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E3520 Sigma-Aldrich

Ebselen

cysteine modifier

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

  • CAS Number 60940-34-3

  • Empirical Formula (Hill Notation) C13H9NOSe

  • Molecular Weight 274.18

  •  MDL number MFCD00210937

  •  PubChem Substance ID 24278417

  •  NACRES NA.77

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Properties

Related Categories Antioxidants and Cytoprotectants, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Cell Stress,
Quality Level   200
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

Description

General description

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

Packaging

100 mg in glass bottle

25 mg in poly bottle

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3283 6.1 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Dietary Antioxidants

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.1 During the oxi...
Biofiles Volume 2 Article 2
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Peer-Reviewed Papers
15

References

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