- Atom arrangement strategy for designing a turn-on 1H magnetic resonance probe: A dual activatable probe for multimodal detection of hypochlorite
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The first dual activatable hypochlorite (-OCl)-sensing probe was developed, based on a new proof-of-concept design involving signal-activatable 1H chemical probes using the triple-resonance NMR technique. The probe enabled fluorescen
- Doura, Tomohiro,Nonaka, Hiroshi,Sando, Shinsuke
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Read Online
- Marine natural products as inhibitors of cystathionine beta-synthase activity
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A library consisting of characterized marine natural products as well as synthetic derivatives was screened for compounds capable of inhibiting the production of hydrogen sulfide (H2S) by cystathionine beta-synthase (CBS). Eight hits were valid
- Thorson, Megan K.,Van Wagoner, Ryan M.,Harper, Mary Kay,Ireland, Chris M.,Majtan, Tomas,Kraus, Jan P.,Barrios, Amy M.
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Read Online
- O-fluorination of aromatic azides yields improved azido-based fluorescent probes for hydrogen sulfide: Synthesis, spectra, and bioimaging
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Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. To visualize the endogenous in situ production of H2S in real time, new coumarin- and boron-dipyrromethene- based fluorescent turn-on probes were developed for fast sensing of H2S in aqueous buffer and in living cells. Introduction of a fluoro group in the ortho position of the aromatic azide can lead to a greater than twofold increase in the rate of reaction with H2S. On the basis of o-fluorinated aromatic azides, fluorescent probes with high sensitivity and selectivity toward H2S over other biologically relevant species were designed and synthesized. The probes can be used to in situ to visualize exogenous H2S and d-cysteine-dependent endogenously produced H2S in living cells, which makes them promising tools for potential applications in H2S biology.
- Wei, Chao,Wang, Runyu,Wei, Lv,Cheng, Longhuai,Li, Zhifei,Xi, Zhen,Yi, Long
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Read Online
- Multicolor GLUT5-permeable fluorescent probes for fructose transport analysis
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The specificity of carbohydrate transporters towards their substrates poses a significant challenge for the development of molecular probes to monitor sugar uptake in cells for biochemical and biomedical applications. Herein we report a new set of coumarin-based fluorescent sugar conjugates applicable for the analysis of fructose uptake due to their free passage through the fructose-specific transporter GLUT5. The reported probes cover a broad range of the fluorescence spectrum providing essential tools for the evaluation of fructose transport capacity in live cells.
- Begoyan,Weseliński,Xia,Fedie,Kannan,Ferrier,Rao,Tanasova
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Read Online
- A Suite of Activity-Based Probes to Dissect the KLK Activome in Drug-Resistant Prostate Cancer
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Kallikrein-related peptidases (KLKs) are a family of secreted serine proteases, which form a network (the KLK activome) with an important role in proteolysis and signaling. In prostate cancer (PCa), increased KLK activity promotes tumor growth and metastasis through multiple biochemical pathways, and specific quantification and tracking of changes in the KLK activome could contribute to validation of KLKs as potential drug targets. Herein we report a technology platform based on novel activity-based probes (ABPs) and inhibitors enabling simultaneous orthogonal analysis of KLK2, KLK3, and KLK14 activity in hormone-responsive PCa cell lines and tumor homogenates. Importantly, we identifed a significant decoupling of KLK activity and abundance and suggest that KLK proteolysis should be considered as an additional parameter, along with the PSA blood test, for accurate PCa diagnosis and monitoring. Using selective inhibitors and multiplexed fluorescent activity-based protein profiling (ABPP), we dissect the KLK activome in PCa cells and show that increased KLK14 activity leads to a migratory phenotype. Furthermore, using biotinylated ABPs, we show that active KLK molecules are secreted into the bone microenvironment by PCa cells following stimulation by osteoblasts suggesting KLK-mediated signaling mechanisms could contribute to PCa metastasis to bone. Together our findings show that ABPP is a powerful approach to dissect dysregulation of the KLK activome as a promising and previously underappreciated therapeutic target in advanced PCa.
- Bakker, Alexander T.,Bevan, Charlotte L.,Bock, Nathalie,Clements, Judith A.,De Vita, Elena,Engelsberger, Elisabeth,Kryza, Thomas,Lovell, Scott,Maneiro, Maria,Neodo, Anna,Tanaka, Reiko J.,Tate, Edward W.,Williams, Elizabeth D.,Xu, Congyi,Zhang, Leran
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supporting information
p. 8911 - 8924
(2021/06/28)
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- Targeting of glut5 for transporter-mediated drug-delivery is contingent upon substrate hydrophilicity
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Specific link between high fructose uptake and cancer development and progression highlighted fructose transporters as potential means to achieve GLUT-mediated discrimination between normal and cancer cells. The gained expression of fructose-specific transporter GLUT5 in various cancers offers a possibility for developing cancer-specific imaging and bioactive agents. Herein, we explore the feasibility of delivering a bioactive agent through cancer-relevant fructose-specific transporter GLUT5. We employed specific targeting of GLUT5 by 2,5-anhydro-D-mannitol and investigated several drug conjugates for their ability to induce cancer-specific cytotoxicity. The proof-of-concept analysis was carried out for conjugates of chlorambucil (CLB) in GLUT5-positive breast cancer cells and normal breast cells. The cytotoxicity of conjugates was assessed over 24 h and 48 h, and significant dependence between cancer-selectivity and conjugate size was observed. The differences were found to relate to the loss of GLUT5-mediated uptake upon increased conjugate size and hydrophobicity. The findings provide information on the substrate tolerance of GLUT5 and highlight the importance of maintaining appropriate hydrophilicity for GLUT-mediated delivery.
- Nahrjou, Nazanin,Ghosh, Avik,Tanasova, Marina
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- Novel coumarin-based pH sensitive fluorescent probes for the highly alkaline pH region
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The design, synthesis and spectroscopic properties of novel polymerizable coumarin-based pH indicators are reported. They show a fluorescence response to pH in the highly alkaline pH region with calculated pKa values in the range of 12.2–12.5. Covalent immobilization of the indicators to polymer supports provides novel pH-sensitive materials that possess excellent photostability. The materials are sensitive to pH in a similar range and can be applied in optical pH sensors for measuring pH in various alkaline media.
- Grattan, Kenneth T. V.,Nguyen, T. Hien,Sun, Tong
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- Coumarin Schiff base derivative as well as preparation method and application thereof
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The invention relates to a coumarin Schiff base derivative as well as a preparation method and application thereof, belonging to the technical field of metal ion detection. The coumarin Schiff base compound is 2-hydroxyl Schiff base-4-methylcoumarin. The specific structural formula of the coumarin Schiff base derivative is as shown in the specification. The invention further relates to a preparation method and application of the coumarin Schiff base derivative. The coumarin Schiff base derivative is high in Cr selectivity and Cr sensitivity, high in binding capacity and beneficial forCr detection.
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Paragraph 0022; 0053; 0055-0080
(2020/11/25)
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- Gasotransmitter Regulation of Phosphatase Activity in Live Cells Studied by Three-Channel Imaging Correlation
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Enzyme activity in live cells is dynamically regulated by small-molecule transmitters for maintaining normal physiological functions. A few probes have been devised to measure intracellular enzyme activities by fluorescent imaging, but the study of the re
- Ou, Pan,Zhang, Ruilong,Liu, Zhengjie,Tian, Xiaohe,Han, Guangmei,Liu, Bianhua,Hu, Zhangjun,Zhang, Zhongping
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supporting information
p. 2261 - 2265
(2019/01/29)
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- Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents
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Cancer and diabetes are considered as two major diseases affecting human health worldwide. Various therapies are available for treatment of cancer and diabetes individually, peptide linkage containing proline sulfonamide can be a promising therapy for treatment of both cancer as well as diabetes. Here, we report design and synthesis of novel coumarin-proline sulfonamide derivatives as anticancer and antidiabetic agents. All the synthesized compounds were screened for their anticancer activity against lungs cancer cell line (A549) and breast cancer cell line (MCF7) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide dye (MTT)assay and antidiabetic activity using DPP-IV inhibition assay. Compound 16b showed excellent activity against breast cancer cell line (MCF7) with IC50 value of 1.07 μM. All compounds showed moderate DPP-IV inhibition.
- Durgapal, Sunil Dutt,Soman, Shubhangi S.
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supporting information
p. 2869 - 2883
(2019/08/22)
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- Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S)donors for lowering blood pressure
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Hydrogen sulfide (H2S)is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides, thiolactams and thioureas. Three different thionation methods based on the usage of a phosphorus pentasulfide and Lawesson reagent were applied to prepare the target thioamides and thiolactams. Furthermore, obtained H2S donors were evaluated both in in vivo and in vitro studies. The kinetic parameters of the liberating H2S was determined and compared with NaHS and GYY4137 using two different detection technics i.e.; fluorescence labeling 7-azido-4-methyl-2H-chromen-2-one and 5,5‘-dithiobis (2-nitrobenzoic acid), sulfhydryl probe, also known as the Ellman's reagent. We have proved that the amount of releasing H2S from these compounds is controllable through structural modifications. Finally, the present study shows a hypotensive response to an intravenous administration of the developed donors in the anesthetized rats.
- Zaorska, Ewelina,Hutsch, Tomasz,Gawry?-Kopczyńska, Marta,Ostaszewski, Ryszard,Ufnal, Marcin,Koszelewski, Dominik
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supporting information
(2019/04/29)
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- Design and synthesis of aminocoumarin derivatives as DPP-IV inhibitors and anticancer agents
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DPP-IV “a moonlighting protein” has immerged as promising pathway to control Type 2 diabetes as well as found to play key role in earlier stages of cancer. Here we have reported design, synthesis and applications of aminocoumarin derivatives as DPP-IV inhibitors. Compounds have been synthesized and studied for their DPP-IV inhibition activity. Three compounds have shown moderate inhibition at 100 μM concentration. All compounds were also screened for their anticancer activity against A549 (Lung cancer cell line), MCF-7 (Breast cancer cell line) using MTT assay. One of the compounds has shown very good anticancer activity with IC50 value 24 ± 0.1 nM against A549 cell line.
- Soni, Rina,Soman, Shubhangi S.
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p. 277 - 284
(2018/05/24)
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- Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents
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To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G0/G1 phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis.
- Yu, Haonan,Hou, Zhuang,Tian, Ye,Mou, Yanhua,Guo, Chun
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p. 434 - 449
(2018/04/14)
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- A dual-analyte probe: Hypoxia activated nitric oxide detection with phototriggered drug release ability
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A new strategy for the detection of hypoxia and NO succeeded by photocontrolled delivery of an anticancer agent has been demonstrated. The developed system is able to produce distinct responses (dual channel) upon interaction with hypoxia and NO. This probe can also release anticancer drugs upon photoirradiation acting potentially as both a dual-analyte imaging agent and a prodrug.
- Biswas, Sandipan,Rajesh,Barman, Shrabani,Bera, Manoranjan,Paul, Amrita,Mandal, Mahitosh,Pradeep Singh
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p. 7940 - 7943
(2018/07/25)
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- Synthesis and characterization of new inhibitors of cholinesterases based on N-phenylcarbamates: In vitro study of inhibitory effect, type of inhibition, lipophilicity and molecular docking
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Based on current treatment of Alzheimer's disease, where the carbamate inhibitor Rivastigmine is used, two series of carbamate derivatives were prepared: (i) N-phenylcarbamates with additional carbamate group (1–12) and (ii) N-phenylcarbamates with monosaccharide moiety (13–24). All compounds were tested for the inhibitory effect on both of the cholinesterases, electric eel acetylcholinesterase (eeAChE) and butyrylcholinesterase from equine serum (eqBChE) and the inhibitory activity (expressed as IC50 values) was compared with that of the established drugs Galanthamine and Rivastigmine. The compounds with two carbamate groups 1–12 revealed higher inhibitory efficiency on both cholinesterases in compared with monosaccharide derived carbamates 13–24 and with Rivastigmine. The significant decrease of inhibitory efficiency on eqBChE (also for eeAChE but in less manner) was observed after deacetalization of monosaccharide. Moreover, the type of inhibitory mechanism of five chosen compounds was studied. It was found, that compounds with two carbamate groups act presumably via a mixed inhibitory mechanism and the compounds with monosaccharide moiety act as non-competitive inhibitors. The lipophilicity of tested compounds was determined using partition coefficient. Specific positions of the inhibitors in the binding sites of cholinesterases were determined using molecular modeling and the results indicate the importance of phenylcarbamate orientation in the catalytic gorges of both enzymes.
- Vor?áková, Katarína,Májeková, Magdaléna,Horáková, Eva,Drabina, Pavel,Sedlák, Milo?,?těpánková, ?árka
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p. 280 - 289
(2018/04/06)
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- Intracellular detection of hazardous Cd2+ through a fluorescence imaging technique by using a nontoxic coumarin based sensor
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A new coumarin based turn on fluorescent sensor (R1) was reported for the detection of highly hazardous Cd2+ with excellent selectivity and sensitivity without any interference of other metal ions. The single crystal X-ray structure analysis of
- Kumari, Chanda,Sain, Dibyendu,Kumar, Ashish,Debnath, Sushanta,Saha, Partha,Dey, Swapan
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p. 2524 - 2531
(2017/03/08)
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- Ubiquitin 7-amino-4-carbamoylmethylcoumarin as an improved fluorogenic substrate for deubiquitinating enzymes
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A new fluorogenic substrate Ub-ACC (ubiquitin C-terminal 7-amino-4-carbamoylmethyl-coumarin) was developed for DUB (deubiquitinating enzyme) activity assays. This substrate can be synthesized with higher efficiency than the classical DUB substrate, Ub-AMC (ubiquitin C-terminal 7-amino-4-methylcoumarin). DUB assays using UCH-L3, OTUD2 and USP30 demonstrated that Ub-ACC shows nearly 2-fold higher sensitivity than Ub-AMC.
- Li, Yi-Tong,Huang, Yi-Chao,Xu, Yang,Pan, Man,Li, Yi-Ming
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p. 4085 - 4090
(2016/07/06)
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- Dual-Reactable Fluorescent Probes for Highly Selective and Sensitive Detection of Biological H2S
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Hydrogen sulfide (H2S) is an important endogenous signaling molecule with a variety of biological functions. Development of fluorescent probes for highly selective and sensitive detection of H2S is necessary. We show here that dual-reactable fluorescent H2S probes could react with higher selectivity than single-reactable probes. One of the dual-reactable probes gives more than 4000-fold turn-on response when reacting with H2S, the largest response among fluorescent H2S probes reported thus far. In addition, the probe could be used for high-throughput enzymatic assays and for the detection of Cys-induced H2S in cells and in zebrafish. These dual-reactable probes hold potential for highly selective and sensitive detection of H2S in biological systems. Two heads are better than one: Fluorescent probes with two types of reactive heads (R1 and R2) for H2S can lead to a higher selectivity than that of single-reactable probes (See Figure). The probe was used for highly selective and sensitive detection of biological H2S.
- Wei, Chao,Wang, Runyu,Zhang, Changyu,Xu, Guoce,Li, Yanyan,Zhang, Qiang-Zhe,Li, Lu-Yuan,Yi, Long,Xi, Zhen
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supporting information
p. 1376 - 1381
(2016/05/19)
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- Synthesis and fluorescence study of 6,7-diaminocoumarin and its imidazolo derivatives
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Novel 6,7-diamino-4-methylcoumarin and derived imidazolocoumarins were synthesized and their absorption and fluorescence properties were recorded in solvents of varying polarity. 6,7-Diamino-4-methylcoumarin is highly fluorescent, with a quantum yield of
- Sheshashena Reddy,Ram Reddy
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p. 525 - 534
(2013/02/22)
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- PET-dependent fluorescence sensing of enzyme reactions using the large and tunable pKa shift of aliphatic amines
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A fluorescence sensing system exploiting the large and finely tunable pKa shift of aliphatic amines was developed. The amine-containing fluorescent probes with distinct pKa values in a wide pH range were successfully applied to detect a variety of enzyme reactions with a large and real-time fluorescence enhancement.
- Oshikawa, Yuji,Ojida, Akio
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supporting information
p. 11373 - 11375
(2013/12/04)
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- Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function
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Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions.
- Kathuria, Abha,Priya, Nivedita,Chand, Karam,Singh, Prabhjot,Gupta, Anjali,Jalal, Sarah,Gupta, Shilpi,Raj, Hanumantharao G.,Sharma, Sunil K.
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experimental part
p. 1624 - 1638
(2012/05/04)
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- COUMARIN COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS
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The present invention relates to method for treating mycobacterial infection/disease by administration of a therapeutically effective amount of compound of formula I.
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Page/Page column 13-14
(2012/10/18)
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- Non-conjugated dendrimers with a porphyrin core and coumarin chromophores as peripheral units: Synthesis and photophysical properties
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Three porphyrin-cored dendrimers with non-conjugated coumarins as dendrons have been synthesized and characterized. The photophysical properties of the title compounds were investigated by means of UV/Vis absorption and fluorescence spectroscopy in dilute CH2Cl2 solutions and in thin neat films. The intramolecular energy transfer from the coumarin units to the porphyrin core clearly reveals two factors influencing energy-transfer efficiency. Firstly, a better spectral overlap between the absorption spectrum of porphyrin core and the emission spectrum of the coumarin moiety results in high energy-transfer efficiency. Secondly, a long alkyl side-chain improves solubility of dendrimers, but also prevents the coumarins from self-quenching. Hence, the dendrimer with N-octyl groups possesses a higher efficiency than that with N-ethyl groups. The dendrimers emit red light with higher fluorescence quantum yields over the free porphyrin.
- Mao, Mao,Song, Qin-Hua
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scheme or table
p. 975 - 981
(2012/03/27)
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- A macrocyclic coumarin-containing tripeptide via CuAAC chemistry
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A Cu-catalysed macrocyclisation was performed to obtain a macrocyclic coumarin-containing tripeptide for use in thrombin activity measurements.
- Van Berkel, Sander S.,Van Der Lee, Bas,Van Delft, Floris L.,Rutjes, Floris P. J. T.
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supporting information; experimental part
p. 4272 - 4274
(2011/03/19)
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- Synthesis and evaluation of antiinflammatory and analgesic activities of a novel series of substituted-N-(4-methyl-2-oxo-2H-chromen-7-yl) benzamides
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A novel series of coumarinyl amides (IVa-1) have been synthesized by reacting 7-amino-4-methylcoumarin (III) with various substituted aromatic acid chlorides. IR, 1H NMR, 13C NMR and HRMS spectral data characterized the structure of the synthesized compounds. The title compounds were screened for in vivo acute anti-inflammatory activity using the carrageenan-induced rat paw edema assay model. Among the compounds tested, 2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVb) and 4-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVc) showed 60.5 and 62.3% edema protection, respectively, as compared to the standard drug diclofenac (CAS 15307-86-5) (63.5%) after third hour. Compounds N-(4-methyl-2-oxo-2H- chromen-7-yl)-4-nitrobenzamide (IVf) and N-(4-methyl-2-oxo-2H-chromen-7-yl) cinnamamide (IVg) showed moderate activity. The new compounds have been also tested for in vivo analgesic activity. Quantitative structure-activity relationship studies indicated that the chloro substitution at the aromatic ring enhanced the anti-inflammatory activity (IVb and IVc). These compounds were also found to provide significant protection in acetic acid induced writhing animal model, showing remarkable analgesic activity. Compounds IVb and IVc showed 55.1% and 56.3% protection, respectively, as compared to acetylsalicylic acid (CAS 50-78-2) (57.7%). ECV - Editio Cantor Verlag.
- Ronad, Pradeepkumar M.,Hunashal, Rajesh D.,Darbhamalla, Satyanarayana,Maddi, Veeresh S.
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experimental part
p. 641 - 646
(2009/04/10)
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- Coumarin-coupled receptor as a membrane-permeable, Cu2+- selective fluorescent chemosensor for imaging copper(II) in HEPG-2 cell
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A novel fluorescent chemosensor 1 for imaging labile Cu2+ in living biological samples was designed and synthesized; it exhibits very strong fluorescence responses to Cu2+, and its LSM images strongly support the existence of Cu2+ in HEGP-2 cell. Copyright
- Wang, Mao-Xiang,Huang, Sheng-Hai,Meng, Xiang-Ming,Zhu, Man-Zhou,Guo, Qing-Xiang
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p. 462 - 465
(2008/09/20)
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- Synthesis, photophysical, photochemical and biological properties of caged GABA, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] butanoic acid
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The photorelease of a caged neurotransmitter can be used to investigate the function of neuronal circuits in tissues. We have designed and synthesized a stable, caged γ-aminobutyric acid (GABA) derivative, 4-[[(2H-l-benzopyran- 2-one-7-amino-4-methoxy)carbonyl]amino] butanoic acid (BC204), that releases the neurotransmitter in physiological medium when irradiated with UV light at 300-400 nm in PBS at pH 7.4. The release of GABA occurs with the formation of the major photoproduct, 7-amino-4-(hydroxymethyl)-2H-1-benzopyran-2-one, via a solvolytic photodegradation mechanism of the coumarin moiety and was confirmed by electrospray mass spectrometry/mass spectrometry (ESI MS/MS). BC204 is chemically stable and shows no intrinsic activity after many hours under physiological dark conditions. These properties suggest that BC204 is an excellent form of caged GABA that is well suited for long-term biological studies.
- Cuerten, Beate,Kullmann, Paul H. M.,Bier, Mark E.,Kandler, Karl,Schmidt, Brigitte F.
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p. 641 - 648
(2008/02/03)
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- Expedient solid-phase synthesis of fluorogenic protease substrates using the 7-amino-4-carbamoylmethylcoumarin (ACC) fluorophore
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A highly efficient solid-phase synthesis method for the preparation of fluorogenic protease substrates based upon the bifunctional leaving group 7-amino-4-carbamoylmethylcoumarin (ACC) is reported. Methods for the large-scale preparation of the novel fluorogenic leaving-group ACC are provided (Scheme 1). Detailed procedures are also provided for loading a diverse set of amino acids to support-bound ACC in good yields and with minimal racemization. Finally, procedures are included for the preparative synthesis of optimized ACC substrates for HIV-1 protease and plasmin.
- Maly, Dustin J.,Leonetti, Francesco,Backes, Bradley J.,Dauber, Deborah S.,Harris, Jennifer L.,Craik, Charles S.,Ellman, Jonathan A.
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p. 910 - 915
(2007/10/03)
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- A labeled guanidine ligand for studying sweet taste
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A synthesis of a biotinylated-, coumarin-substituted-N,N'-diarylguanidin 1 is reported. This ligand has structural features conducive to studying sweet taste including a fluorescent tag to facilitate spectroscopic studies of binding to protein-receptors f
- Feng, Yangbo,Burgess, Kevin,Pledger, David,Cairns, Nick,Linthicum, D. Scott
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p. 881 - 884
(2007/10/03)
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- Synthesis and structure-activity relationships of new β-adrenoreceptor antagonists. Evidence for the electrostatic requirements for β-adrenoreceptor antagonists
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A series of mono- and disubstituted phenoxypropanolamines, structurally related to practolol and acebutolol, has been synthesized and tested for β-adrenoreceptor blocking activity. Structure-activity relationships are discussed. The reasons for the lack of activity of compounds 3n and 4n have also been examined. The results suggest that the negative electrostatic potential above the phenyl ring of phenoxypropanolamines is essential for binding activity and point to the presence of an electropositive residue in the β-adrenoreceptor binding site.
- Kettmann,Csollei,Racanska,Svec
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p. 843 - 851
(2007/10/02)
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- Process for the preparation of herbicidally active phenyl carbamates
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Herbicidally active substituted phenyl carbamates I STR1 in which R1 represents a C1 -C6 alkyl group, a C3 -C6 cycloalkyl group or an aryl group, which aryl group may be substituted by a halogen atom and/or a C1 -C6 alkyl group and/or a trifluoromethyl group, and R2 represents a C1 -C6 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl group that may be substituted by a terminal halogen atom, are prepared by reacting N-hydroxyphenyl carbamates II STR2 with either isocyanates R1 --N=C=O or amino chlorides R1 --NH--COCl in an aqueous medium thus avoiding the use of organic solvents. The end product I may be extracted from the aqueous slurry into a water-immiscible solvent. The N-hydroxyphenyl carbamates II can be prepared by reacting 3-aminophenol with chloroformates in an aqueous medium, and the resulting product may be reacted in situ, without isolation, with isocyanates, in the same reaction vessel. Stabilized herbicidal compositions containing compounds I may be prepared by suspending the compounds I in a liquid phase comprising one or more oily components and one or more surfactants.
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