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https://www.readbyqxmd.com/read/28285521/exploring-covalent-allosteric-inhibition-of-antigen-85c-from-mycobacterium-tuberculosis-by-ebselen-derivatives
#1
Christopher M Goins, Steven J Dajnowicz, Sandeep Thanna, Steven J Sucheck, Jerry Matthew Parks, Donald R Ronning
Previous studies identified ebselen as a potent in vitro and in vivo inhibitor of the Mycobacterium tuberculosis (Mtb) antigen 85 (Ag85) complex, comprising three homologous enzymes required for the biosynthesis of the mycobacterial cell wall. In this study, the Mtb Ag85C enzyme was co-crystallized with azido and adamantyl ebselen derivatives, resulting in two crystallographic structures of 2.01 and 1.30 Å resolution, respectively. Both structures displayed the anticipated covalent modification of the solvent accessible, non-catalytic Cys209 residue forming a selenenylsulfide bond...
March 13, 2017: ACS Infectious Diseases
https://www.readbyqxmd.com/read/28273423/thermal-and-photoinduced-copper-promoted-c-se-bond-formation-synthesis-of-2-alkyl-1-2-benzisoselenazol-3-2h-ones-and-evaluation-against-mycobacterium-tuberculosis
#2
Sandeep Thanna, Christopher M Goins, Susan E Knudson, Richard A Slayden, Donald R Ronning, Steven J Sucheck
2-Alkyl-1,2-benzisoselenazol-3(2H)-ones, represented by ebselen (1a), are being studied intensively for a range of medicinal applications. We describe both a new thermal and photoinduced copper-mediated cross-coupling between potassium selenocyanate (KSeCN) and N-substituted ortho-halobenzamides to form 2-alkyl-1,2-benzisoselenazol-3(2H)-ones containing a C-Se-N bond. The copper ligand (1,10-phenanthroline) facilitates C-Se bond formation during heating via a mechanism that likely involves atom transfer (AT), whereas, in the absence of ligand, photoinduced activation likely proceeds through a single electron transfer (SET) mechanism...
March 20, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28242720/fluorescence-high-throughput-screening-for-inhibitors-of-tonb-action
#3
Brittany L Nairn, Olivia S Eliasson, Dallas R Hyder, Noah J Long, Aritri Majumdar, Somnath Chakravorty, Peter McDonald, Anuradha Roy, Salete M Newton, Phillip E Klebba
Gram (-) bacteria acquire ferric siderophores through TonB-dependent outer membrane transporters (TBDT). By fluorescence spectroscopic high-throughput screening (FLHTS) we identified inhibitors of TonB-dependent ferric enterobactin (FeEnt) uptake through E. coli FepA (EcoFepA). Among 165 inhibitors found in a primary screen of 17,441 compounds, we evaluated 20 in secondary tests: TonB-dependent ferric siderophore uptake and colicin killing; proton-motive force-dependent lactose transport. 6 of 20 primary hits inhibited TonB activity in all tests...
February 27, 2017: Journal of Bacteriology
https://www.readbyqxmd.com/read/28212823/cyp-epoxygenase-derived-h2o2-is-involved-in-the-endothelium-derived-hyperpolarization-edh-and-relaxation-of-intrarenal-arteries
#4
Mercedes Muñoz, Maria Elvira López-Oliva, Estéfano Pinilla, María Pilar Martínez, Ana Sánchez, Claudia Rodríguez, Albino García-Sacristán, Medardo Hernández, Luis Rivera, Dolores Prieto
Reactive oxygen species (ROS) like hydrogen peroxide (H2O2) are involved in the in endothelium-derived hyperpolarization (EDH)-type relaxant responses of coronary and mesenteric arterioles. The role of ROS in kidney vascular function has mainly been investigated in the context of harmful ROS generation associated to kidney disease. The present study was sought to investigate whether H2O2 is involved in the endothelium-dependent relaxations of intrarenal arteries as well the possible endothelial sources of ROS generation involved in these responses...
February 14, 2017: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/28208301/biomolecular-interaction-assays-identified-dual-inhibitors-of-glutaminase-and-glutamate-dehydrogenase-that-disrupt-mitochondrial-function-and-prevent-growth-of-cancer-cells
#5
Min Zhu, Jinzhang Fang, Jingjing Zhang, Zheng Zhang, Jianhui Xie, Yan Yu, Jennifer Jin Ruan, Zhao Chen, Wei Hou, Gensheng Yang, Weike Su, Benfang Helen Ruan
Glutaminase (KGA/isoenzyme GAC) is an emerging and important drug target for cancer. Traditional methods for assaying glutaminase activity are coupled with several other enzymes. Such coupled assays do not permit the direct and stringent characterization of specific glutaminase inhibitors. Ebselen was identified as a potent 9 nM KGA inhibitor in the KGA/glutamate oxidase (GO)/horse radish peroxidase (HRP) coupled assay but showed very weak activity in inhibiting the growth of glutamine-dependent cancer cells...
February 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28151580/in-vitro-assessment-of-the-growth-and-plasma-membrane-h-atpase-inhibitory-activity-of-ebselen-and-structurally-related-selenium-and-sulfur-containing-compounds-in-candida-albicans
#6
Natalie N Orie, Andrew R Warren, Jovana Basaric, Cesar Lau-Cam, Magdalena Piętka-Ottlik, Jacek Młochowski, Blase Billack
Ebselen (EB, compound 1) is an investigational organoselenium compound that reduces fungal growth, in part, through inhibition of the fungal plasma membrane H(+) -ATPase (Pma1p). In the present study, the growth inhibitory activity of EB and of five structural analogs was assessed in a fluconazole (FLU)-resistant strain of Candida albicans (S2). While none of the compounds were more effective than EB at inhibiting fungal growth (IC50  ∼ 18 μM), two compounds, compounds 5 and 6, were similar in potency...
February 2, 2017: Journal of Biochemical and Molecular Toxicology
https://www.readbyqxmd.com/read/28043795/evaluation-of-substituted-ebselen-derivatives-as-potential-trypanocidal-agents
#7
Heeren M Gordhan, Stephen L Patrick, Maria I Swasy, Amber L Hackler, Mark Anayee, Jennifer E Golden, James C Morris, Daniel C Whitehead
Human African trypanosomiasis is a disease of sub-Saharan Africa, where millions are at risk for the illness. The disease, commonly referred to as African sleeping sickness, is caused by an infection by the eukaryotic pathogen, Trypanosoma brucei. Previously, a target-based high throughput screen revealed ebselen (EbSe), and its sulfur analog, EbS, to be potent in vitro inhibitors of the T. brucei hexokinase 1 (TbHK1). These molecules also exhibited potent trypanocidal activity in vivo. In this manuscript, we synthesized a series of sixteen EbSe and EbS derivatives bearing electron-withdrawing carboxylic acid and methyl ester functional groups, and evaluated the influence of these substituents on the biological efficacy of the parent scaffold...
February 1, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28029457/new-glutathione-peroxidase-mimetics-insights-into-antioxidant-and-cytotoxic-activity
#8
Agata J Pacuła, Katarzyna B Kaczor, Angelika Wojtowicz, Jędrzej Antosiewicz, Anna Janecka, Angelika Długosz, Tomasz Janecki, Jacek Ścianowski
A series of N-alkyl benzisoselenazol-3(2H)-ones has been obtained and transformed to corresponding diselenides by the reduction with sodium borohydride. Additionally, efficient methodology for the oxidative Se-N bond formation by potassium iodate has been presented, new conversion of diselenide to benzisoselenazolone was observed. The GPx-like activity of all synthetized derivatives has been evaluated by NMR. N-Allyl diselenide was up to five times better antioxidant than ebselen. Anticancer capacity towards MCF7 and DU145 cancer cells has been also tested...
October 18, 2016: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28003551/response-to-comment-on-a-small-molecule-antivirulence-agent-for-treating-clostridium-difficile-infection
#9
Kristina Oresic Bender, Megan Garland, Matthew Bogyo
Ebselen's antivirulence activity in Clostridium difficile infection is likely due to multiple modes of action, but the contribution of each to its efficacy remains unclear.
December 21, 2016: Science Translational Medicine
https://www.readbyqxmd.com/read/28003550/comment-on-a-small-molecule-antivirulence-agent-for-treating-clostridium-difficile-infection
#10
Greg L Beilhartz, John Tam, Zhifen Zhang, Roman A Melnyk
New insights into the mechanism of action of ebselen, a small-molecule antivirulence agent that reduces disease pathology in a mouse model of Clostridium difficile infection, suggest a different molecular target may be responsible for its efficacy.
December 21, 2016: Science Translational Medicine
https://www.readbyqxmd.com/read/27997177/nitro-azo-and-amino-derivatives-of-ebselen-synthesis-structure-and-cytoprotective-effects
#11
Vijay P Singh, Jia-Fei Poon, Jiajie Yan, Xi Lu, Marjam Karlsson Ott, Ray J Butcher, Paul J Gates, Lars Engman
Novel azo-bis-ebselen compounds 7 were prepared by reduction of 7-nitro-2-aryl-1,2-benzisoselenazol-3(2H)-ones 3 and 6 with sodium benzenetellurolate, NaTeC6H5, and by reaction of 2-bromo-3-nitrobenzamides with Na2Se2. The X-ray structure of 7b showed that the molecule, due to strong intramolecular secondary Se···N interactions, is completely planar. Azo-compounds 7 upon further reaction with NaTeC6H5 were reductively cleaved to provide 2 equiv of the corresponding aromatic amine. The weak Se-N bond was not stable enough to survive the reaction conditions, and diselenides 8 were isolated after workup...
December 20, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27983850/computational-modeling-of-the-catalytic-cycle-of-glutathione-peroxidase-nanomimic
#12
Ramesh Kheirabadi, Mohammad Izadyar
To elucidate the role of a derivative of ebselen as a mimic of the antioxidant selenoenzyme glutathione peroxidase, density functional theory and solvent-assisted proton exchange (SAPE) were applied to model the reaction mechanism in a catalytic cycle. This mimic plays the role of glutathione peroxidase through a four-step catalytic cycle. The first step is described as the oxidation of 1 in the presence of hydrogen peroxide, while selenoxide is reduced by methanthiol at the second step. In the third step of the reaction, the reduction of selenenylsulfide occurs by methanthiol, and the selenenic acid is dehydrated at the final step...
December 29, 2016: Journal of Physical Chemistry. A
https://www.readbyqxmd.com/read/27966584/ebselen-preserves-tissue-engineered-cell-sheets-and-their-stem-cells-in-hypothermic-conditions
#13
Ryosuke Katori, Ryuhei Hayashi, Yuki Kobayashi, Eiji Kobayashi, Kohji Nishida
Clinical trials have been performed using autologous tissue-engineered epithelial cell sheets for corneal regenerative medicine. To improve stem cell-based therapy for convenient clinical practice, new techniques are required for preserving reconstructed tissues and their stem/progenitor cells until they are ready for use. In the present study, we screened potential preservative agents and developed a novel medium for preserving the cell sheets and their stem/progenitor cells; the effects were evaluated with a luciferase-based viability assay...
December 14, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27864790/understanding-pacing-postconditioning-mediated-cardiac-protection-a-role-of-oxidative-stress-and-a-synergistic-effect-of-adenosine
#14
Fawzi A Babiker, Aishah Al-Jarallah, Shaji Joseph
We and others have demonstrated a protective role for pacing postconditioning (PPC) against ischemia/reperfusion (I/R) injury in the heart; however, the underlying mechanisms behind these protective effects are not completely understood. In this study, we wanted to further characterize PPC-mediated cardiac protection, specifically identify optimal pacing sites; examine the role of oxidative stress; and test the existence of a potential synergistic effect between PPC and adenosine. Isolated rat hearts were subjected to coronary occlusion followed by reperfusion...
November 19, 2016: Journal of Physiology and Biochemistry
https://www.readbyqxmd.com/read/27777322/the-potential-toxicological-insights-about-the-anti-hiv-drug-azidothymidine-derived-monoselenides-in-human-leukocytes-toxicological-insights-of-new-selenium-azidothymidine-analogs
#15
Doc Mariano, D de Souza, D F Meinerz, J Allebrandt, A F de Bem, W Hassan, Oed Rodrigues, Jbt da Rocha
Acquired immunodeficiency syndrome (AIDS) is a worldwide disease characterized by impairments of immune function. AIDS can be associated with oxidative stress (OS) that can be linked to selenium (Se) deficiency. Se is fundamental for the synthesis of selenoproteins, such as glutathione peroxidase and thioredoxin reductase. These enzymes catalyze the decomposition of reactive oxygen species and contribute to maintain equilibrium in cell redox status. Literature data indicate that organoselenium compounds, such as ebselen and diphenyl diselenide, have antioxidant properties in vitro and in vivo models associated with OS...
October 24, 2016: Human & Experimental Toxicology
https://www.readbyqxmd.com/read/27777006/inhibition-of-plasma-lipid-oxidation-induced-by-peroxyl-radicals-peroxynitrite-hypochlorite-15-lipoxygenase-and-singlet-oxygen-by-clinical-drugs
#16
Mayuko Morita, Yuji Naito, Toshikazu Yoshikawa, Etsuo Niki
With increasing evidence showing the involvement of oxidative stress in the pathogenesis of various diseases, the effects of clinical drugs possessing antioxidant functions have received much attention. The unregulated oxidative modification of biological molecules leading to diseases is mediated by multiple oxidants including free radicals, peroxynitrite, hypochlorite, lipoxygenase, and singlet oxygen. The capacity of antioxidants to scavenge or quench oxidants depends on the nature of oxidants. In the present study, the antioxidant effects of several clinical drugs against plasma lipid oxidation induced by the aforementioned five kinds of oxidants were investigated from the production of lipid hydroperoxides, which have been implicated in the pathogenesis of various diseases...
November 15, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27765750/ebselen-does-not-improve-oxidative-stress-and-vascular-function-in-patients-with-diabetes-a-randomized-crossover-trial
#17
Joshua A Beckman, Allison B Goldfine, Jane A Leopold, Mark A Creager
Oxidative stress is a key driver of vascular dysfunction in diabetes mellitus. Ebselen is a glutathione peroxidase mimetic. A single-site, randomized, double-masked, placebo-controlled, crossover trial was carried out in 26 patients with type 1 or type 2 diabetes to evaluate effects of high-dose ebselen (150 mg po twice daily) administration on oxidative stress and endothelium-dependent vasodilation. Treatment periods were in random order of 4 wk duration, with a 4-wk washout between treatments. Measures of oxidative stress included nitrotyrosine, plasma 8-isoprostanes, and the ratio of reduced to oxidized glutathione...
December 1, 2016: American Journal of Physiology. Heart and Circulatory Physiology
https://www.readbyqxmd.com/read/27759382/identifying-and-tackling-emergent-vulnerability-in-drug-resistant-mycobacteria
#18
Jyothi Padiadpu, Priyanka Baloni, Kushi Anand, MohamedHusen Munshi, Chandrani Thakur, Abhilash Mohan, Amit Singh, Nagasuma Chandra
The global mechanisms and associated molecular alterations that occur in drug-resistant mycobacteria are poorly understood. To address this, we obtain genomics data and then construct a genome-scale response network in isoniazid-resistant Mycobacterium smegmatis and apply a network-mining algorithm. Through this, we decipher global alterations in an unbiased manner and identify emergent vulnerabilities in resistant bacilli, of which redox response was prominent. Using phenotypic profiling, we find that resistant bacilli exhibit collateral sensitivity to several compounds that block antioxidant responses...
September 9, 2016: ACS Infectious Diseases
https://www.readbyqxmd.com/read/27752786/selenite-and-ebselen-supplementation-attenuates-d-galactose-induced-oxidative-stress-and-increases-expression-of-selr-and-sep15-in-rat-lens
#19
Jie Dai, Jun Zhou, Hongmei Liu, Kaixun Huang
Selenite and ebselen supplementation has been shown to possess anti-cataract potential in some experimental animal models of cataract, however, the underlying mechanisms remain unclear. The present study was designed to evaluate the anti-cataract effects and the underlying mechanisms of selenite and ebselen supplementation on galactose induced cataract in rats, a common animal model of sugar cataract. Transmission electron microscopy images of lens fiber cells (LFC) and lens epithelial cells (LEC) were observed in D-galactose-induced experimental cataractous rats treated with or without selenite and ebselen, also redox homeostasis and expression of proteins such as selenoprotein R (SELR), 15kD selenoprotein (SEP15), superoxide dismutase 1 (SOD1), catalase (CAT), β-crystallin protein, aldose reductase (AR) and glucose-regulated protein 78 (GRP78) were estimated in the lenses...
October 17, 2016: Journal of Biological Inorganic Chemistry: JBIC
https://www.readbyqxmd.com/read/27727401/antifungal-activities-of-diphenyl-diselenide-and-ebselen-against-echinocandin-susceptible-and-resistant-strains-of-candida-parapsilosis
#20
Francieli Chassot, Tarcieli Pozzebon Venturini, Fernanda Baldissera Piasentin, Janio Morais Santurio, Terezinha Inez Estivalet Svidzinski, Sydney Hartz Alves
We evaluated the in vitro antifungal activity of diphenyl diselenide and ebselen against echinocandin-susceptible and -resistant strains of Candida parapsilosis using the broth microdilution method. Diphenyl diselenide (MIC range =1-8 µg/mL) and ebselen (MIC range =0.25-4 µg/mL) showed in vitro activity against echinocandin-susceptible isolates. However, ebselen also showed the highest antifungal activity against echinocandin-resistant strains (MIC range =0.06-4 µg/mL). This study demonstrated that the antifungal potential of diphenyl diselenide and ebselen deserves further investigation using in vivo experimental protocols...
October 2016: New Microbiologica
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