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Principaux documents

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:
Poids moléculaire :
274.18
Numéro MDL:
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.77

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product name

Ebselen, cysteine modifier

Niveau de qualité

Pureté

≥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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BAH131820810BAH131852436BAH131820812
packaging

pack of 100 ea

packaging

pack of 100 ea

packaging

pack of 100 ea

packaging

pack of 100 ea

manufacturer/tradename

Bel-Art H13182-1012

manufacturer/tradename

Bel-Art H13182-0810

manufacturer/tradename

Bel-Art H13185-2436

manufacturer/tradename

Bel-Art H13182-0812

width × H × thickness

10 in. (250 mm) × 12 in. (300 mm) × 2 mil (0.05 mm)

width × H × thickness

-

width × H × thickness

-

width × H × thickness

-

Description générale

Ebselen is a sympathomimetic amine.[1]

Application

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

extensor digitorum longus (fast-twitch) muscle[3]
  • glucocerebrosidase inhibitor[1]
  • hepatitis C virus helicase inhibitor[4]

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.[5] Inhibits oxidation of low density lipoproteins (LDL).
Ebselen, a glutathione-peroxidase-mimic, elicits anti-inflammatory activity.[1] 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.[6] It is regarded as neuroprotective agent and elicits chemopreventive functionality in inflammation-associated carcinogenesis.[7]

Pictogrammes

Skull and crossbonesHealth hazardEnvironment

Mention d'avertissement

Danger

Mentions de danger

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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Les clients ont également consulté

N Noguchi et al.
Biochimica et biophysica acta, 1213(2), 176-182 (1994-07-14)
The oxidative modification of low density lipoprotein (LDL) is accepted to be an important early event of atherosclerosis, but it has not yet been well understood. The preventive effects of two antioxidants with different functions, ebselen and probucol, against the
Ebselen, a glutathione peroxidase mimetic seleno-organic compound, as a multifunctional antioxidant implication for inflammation-associated carcinogenesis
Nakamura Y, et al.
The Journal of Biological Chemistry, 277(4), 2687-2694 (2002)
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
Sourav Mukherjee et al.
ACS chemical biology, 9(10), 2393-2403 (2014-08-16)
The hepatitis C virus (HCV) nonstructural protein 3 (NS3) is both a protease, which cleaves viral and host proteins, and a helicase that separates nucleic acid strands, using ATP hydrolysis to fuel the reaction. Many antiviral drugs, and compounds in
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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