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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

product name

Ebselen, cysteine modifier

Niveau de qualité

200

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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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

Certificats d'analyse (COA)

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Electrical Stimulation Degenerated Cochlear Synapses Through Oxidative Stress in Neonatal Cochlear Explants
Liang Q, et al.
Frontiers in Neuroscience, 13, 1073-1073 (2019)
Lili Zou et al.
EMBO molecular medicine, 9(8), 1165-1178 (2017-06-14)
Multidrug-resistant (MDR) Gram-negative bacteria account for a majority of fatal infections, and development of new antibiotic principles and drugs is therefore of outstanding importance. Here, we report that five most clinically difficult-to-treat MDR Gram-negative bacteria are highly sensitive to a
Role of reactive oxygen species in contraction-mediated glucose transport in mouse skeletal muscle
Sandstrom ME, et al.
The Journal of Physiology, 575(1), 251-262 (2006)
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
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)
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