cas 1214-24-0, 3,6-Dimethoxyxanthone | Articles data

Articles about 1214-24-0Total 51 be found

Article title
Article abstract
Author
Journal number and time
Download

Multiligand interactions at the combining site of anti-fluorescyl antibodies. Molecular recognition and connectivity
Partitioning of binding energy among the constituent subsites in a ligand-antibody complex can be useful in assessment of bimolecular processes in the combining site. Binding affinities of five anti-fluorescyl monoclonal antibodies for fluorescein (1) and two compounds representing its component parts, xanthenone (2) and benzoate, were studied by the fluorescence quenching technique. Dissociation constants were found to be in the range 10-12- 10-10 M for 1, 10-8- 10-7 M for 2, and 10-3- 10-1 M for benzoate. Binding at both subsites was found to depend strongly on the recognition of polar or charged groups. The carboxylate accounts for ca. 4 kcal/mol for binding at the benzoate site whereas two hydroxyl groups contribute at least 5.5 kcal/mol toward binding of xanthene derivatives. The thermodynamic changes associated with ligand binding were described in terms of the intrinsic (ΔG(i)) and the 'connection' (ΔG(S)) free energies. The connection free energies, estimated at 1.0-2.5 kcal/mol, represent a lower limit for reduction of the entropic energy barrier to bimolecular reactions that would ensue from binding of two reactants prior to chemical transformation. Study of this model system provides a thermodynamic rationale for the utility of monoclonal antibodies as catalysts for bimolecular processes.
Janjic,Schloeder,Tramontano
p. 6374 - 6377
(1989)
Read Online

Polysulfated xanthones: Multipathway development of a new generation of dual anticoagulant/antiplatelet agents
A multipathway strategy was used to evaluate the in vitro and in vivo antithrombotic effects of a new synthetic family of sulfated small molecules. Polysulfated xanthonosides showed highly effective anticoagulation effects in vitro, both in plasma (clotting times) and in whole human blood (thromboelastography), as well as in vivo (ip administration, mice). Physicochemical properties were assessed for mangiferin heptasulfate (7), which showed high solubility and stability in water and in human plasma and no putative hepatotoxicity in vivo. Mangiferin heptasulfate (7) was found to be a direct inhibitor of FXa, while persulfated 3,6-(O-β-glucopyranosyl)xanthone (13) acted as a dual inhibitor of FXa (directly and by antithrombin III activation). By impedance aggregometry, compounds 7 and 13 exhibited the antiplatelet effect by inhibition of both arachidonic acid and ADP-induced platelet aggregation. Dual anticoagulant/antiplatelet agents, such as sulfated xanthonosides 7 and 13, are expected to lead to a new therapeutic approach for the treatment of both venous and arterial thrombosis.
Correia-Da-Silva, Marta,Sousa, Emília,Duarte, Bárbara,Marques, Franklim,Carvalho, Félix,Cunha-Ribeiro, Luís M.,Pinto, Madalena M. M.
p. 5373 - 5384
(2011)
Read Online

Mitochondria-anchored colorimetric and ratiometric fluorescent chemosensor for visualizing cysteine/homocysteine in living cells and daphnia magna model
Cysteine (Cys) and homocysteine (Hcy) are essential for maintaining the cellular redox homeostasis and play critical roles in pathological and physiological processes. The development of Cys/Hcy-specific responsive fluorescent probes that are independent
Yang, Mingwang,Fan, Jiangli,Sun, Wen,Du, Jianjun,Peng, Xiaojun
p. 12531 - 12537
(2019)
Read Online

Fluorescein analogue xanthene-9-carboxylic acid: A transition-metal-free CO releasing molecule activated by green light
6-Hydroxy-3-oxo-3H-xanthene-9-carboxylic acid is introduced as the first transition-metal-free carbon monoxide releasing molecule activated by visible light (photoCORM). This water-soluble fluorescein analogue releases carbon monoxide in both water and methanol upon irradiation at 500 nm. When selectively irradiated in the presence of hemoglobin (Hb) under physiological conditions, released CO is quantitatively trapped to form carboxyhemoglobin (COHb). The reaction progress can be accurately monitored by characteristic absorption and emission properties of the reactants and products.
Antony, Lovely Angel Panamparambil,Slanina, Tomas,Sebej, Peter,Solomek, Tomas,Klan, Petr
p. 4552 - 4555
(2013)
Read Online

A Cu-free clickable fluorescent probe for intracellular targeting of small biomolecules
We synthesized a novel cyclooctyne-based clickable fluorescent probe with versatile properties such as high cell-membrane permeability and free diffusibility in the cell. Our probe "FC-DBCO" was conjugated to an azide-modified mannose via a Cu-free click
Yamagishi, Kento,Sawaki, Kazuaki,Murata, Atsushi,Takeoka, Shinji
p. 7879 - 7882
(2015)
Read Online

-
-
Pomerantz et al.
p. 2183,2189
(1972)
Read Online

Xanthene and xanthone derivatives as G-quadruplex stabilizing ligands
Following previous studies on anthraquinone and acridine-based G-quadruplex ligands, here we present a study of similar aromatic cores, with the specific aim of increasing G-quadruplex binding and selectivity with respect to duplex DNA. Synthesized compounds include two and three-side chain xanthone and xanthene derivatives, as well as a dimeric "bridged" form. ESI and FRET measurements suggest that all the studied molecules are good G-quadruplex ligands, both at telomeres and on G-quadruplex forming sequences of oncogene promoters. The dimeric compound and the three-side chain xanthone derivative have been shown to represent the best compounds emerging from the different series of ligands presented here, having also high selectivity for G-quadruplex structures with respect to duplex DNA. Molecular modeling simulations are in broad agreement with the experimental data.
Altieri, Alessandro,Alvino, Antonello,Ohnmacht, Stephan,Ortaggi, Giancarlo,Neidle, Stephen,Nocioni, Daniele,Franceschin, Marco,Bianco, Armandodoriano
p. 13446 - 13470
(2013)
Read Online

Design, molecular docking study and synthesis of 3,6-bis(3'-substituted propoxy)xanthone derivatives as COX-2 inhibitors
New drug discovery is considered broadly in terms of two kinds of investigational activities such as exploration and exploitation. Docking of small molecules in the receptor binding site and estimation of binding affinity of the complex is a vital part of
Shankar, Brajesh,Das, Aparoop,Parida, Pratap
p. 4634 - 4640
(2015)
Read Online

Antihypertensive activity, toxicity and molecular docking study of newly synthesized xanthon derivatives (xanthonoxypropanolamine)
Context Xanthone derivatives have been reported to possess a wide range of biological properties. In effort to search new effective antihypertensive compounds, we have synthesizednovel xanthone derivatives (xanthonoxypropanolamines) and got patent for these compounds (The Patent Office, Government of India, S. No.: 011–016308, Patent No.: 250538). Objective In the present work, we attempted to establish the antihypertensive activity, toxicity and molecular docking study forthese newly synthesized compounds (1a, 1b and 2). Materials and method The preliminary antihypertensive screening was performed by administering synthesized compounds and standard drugs intraperitonially and orally into wistar rats. The change in systolic, diastolic and the mean blood pressure before and after the treatment of the drugs was measured on a Digital LE-S100 Blood Pressure Meter by Tail-cuff method non-invasively. Toxicity studies were carried out after oral administration of synthesized compounds to rats at doses of 25, 50, and 100mg/kg. The serum samples were tested for different toxicity parameters such as liver function test, kidney function test etc. The docking simulations of all the compounds were performed using Maestro, version 9.4 implemented from Schrodinger software suite. Results and discussion The result showed that the compound 1a, 1b and 2 have greater antihypertensive activity with almost equal or less toxicity profile in comparison to standard drug Propranolol and Atenolol. The docking score for the compound 1b was found -9.1 while for compound 1a and 2 were found -8.7 and -8.6 respectively. Conclusion These novel compounds i.e. 1a, 1b, and 2 have greater antihypertensive activity in comparison to standard drugs Propranolol and Atenolol. All these compounds do not have any toxicity.
Goshain, Omprakash,Ahmed, Bahar
(2019)
Read Online

Antifungal Activity of Xanthones: Evaluation of their Effect on Ergosterol Biosynthesis by High-performance Liquid Chromatography
The increasing resistance of pathogenic fungi to antifungal compounds and the reduced number of available drugs led to the search for therapeutic alternatives among natural products, including xanthones. The antifungal activity of 27 simple oxygenated xanthones was evaluated by determination of their minimal inhibitory concentration on clinical and type strains of Candida, Cryptococcus, Aspergillus and dermatophytes, and their preponderance on the dermatophytic filamentous fungi was observed. Furthermore, a simple and efficient HPLC method with UV detection to study the effect of the active xanthones on the biosynthesis of ergosterol was developed and validated. Using this methodology, the identification and quantification of fungal sterols in whole cells of Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, and Trichophyton mentagrophytes were accomplished. In summary, 1,2-dihydroxyxanthone was found to be the most active compound against all strains tested, showing its effect on sterol biosynthesis by reducing the amount of ergosterol detected.
Pinto, Eugenia,Afonso, Carlos,Duarte, Serafim,Vale-Silva, Luis,Costa, Elisangela,Sousa, Emilia,Pinto, Madalena
p. 212 - 222
(2011)
Read Online

A Turn-On Fluorescent Probe for Detection of Sub-ppm Levels of a Sulfur Mustard Simulant with High Selectivity
A new type of fluorescent probe capable of detecting a sulfur mustard (SM) simultant at a concentration of 1.2 μM in solution and 0.5 ppm in the gas phase has been developed. Owing to its molecular structure with a thiocarbonyl component and two piperidyl
Zhang, Yuanlin,Lv, Yanlin,Wang, Xuefei,Peng, Aidong,Zhang, Kaiquan,Jie, Xiaoke,Huang, Jijun,Tian, Zhiyuan
p. 5481 - 5488
(2018)
Read Online

Synthesis and anticancer potential of novel xanthone derivatives with 3,6-substituted chains
In an effort to develop new drug candidates with enhanced anticancer activity, our team synthesized and assessed the cytotoxicity of a series of novel xanthone derivatives with two longer 3,6-disubstituted amine carbonyl methoxy side chains on either benzene ring in selected human cancer cell lines. An MTT assay revealed that a set of compounds with lower IC50values than the positive control, 5-FU, exhibited greater anticancer effects. The most potent derivative (XD8) exhibited anticancer activity in MDA-MB-231, PC-3, A549, AsPC-1, and HCT116 cells lines with IC50values of 8.06, 6.18, 4.59, 4.76, and 6.09?μM, respectively. Cell cycle analysis and apoptosis activation suggested that the mechanism of action of these derivatives includes cell cycle regulation and apoptosis induction.
Liu, Chaomei,Zhang, Mei,Zhang, Zhenhuan,Zhang, Steven B.,Yang, Shanmin,Zhang, Amy,Yin, Liangjie,Swarts, Steven,Vidyasagar, Sadasivan,Zhang, Lurong,Okunieff, Paul
p. 4263 - 4271
(2016)
Read Online

Fluorescently Labeled Cyclodextrin Derivatives as Exogenous Markers for Real-Time Transcutaneous Measurement of Renal Function
Evaluation of renal function is crucial for a number of clinical situations. Here, we reported a novel exogenous fluorescent marker (FITC-HPβCD) to real-time assess renal function by using a transcutaneous fluorescent detection technique. FITC-HPβCD was designed based on the principle of renal clearance of designed drugs. It displays favorable fluorescent properties, high hydrophilicity, low plasma protein binding, and high stability in porcine liver esterase as well as in plasma and nontoxicity. More importantly, FITC-HPβCD can be efficiently and rapidly filtered by glomerulus and completely excreted into urine without proximal tubular reabsorption or secretion in rat models. Additionally, the marker was well-tolerated, with nearly 100% urinary recovery of the given doses, and no metabolism were found. Relying on this novel kidney function marker and transcutaneous devices, we demonstrate a rapid, robust, and convenient approach for real-time assessing renal function without the need of time-consuming blood and urine sample preparation. Our work provides a promising tool for noninvasive real-time monitoring of renal function in vivo.
Huang, Jiaguo,Weinfurter, Stefanie,Pinto, Pedro Caetano,Pretze, Marc,Kr?nzlin, Bettina,Pill, Johannes,Federica, Rodeghiero,Perciaccante, Rossana,Ciana, Leopoldo Della,Masereeuw, Rosalinde,Gretz, Norbert
p. 2513 - 2526
(2016)
Read Online

Xanthone as antimalarial: QSAR analysis, synthesis, molecular docking and in-vitro antimalarial evaluation
The rational design of eighteen new antimalarial compounds from xanthone derivatives has been conducted based on Quantitative Structure-Activity Relationship (QSAR) calculation using semiempirical AM1 methods. The best equation model obtained from QSAR calculation was Log pIC50 = 2.997 - 29.256 (qO8) - 138.234 (qC9) - 6.882 (qC12) - 107.836 (qC14) + 48.764 (qO15). Among the designed compounds, 3,6-dihydroxy-9H-xanthen-9-one (26) and 3,4,6-trihydroxy-9H-xanthen-9-one (27) have been synthesized and investigated their in-vitro antimalarial activities against the chloroquine-sensitive 3D7 strain. An in-vitro antimalarial activity of compound 26 and 27 showed to be highly potential as antimalarial compounds with IC50 of 0.71 and 0.11 μM respectively. Molecular docking studies of compound 26 and 27 showed the formation of a binding interaction between the compounds with the amino acids Ala16, Ser108, Phe58, Asp54 and Leu46, which is the crucial amino acids for antimalarial activity based on the protein-ligand co-crystal structure of WR99210 (1,3,5-triazine, a pre-clinical molecule as P. falciparum DHFR-TS inhibitor).
Syahri, Jufrizal,Yuanita, Emmy,Nurohmah, Beta Achromi,Wathon, Muhammad Hizbul,Syafri, Rahmadini,Armunanto, Ria,Purwono, Bambang
p. 29 - 40
(2017)
Read Online

Development of azo-based fluorescent probes to detect different levels of hypoxia
Let it shine: New hypoxia-sensitive fluorescent probes were developed; they consist of a rhodamine moiety with an azo group directly conjugated to the fluorophore. Because of an ultrafast conformational change around the N=N bond, the compounds are nonflu
Piao, Wen,Tsuda, Satoru,Tanaka, Yuji,Maeda, Satoshi,Liu, Fengyi,Takahashi, Shodai,Kushida, Yu,Komatsu, Toru,Ueno, Tasuku,Terai, Takuya,Nakazawa, Toru,Uchiyama, Masanobu,Morokuma, Keiji,Nagano, Tetsuo,Hanaoka, Kenjiro
p. 13028 - 13032
(2013)
Read Online

A highly selective reaction-based two-photon probe for Copper(I) in aqueous media
Out of the blue: A reaction-based two-photon probe XanCu (see scheme) is reported for the selective detection of Cu+ in reducing aqueous environments. Copper(I)-mediated oxidative benzylic ether (Ci￡ O) bond cleavage offers switch-on detection of the metal ion. Copyright
Maity, Debabrata,Sarkar, Bidyut,Maiti, Sudipta,Govindaraju
p. 785 - 788
(2013)
Read Online

Design, synthesis and biological evaluation of Rose Bengal analogues as SecA inhibitors
SecA, a key component of bacterial Sec-dependent secretion pathway, is an attractive target for exploring novel antimicrobials. Rose bengal (RB), a polyhalogenated fluorescein derivative, was found from our previous study as a potent SecA inhibitor. Here we describe the synthesis and structure-activity relationships (SAR) of 23 RB analogues that were designed by systematical dissection of RB. Evaluation of these analogues allowed us to establish an initial SAR in SecA inhibition. The antimicrobial effects of these SecA inhibitors are confirmed in experiments using E.coli and B.subtilis.
Cui, Jianmei,Jin, Jinshan,Hsieh, Ying-Hsin,Yang, Hsiuchin,Ke, Bowen,Damera, Krishna,Tai, Phang C.,Wang, Binghe
p. 1384 - 1393
(2013)
Read Online

Microwave-assisted efficient and green synthesis of hydroxyxanthone in water
An efficient and green procedure has been developed for the synthesis of hydroxyxanthones from substituted 2,2-dihydroxybenzophenone precursors via microwave-assisted base-catalyzed cyclization in water. This method provides excellent yields of products in a short time, making it a useful strategy for the synthesis of structurally diverse hydroxyxanthones.
Zhang, Xiao-Jin,Ye, Suo-Fu,Zhang, Yu,Meng, Hu-Yan,Zhang, Ming-Qian,Gao, Wen-Lei,You, Qi-Dong
p. 2952 - 2958
(2012)
Read Online

A palate of fluorescent corannulene derivatives: Synthesis, spectroscopic properties, and bio-imaging application
Reported here is a palate of fluorescent corannulene derivatives suitable for cellular imaging. They are derived from "tagging"corannulene with known fluorophores. The tagged corannulenes display strong fluorescence (?F > 0.25 in MeOH), good photostability and long emission wavelength (500 nm to 600 nm). Cell staining experiments indicate that several of them have excellent cell membrane permeability and targeting ability. In addition, we have found an unexpected, highly efficient energy transfer from corannulene to the pendant fluorophore. This has implications for many areas of corannulene research.
Finney, Nathaniel S.,Gao, Yan,Jiang, Haiyan,Liu, Xueling,Wang, Yali,Xu, Jun
supporting information
p. 5818 - 5821
(2021/06/16)

Optical detection of sulfur mustard contaminated surfaces based on a sprayable fluorescent probe
Chemical warfare agents (CWAs) pose an inevitable threat, both to soldiers and civilians. There have been many incidents where CWAs have claimed thousands of lives and contaminated many more people. In this regard, strict control and proper decontamination are equally important. Here, we present a visualization method to locate sulfur mustard (HD)-contaminated surfaces using a water-based sprayable polymer containing a sulfur mustard fluorescent probe (DPXT). After confirming the high sensitivity (0.9 μM) and selectivity of DPXT in aqueous solution toward sulfur mustard, a sprayable material was developed by immobilizing the DPXT in a water-soluble polymer. This method enables the localization of HD-contaminated areas through a fluorescence response detectible by the naked eye. Sprayable HD sensors present obvious advantages over other sensors since they do not necessitate damage to the surface of interest. In our perception, this sensing protocol also holds great potential in sensing and localizing other CWAs, and will be a powerful tool for monitoring decontamination processes. This journal is
Dong, Bin,Gao, Shi,Ma, Bin,Wang, Xuefeng,You, Lijuan,Zuo, Guomin
supporting information
p. 20569 - 20574
(2021/11/27)

ORGANIC ELECTROLUMINESCENT ELEMENT AND POLYCYCLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENT ELEMENT
PROBLEM TO BE SOLVED: To provide an organic electroluminescent element with high efficiency and a polycyclic compound used for the same. SOLUTION: An organic electroluminescent element includes a first electrode EL1, an organic layer OL, and a second electrode EL2, and the organic layer OL includes a polycyclic compound expressed by Chemical Formula 1 (Chemical Formula 1). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2021,JPOandINPIT
-
Paragraph 0171-0172

(2021/09/10)

New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms
Recently, we reported the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently bonded to a chromatographic support and further packed into LC stainless-steel columns (150?×?2.1?mm I.D.). The enantioselective performance of the new CSPs was evaluated by LC using different classes of chiral compounds. Specificity for enantioseparation of some CDXs was observed in the evaluation of the new CSPs. Besides, assessment of chiral recognition mechanisms was performed by computational studies using molecular docking approach, which are in accordance with the chromatographic parameters. X-Ray analysis was used to establish a chiral selector 3D structure.
Phyo, Ye' Zaw,Teixeira, Joana,Tiritan, Maria Elizabeth,Cravo, Sara,Palmeira, Andreia,Gales, Luís,Silva, Artur M.S.,Pinto, Madalena M.M.,Kijjoa, Anake,Fernandes, Carla
supporting information
p. 81 - 97
(2019/11/28)

Single-Molecule Imaging of Active Mitochondrial Nitroreductases Using a Photo-Crosslinking Fluorescent Sensor
Many biomacromolecules are known to cluster in microdomains with specific subcellular localization. In the case of enzymes, this clustering greatly defines their biological functions. Nitroreductases are enzymes capable of reducing nitro groups to amines,
Thiel, Zacharias,Rivera-Fuentes, Pablo
supporting information
p. 11474 - 11478
(2019/07/10)

Polyphosphoric acid terminal fluorescence labeled nucleotide and application thereof
The invention relates to a 5 '-end phosphoric acid fluorescent labeled nucleotide, and provides a molecular structure and a synthesis method. The molecule can be better identified by DNA polymerase, and after the molecule is identified by the DNA polymerase, and reacted with the DNA polymerase for combination, and with the aid of alkaline phosphatase, the transform from the close to open state of a fluorescence signal can be rapidly realized, so that the 5 '-end phosphoric acid fluorescent labeled nucleotide as a polymerase substrate can be used in the nucleic acid sequence determination and other fields.
-
Paragraph 0046-0049

(2019/11/29)

XANTHINE COMPOUND AND USE THEREOF
A fluorescent probe for measurement of CYP3A activity, having an excellent CYP molecular species selectivity and detection sensitivity represented is represented by the following formula: In the formula, R1 represents a monovalent group, R2 represents a hydrogen atom or a monovalent group, R3 and R4 each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, R5 represents a monovalent group selected so that the ether bond of the O-benzyl moiety at the 6th position of the compound represented by formula (I) is oxidatively cleavable by the molecular species 3A of the cytochrome P-450, n represents an integer from 1 to 5, and when n is 2 or more, all or a part of the plurality of R5s may be the same as each other or different from each other.
-
Paragraph 0058; 0061

(2018/11/21)

Development of xanthene dyes containing arylacetylenes: The role of acetylene linker and substituents on the aryl group
Fluorescent dyes possessing a variety of arylacetylenes at the 9-position of a xanthene skeleton were synthesized and their optical properties were investigated. The π system effectively expanded over the xanthene skeleton and the aryl group through the triple bond. Starting from the emission wavelength (λem) of 9-methyl xanthene 20 in basic DMSO solution at 536 nm, the emission wavelengths gradually shifted to the red region for methylacetylene 17 (λem = 600 nm), phenylacetylene 5 (λem = 636 nm), and p-CF3-phenylacetylene 11 (λem = 660 nm). On the basis of these data, we estimated the substituent effects for the red shift on the emission wavelength and rationally explained the results by DFT calculations. Furthermore, potential applicability of these fluorescent dyes to cell staining was exemplified.
Hirata, Ryo,Torii, Ayame,Kawano, Kenichi,Futaki, Shiroh,Imayoshi, Ayumi,Tsubaki, Kazunori
p. 3608 - 3615
(2018/05/26)

Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them
34 Xanthones were synthesized by microwave assisted technique. Their in?vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231?cell line growth with an IC50 of 0.46?±?0.03?μM. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.
Liu, Jie,Zhang, Jianrun,Wang, Huailing,Liu, Zhijun,Zhang, Cao,Jiang, Zhenlei,Chen, Heru
p. 50 - 61
(2017/04/06)

Synthesis of 1,2-Dioxetanes as Thermochemiluminescent Labels for Ultrasensitive Bioassays: Rational Prediction of Olefin Photooxygenation Outcome by Using a Chemometric Approach
Great interest in new thermochemiluminescent (TCL) molecules, for example, in bioanalytical assays, has prompted the design and synthesis of a small library of more than 30 olefins to be subjected to photooxygenation, with the aim of obtaining new 1,2-dioxetane-based TCL labels with optimized properties. Fluorine atoms on the acridan system remarkably stabilize 1,2-dioxetanes when they are located in the 3- and/or 6-position (4 h and 4 i). On the other hand, 2,7-difluorinated acridan dioxetane (4 j) showed a significantly enhanced fluorescence quantum yield with respect to the unsubstituted dioxetane (4 a). Some of the synthesized olefins did not undergo singlet oxygen addition and a rationale was sought to ease the photooxygenation step, leading to the TCL dioxetanes. A chemometric approach has been adopted to exploit principal component analysis and linear discriminant analysis of the structural and electronic molecular descriptors obtained by DFT optimizations of olefins 3. This approach allows the steric and electronic parameters that govern dioxetane formation to be revealed.
Andronico, Luca A.,Quintavalla, Arianna,Lombardo, Marco,Mirasoli, Mara,Guardigli, Massimo,Trombini, Claudio,Roda, Aldo
supporting information
p. 18156 - 18168
(2016/12/16)

Rh-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones
An efficient rhodium-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones was developed from functionalized salicylaldehydes. This approach provides an easy access to various functionalized 2,2′-dihydroxybenzophenone and xanthone core s
Rao, Maddali L. N.,Ramakrishna, Boddu S.
p. 75505 - 75511
(2016/08/24)

XANTHENE COMPOUND AND USE THEREOF
PROBLEM TO BE SOLVED: To provide a fluorescence probe for measuring activity of molecular species 3A of cytochrome P-450 having excellent cytochrome P-450 molecular species selectivity and excellent detection sensitivity. SOLUTION: There is provided a xanthene-based fluorescent compound represented by the formula (I), where R1 is a monovalent group, R2 is H or a monovalent group, R3 and R4 are H, a halogen atom or the like, R5 is a monovalent group in which an ether bond of 6-position O-benzyl part of the formula (I) can be oxidation cleaved by cytochrome P-450 molecular species 3A, n is an integer of 1 to 5 and R5s may be same or different when n is 2 or more. COPYRIGHT: (C)2016,JPOandINPIT
-
Paragraph 0037

(2016/10/10)

NOVEL PROBES AND TARGETING COMOUNDS FOR MITOCHONDRIA
The present invention provides novel compounds which are fluorescent and target the mitochondria and methods of using them.
-
Paragraph 00163

(2014/05/07)

Fluorescein analogues as photoremovable protecting groups absorbing at ～520 nm
A new photoremovable protecting group, (6-hydroxy-3-oxo-3H-xanthen-9-yl) methyl (1), with a molar absorption coefficient ε of ～4 × 10 4 m-1 cm-1 at ～520 nm for the release of carboxylates or phosphates is reported. Three derivatives of 1 (diethyl phosphate, acetate, and bromide) were isolated as complexes with DDQ and shown to release the ligands with quantum yields ≤2.4% in aqueous solution.
?ebej, Peter,Wintner, Jürgen,Müller, Pavel,Slanina, Tomá?,Al Anshori, Jamaludin,Antony, Lovely Angel Panamparambil,Klán, Petr,Wirz, Jakob
p. 1833 - 1843
(2013/04/10)

SECA INHIBITORS AND METHODS OF MAKING AND USING THEREOF
Inhibitors of SecA, and methods of making and using thereof, are described herein. The compounds described herein can be used to treat or prevent microbial infections, such as bacterial infections.
-
Page/Page column 125

(2014/01/08)

FUSED PENTACYCLIC ANTI - PROLIFERATION COMPOUNDS
The present invention relates to novel compounds of formula (I) wherein X, Q, R1, R2, R3, R4, R5, R6, R7, R8, R21, R22 and R23 are as defined herein. The compounds of formula (I) are inhibitors of telomerase enzyme function and are accordingly useful for the treatment cellular proliferation disorders, such as cancer
-
Page/Page column 73-74

(2013/02/28)

Synthesis, SAR and biological evaluation of natural and non-natural hydroxylated and prenylated xanthones as antitumor agents
In order to explore the detailed structure-activity relationship (SAR) around xanthone scaffold bearing hydroxyl and prenyl moieties, twenty-nine natural and non-natural hydroxylated and prenylated xanthones have been synthesized and evaluated for their in vitro anti-proliferative activities against five human cancer cell lines, including HepG2 (hepatocelluar carcinoma), HCT-116 (colon carcinoma), A549 (lung carcinoma), BGC823 (gastric carcinoma) and MDAMB- 231 (breast carcinoma). The SAR analysis revealed that the anti-proliferative activity of the xanthones is substantially influenced by the position and number of attached hydroxyl and prenyl groups, and the presence of hydroxyl group ortho to the carbonyl function of xanthone scaffold contributes significantly to their cytotoxicity. The new prenylated xanthone 20 with a relatively simple structure, namely 1,3,8-trihydroxy-2-prenylxanthone, was found to exhibit potent antitumor activities comparable to mangostin against all the five cancer cell lines. Further mechanistic studies suggested that compound 20 induces apoptosis and causes cell cycle arrest at S phase in HepG2 cells. These results have highlighted compound 20 as a new potential lead candidate for future development of novel potent broad-spectrum antitumor agents.
Zhang, Xiaojin,Li, Xiang,Tao, Lei,Gao, Yuan,Gong, Dandan,Xi, Meiyang,Xu, Xiaoli,Guo, Qinglong,You, Qidong,Ye, Suofu,Zhang, Yu,Meng, Huyan,Zhang, Mingqian,Gao, Wenlei
p. 1012 - 1025,14
(2012/12/12)

9-Aryl-9-xanthenols: A convenient platform for the design of fluorimetric and colorimetric pH indicators
In aqueous and alcohol solutions, colorless and non-fluorescent derivatives of 9-aryl-9H-xanthen-9-ol equilibrate with brightly colored and fluorescent 9-arylxanthylium cations, thus offering a convenient platform for the design of dual-mode indicators for emission and absorption-based pH measurements. The position of the prototropic equilibrium depends only on the hydronium ion concentration and is not affected by general acids or other ions. Furthermore, the equilibrium equivalence point can be readily adjusted by introducing substituents in the xanthenol core. As dehydroxylation of 3,6-dialkoxy-9-(o- tolyl)-9-xanthenol occurs at pH = 6.5, indicators of this type are well suited for biological applications as illustrated by in vitro cell culture studies with NIH 3T3 cells.
Nekongo, Emmanuel E.,Bagchi, Pritha,Fahrni, Christoph J.,Popik, Vladimir V.
supporting information
p. 9214 - 9218
(2013/01/15)

Fluorogenic azidofluoresceins for biological imaging
Fluorogenic probes activated by bioorthogonal chemical reactions can enable biomolecule imaging in situations where it is not possible to wash away unbound probe. One challenge for the development of such probes is the a priori identification of structure
Shieh, Peyton,Hangauer, Matthew J.,Bertozzi, Carolyn R.
supporting information
p. 17428 - 17431
(2013/01/15)

Carbon-carbon bond cleavage in fluorescent pyronin analogues induced by yellow light
A novel class of pyronin analogues, which undergoes a photochemically induced cleavage of the C-C bond in the presence of water in both solution and on a silica gel surface upon direct irradiation with visible light, is reported. The reaction course can be monitored by characteristic fluorescence of both the starting compound and the final product. This system could find useful applications in the field of photoremovable protecting groups or caged fluorophores.
?tacko, Peter,?ebej, Peter,Veetil, Aneesh Tazhe,Klán, Petr
supporting information
p. 4918 - 4921
(2013/01/15)

Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS
In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G1 phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect.
Cheng, Jen-Hao,Huang, A-Mei,Hour, Tzyh-Chyuan,Yang, Shyh-Chyun,Pu, Yeong-Shiau,Lin, Chun-Nan
p. 1222 - 1231
(2011/04/22)

Synthesis of xanthones and benzophenones as inhibitors of tumor cell growth
The synthesis of two new sulfated xanthones and two O-substituted benzophenones was carried out to evaluate for their inhibitory effect on growth of human tumor cell lines. The sulfation of 3,6-(2) and 3,4-dihydroxyxanthone (3) was accomplished using sulfur trioxide-pyridine to give, respectively, xanthone-3,6-O,O-bis(sulfate) (4) and xanthone- 3,4-O,O-bis(sulfate) (5). Treatment of 2,2',4,4'-tetrahydroxybenzophenone (6) with acetic acid and prenyl bromide furnished 2,2',4,4'- tetraacetoxybenzophenone (7) and (5-hydroxy-2,2-dimethylchroman-6-yl)(2'-hydroxy-4'-(tertpentyloxy) phenyl)methanone (8), respectively. Compounds 2-8 were tested for their effect on the in vitro growth of four representative human tumor cell lines: MCF-7 ER(+) (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), SF-268 (glioma), and A375-C5 (melanoma). Compounds 2 and 7-8 showed an inhibitory activity in the μM range.
Costa, Elisangela,Sousa, Emilia,Nazareth, Nair,Nascimento, Maria S.J.,Pinto, Madalena M.M.
scheme or table
p. 487 - 493
(2011/11/12)

Fluorescent probe
A fluorescent probe which is represented by the following formula (I): (wherein, R1 and R2 represent hydrogen atom, or a substituent for trapping proton, a metal ion, or an active oxygen species, or the like; R3 represents
-
Page/Page column 13-14; 17

(2009/05/29)

TRICYCLIC DELTA- OPIOID MODULATORS
The invention is directed to delta opioid receptor modulators. More specifically, the invention relates to tricyclic δ-opioid modulators, of formula (I). Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.
-
Page/Page column 105

(2010/11/26)

Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation
We have developed novel fluorescence probes for sodium cation based on photoinduced electron transfer (PeT). In this study, we rationally designed new probes and succeeded in achieving fluorescence enhancement upon sodium ion binding by reducing the HOMO
Kenmoku, Suguru,Urano, Yasuteru,Kanda, Koujirou,Kojima, Hirotatsu,Kikuchi, Kazuya,Nagano, Tetuso
p. 11067 - 11073
(2007/10/03)

Fluorone and pyronin Y derivatives
A compound of the formula (I) or (II): STR1 where R1, R2, R5 and R6 are the same or different and represent a hydrogen atom or a halogen atom and R1 and R2 may combine to form a ring; R3, and R4 are the same or different and represent a hydrogen atom, a halogen atom, a benzoyl group, a group of the formula --L(CH2)n R8 where n is 1 to 8, R8 is a hydrogen, hydroxy, amino, dialkylamino, --COR16 or --COOR14 where R16 is a hydrogen, chlorine, COCl, C1 -C8 alkyl, --NR2 or aryl and R14 is a hydrogen, C1 -C8 alkyl, aryl, COR, 2,4-dinitrophenyl, N-imido or --NR2 and L is a direct bond or C=O; W is =O; W1 is hydrogen or --OR9, where R9 is hydrogen, C1 -C8 alkyl, acyl or a group of the formula --(CH2)n R10 where n is 1 to 8 and R10 is amino, dialkylamino, hydroxy, acryloyl or methacryloyl; Y is oxygen, sulfur, selenium, tellurium, C=O, or >N--R13 is where R13 is 4-methylphenyl, and A is hydrogen, alkenyl, dichlorotriazinylamino, or an electron withdrawing group selected from the group consisting of COOR11, C(O)OCOR11, CONR2, CN, NO2, NCS, NCO, SO2 R12, SO3, R12, SO3 R11, SO2 NR2 and CX32 where X2 is the same or different and is a halogen atom and R11 is hydrogen, alkyl, aryl, or aralkyl, and R12 is hydrogen, alkyl, aryl, or aralkyl; provided that when R1 -R6 are all hydrogen, A is not hydrogen.
-
(2008/06/13)

γ-Pyrone compounds. IV: Synthesis and antiplatelet effects of mono- and dioxygenated xanthones and xanthonoxypropanolamine
Xanthodilol, mono- and dioxygenated xanthones, and 1,3-, 2,3-, 3,4-, 3,5- , 1,6-, 2,6-, and 3,6-dioxygenated xanthones were synthesized from benzophenone precursors by Friedel-Crafts acylation and subsequent base- catalyzed cyclization to eliminate methanol. 3-Hydroxyxanthone, xanthodilol, 2,3-dihydroxyxanthone diacetate, and 3,4-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate- and collagen-induced aggregation. 3,5-Dihydroxyxanthone and its diacetate, 1,6-dimethoxyxanthone, and 3,6-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate-induced aggregation.
Lin,Liou,Ko,Teng
p. 11 - 16
(2007/10/02)

Xanthenes: Fluorone Derivatives. 1
Several new fluorone derivatives including 2,4,5,7-tetraiodo-6-hydroxy-3-fluorone, 2,4,5,7-tetrabromo-6-hydroxy-3-fluorone, and 2,4-diiodo-8-methoxy-3-fluorone were synthesized and their spectral and photophysical properties investigated.
Shi, Jianmin,Zhang, Xianping,Neckers, Douglas C.
p. 4418 - 4421
(2007/10/02)

Studies in synthesis of xanthones: Part VIII
Thermal condensation of the methyl esters of 2,6-dihydroxy-, 2,4-dihydroxy- and 2,4,6-trihydroxy-benzoic acids has been carried out with different phenols in refluxing diphenyl ether to give various xanthones in good yields.Condensation of methyl 5-bromo-2-hydroxybenzoate with hydroquinone gives 7-bromo-1,4-dihydroxyxanthone (19) and 7-bromo-2-hydroxyxanthone (20).However, condensation of methyl 5-chloro-2,6-dihydroxybenzoate with phloroglucinol gives 5-chloro-1,3,8-trihydroxyxanthone (21).The structures of these products have been established by IR, mass and PMR spectral studies.
Patel G N,Trivedi K N
p. 437 - 439
(2007/10/02)

Attempted synthesis of 3,3'-linked biflavonoids
-
Khan,Khan,Javed
p. 1101 - 1106
(2007/10/02)

STRUCTURES OF MOLECULAR AND IONIC FORMS OF SUCCINYLFLUORESCEIN IN SOLUTION AND IN THE SOLID STATE
-
Amat-Guerri, F.,Martin, M. E.,Martinez-Utrilla, R.,Pascual, C.
p. 1447 - 1465
(2007/10/02)

Studies in Synthesis of Xanthone Derivatives: Part VI - Synthesis of Furano- and Difurano-xanthones
2-Methylresorcinol, resorcinol and 5-methylresorcinol on thermal condensation with methyl 2,4-dihydroxybenzoate in diphenyl ether afford 3,6-dihydroxy-4-methylxanthone (I), 3,6-dihydroxyxanthone (VII) and 1,6-dihydroxy-3-methylxanthone (XII), respectively.I, VII and XII on allylation, Claisen migration, cyclisation with sulphuric acid and dehydrogenation with palladised charcoal give 2,9,11-trimethyldifuroxanthen-6(H)-one (VI), 2,10-dimethyldifuroxanthen-6(H)-one (XI) and 7-hydroxy-2,9-dimethylfuroxanthen-6(H)-one (XVI), respectively.Structures of final and intermediate products have been established by PMR spectral data.
Patel, G. N.,Patolia, R. J.,Trivedi, K. N.
p. 1035 - 1038
(2007/10/02)

Bis basic substituted polycyclic aromatic compounds. A new class of antiviral agents. 7. Bisalkamine esters, 3,6 bis basic ethers and 2,7 bis(aminoacyl)xanthen 9 ones
3,6 Bis[2(dimethylamino)ethoxy] 9H xanthen 9 one dihydrochloride (4, RMI 0874DA) and 1,1' (9H xanthene 2,7 diyl)bis[2 (dimethylamino)ethanone] dihydrochloride (16, RMI 11513DA) were found to prolong survival of mice infected with lethal challenges of encephalomyocarditis (EMC) virus. They were effective by oral as well as subcutaneous administration and showed broad spectrum antiviral activity. They were selected for preclinical evaluation from the five series of compounds named in the title that were synthesized in analogy to tilorone and related fluorenone derivatives, described earlier. In addition to 4 and 16, compounds 11, 12, 17, and 18 showed high antiviral activity on oral as well as subcutaneous administration. High antiviral activity on subcutaneous administration was found in the bisalkamine esters 1, 2, and 14, the bis(aminoacyl)xanthenes 23 and 26, the bis(aminoalkylene)xanthene 31, the bis(aminoacyl)thioxanthenes 34-40, and the bis basic ethers of 9 benzylidenexanthenes 41 and 42. Structure activity relationships showed a decrease of oral activity with increased length of side chains and increased molecular weight of dialkylamino substituents of 3,6 bis basic ethers of xanthen 9 one and of 2,7 bis(aminoacyl) xanthenes and xanthen 9 ones. At least one carbonyl or alkenyl function in conjugation to the xanthene nucleus either at the 9 position of the nucleus or in the side chains is required for high antiviral activity.
Carr,Grunwell,Sill
p. 1142 - 1148
(2007/10/07)