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E3520

Sigma-Aldrich

Ebselen

powder, ≥98% (TLC)

Sinónimos:

2-Phenyl-1,2-benzisoselenazol-3(2H)-one

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About This Item

Fórmula empírica (notación de Hill):
C13H9NOSe
Número de CAS:
60940-34-3
Peso molecular:
274.18
MDL number:
MFCD00210937
UNSPSC Code:
12352202
PubChem Substance ID:
24278417
NACRES:
NA.77

product name

Ebselen, cysteine modifier

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

176-182  °C

solubility

chloroform: 19.60-20.40 mg/mL, clear, yellow

storage temp.

2-8°C

SMILES string

O=C1N([Se]c2ccccc12)c3ccccc3

InChI

1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H

InChI key

DYEFUKCXAQOFHX-UHFFFAOYSA-N

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General description

Ebselen is a sympathomimetic amine.

Application

Ebselen has been used as a:
  • voltage-dependent calcium channels (VDCCs) blocker
  • glutathione peroxidase mimetic to test its inhibitory effect on contraction-mediated deoxy glucose (2-DG) uptake in mouse

extensor digitorum longus (fast-twitch) muscle
  • glucocerebrosidase inhibitor
  • hepatitis C virus helicase inhibitor

Biochem/physiol Actions

An organo-selenium compound possessing antioxidant properties. Inhibits mammalian lipoxygenases in the absence of thiol groups, and glutathione S-transferase and papain via the interaction with cysteine residues. Also inhibits indoleamine 2,3-dioxygenase by covalently modifying a cysteine residue, the effect being reversible with dithiothreitol. Inhibits oxidation of low density lipoproteins (LDL).
Ebselen, a glutathione-peroxidase-mimic, elicits anti-inflammatory activity. It also has anti-atherosclerotic functionality. Ebselen displays antibacterial action on) multidrug-resistant Staphylococcus aureus (MRSA) infections and could be a potential therapeutic target for treating MRSA based skin infection. It is regarded as neuroprotective agent and elicits chemopreventive functionality in inflammation-associated carcinogenesis.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Repurposing ebselen for treatment of multidrug-resistant staphylococcal infections
Thangamani S, et al.
Scientific reports, 5, 11596-11596 (2015)
Optimization and validation of two miniaturized glucocerebrosidase enzyme assays for high throughput screening
Urban DJ, et al.
Combinatorial Chemistry & High Throughput Screening, 11(10), 817-824 (2008)
Diana Islam et al.
American journal of respiratory and critical care medicine, 199(10), 1214-1224 (2018-12-07)
Rationale: There are controversial reports on applications of mesenchymal stromal cells (MSCs) in patients with acute respiratory distress syndrome (ARDS). Objectives: We hypothesized that lung microenvironment was the main determinant of beneficial versus detrimental effects of MSCs during ARDS. Methods:
Chuanjiang Dong et al.
Frontiers in microbiology, 10, 3016-3016 (2020-02-06)
As a thiol-dependent enzyme, thioredoxin reductase (TrxR) is a promising antibacterial drug target. Ebselen, an organo-selenium with well-characterized toxicology and pharmacology, was recently reported to have potent antibacterial activity against Staphylococcus aureus. In this paper, we demonstrated that ebselen has
Selcuk Yatmaz et al.
American journal of respiratory cell and molecular biology, 48(1), 17-26 (2012-09-25)
Oxidative stress caused by excessive reactive oxygen species production is implicated in influenza A virus-induced lung disease. Glutathione peroxidase (GPx)-1 is an antioxidant enzyme that may protect lungs from such damage. The objective of this study was to determine if
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