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E3520

Sigma-Aldrich

Ebselen

powder, ≥98% (TLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C13H9NOSe
Numero CAS:
60940-34-3
Peso molecolare:
274.18
Numero MDL:
MFCD00210937
Codice UNSPSC:
12352202
ID PubChem:
24278417
NACRES:
NA.77

product name

Ebselen, cysteine modifier

Livello qualitativo

200

Saggio

≥98% (TLC)

Forma fisica

powder

Punto di fusione

176-182  °C

Solubilità

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

Temperatura di conservazione

2-8°C

Stringa SMILE

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
DYEFUKCXAQOFHX-UHFFFAOYSA-N

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Descrizione generale

Ebselen is a sympathomimetic amine.

Applicazioni

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

Azioni biochim/fisiol

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.

Avvertenze

Danger

Indicazioni di pericolo

H301 + H331,H373,H410

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Certificati d'analisi (COA)

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Selenomethionine United States Pharmacopeia (USP) Reference Standard

USP

1611955

Selenomethionine

Seleno-L-cystine 95%

Sigma-Aldrich

545996

Seleno-L-cystine

Xanthine Oxidase, Buttermilk Native xanthine oxidase from buttermilk. Complex metalloprotein that catalyzes oxidative hydroxylation of a variety of aromatic heterocycles and simple aldehydes. Catalyzes the oxidation of xanthine to uric acid.

Sigma-Aldrich

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Xanthine Oxidase, Buttermilk

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
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
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
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)
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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