN? ions. The possible sensing mechanism of FCBH toward Cu2?+ was derived from experimental and theoretical examinations.
- Mergu, Naveen,Kim, Myeongjin,Son, Young-A.
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- Highly selective fluorescent sensor for homocysteine and cysteine
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A new fluorescent sensor (1) based on a coumarin was synthesized for the selective detection of homocysteine (Hcy) and cysteine (Cys). The chemosensor has shown a selective response to Hcy or Cys over other various amino acids via a ring formation of thiazinane or thiazolidine. When Hcy or Cys was added, the fluorescent intensity of 1 was completely quenched through a photo-induced electron transfer with the sensitivity of sub-millimolar concentration.
- Kim, Tae-Ki,Lee, Dong-Nam,Kim, Hae-Jo
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- The ferroquine antimalarial conundrum: Redox activation and reinvasion inhibition
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Metal health: Ferroquine is a ferrocene-based analogue of the antimalarial drug chloroquine. In addition to the primary mechanism of quinoline action, fluorescent probe studies in infected red blood cells show another mechanism is at work. It is based on the production of HO. in the acidic and oxidizing environment of the digestive vacuole of the malaria parasite and implies that, with ferroquine, reinvasion can be inhibited. Copyright
- Dubar, Faustine,Slomianny, Christian,Khalife, Jamal,Dive, Daniel,Kalamou, Hadidjatou,Guerardel, Yann,Grellier, Philippe,Biot, Christophe
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- Mitochondria-targeted reversible ratiometric fluorescent probe for monitoring SO2/HCHO in living cells
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Sulfur dioxide (SO2) maintains a certain steady state balance in the body, high concentration SO2 will be harmful to human health. Seeking a suitable detection method to monitor sulfur dioxide in real time becomes an urgent requirement owing to the transient nature of sulfur dioxide in organisms. Here, a novel NIR ratiometric fluorescent probe for detection of SO2 was developed based on a conjugation of coumarin and indol salt with excellent water solubility. The probe Mito-CI displayed highly sensitive (69 nM), fast response time (30 s), large Stokes shift (174 nm) and the NIR fluorescence emission wavelength (655 nm). In the reversibility process of the SO3 ?-probe Mito-CI system induced by HCHO in vitro was also detected. Besides, cell imaging showed that Mito-CI possesses mitochondria-targeted ability. Particularly, Mito-CI was proved to reversibly detect SO2/HCHO in living cells.
- Chao, Jianbin,Huo, Fangjun,Wen, Guangming,Yin, Caixia,Zhang, Tao,Zhang, Yongbin
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- Synthesis and evaluation of 11C-labeled coumarin analog as an imaging probe for detecting monocarboxylate transporters expression
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Upregulated monocarboxylate transporters (MCTs) in tumors are considered diagnostic imaging targets. Herein, we synthesized the positron emission tomography probe candidates coumarin analogs 2 and 3, and showed 55 times higher affinity of 2 for MCTs than a representative MCT inhibitor. Whereas [11C]2 showed low tumor accumulation, probably due to adduct formation with plasma proteins, [11C]2 showed high initial brain uptake, suggesting that the scaffold of 2 has properties that are preferable in imaging probes for the astrocyte–neuron lactate shuttle. Although further optimization of 2 is required, our findings can be used to inform the development of MCT-targeted imaging agents.
- Tateishi, Hiroyuki,Tsuji, Atsushi B.,Kato, Koichi,Sudo, Hitomi,Sugyo, Aya,Hanakawa, Takashi,Zhang, Ming-Rong,Saga, Tsuneo,Arano, Yasushi,Higashi, Tatsuya
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- A fluorescence "turn-on" chemodosimeter for Cu2+ in aqueous solution based on the ion promoted oxidation
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We developed a novel method for Cu2+ detection based on the ion promoted oxidation reaction. Chemodosimeter L (weak fluorescence) can be oxidized into 3-benzothiazoly-7-N,N-diethylaminocoumarin (strong green fluorescence, coumarin 6) by Cu2+ with high selectivity and sensitivity in HEPES (10 mM, pH = 7.4) buffer containing 50% (v/v) water-CH 3CN solution. The Royal Society of Chemistry 2012.
- Li, Junbo,Zeng, Yang,Hu, Qihui,Yu, Xianglin,Guo, Jia,Pan, Zhiquan
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- Optimizing the framework of indolium hemicyanine to detect sulfur dioxide targeting mitochondria
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Endogenous sulfur dioxide (SO2) is mainly produced by the enzymatic reaction of sulfur-containing amino acids in mitochondria, which has unique biological activity in inflammatory reaction, regulating blood pressure and maintaining the homeostasis of biological sulfur. It is more and more common to detect monitor SO2 levels by fluorescence probe. In recent years, the indolium hemicyanine skeleton based on the D-π-A structure has been widely used in the development of fluorescent sensors for the detection of SO2. However, subtle changes in the chemical structure of indolium may cause significant differences in SO2 sensing behavior. In this article, we designed and synthesized two probes with different lipophilicities to further study the relationship between the structure and optical properties of hemicyanine dyes. On the basis of previous studies, the structure of indolium hemicyanine skeleton was optimized by introducing –OH group, so that MC-1 and MC-2 had the best response to SO32- in pure PBS system. In addition, the lipophilicity of MC-2 was better than that of MC-1, which enabled it to respond quickly to SO32- and better target mitochondria for SO2 detection. Most importantly, the low detection limits of MC-1 and MC-2 conducive to the detection of endogenous SO2. This work provided an idea for developing SO2 fluorescent sensors with excellent water solubility and low detection limit.
- Chao, Jianbin,Huo, Fangjun,Wang, Zhuo,Zhang, Ting,Zhang, Yongbin
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supporting information
(2021/10/04)
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- Effect of the π-bridge on the light absorption and emission in push-pull coumarins and on their supramolecular organization
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A family of eight π-extended push–pull coumarins with cross-conjugated (amide) and directly conjugated (p-phenylene, alkyne, alkene) bridges were synthesized through a convergent strategy. Using an experimentally calibrated computational protocol, their UV–Visible light absorption and emission spectra in solution were investigated. Remarkably, amide-, alkyne- and alkene-bridges undergo comparable vertical excitations. The different nature of these bridges manifests during excited-state relaxation and fluorescence. We predict that these molecules can serve as building blocks for p-type semiconductors with low reorganization energies, below 0.2 eV. Since solid-state self-assembly is crucial for this application, we examined the effect of the π-bridge over the supramolecular organization in this family of compounds to determine if stacking prevails in these π-extended coumarin derivatives. Amide and alkyne spacers allow coplanar conformations which crystallize readily; p-phenylene hinders planarity yet allows facile crystallization; alkene-bridged molecules eluded all crystallization attempts. All the crystals obtained feature dense face-to-face π-stacking with 3.5–3.7 ? interlayer distances, expected to facilitate charge transfer processes in the solid state.
- Arcos-Ramos, Rafael,Carreón-Castro, María del Pilar,Farfán, Norberto,González-Rodríguez, Edgar,Guzmán-Juárez, Brenda,Maldonado-Domínguez, Mauricio,Miranda-Olvera, Montserrat,Santillan, Rosa
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- PHENANTHROLINE, CARBAZOLE AND FLAVYLIUM BASED CYANINES AND COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME
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The present disclosure is in the field of pharmaceutical and chemical sciences, including the synthesis of theranostic agents and processes for preparing such agents. In particular, the disclosure relates to important phenanthroline, carbazole and flavylium based cyanine group containing chemical compounds, method of preparing such molecules and compositions thereof, and the use of such molecules and compositions as a probe and diagnostic agent in the diagnosis and treatment of diseases including cancer.
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- Coumarin-containing selective recognition Hg2 + Fluorescent probe and preparation method thereof
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The invention discloses a coumarin-containing selective recognition Hg. 2 + The fluorescent probe and the preparation method thereof adopt coumarin as a fluorescent group and serve as a building unit of a molecular probe. In addition, the fluorescence difference between molecules and mercury ions is enlarged, the sensitivity of the probe is further improved, and the minimum detection limit can reach 7.84 ×10. -9 Mol/l. The series of probes has the advantages of simple structure, convenient synthesis and low cost, and can be used for detecting mercury ions with high selectivity and fluorescence intensity.
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(2021/11/21)
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- Fluorescent probe for selectively identifying fluorine ions and preparation method thereof
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The invention discloses a fluorescent probe capable of selectively identifying fluoride ions and a preparation method thereof. It uses coumarin as a fluorescent group, and further widens the functionality of the fluorescent group as a fluorescent group. A benzimidazole group containing different substituents is modified on the coumarin fluorescent group, H of the imidazole ring and the carbonyl oxygen of coumarin form intramolecular hydrogen bonds to maintain the planarity of the molecule. Ferroelectric negative electrode using fluoride ion Due to the high charge density, fluorine passes through hydrogen bonds with hydrogen on the imidazole ring, the original intramolecular hydrogen bonding is broken, and the intramolecular structure changes. The synthesized compound 10 has good selectivity and faster response speed for fluoride ions as a fluorescent probe, and the detection limit is 3 . 50μmol/L.
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Paragraph 0008-0009
(2021/11/19)
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- Preparation method and application of fluorescent probe for ultrafast detection of biological mercaptan
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The invention relates to the field of optical imaging, in particular to a preparation method and application of a fluorescent probe for ultrafast detection of biological mercaptan. According to the invention, a pink solid probe, namely [2-(7-diethylaminocoumarin)methylene-7-methyl-1-oxo-3,3a-dihydrocyclopenta[b]chroman-cycl-5-yl]-methyl-N,N-dimethyl-4(1H)-pyridylidene carbonic ester, is finally synthesized through a series of chemical reactions on the basis of 2,6-bis(hydroxymethyl)-p-cresol and 4-(diethylamino)salicylaldehyde. The fluorescent probe has the advantages of simple synthesis route, easily available raw materials, low cost and very short reaction time, can realize the detection of certain micromolecular biological mercaptans at a very high speed, and has very strong sensitivity and selectivity; and in addition, the probe can be targeted to and positioned in mitochondria, so rapid imaging at a specific position is realized.
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Paragraph 0036; 0043-0045
(2021/05/29)
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- Light-up lipid droplets for the visualization of lipophagy and atherosclerosis by coumarin-derived bioprobe
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Lipid droplets (LDs) are intracellular lipid-metabolism organelles that involved in many physiological processes, metabolic disorders as well as diseases such as atherosclerosis. However, the specific probes that can visually locate abnormal LDs-rich tissues and track LDs-associated behavior to the naked eye with adequate biosafety still are rare. Herein, we develop a new design strategy of LDs-targeted probe based on the solvatochromism of coumarin derivatives. The results revealed that the emission wavelength of coumarin fluorophores gradually red shift in different solvents with increasing polarity, while absorption wavelength almost unchanged. As a result, the enlarged stokes shift of coumarin was emerged from oil to water. Furthermore, properly reducing water solubility and adding electronic donor at the structure of coumarins can enlarge this type of solvatochromism. This discovery was utilized to develop suitable probe for the image of LDs and LDs-rich tissues with high resolution and biosafety. Therefore, LDs-associated behavior was visible to the naked eye during the process of lipophagy and atherosclerosis. We deem that the developed probe here offers a new possibility to accurately diagnosis and analyse LDs-related diseases in clinic and preclinical study.
- Zheng, Jinrong,Qin, Shuheng,Gui, Lijuan,Li, Hua,Fan, Lixue,Yang, Yifei,Chen, Haiyan,Xu, Hui,Yuan, Zhenwei
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supporting information
p. 2385 - 2389
(2021/03/17)
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- A fluorescent probe based on coumarin and p-bromobenzoylhydrazide and preparation method thereof
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The present application belongs to the field of fluorescent probes, specifically relates to a fluorescent probe based on coumarin and p-bromobenzohydrazide and a method for preparing them. The fluorescent probe can form a complex with Cu2+ when detectingcu2+, redshifting occurs in ultraviolet absorption, fluorescence is rapidly quenched, after detectingCu2+, the color of the solution changes from yellow to brown, and the naked eye is obvious; and the fluorescent probe has the characteristics of good selectivity, strong anti-interference ability, rapid response, etc., and is an excellentCu2+ specific detection reagent, which can be applied to the field of materials or sensors.
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Paragraph 0008; 0032-0033; 0036-0037; 0040-0041; ...
(2022/01/10)
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- 3-carboxylic acid and formyl-derived coumarins as photoinitiators in photo-oxidation or photo-reduction processes for photopolymerization upon visible light: Photocomposite synthesis and 3d printing applications
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In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical pho-topolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2 ) was also examined.
- Dumur, Frédéric,Gigmes, Didier,Graff, Bernadette,Hamieh, Tayssir,Lalevée, Jacques,Noirbent, Guillaume,Rahal, Mahmoud,Toufaily, Joumana
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- AIE type coumarin derivative fluorescent probe and preparation method and application thereof
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The invention discloses an AIE type coumarin derivative fluorescent probe and a preparation method and application thereof in cell imaging, and belongs to the field of small organic molecule biological fluorescent probes. The chemical name of the fluorescent probe molecule is (Z)-4-(1-cyano-2-(7-(diethylamino) -2-oxo-2H-chromene-3-yl) vinyl) benzonitrile, and the molecular formula of the fluorescent probe molecule is C23H19N3O2. The fluorescent probe provided by the invention shows large Stokes shift (118 nm), and can effectively solve the problem that the fluorescent probe is blocked in the aspect of biological application due to fluorescence self-absorption. Fluorescence analysis research shows that the probe molecule can be used for high-sensitivity detection of glutathione, the detection limit of the probe molecule is 0.38 [Mu]m, and interferents cysteine and homocysteine of glutathione in a living body can be effectively distinguished.
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Paragraph 0040; 0042-0045
(2021/01/11)
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- Quenched fluorescent probe based on coumarin and preparation method thereof
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The present application belongs to the field of fluorescent probes, specifically relates to a fluorescent probe based on coumarin and 4-biphenylcarboxylic acid hydrazine and preparation method thereof. The fluorescent probe can form a complex with Cu2+ when detectingcu2+, redshifting occurs in ultraviolet absorption, fluorescence is rapidly quenched, after detectingCu2+, the color of the solution changes from yellow to brown, and the naked eye is obvious; and the fluorescent probe has the characteristics of good selectivity, strong anti-interference ability, rapid response, etc., and is an excellentCu2+ specific detection reagent, which can be applied to the field of materials or sensors.
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Paragraph 0008; 0032-0033; 0036-0037; 0040-0041; 0044; ...
(2022/01/10)
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- Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties
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High level time-dependent density functional theory (TD-DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values reported for a few candidates has been used for assessing the level of theory. On the basis of the results obtained, new strongly reducing PCs [Eox(PC.+/PC*)=?2.1 – ?2.0 V vs SCE] were discovered. Through the computational study of structure-properties relationships, a number of coumarins derivatives have been synthesized and evaluated in the pinacol coupling of aldehydes as the model reaction. The new organic photoredox catalysts show experimental photophysical and electrochemical data in accordance with the ones predicted by calculation, with excited state reduction potentials surpassing those of highly reducing transition metal-based PCs. A careful investigation of their behavior as PC has revealed crucial issues that need to be taken into consideration in the general photoredox catalysis, shedding light on the use of these PC in the pinacol, as well as, in other photoredox reactions.
- Gualandi, Andrea,Nenov, Artur,Marchini, Marianna,Rodeghiero, Giacomo,Conti, Irene,Paltanin, Ettore,Balletti, Matteo,Ceroni, Paola,Garavelli, Marco,Cozzi, Pier Giorgio
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p. 981 - 989
(2020/12/07)
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- Application of merocyanine-coumarin fluorophore to detection of hydrogen sulfide in mitochondria
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The invention discloses application of a merocyanine-coumarin fluorophore serving as a hydrogen sulfide fluorescent probe to detection of hydrogen sulfide in mitochondria. The structure of the merocyanine-coumarin fluorophore is shown in a formula defined in the description, wherein C6H13 refers to linear or branched hexyl. The merocyanine-coumarin fluorophore is not prone to being influenced by adetection environment, such as a probe concentration and other conditions, is not disturbed by biological mercaptan, can selectively react with hydrogen sulfide, has the advantages of fluorescence ratio response effects, strong selectivity, high sensitivity, rapid response and the like and realizes intracellular exogenous and endogenous hydrogen sulfide ratio imaging; and besides, the probe can perform mitochondrial locating, is expected to play a role in bioscience and has broad application prospects.
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Paragraph 0026-0028
(2020/02/27)
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- A novel near-infrared ratiometric fluorescent probe for SO2 detection with a large emission shift
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Due to the toxicity of SO2 to the respiratory tract, ingesting an excess of SO2 can cause some respiratory diseases and lung cancer. Thus, the development of efficient methods for the detection of SO2 in biological environments is of great importance. In this work, a ratiometric fluorescent probe, MQC, was constructed and applied for SO2 detection with good selectivity and sensitivity. Probe MQC displayed a near-infrared emission at 715 nm, which underwent a 245 nm blue-shift (470 nm) upon the addition of SO2. Meanwhile, a color change from fuchsia to colorless was observed before and after the treatment of probe MQC with SO2. Biological imaging experiments were performed on probe MQC to detect intracellular SO2 in living cells.
- Han, Shaohui,Song, Xiangzhi,Wang, Benhua,Wang, Jingpei,Yue, Xiuxiu,Zhang, Yun
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supporting information
p. 4554 - 4557
(2020/04/03)
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- Indole-salt-coumarin derivative as well as synthesis method and application thereof (by machine translation)
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The invention provides an indole salt (E)-1 - (2 - (diethylamino) -2 - oxo - 222H-chromium 2 - yl) vinyl) 7 -2 - dimethyl - 333H-indole -3 - cation and an English name called (E)-3 (3 -) -1 - (-1 - (diethyethylamino) 2 - carboxyethyl 7 -) 3 - dimethyl - 3H - indol - 1 - ium vinyl -2 -2 - oxo - 2H - chromen - 3 - yl 2 - named Mito-CI, which can be used for efficiently and reversibly detecting sulfur dioxide -3. The detection method is in a buffer solution of pure PBS pH of 7.4, and sulfur dioxide is detected through a fluorescence spectrophotometer. The detection process is simple, sensitive and quick, and the detection result is accurate. (by machine translation)
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Paragraph 0039; 0040; 0041
(2020/06/17)
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- Application of coumarin-cyanopyridine derivative in ratio detection of sulfur dioxide
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The invention provides an application of a coumarin cyanopyridine derivative in ratio detection of sulfur dioxide, and the Chinese name of the coumarin cyanopyridine derivative is (Z)- 4- (1-cyano -2-(7- (diethylamino)- 2-oxo -2H-chromium- 3-yl) vinyl) -1-methylpyridine -1-cation. Its English name is (Z)-4-(1-cyano-2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-1-methylpyridin-1-ium, also knownas CPA-I, and another is (Z)-4-(1-cyano-2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-1-nonylpyridin-1-ium, known as CPA-II. The two reagents can be used for detecting sulfur dioxide in a ratio, the method is simple, sensitive and rapid, and the detection result is accurate.
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Paragraph 0052-0054
(2020/12/31)
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- Interface targeting type mitochondrial probe as well as preparation method and application thereof
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The invention discloses an interface targeting type mitochondrial probe as well as a preparation method and application thereof in living cells and tissues, and belongs to the technical field of mitochondrial fluorescent probes. The structural formula of the interface targeting type mitochondrial probe is shown in the specification. The chemical name of the interface targeting type mitochondrial probe is (E)-4-(2-(7-diethylamino-coumarin) vinyl)-1-dodecyl pyridine iodate. The probe is named as CVP-12. The interface targeting type mitochondrial probe has the characteristics of no need of washing, high selectivity, good biocompatibility, excellent membrane permeability and low cytotoxicity, and has good application prospects in the field of biomarkers.
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Paragraph 0038-0040
(2020/07/15)
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- Coumarin derivative Th-HM1 as well as synthesis method and application thereof (by machine translation)
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The invention provides a coumarin derivative Th-HM1 as well as a synthesis method and application thereof. The literature names of the coumarin derivatives are referred to as (E)-4 - (2 - (7 - (diethylamino) -2 - oxo - 222H-chromen -3 - vinyl) -2, 2 - difluoro -7 - methyl - 22H, 5H - 1l3, 2 l4 pyrano [3, 4-e] [1,dioxopyrine -5 - ketone. The invention also provides a method for stepwise detecting the down-regulation of the cysteine concentration so as to reduce the glutathione concentration, and the method is based on the coumarin derivatives in PBS and acetonitrile. v/v ＝ 1/1) The concentration of cysteine and glutathione in the solution was qualitatively detected by an ultraviolet-visible spectrophotometer and a fluorescence spectrometer. The method achieves down-regulation of cysteine concentration and further step-by-step detection of glutathione concentration reduction at the cell level. (by machine translation)
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Paragraph 0036-0039
(2020/12/30)
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- Bifunctional fluorescent probe for detecting hypochlorite ions and/or singlet oxygen in cell mitochondria as well as preparation method and application thereof
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The invention belongs to the technical field of fluorescence detection, and discloses a bifunctional fluorescent probe for detecting hypochlorite ions and/or singlet oxygen in cell mitochondria as well as a preparation method and application thereof. After a series of steps of preparing 7-(diethylamino) coumarin, 7-(diethylamino) coumarin aldehyde and the like, the bifunctional fluorescent probe for detecting hypochlorite ions and/or singlet oxygen in cell mitochondria is obtained. After the synthesis method is improved, side reactions can be effectively prevented, and impurities difficult toseparate in the reaction process are greatly reduced, so that a high-purity target product can be obtained. The prepared bifunctional fluorescent probe not only can independently detect hypochlorite ions or singlet oxygen, but also can distinguish the levels of hypochlorite ions and singlet oxygen at the same time, and can also be used for fluorescence imaging of endogenous hypochlorite ions and/or singlet oxygen in cells.
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Paragraph 0064; 0076
(2020/11/26)
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- A novel fluorescent chemosensor based on coumarin and quinolinyl-benzothiazole for sequential recognition of Cu2+ and PPi and its applicability in live cell imaging
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In this study, a highly selective fluorescent sensor (E)-2-((2-(benzo[d]thiazol-2-yl)quinolin-8-yl)oxy)-N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)acetohydrazide (TQC) was synthesized from 2-methylquinolin-8-ol and 4-(diethylamino)-2-hydroxybenzaldehyde and its structure was characterized by 1H NMR, 13C NMR, ESI-HR-MS and density functional theory (DFT) calculation. Sensor TQC showed an obvious “on-off-on” fluorescence response to Cu2+ and PPi in a DMSO/HEPES (3:2 v/v, pH = 7.4) buffer system. The detection limits of sensor TQC were 0.06 μM to Cu2+ and 0.01 μM to PPi. In addition, sensor TQC showed a 1:1 binding stoichiometry to Cu2+ and TQC-Cu2+ complex showed a 2:1 binding stoichiometry to PPi. The optimum pH range of sensor TQC and TQC-Cu2+ was 3–8. Further studies demonstrated that sensor TQC could be made into test paper strips for the qualitative of Cu2+ and PPi and showed sequentially “on-off-on” fluorescent bio-imaging of Cu2+ and PPi in HeLa cells.
- Li, Shengling,Cao, Duanlin,Meng, Xianjiao,Hu, Zhiyong,Li, Zhichun,Yuan, Changchun,Zhou, Tao,Han, Xinghua,Ma, Wenbing
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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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p. 5608 - 5616
(2020/08/21)
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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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supporting information
p. 2917 - 2920
(2020/03/13)
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- Water-soluble ratio type fluorescent probe for detecting hydrazine hydrate
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The invention discloses a water-soluble ratio type fluorescent probe for detecting hydrazine hydrate. The water-soluble ratio type fluorescent probe has a chemical structure shown as follows, has excellent fluorescence and ultraviolet selectivity to hydrazine hydrate, is capable of realizing detection in pure water phase, has a bright biological application prospect and is capable of realizing ratio type fluorescent imaging in cells and zebra fish body.
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Paragraph 0030
(2019/08/06)
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- Single-Atom Fluorescence Switch: A General Approach toward Visible-Light-Activated Dyes for Biological Imaging
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Photoactivatable fluorophores afford powerful molecular tools to improve the spatial and temporal resolution of subcellular structures and dynamics. By performing a single sulfur-for-oxygen atom replacement within common fluorophores, we have developed a facile and general strategy to obtain photoactivatable fluorogenic dyes across a broad spectral range. Thiocarbonyl substitution within fluorophores results in significant loss of fluorescence via a photoinduced electron transfer-quenching mechanism as suggested by theoretical calculations. Significantly, upon exposure to air and visible light residing in their absorption regime (365-630 nm), thio-caged fluorophores can be efficiently desulfurized to their oxo derivatives, thus restoring strong emission of the fluorophores. The effective photoactivation makes thio-caged fluorophores promising candidates for super-resolution imaging, which was realized by photoactivated localization microscopy (PALM) with low-power activation light under physiological conditions in the absence of cytotoxic additives (e.g., thiols, oxygen scavengers), a feature superior to traditional PALM probes. The versatility of this thio-caging strategy was further demonstrated by multicolor super-resolution imaging of lipid droplets and proteins of interest.
- Tang, Juan,Robichaux, Michael A.,Wu, Kuan-Lin,Pei, Jingqi,Nguyen, Nhung T.,Zhou, Yubin,Wensel, Theodore G.,Xiao, Han
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supporting information
p. 14699 - 14706
(2019/10/11)
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- Pyridine triazole modified coumarin Cu2 + The preparation method of the fluorescent probe (by machine translation)
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Pyridine triazole modified coumarin Cu2 + fluorescent probe preparation method, the invention relates to a triazole modified coumarin Cu pyridine2 + Fluorescent probe is 3 - formyl - 7 - (diethylamino) coumarin Schiff base, the preparation method comprises preparing a compound (A), compound (B) and compound (C) 3 - formyl - 7 - (diethylamino) coumarin Schiff base three steps. 3 - Formyl - 7 - (diethylamino) coumarin Schiff base as a fluorescent probe in the detection of copper, has good light stability, high fluorescence quantum yield, storck large displacement and the like, can be fast, efficient, single-minded identification in an aqueous solution of copper ion, which is a fast high sensitivity fluorescence probe, other common metal ion has a stronger anti-interference capability, real-time monitoring and detecting the stability is high, can be used for qualitative, quantitative detection environment in the copper ion, to the cupric ion detection has very good application value. The reaction of the invention easy control of the condition, the operation is convenient, and the yield is high. (by machine translation)
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Paragraph 0012; 0036-0039; 0049-0051
(2019/04/17)
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- Preparation method of novel pyrazolyl coumarin Schiff base copper ion fluorescence probe
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The invention discloses a preparation method of a novel pyrazolyl coumarin Schiff base copper ion fluorescence probe. Novel pyrazolyl coumarin Schiff base is provided with a rapid, high sensitivity and stability copper ion fluorescence probe, has high anti-interference effects on other common metal ions, can be used for qualitatively and quantitatively detecting copper ions in environments and canovercome the shortcomings that an existing fluorescence probe for detecting Cu is slow in response and cannot uniquely identify one positive ion, cytotoxicity of a ligand is high, Stock transferis small, fluorescence quantum yield in a water-based medium is low and the like. The fluorescence probe is easy to implement and popularize and has excellent application value. The preparation methodis simple and convenient to operate, reaction conditions are easily controlled, and the yield of a product is high.
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Paragraph 0031; 0035; 0036
(2019/04/17)
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- Tuning lipophilicity for optimizing the H2S sensing performance of coumarin-merocyanine derivatives
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Hydrogen sulfide (H2S) is an endogenous signaling molecule involved in various physiopathological processes; coumarin-based merocyanines have been successfully utilized for developing fluorescent H2S sensors. However, subtle changes in the chemical structure of merocyanines could induce distinct difference in the H2S sensing behavior. Investigation of the structure-property relationship of merocyanine dyes is of great importance for the development of ideal sensors with desirable performance. In this work, a series of coumarin/merocyanine (CMC) hybrid fluorescent probes with different lipophilicities have been developed. By altering the N-alkyl chain, the reaction rate with H2S and intracellular distribution of CMC sensors are optimized. The results showed that increasing the lipophilicity by attaching longer N-alkyl chains leads to a faster sensing response as well as a higher efficiency of the mitochondrial targeting ability. By virtue of rapid sensing of H2S and impressive mitochondrial co-localization ability, CM-NC6 could monitor H2S levels via a dual channel ratiometric mode. In addition, CM-NC6 is also capable of in vivo imaging of exogenous H2S. The work provided a powerful strategy for developing H2S sensors with optimized performance, which would be helpful for understanding the complicated roles of H2S in various physiological processes.
- Fang, Hongbao,Chen, Yuncong,Shi, Xiangchao,Bai, Yang,Chen, Zhongyan,Han, Zhong,Zhang, Yuming,He, Weijiang,Guo, Zijian
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supporting information
p. 14800 - 14805
(2019/09/30)
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- Novel fluorescent probe for detecting cysteine as well as preparation method and application of novel fluorescent probe
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The invention discloses a novel fluorescent probe for detecting cysteine as well as a preparation method and application of the novel fluorescent probe. The novel fluorescent probe is 4-(7-diethylaminocoumarin-3-vinyl)-1-(4-acryloyloxy)benzylpyridine bromide. The preparation method comprises the following steps: carrying out a reaction between p-hydroxybenzyl alcohol and acryloyl chloride; carrying out a reaction between the obtained phenyl 4-(hydroxymethyl)acrylate and phosphorus tribromide to obtain phenyl 4-(bromomethyl)acrylate; carrying out a reaction between 4-diethylaminosalicylaldehydeand diethyl malonate, and carrying out a Vilsmeier reaction of the obtained 7-diethylaminocoumarin; carrying out a dehydration condensation reaction between the obtained 7-diethylaminocoumarin-3-formaldehyde and 4-methylpyridine; carrying out a reaction between obtained 7-diethylamino-3-(4-pyridyl)vinylcoumarin and the phenyl 4-(bromomethyl)acrylate to obtain the novel fluorescent probe. The novel fluorescent probe has relatively high selectivity and sensitivity during cysteine detection.
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Paragraph 0059; 0077-0081
(2019/01/23)
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- Design and Synthesis of Coumarin–Imidazole Hybrid Chromophores: Solvatochromism, Acidochromism and Nonlinear Optical Properties
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A set of linear and asymmetric coumarin–imidazole hybrid compounds having a N,N-diethylamine at 7-position and imidazole at 3-position on the coumarin were synthesized. Insertion of thiophene π-spacer between coumarin and imidazole moieties (5b, 5d) leads to redshifted absorption and emission compared to 5a and 5c. All the compounds show a noticeable response to trifluoroacetic acid with a redshifted absorption and an increase in emission intensity by twofold. The ratio of ground and excited state acidity constant was calculated using F?rster energy cycle, and the ratios were found to be 0.25, 0.96, 0.52 and 1.87, respectively, for 5a-5d. Due to the thiophene π-spacer, elongation of π-conjugation in 5b and 5d leads to high values of polarizability (α), first-order hyperpolarizability (β) and second-order hyperpolarizability (γ). Compound 5b exhibits a high value (895 GM) of two-photon absorption cross section (σ2PA), measured using two-level model.
- Bhagwat, Archana A.,Avhad, Kiran C.,Patil, Dinesh S.,Sekar, Nagaiyan
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p. 740 - 754
(2018/11/02)
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- A method for detecting the ratio of cyanide-near-infrared fluorescent probe preparation method and use thereof (by machine translation)
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The invention relates to a fluorescence detection technology field, in particular to a method for detecting food cyanide in the ratio-type near-infrared fluorescent probe preparation method and use; preparation steps are as follows: first preparation to obtain 7 - (diethylamino) coumarin and 7 - (diethylamino) coumarin aldehydes; then the 7 - (diethylamino) coumarin aldehyde (1, 3 - dioxo of vinyl - 2 - methyl) phenyl [...] three to dissolved in methylene chloride, sodium hydroxide solution, adding hydrochloric acid neutralization, by extraction of the liquid, column chromatography purification to obtain the intermediate product; and acetophenone to the intermediate product in the mixed solvent of methylene chloride and methanol, drip and [...] pyrrole, sodium chloride is added, stirring, distillation, column chromatography purification to obtain the detected cyanide of ratio-type near-infrared fluorescent probe; the invention has developed a novel high-performance ratio-type near-infrared fluorescent probe, the synthetic method is simple, the cyanide has very good selectivity, and successfully applied to the cyanide in the detection of the food. (by machine translation)
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Paragraph 0041; 0042; 0046; 0047; 0051; 0052; 0058
(2019/05/15)
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