20571-42-0Relevant articles and documents
Silver-catalyzed facile decarboxylation of coumarin-3-carboxylic acids
Jafarpour, Farnaz,Jalalimanesh, Nafiseh,Olia, Mina Barzegar Amiri,Kashani, Asieh Otaredi
, p. 9508 - 9511 (2010)
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.
A novel hydrazide Schiff base self-assembled nanoprobe for selective detection of human serum albumin and its applications in renal disease surveillance
Li, Qing-Zhong,Liu, Hai-Bo,Liu, Wei,Wang, Zhi-Gang,Xie, Cheng-Zhi,Xu, Jing-Yuan,Yan, Xiao-Jing,Zhang, De-Long
, p. 8346 - 8355 (2020)
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.
A colorimetric and ratiometric fluorescence probe for rapid detection of SO2 derivatives bisulfite and sulfite
Xiang, Kaiqiang,Chang, Shunzhou,Feng, Jingjing,Li, Changjiang,Ming, Wei,Liu, Ziyan,Liu, Yunchang,Tian, Baozhu,Zhang, Jinlong
, p. 190 - 197 (2016)
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.
A coumarin-fused ‘off-on’ fluorescent probe for highly selective detection of hydrazine
Wang, Mei,Wang, Xiaoli,Li, Xueyan,Yang, Ziqi,Guo, Zhenbo,Zhang, Jiangyan,Ma, Jingjun,Wei, Chao
, (2020)
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.
A selective thioxothiazolidin-coumarin probe for Hg2+ based on its desulfurization reaction. Exploring its potential for live cell imaging
Aliaga, Margarita E.,Gazitua, Marcela,Rojas-Bola?os, Andrea,Fuentes-Estrada, Marcial,Durango, Diego,García-Beltrán, Olimpo
, (2020)
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.
Synthesis and combined experimental and computational investigations on spectroscopic and photophysical properties of red emitting 3-styryl coumarins
Tathe, Abhinav B.,Gupta, Vinod D.,Sekar, Nagaiyan
, p. 49 - 55 (2015)
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.
Bifunctional Fluorescent Probe for Sequential Sensing of Thiols and Primary Aliphatic Amines in Distinct Fluorescence Channels
Huang, Meiyu,Long, Lingliang,Wang, Ning,Yuan, Xiangqi,Cao, Siyu,Gong, Aihua,Wang, Kun
, p. 560 - 567 (2018)
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.
A thiocoumarin-based colorimetric and ratiometric fluorescent probe for Hg2+ in aqueous solution and its application in live-cell imaging
Qin, Siyao,Chen, Bo,Huang, Jing,Han, Yifeng
, p. 12766 - 12772 (2018)
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.
A novel coumarin Schiff-base as a Ni(II) ion colorimetric sensor
Wang, Lingyun,Ye, Decheng,Cao, Derong
, p. 40 - 44 (2012)
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.
A new coumarin based chromo-fluorogenic probe for selective recognition of cyanide ions in an aqueous medium
Sun, Xueyi,Wang, Yu,Zhang, Xiaofeng,Zhang, Shihong,Zhang, Zhao
, p. 96905 - 96910 (2015)
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.
A mitochondria-specific fluorescent probe for visualizing endogenous hydrogen cyanide fluctuations in neurons
Long, Lingliang,Huang, Meiyu,Wang, Ning,Wu, Yanjun,Wang, Kun,Gong, Aihua,Zhang, Zhijian,Sessler, Jonathan L.
, p. 1870 - 1875 (2018)
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.
A new ratiometric and colorimetric chemosensor for cyanide anion based on Coumarin-hemicyanine hybrid
Yang, Zhenghao,Liu, Zhipeng,Chen, Yuncong,Wang, Xiaoqing,He, Weijiang,Lu, Yi
, p. 5073 - 5076 (2012)
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.
A novel coumarin-based colorimetric and fluorescent probe for detecting increasing concentrations of Hg2+in vitroandin vivo
Chi, Liqun,Duan, Hongdong,Huang, Li,Meng, Xia,Sheng, Wenlong,Wang, Lizhen
, p. 23597 - 23606 (2021)
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.
Synthesis and fluorescent properties of coumarin-benzimidazole and coumarin–phenanthroimidazole hybrids
Fan, Hongli,Wang, Lingqiang,Wang, Xiaolong
, p. 9 - 13 (2020)
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.
Turn on fluorescent detection of hydrazine with a 1,8-naphthalimde derivative
Shi, Bingjie,He, Yangyang,Zhang, Panpan,Wang, Yulong,Yu, Mingming,Zhang, Hongyan,Wei, Liuhe,Li, Zhanxian
, p. 152 - 159 (2017)
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.
Ratiometric fluorescence imaging of cellular polarity: Decrease in mitochondrial polarity in cancer cells
Jiang, Na,Fan, Jiangli,Xu, Feng,Peng, Xiaojun,Mu, Huiying,Wang, Jingyun,Xiong, Xiaoqing
, p. 2510 - 2514 (2015)
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.
Functionalized coumarin derivatives containing aromatic-imidazole unit as organic luminescent materials
Wang, Youjia,Li, Yanmei,Yu, Tianzhi,Su, Wenming,Ma, Hailin,Zhao, Yuling,Li, Xinyu,Zhang, Hui
, (2020)
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%.
Synthesis of Functionalized Benzopyran/Coumarin-Derived Aryne Precursors and Their Applications
Nakamura, Yu,Sakata, Yuki,Hosoya, Takamitsu,Yoshida, Suguru
, p. 8505 - 8510 (2020)
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.
Spectral Properties of Highly Emissive Derivative of Coumarin with N,N-Diethylamino, Nitrile and Tiophenecarbonyl Moieties in Water-Methanol Mixture
Kolbus, Anna,Danel, Andrzej,Grabka, Danuta,Kucharek, Mateusz,Szary, Karol
, p. 1393 - 1399 (2019)
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.
Di–thioether amide–Pd2+ complex based-methionine fluorescent chemosensor with selectivity over cysteine and histidine
Lee, Minah,Lim, Taeho,Lee, Youngkeun,Kang, Seungyoon,Han, Min Su
, p. 69 - 75 (2017)
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.
A novel ratiometric near-infrared fluorescent probe for monitoring cyanide in food samples
Long, Lingliang,Han, Yuanyuan,Yuan, Xiangqi,Cao, Siyu,Liu, Weiguo,Chen, Qian,Wang, Kun,Han, Zhixiang
, (2020)
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.
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
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
, (2020)
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.
A coumarin-derived Cu2?+-fluorescent chemosensor and its direct application in aqueous media
Mergu, Naveen,Kim, Myeongjin,Son, Young-A.
, p. 571 - 580 (2018)
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.
The ferroquine antimalarial conundrum: Redox activation and reinvasion inhibition
Dubar, Faustine,Slomianny, Christian,Khalife, Jamal,Dive, Daniel,Kalamou, Hadidjatou,Guerardel, Yann,Grellier, Philippe,Biot, Christophe
, p. 7690 - 7693 (2013)
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
Synthesis and evaluation of 11C-labeled coumarin analog as an imaging probe for detecting monocarboxylate transporters expression
Tateishi, Hiroyuki,Tsuji, Atsushi B.,Kato, Koichi,Sudo, Hitomi,Sugyo, Aya,Hanakawa, Takashi,Zhang, Ming-Rong,Saga, Tsuneo,Arano, Yasushi,Higashi, Tatsuya
, p. 4893 - 4897 (2017)
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.
Effect of the π-bridge on the light absorption and emission in push-pull coumarins and on their supramolecular organization
Arcos-Ramos, Rafael,Carreón-Castro, María del Pilar,Farfán, Norberto,González-Rodríguez, Edgar,Guzmán-Juárez, Brenda,Maldonado-Domínguez, Mauricio,Miranda-Olvera, Montserrat,Santillan, Rosa
, (2021/11/08)
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.
PHENANTHROLINE, CARBAZOLE AND FLAVYLIUM BASED CYANINES AND COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME
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Page/Page column 69, (2021/09/11)
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.
AIE type coumarin derivative fluorescent probe and preparation method and application thereof
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Paragraph 0040; 0042-0045, (2021/01/11)
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.
