1214-24-0Relevant articles and documents
Multiligand interactions at the combining site of anti-fluorescyl antibodies. Molecular recognition and connectivity
Janjic,Schloeder,Tramontano
, p. 6374 - 6377 (1989)
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.
Polysulfated xanthones: Multipathway development of a new generation of dual anticoagulant/antiplatelet agents
Correia-Da-Silva, Marta,Sousa, Emília,Duarte, Bárbara,Marques, Franklim,Carvalho, Félix,Cunha-Ribeiro, Luís M.,Pinto, Madalena M. M.
, p. 5373 - 5384 (2011)
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.
Mitochondria-anchored colorimetric and ratiometric fluorescent chemosensor for visualizing cysteine/homocysteine in living cells and daphnia magna model
Yang, Mingwang,Fan, Jiangli,Sun, Wen,Du, Jianjun,Peng, Xiaojun
, p. 12531 - 12537 (2019)
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
Fluorescein analogue xanthene-9-carboxylic acid: A transition-metal-free CO releasing molecule activated by green light
Antony, Lovely Angel Panamparambil,Slanina, Tomas,Sebej, Peter,Solomek, Tomas,Klan, Petr
, p. 4552 - 4555 (2013)
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.
A Cu-free clickable fluorescent probe for intracellular targeting of small biomolecules
Yamagishi, Kento,Sawaki, Kazuaki,Murata, Atsushi,Takeoka, Shinji
, p. 7879 - 7882 (2015)
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
Xanthene and xanthone derivatives as G-quadruplex stabilizing ligands
Altieri, Alessandro,Alvino, Antonello,Ohnmacht, Stephan,Ortaggi, Giancarlo,Neidle, Stephen,Nocioni, Daniele,Franceschin, Marco,Bianco, Armandodoriano
, p. 13446 - 13470 (2013)
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.
Design, molecular docking study and synthesis of 3,6-bis(3'-substituted propoxy)xanthone derivatives as COX-2 inhibitors
Shankar, Brajesh,Das, Aparoop,Parida, Pratap
, p. 4634 - 4640 (2015)
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
Antihypertensive activity, toxicity and molecular docking study of newly synthesized xanthon derivatives (xanthonoxypropanolamine)
Goshain, Omprakash,Ahmed, Bahar
, (2019)
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.
Antifungal Activity of Xanthones: Evaluation of their Effect on Ergosterol Biosynthesis by High-performance Liquid Chromatography
Pinto, Eugenia,Afonso, Carlos,Duarte, Serafim,Vale-Silva, Luis,Costa, Elisangela,Sousa, Emilia,Pinto, Madalena
, p. 212 - 222 (2011)
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.
A Turn-On Fluorescent Probe for Detection of Sub-ppm Levels of a Sulfur Mustard Simulant with High Selectivity
Zhang, Yuanlin,Lv, Yanlin,Wang, Xuefei,Peng, Aidong,Zhang, Kaiquan,Jie, Xiaoke,Huang, Jijun,Tian, Zhiyuan
, p. 5481 - 5488 (2018)
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
