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E3520

Ebselen

powder, ≥98% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C13H9NOSe
CAS Number:
60940-34-3
Molecular Weight:
274.18
UNSPSC Code:
12352202
PubChem Substance ID:
24278417
NACRES:
NA.77
MDL number:
MFCD00210937
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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

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

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.
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).

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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

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
108K4100
018K4114
117K4123
067K4100
096K4115

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Articles

Papain, Cysteine Protease, Properties & Products

Uncover properties and applications of the cysteine protease papain and find inhibitors, substrates, and other papain products.

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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:
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Global Trade Item Number

SKUGTIN
E3520-100MG04061833603314
E3520-25MG04061833603321