- 3-Hydroxy-(4H)-benzopyran-4-ones as potential iron chelating agents in vivo
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Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalised from specific carriers or intracellular sites (inflammation, eurodegenerative diseases, post-ischaemic reperfusion, etc.). In order to be used for therapeutical purposes in vivo, a reliable iron chelator should be capable of preventing the undesired effects that follow the electrochemical activation of iron (see below). Bearing in mind the molecular structure of some flavonols that are able to chelate iron, we synthesised a new oral iron-chelator, 2-methyl-3-hydroxy-4H-benzopyran-4-one (MCOH). We demonstrate that MCOH chelates iron in a 2:1 ratio showing a stability constant of ~1010. MCOH is able to cross cell membranes (erythrocytes, ascite tumour cells) in both directions. Following intraperitoneal administratio to rats, it is quickly taken up by the liver and excreted in the urine withi 24 h. A similar behaviour has bee documented after oral administration. We propose that MCOH may represent the prototype of a new class of iron chelating agents to be developed for iron-removal therapy in vivo with the goal of preventing tissue damage caused by the iron redox cycle. Copyright
- Ferrali, Marco,Donati, Donato,Bambagioni, Sabrina,Fontani, Marco,Giorgi, Gianluca,Pietrangelo, Antonello
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Read Online
- A novel near-infrared fluorescent probe for detection of early-stage Aβ protofibrils in Alzheimer's disease
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Detection of Aβ protofibrils at the early stage of Alzheimer's disease was realized by a novel near-infrared probe (DCM-AN) based on dicyanomethylene-4H-pyran. This probe exhibits high affinity towards Aβ protofibrils in vitro and in brain sections of tra
- Li, Ruohan,Lv, Guanglei,Sun, Anyang,Wang, Minqi,Wei, Peng,Yi, Tao
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Read Online
- A “turn-on” fluorescent probe with high selectivity and large stokes shift for the detection of hydrogen peroxide and its bioimaging applications
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Hydrogen peroxide (H2O2) plays pivotal roles in various biological functions and pharmacological activities. High selectivity and sensitivity remain challenges for fluorescent probes to detection of H2O2 with a large stokes shift. Herein, a new “turn-on” fluorescent probe (DCM-C) was designed based on the mechanism of intramolecular charge transfer (ICT). In PBS buffer (10 mM, pH 7.4, with 20% DMSO, v/v), DCM-C exhibited high selectivity and sensitivity for H2O2 over other interfering analytes with a large stokes shift (187 nm), and the detection limit was as low as 35.5 nM. In addition, the probe was effective for detecting exogenous and endogenous H2O2 in living cells, and identifying stained in cytoplasm. Moreover, the probe has been used successfully for determining H2O2 in zebrafish by fluorescence imaging.
- Gao, Mengjiao,Hua, Yun,Kang, Yanfei,Li, Jin,Shang, Yajing
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supporting information
(2021/09/11)
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- Near-infrared hydrazine fluorescence sensor as well as preparation method and application thereof
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The invention discloses a near-infrared hydrazine fluorescence sensor as well as a preparation method and application thereof. According to the method, a target product (E) 4-(2-(4-(dicyanomethylene) chroman-2-yl) vinyl) phenyl 4-bromobutyric acid is synthesized. An ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer are adopted to determine the intensity change of a characteristic peak of a probe in a water phase, so as to determine the existence of hydrazine. The invention provides application of the hydrazine fluorescence sensor in hydrazine detection, and the hydrazine fluorescence sensor can be used for high-selectivity and high-sensitivity detection of hydrazine in a water phase. It is found that thehydrazine fluorescence sensor has a good hydrazine detection effect. Compared with the prior art, the hydrazine fluorescence sensor has the advantages of easily available raw materials, simple synthesis steps, convenient post-treatment, easy realization of large-scale production, and great application prospect in hydrazine detection.
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Paragraph 0042; 0048-0051
(2021/04/21)
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- Design, synthesis, and evaluation of near-infrared fluorescent molecules based on 4h-1-benzopyran core
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A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules M-1, M-2, M-3 varied significantly with the increasing polarities of solvents, where M-3 showed high viscosity sensitivity in glycerol-ethanol system with a 3-fold increase in emission intensity. Increasing concentrations of compound M-3 to 5% BSA in PBS elicited a 4-fold increase in fluorescence intensity, exhibiting a superior environmental sensitivity. Furthermore, the in vitro cellular uptake behavior and CLSM assay of cancer cell lines demonstrated that M-3 could easily enter the cell nucleus and bind to proteins with low toxicity. Therefore, the synthesized near-infrared fluorescent molecules could provide a new direction for the development of optical imaging probes and potential further drugs.
- Li, Chuchu,Lu, Wei,Ma, Mingliang,Tanzeng, Yawen,Wang, Shuting,Zhang, Yuexing,Zhu, Shulei
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- A matrix targeted fluorescent probe to monitor mitochondrial dynamics
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Mitochondria are an indispensable organelle for energy production and regulation of cellular metabolism. The structural and functional alterations to mitochondria instigate pathological conditions of cancer, and aging-associated and neurodegenerative disorders. The normal functioning of mitochondria is maintained by quality control mechanisms involving dynamic fission, fusion, biogenesis and mitophagy. Under conditions of mitophagy and neurodegenerative diseases, mitochondria are exposed to different acidic environments and high levels of reactive oxygen species (ROS). Therefore stable molecular tools and methods are required to monitor the pathways linked to mitochondrial dysfunction and disease conditions. Herein, we report a far-red fluorescent probe (Mito-TG) with excellent biocompatibility, biostability, photostability, chemical stability and turn on emission for selective targeting of the mitochondrial matrix in different live cells. The probe was successfully employed for monitoring dynamic processes of mitophagy and amyloid beta (Aβ) induced mitochondrial structural changes.
- Ramesh, Madhu,Rajasekhar, Kolla,Gupta, Kavya,Babagond, Vardhaman,Saini, Deepak Kumar,Govindaraju, Thimmaiah
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supporting information
p. 801 - 808
(2021/02/09)
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- Near-infrared compound with aggregation-induced emission property as well as preparation method and application thereof
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The invention discloses a near-infrared compound with an aggregation-induced emission property as well as a preparation method and application of the near-infrared compound. The near-infrared compoundhas high-brightness far-infrared and near-infrared fluorescence emission characteristics, has aggregation-induced emission and crystallization-induced emission characteristics in a near-infrared region, and has the characteristic of aggregation-induced nonlinear optical effect. The nanocrystal can be used for biological imaging and can be prepared into nanocrystals for living body deep high-resolution multi-photon fluorescence and third harmonic imaging. The material synthesized by the method shows the properties of aggregation-induced emission and crystallization-induced emission, while thetraditional fluorescent dye has the phenomenon of aggregation-induced fluorescence quenching under the condition of high concentration, so that the defects of the traditional fluorescent dye are effectively overcome.
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Paragraph 0021
(2021/02/10)
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- Rational Design of a Highly Selective Near-Infrared Two-Photon Fluorogenic Probe for Imaging Orthotopic Hepatocellular Carcinoma Chemotherapy
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Selective fluorescence imaging of biomarkers in vivo and in situ for evaluating orthotopic hepatocellular carcinoma (HCC) chemotherapy remains a great challenge due to current imaging agents suffering from the potential interferences of other hydrolases. Herein, we observed that carbamate unit showed a high selectivity toward the HCC-related biomarker carboxylesterase (CE) for evaluation of treatment. A near-infrared two-photon fluorescent probe was developed to not only specially image CE activity in vivo and in situ but also target orthotopic liver tumor after systemic administration. The in vivo signals of the probe correlate well with tumor apoptosis, making it possible to evaluate the status of treatment. The probe enables the imaging of CE activity in situ with a high-resolution three-dimensional view for the first time. This study may promote advances in optical imaging approaches for precise imaging-guided diagnosis of HCC in situ and its evaluation of treatment.
- Han, Jingjing,Kim, Heejeong,Kwon, Nahyun,Li, Haidong,Qi, Sujie,Wang, Rui,Wu, Xiaofeng,Yoon, Juyoung,Yu, Fabiao
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supporting information
p. 15418 - 15425
(2021/06/18)
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- Molecular Aggregation of Naphthalene Diimide(NDI) Derivatives in Electron Transport Layers of Inverted Perovskite Solar Cells and Their Influence on the Device Performance
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One of key factors to design applicable electron transport layers (ETLs) for perovskite solar cells is the morphology of ETLs since a good morphology would help to facilitate the carrier transport at two interfaces (perovskiteETL and ETLcathode). However, one drawback of most organic ETL small molecules is the internal undesired accumulation, which would cause the formation of inappropriate morphology and rough ETL surface. Here, by elaborately designing the side chains of NDI derivatives, the molecular interaction could be modified to achieve the aggregation in different degrees, which would eventually affect the accumulation of molecules and surface qualities of ETLs. By speculating from the comparison between the absorption spectra of solutions and films, the sequence of extent of molecule interaction and aggregation was built among three NDI derivatives, which is further confirmed by direct evidence of atomic force microscopy (AFM) images. Then, carrier exaction abilities are simply studied by steady-state photoluminescence spectroscopy. The carrier transport process is also discussed based on cyclic voltammetry, time-resolved photoluminescence spectroscopy and mobility. NDIF1 are proven to have the appropriate internal aggregation to smooth the contact with cathode and low series resistance, and a device performance of 15.6 % is achieved. With the ability of preventing the thermal diffusion of Ag towards the perovskite surface due to the strong interaction between molecules, NDIF2 at high concentration shows the highest fill factor (80 %).
- Liu, Wenbo,Shaikh, Dada B.,Rao, Pedada Srinivasa,Bhosale, Rajesh S.,Said, Ahmed Ali,Mak, Adrian M.,Wang, Zongrui,Zhao, Mu,Gao, Weibo,Chen, Bingbing,Lam, Yeng Ming,Fan, Weijun,Bhosale, Sidhanath V.,Bhosale, Sheshanath V.,Zhang, Qichun
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supporting information
p. 112 - 121
(2019/12/03)
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- Preparation method and application of novel photosensitizer
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The invention relates to a preparation method and application of a novel photosensitizer. The photosensitizer is synthesized for the first time. A general formula compound represented by an intermediate formula (I) is used as a mother core, and is subjected to a Knoevenagel reaction with 4-hydroxybenzaldehyde, 3,5-dibromo-4-hydroxybenzaldehyde and 3,5-diiodo-4-hydroxybenzaldehyde to obtain the general formula photosensitizer represented by a formula (II). The method creatively reserves functional groups (R1, R2) on the intermediate formula (I) and the photosensitizer formula (II), and synthesizes the intermediate and the photosensitizer with S and Se as central atoms (Q) for the first time. The novel photosensitizer provided by the invention solves the technical problems that an existing photosensitizer has a narrow absorption range, a poor therapeutic effect in the visible light range, excessive power of a used light source, and inability to introduce functional groups.
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Paragraph 0022; 0029-0030
(2020/02/14)
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- Visualization of carboxylesterase 2 with a near-infrared two-photon fluorescent probe and potential evaluation of its anticancer drug effects in an orthotopic colon carcinoma mice model
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We establish a near-infrared two-photon fluorescent probe for the detection of CE2 with high selectivity and sensitivity. This probe exhibits low cytotoxicity and superior tissue penetration ability for evaluating the real-time activity of CE2 in living cells, in cancer tissues, and in a colon carcinoma mice model.
- Li, Mingshun,Luo, Xianzhu,Wang, Yan,Yu, Fabiao,Yu, Feifei,Zhao, Linlu
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supporting information
p. 4412 - 4415
(2020/05/05)
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- An Activatable AIEgen Probe for High-Fidelity Monitoring of Overexpressed Tumor Enzyme Activity and Its Application to Surgical Tumor Excision
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Monitoring fluctuations in enzyme overexpression facilitates early tumor detection and excision. An AIEgen probe (DQM-ALP) for the imaging of alkaline phosphatase (ALP) activity was synthesized. The probe consists of a quinoline-malononitrile (QM) core decorated with hydrophilic phosphate groups as ALP-recognition units. The rapid liberation of DQM-OH aggregates in the presence of ALP resulted in aggregation-induced fluorescence. The up-regulation of ALP expression in tumor cells was imaged using DQM-ALP. The probe permeated into 3D cervical and liver tumor spheroids for imaging spatially heterogeneous ALP activity with high spatial resolution on a two-photon microscopy platform, providing the fluorescence-guided recognition of sub-millimeter tumorigenesis. DQM-ALP enabled differentiation between tumor and normal tissue ex vivo and in vivo, suggesting that the probe may serve as a powerful tool to assist surgeons during tumor resection.
- Baek, Gain,Chung, Jeewon,Fan, Jiangli,Ge, Haoying,Hillman, Prima Fitria,Kim, Dayeh,Lee, Eun Young,Li, Haidong,Li, Yueqing,Nam, Sang-Jip,Peng, Xiaojun,Wang, Jingyun,Wu, Xiaofeng,Xu, Feng,Yao, Qichao,Yoon, Juyoung
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supporting information
p. 10186 - 10195
(2020/03/23)
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- Targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system
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The invention relates to a targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system. Sugar functionalized column [5] arene with targeted selectivity isused as a host molecule, a trimethylamine derivative of disulfide bond bridged dicyanomethylene 4H pyran with GSH response fluorescence tracing is used as a guest molecule, a GSH responsive column [5] arene amphiphilic molecule with targeted and fluorescence tracing is prepared through host-guest interaction, nano-vesicles are formed in a solution through hydrophilic-hydrophobic interaction, andan anticancer drug is encapsulated in a vesicle cavity. Mannose is specifically bound with a mannose receptor overexpressed on the surface of a breast cancer cell, so that targeted selective entry into the cancer cell is realized; meanwhile, a disulfide bond is quickly broken under the action of GSH with relatively high concentration in the cancer cell, so that the vesicles are promoted to break to quickly release the anticancer drug; and in addition, the dicyanomethylene 4H pyran is used as a fluorescent chromogenic group to realize fluorescence tracing. The system can be applied to transportation and tracing of the anticancer drug.
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Paragraph 0063-0066
(2020/10/12)
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- Hydrogen peroxide activated aspirin visual prodrug, preparation method and application thereof
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The invention discloses a hydrogen peroxide activated aspirin visual prodrug, a preparation method and application thereof. Salicylic acid is used as a new response group of hydrogen peroxide (H2O2),aspirin is integrated into a pyranonitrile (DCM) dye structure, and a new hydrogen peroxide responsive aspirin prodrug (DA) is synthesized. The prodrug molecule is activated by H2O2, releases an active drug aspirin, and has high-selectivity cell imaging on endogenous and exogenous H2O2. The prodrug DA not only can be used as an effective tool to track pathological reaction related to H2O2 in a living body system, but also a disconnected aspirin part has a potential prospect of being applied as a therapeutic drug to related disease treatment after reaction.
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Paragraph 0025-0027
(2020/10/04)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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Page/Page column 66
(2020/01/08)
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- Based on benzo [...] detection diaphorases fluorescent probe molecule, preparation and use (by machine translation)
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The invention relates to a detection based on benzo [...] diaphorases fluorescence probe molecule, preparation method and use thereof. The fluorescence probe molecule structure is shown as follows: The invention also discloses the [...] based detection di
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Paragraph 0032; 0043; 0045
(2019/05/02)
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- An I6P7 peptide modified fluorescent probe for bio-imaging
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The I6P7 peptide was proved to specifically bind to the interleukin-6 receptor, which can be exploited as an effective tumor-targeting moiety. Herein, a novel tumor-targeting fluorescent probe (DMP) conjugated with the I6P7 peptide was designed and synthesized. This probe was validated to possess valuable photophysical properties. The biocompatibility was evaluated by investigating its cytotoxicity on HUVEC and U87 cells, respectively. The tumor cell affinity has been confirmed by bio-imaging of this probe on different human cancer cells (U87, A549 and MCF-7 cells) and normal cells (HUVEC cell). The probe demonstrates low cytotoxicity, high tumor cell affinity and favorable mitochondria-targeting capability. Overall, these results revealed that DMP can serve as an important fluorescent probe for tumor-targeted bio-imaging.
- Yao, Yuxin,Gui, Lijuan,Gao, Beike,Yuan, Zhenwei,Chen, Yisha,Wei, Chen,He, Qing,Wang, Fei,Xu, Mingjun,Chen, Haiyan
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supporting information
p. 1785 - 1790
(2019/01/28)
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- A detection Cys benzo pyrane nitrile class of fluorescent probe molecule preparation process (by machine translation)
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The invention discloses a method for selectively detecting Cys benzo pyrane nitrile class of fluorescent probe molecule preparation process, its preparation process characteristic as follows: under nitrogen conditions, accurate weighing compound I (48 mg, 0 . 14 mmol) is dissolved in the water removal of dichloromethane (10 ml) in, fetch trifluoromethanesulfonic acid methyl ester (92 mg, 0 . 56 mmol) in the mixed solution, stirring at room temperature of not less than 12 hours. After the reaction is filtered and precipitated, absolute ethanol and ethyl ether washing, to get the crude product red powder, column chromatography separation and purification, eluent: dichloromethane/methanol=20/1, orange red powder obtained DCM - q (36 mg, 50%). Said product of this invention DCM - q relatively easy to obtain, the probe molecule mainly used for selectively detecting biological thiol of cysteine (Cys). (by machine translation)
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Paragraph 0017; 0018
(2019/01/20)
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- 2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors
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A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B inhibitory activity (IC50 = 17 ± 2.4 nM) and the best MAO-B selectivity (IC50 for MAO-A/IC50 for MAO-B = 1500). The mode of inhibition of compound 9 against MAO-B was competitive and reversible. Quantitative structure–activity relationship (QSAR) analyses of the 2-styrylchromone derivatives were conducted using their pIC50 values with the use of Molecular Operating Environment (MOE) and Dragon, demonstrating that the descriptors of MAO-B inhibitory activity and MAO-B selectivity were 1734 and 121, respectively, that showed significant correlations (P 50 value indexes for MAO-B exhibited a determination coefficient (R2) of 0.873 as well as a Leave-One-Out cross-validated determination coefficient (Q2) of 0.675. These data suggested that the 2-styrylchromone structure might be a useful scaffold for the design and development of novel MAO-B inhibitors.
- Takao, Koichi,Endo, Saki,Nagai, Junko,Kamauchi, Hitoshi,Takemura, Yuri,Uesawa, Yoshihiro,Sugita, Yoshiaki
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- New chromophores based on 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile
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New derivatives of 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile were synthesized using the Knoevenagel reaction of 2-(4-methyl-chromen-2-ylidene)malononitrile and 2-(2-methylchromen-4-ylidene)malononitrile, respectively, with the participation of [1-(2-n-butoxyethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)]-carbaldehyde. First hyperpolarizability (β) was calculated for the obtained compounds using the M05-2X functional and 6-31+G (d) basis. Optical properties and solvatochromism in solvents of different polarity (toluene, 1,4-dioxane, chlorobenzene, dichloromethane, DMF, and ethanol) were also investigated.
- Levchenko,Chudov,Demin, D. Yu.,Adamov,Zinoviev,Lyssenko,Shokurov,Shmelin,Grebennikov
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p. 1883 - 1888
(2019/10/22)
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- Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo
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A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.
- Dan, Wen-Jia,Tuong, Thi-Mai-Luong,Wang, Da-Cheng,Li, Ding,Zhang, An-Ling,Gao, Jin-Ming
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supporting information
p. 2861 - 2864
(2018/07/25)
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- Dicyanomethylene-4H-pyran-based NIR fluorescent ratiometric chemosensor for pH measurement
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Abstract: A D-π-A featured dicyanomethylene-4H-pyran-based dye (DCM-OH) is designed as a pH-sensitive fluorescent chemosensor. In neutral conditions, DCM-OH shows a long absorption wavelength at 431?nm attributed to the DCM chromophore via the intramolecular charge transfer (ICT), but very weak fluorescence around 574?nm. While pH increases from 7.15 to 11.00, DCM-OH shows a bathochromic absorption band at 574?nm due to the increase of the ICT process from the oxygen anion group, shifting the emission band to the NIR region. A DFT calculation has been performed to confirm the ICT enhancement. In this way, an obvious ratiometric fluorescent signal (I692/I574) allows the ratiometric detection of pH, induced by a large Stokes shift of about 118?nm. The fluorescent chemosensor exhibits high sensitivity to H+ with a pKa value of 7.21. The strong change in fluorescence intensity with pH allows the determination of pH over a much wider range (typically 7–11). Furthermore, the reversible absorption and fluorescence conversion was also performed with protonation and deprotonation, which makes DCM-OH a simple naked-eye sensitive NIR fluorescent chemosensor for pH measurement.
- Yang, Jinfeng,Li, Meng,Zhu, Wei-Hong
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p. 3959 - 3969
(2018/03/06)
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- The type of threads[...] Chromone compounds and their production and use (by machine translation)
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The invention provides a xanthone cross-color ketone compound having a structure represented by a general formula I (shown in the specification) or medicinal salt thereof, a preparation method of the xanthone cross-color ketone compound, a pharmaceutical composition containing the xanthone cross-color ketone compound and application of the xanthone cross-color ketone compound in preparation of medicines for treating or preventing diseases relevant with in-vivo energy imbalance, glycometabolism imbalance and/or apoptosis.
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Paragraph 0065; 0069
(2018/04/26)
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- A near-infrared fluorescent probe for rapid detection of carbon monoxide in living cells
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A near-infrared (NIR) and colorimetric fluorescent probe system was developed for Carbon Monoxide (CO) via a Pd0-mediated Tsuji-Trost reaction. In this probe, phenoxide anion formation (DPCO?) was acted as the signal unit and an allyl carbonate group was used as the recognition unit. This non-fluorescent probe molecule can release the relevant fluorophore after conversion of Pd2+ to Pd0 by CO. The probe system including probe 1 and Pd2+ can be used for “naked-eye” detection of CO, and exhibited high selectivity to CO over various other sensing objects. More importantly, the probe system has great potential for fluorescence imaging of intracellular CO in living cells.
- Yan, Liqiang,Nan, Ding,Lin, Cheng,Wan, Yi,Pan, Qiang,Qi, Zhengjian
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p. 284 - 289
(2018/05/28)
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- Hypochlorous acid fluorescent probe, as well as preparation method and application thereof
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The invention provides a hypochlorous acid fluorescent probe with quick response and high selectivity and sensitivity by molecular structure design, as well as a preparation method thereof and application of the hypochlorous acid fluorescent probe to detection of hypochlorous acid in an aqueous solution and a cell. The fluorescent probe can be applied to detection of the hypochlorous acid in the aqueous solution or a biological system, and detection comprises fluorescence detection, cell imaging and visual colorimetry. The fluorescence intensity forms linear positive correlation with the concentration of the hypochlorous acid within a certain concentration range, and the concentration of the hypochlorous acid can be quantitatively measured. The hypochlorous acid fluorescent probe is easy to synthesize, and a posttreatment process is relatively simple; selective and rapid detection of the hypochlorous acid molecular probe is realized, the selectivity is good, and the hypochlorite fluorescent probe is high in resistance to interference of other molecules, is a simple, rapid and sensitive hypochlorous acid molecular specific detection reagent, and has broad application prospect in the field of biomolecular detection.
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Paragraph 0020; 0021
(2017/10/13)
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- Development of a novel near-infrared fluorescent theranostic combretastain A-4 analogue, YK-5-252, to target triple negative breast cancer
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The treatment of triple negative breast cancer (TNBC) is a significant challenge to cancer research. The lack of hormone receptors limits the treatment options available to patients with this diagnosis, forcing them to endure prolonged radiation and chemotherapy. Anti-angiogenesis is a chemotherapeutic strategy that targets the vasculature of tumors. Combretastatin A-4 (CA-4) is a well-known vasculature-disrupting agent, which has been shown to effectively kill a variety of cancers through inhibition of tubulin polymerization. Due to its toxicity, small molecule analogues of CA-4 have been sought out. We have designed a novel dual action CA-4 prodrug, YK-5-252, which releases the drug through a disulfide bond cleavage mechanism and contains a near-infrared (NIR) fluorophore, which allows fluorescence monitoring of cleavage. This disulfide linkage causes CA-4 to become effective only when released by glutathione (GSH) reducing the toxicity of the drug while simultaneously releasing the NIR fluorophore. Therefore the prodrug, YK-5-252, represents a novel CA-4 analogue which has reduced toxicity and can be used for theranostics imaging.
- Kong, Yali,Smith, Jacqueline,Li, Kongwen,Cui, Jake,Han, John,Hou, Shujie,Brown, Milton L.
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p. 2226 - 2233
(2017/03/23)
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- Probing hydrazine with a near-infrared fluorescent chemodosimeter
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Hydrazine is highly toxic to humans and animals when inhaled or in contact with the skin. It is also a very important chemical used as propellant, metal corrosion inhibitor, pharmaceutical and intermediate. The simple detection of hydrazine in solution and biosystems becomes very important as a consequence of the foregoing applications. Herein, we report a two-photon fluorescent probing method using a NIR fluorescent chemodosimeter, displaying turn-on fluorescence and color change after cleaving an O-acetyl moiety by hydrazine, which exhibits good selectivity and sensitively in solution and living cells.
- Ma, Jianhua,Fan, Jiangli,Li, Haidong,Yao, Qichao,Xia, Jing,Wang, Jingyun,Peng, Xiaojun
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- A red-NIR emissive probe for the selective detection of albumin in urine samples and live cells
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A dicyanomethylene-4H-chromene-derived turn-on fluorescence probe (TG-SA) has been designed and synthesised for the selective detection of human serum albumin (HSA). TG-SA exhibits good photostability and selective red-near infrared (NIR) fluorescence enhancement in the presence of HSA in complex samples containing numerous biological analytes. The probe predominantly binds domain II of HSA that accounts for the observed selective fluorescence enhancement. The red-NIR fluorescence probe TG-SA can be effectively used for staining HSA/SA in gel electrophoresis, quantification and validation of HSA in clinical urine samples and monitoring serum albumin in live cells.
- Rajasekhar,Achar, Chaithra J.,Govindaraju, Thimmaiah
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supporting information
p. 1584 - 1588
(2017/02/23)
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- Near infrared fluorescent probe substrate of dipeptidyl peptidase IV enzyme and preparation method and application thereof
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The invention provides a near infrared fluorescent probe substrate of dipeptidyl peptidase IV (DPP-IV) and a preparation method and application thereof, and belongs to the techinical field of biological medicine. The probe substrate is a glycine-based pro
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Paragraph 0015; 0033; 0047; 0048
(2017/08/31)
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- One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential
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A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone-and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations 3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected. Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 3 μM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 μM, whereas normal peripheral blood mononuclear cells were not affected.
- Talhi, Oualid,Brodziak-Jarosz, Lidia,Panning, Jana,Orlikova, Barbora,Zwergel, Clemens,Tzanova, Tzvetomira,Philippot, Stéphanie,Pinto, Diana C. G. A.,Paz, Filipe A. Almeida,Gerhaüser, Clarissa,Dick, Tobias P.,Jacob, Claus,Diederich, Marc,Bagrel, Denyse,Kirsch, Gilbert,Silva, Artur M. S.
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p. 965 - 975
(2016/03/01)
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- Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus
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Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure-activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.
- Dutter, Brendan F.,Mike, Laura A.,Reid, Paul R.,Chong, Katherine M.,Ramos-Hunter, Susan J.,Skaar, Eric P.,Sulikowski, Gary A.
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p. 1354 - 1361
(2016/06/09)
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- Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities
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Chromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O2?-), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen (1O2), and peroxyl radical (ROO?)] and reactive nitrogen species (RNS) [nitric oxide (?NO) and peroxynitrite anion (ONOO-)]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure-activity relationship.
- Proen?a, Carina,Albuquerque, Hélio M.T.,Ribeiro, Daniela,Freitas, Marisa,Santos, Clementina M.M.,Silva, Artur M.S.,Fernandes, Eduarda
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p. 381 - 392
(2016/04/06)
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- One-pot synthesis of 3-(furan-2-yl)-4: H -chromen-4-ones from 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran catalyzed via K10 montmorillonite under solvent-free conditions
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A new, concise and efficient method of one-pot synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was developed using K10 montmorillonite catalysis under solvent-free conditions. The procedure of the synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was that 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran underwent a process of α-alkoxyalkylation in the presence of K10 montmorillonite at 80 °C for 0.5 h and continuously at 120 °C for another 0.5 h. The advantages of this method were that it was solvent-free, the K10 montmorillonite was recyclable and it had an easy work-up.
- Han, Jie,Wang, Tao,Feng, Siqi,Li, Chenchen,Zhang, Zunting
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supporting information
p. 4092 - 4097
(2016/07/21)
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- GLUTATHIONE-CLEAVABLE PRODRUG AND METHODS OF USE THEREOF
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A glutathione-cleavable prodrug is provided herein, as well as methods for its use in treating cancer, including triple negative breast cancer. The prodrug can be cleaved by glutathione under physiological conditions to generate a biologically active agent. The compound described herein is advantageous as the compound is fluorescent and can therefore be monitored within a subject.
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Page/Page column 17
(2016/12/01)
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- A ratiometric fluorescent probe for quantification of alkaline phosphatase in living cells
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A ratiometric fluorescent probe with strong intramolecular charge transfer (ICT) character has been designed for the detection of alkaline phosphatase (ALP). In the presence of ALP, probe 1 showed a dramatic bathochromic shift from 550 to 650 nm in the fluorescence spectrum and an obvious ratiometric signal with an isoemissive point was observed. The spectral change was attributed to the hydrolysis and cleavage of a phosphate group from the probe that changed the ability of the intramolecular charge transfer. The fluorescence intensity ratio displayed a linear relationship against the concentration of ALP in the concentration range from 50 to 200 U L-1. Other biological species, including lysozyme, trypsin, pepsin, acetyl cholinesterase, carboxylesterase, and bovine serum albumin, did not induce distinct spectral changes of the probe, indicating its selective sensing ability to ALP. Furthermore, probe 1 was also successfully applied to image endogenous ALP activity in living cells.
- Lu, Zhenxing,Wu, Jiasheng,Liu, Weimin,Zhang, Guangyou,Wang, Pengfei
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p. 32046 - 32051
(2016/04/26)
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- A near-infrared fluorescent probe for rapid detection of hydrogen peroxide in living cells
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A new near-infrared and colorimetric fluorescent molecular probe was developed for rapid detection of H2O2. The near-infrared fluorescence OFF-ON switch is triggered by transformation of phenylboronic acid unit to phenol in the presence of H2O2. No quinone methides are released in this process, which is preferable for in vivo studies. In addition, probe 1 at low concentration exhibits high quality optical imaging during a short period in in vitro cell study.
- Zhang, Xuan,Zhang, Lun,Liu, Yaqian,Bao, Bin,Zang, Yi,Li, Jia,Lu, Wei
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p. 4842 - 4845
(2015/07/27)
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- A near-infrared chemodosimeter with Pi-selective colorimetric and fluorescent sensing and its application in vivo imaging
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A near-infrared colorimetric and fluorescent chemosensor for detecting phosphate ion (Pi) has been developed. The chemosensor's sensing mechanism is based on the Pi-driven cleavage of an amide bond which releases a fluorophore. The chemosensor exhibits a rapid response and high sensitivity towards Pi in DMSO-HEPES buffer (0.02 M, pH = 7.0) (v/v = 9:1). A colorimetric change with a 70 nm red-shift in the UV-vis absorbance spectrum and a 72-fold enhancement in the ratio of fluorescence intensities at 656 nm and 552 nm were observed. The practical utility of this chemosensor was demonstrated by employing it to detect Pi in Paramecium and C. elegans.
- Zang, Tie Nan,Zhao, Rui Rui,Yang, Xing Zhu,Gao, Yan,Wang, Guang Ke,Zhou, Ying,Liu, Bo,Zhang, Jun Feng
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p. 71756 - 71759
(2015/09/08)
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- TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products
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A concise and facile synthetic protocol for the construction of the 2-γ-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (±)-microdiplodiasone, (±)-lachnone C, and (±)-gonytolides C and G.
- Liu, Jie,Li, Zhanchao,Tong, Pei,Xie, Zhixiang,Zhang, Yuan,Li, Ying
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supporting information
p. 1632 - 1643
(2015/02/19)
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- A fluorescent probe for site i binding and sensitive discrimination of HSA from BSA
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A fluorescent probe DH1 has been successfully developed to detect HSA via site I non-covalent bonding. DH1 shows a dramatic fluorescence enhancement towards HSA without interference from other proteins. The molecular docking method, for the first time, was utilized to provide deep insight into the sensing mechanism of the probe. Moreover, probe DH1 was successfully used to detect trace HSA in healthy human urine. This journal is the Partner Organisations 2014.
- Fan, Jiangli,Sun, Wen,Wang, Zhenkuan,Peng, Xiaojun,Li, Yueqing,Cao, Jianfang
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supporting information
p. 9573 - 9576
(2014/08/18)
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- A two-photon fluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems
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Hydrogen sulfide (H2S) is emerging as an important gasotransmitter but remains difficult to study. Here we report a novel two-photon fluorescent probe with NIR emission for H2S detection. It was successfully used to realize H2S imaging in bovine serum, living cells, tissues as well as in living mice.
- Sun, Wen,Fan, Jiangli,Hu, Chong,Cao, Jianfang,Zhang, Hua,Xiong, Xiaoqing,Wang, Jingyun,Cui, Shuang,Sun, Shiguo,Peng, Xiaojun
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supporting information
p. 3890 - 3892
(2013/07/19)
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- A near-infrared fluorescent probe for hydrogen sulfide in living cells
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Fluorescent probes for hydrogen sulfide have received considerable attention because of the biological significance of H2S recognized recently. However, near-infrared fluorescent probes for H2S are still rare. In this work, a new near-infrared fluorescent probe for H2S was developed based on the reduction reaction of azide with H2S to amine based on the fluorophore of dicyanomethylene-4H-chromene because of its long excitation and emission wavelength. The probe has a high selectivity for H2S over competitive anions and sulfide-containing analytes. Finally, the probe was applied to sense H2S in living cells.
- Zheng, Yi,Zhao, Miao,Qiao, Qinglong,Liu, Huiying,Lang, Haijing,Xu, Zhaochao
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p. 367 - 371
(2013/07/19)
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- Highly efficient organic dyes containing a benzopyran ring as a π-bridge for DSSCs
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A series of novel organic dyes containing a benzopyran ring as a π-bridge have been designed and applied in dye-sensitized solar cells (DSSCs). This series of dyes show the excellent DSSCs' performance, due to their efficient light-to-photocurrent conversion in the region from 380 nm to 600 nm, with the highest IPCE values exceeding 90%. Through modification of the donor units, an efficiency as high as 7.5% has been achieved under standard light illumination (AM 1.5G, 100 mW cm-2) by the dye CC103. The Royal Society of Chemistry 2013.
- Chen, Cheng,Yang, Xichuan,Cheng, Ming,Zhang, Fuguo,Zhao, Jianghua,Sun, Licheng
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p. 12688 - 12693
(2013/08/23)
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- Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols
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Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright
- Zhao, Dongbing,Beiring, Bernhard,Glorius, Frank
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supporting information
p. 8454 - 8458
(2013/09/02)
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- Access to 2-alkyl chromanones via a conjugate addition approach
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The introduction of alkyl substituents at C-2 of chromanones via conjugate addition of silyl enol ethers to a variety of chromenones is reported. In most cases racemic 2-alkyl chromanones were obtained in good yield in the presence of TMSOTf. The copper(II)-promoted conjugate addition of silyl enol ethers to chromenones was also carried out, albeit in low yields and no selectivity. Reliable syntheses of the chromenones via acylation of the corresponding β-diketo-compounds are also described.
- Stubbing, Louise A.,Li, Freda F.,Furkert, Daniel P.,Caprio, Vittorio E.,Brimble, Margaret A.
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experimental part
p. 6948 - 6956
(2012/09/07)
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- Synthesis of novel 1-aryl-9 H -xanthen-9-ones
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A novel route for the synthesis of 1-aryl-9H-xanthen-9-ones is reported. This methodology involves the condensation of 2-methylchromone with cinnamaldehydes leading to (E,E)-2-(4-arylbuta-1,3-dien-1-yl)-4H-chromen-4-ones. The final steps involved electrocyclization and oxidation of the latter compounds, in an one-pot synthesis, giving the desired 1-aryl-9H-xanthen-9-ones. Georg Thieme Verlag Stuttgart - New York.
- Esteves, Cátia I. C.,Santos, Clementina M. M.,Brito, Cristela M.,Silva, Artur M. S.,Cavaleiro, José A. S.
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scheme or table
p. 1403 - 1406
(2011/08/03)
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- Efficient synthesis of chromones with alkenyl functionalities by the heck reaction
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The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl-substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine-free conditions using a phase-transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.
- Patonay, Tams,Vasas, Attila,Kiss-Szikszai, Attila,Silva, Artur M. S.,Cavaleiro, Jos A. S.
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experimental part
p. 1582 - 1593
(2011/08/04)
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- Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells
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A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC50 value of 28.9 μM against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 μM against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 μM induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q2 of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones.
- Shaw, Arthur Y.,Chang, Chun-Yi,Liau, Hao-Han,Lu, Pei-Jung,Chen, Hui-Ling,Yang, Chia-Ning,Li, Hao-Yi
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experimental part
p. 2552 - 2562
(2009/09/30)
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- New synthesis of 2,3-diarylxanthones
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A new synthesis for 2,3-diarylxanthones is described. This was accomplished by aldol condensation of 3-bromo-2-methylchromone with benzaldehydes leading to the formation of 3-bromo-2-styrylchromones, followed by Heck reaction with styrenes. Georg Thieme V
- Santos, Clementina M. M.,Silva, Artur M. S.,Cavaleiro, José A. S.
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p. 3095 - 3098
(2007/10/03)
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- Benzopyrans : Part 40 - Alumina mediated transformations of 4-oxo-4H-1- benzopyran-3-carbaldehyde, -3-carboxylic acid and their 2-methylhomologues
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In contact with alumina, the title aldehyde 1 (R = H, Me, Cl) gives the chromones 5 and 9,12 whereas the acid 2 affords the chromones 7, 10 and acetophenone 23. Alumina converts the aldehyde 3 to the xanthone 14, and the corresponding acid 4 to the chromone 8 and diketone 24.
- Ghosh, Chandra Kanta,Bhattacharyya, Samita
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p. 166 - 172
(2007/10/03)
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- Benzopyrans. Part 41.1 Reactions of 2-(2-dimethylaminovinyl)-lbenzopyran-4-ones with various dienophiles
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Dienamine 1 with W-phenylmaleimide and chromenone 14 as well as 15 produces, through initial [4 + 2]cycloaddition, xanthenones 10 and 18, respectively. Initial Michael addition of 1 to chromenones 14 and 16, and dimethyl acetylenedicarboxylate (DMAD), triggers the formation of xanthenone 19, 4-azaxanthenone 26 and substituted fumarate 49, respectively. Initial [2 + 2]cycloadducts of dienamines 1-3 with electrophilic acetylenes always undergo further transformations. Thus, 1 with DMAD, dibenzoylacetylene and ethyl propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43. Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP. Reaction of 3 with DMAD affords 36 exclusively. The Royal Society of Chemistry 1999.
- Ghosh, Chandra Kanta,Bhattacharyya, Samita,Ghosh, Chandreyi,Patra, Amarendra
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p. 3005 - 3013
(2007/10/03)
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