This product has not been validated for cell-based experiments. However, literature indicates that it has been used successfully in cell-based experiments. For more information, please see references provided on the product web page. https://www.sigmaaldrich.com/en/product/sigma/e3520
Sign In to View Organizational & Contract Pricing.
About This Item
Empirical Formula (Hill Notation):
C13H9NOSe
CAS Number:
Molecular Weight:
274.18
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Skip To
Product Name
Ebselen, cysteine modifier
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
Looking for similar products? Visit Product Comparison Guide
1 of 4
This Item | |||
|---|---|---|---|
| assay ≥98% (TLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay 98% |
| Quality Level 200 | Quality Level 100 | Quality Level 100 | Quality Level 200 |
| form powder | form powder | form powder | form solid |
| solubility chloroform: 19.60-20.40 mg/mL, clear, yellow | solubility DMSO: 2 mg/mL, clear | solubility DMSO: 2 mg/mL, clear | solubility acetone: soluble(lit.), alcohol: slightly soluble(lit.), chloroform: soluble(lit.), diethyl ether: slightly soluble(lit.), water: insoluble(lit.) |
| storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. - |
| mp 176-182 °C | mp - | mp - | mp 104-107 °C (lit.) |
General description
Ebselen is a sympathomimetic amine.
Application
Ebselen has been used as a:
extensor digitorum longus (fast-twitch) muscle
- voltage-dependent calcium channels (VDCCs) blocker[1]
- 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[2]
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.[3] Inhibits oxidation of low density lipoproteins (LDL).
signalword
Danger
hcodes
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
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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)
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
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
Articles
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.
Uncover properties and applications of the cysteine protease papain and find inhibitors, substrates, and other papain products.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| E3520-100MG | 04061833603314 |
| E3520-25MG | 04061833603321 |
-
Hello, we recently ordered this product (Ebselen, Cat# E3520). I dissolved it in DMSO (5 mg/mL) and plan to use it in cell experiments. However, I just noticed that the purity is ≥98% (TLC). Would this be suitable for cell-based experiments.Thank you.
1 answer-
Helpful?
-
Active Filters
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service