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E3520

Sigma-Aldrich

Ebselen

powder, ≥98% (TLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C13H9NOSe
Numéro CAS:
60940-34-3
Poids moléculaire :
274.18
Numéro MDL:
MFCD00210937
Code UNSPSC :
12352202
ID de substance PubChem :
24278417
Nomenclature NACRES :
NA.77

Nom du produit

Ebselen, cysteine modifier

Niveau de qualité

200

Essai

≥98% (TLC)

Forme

powder

Pf

176-182  °C

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

DYEFUKCXAQOFHX-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazardEnvironment
GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H301 + H331,H373,H410

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number
0000384459
0000384459
0000334537
0000195888
0000161739

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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
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:
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)
Andrew C Terentis et al.
Biochemistry, 49(3), 591-600 (2009-12-17)
The heme enzyme indoleamine 2,3-dioxygenase (IDO) plays an important immune regulatory role by catalyzing the oxidative degradation of l-tryptophan. Here we show that the selenezal drug ebselen is a potent IDO inhibitor. Exposure of human macrophages to ebselen inhibited IDO
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