E3520

Ebselen

powder, ≥98% (TLC)

• Synonym(s): 2-Phenyl-1,2-benzisoselenazol-3(2H)-one
• Empirical Formula (Hill Notation): C₁₃H₉NOSe
• CAS Number: 60940-34-3
• Molecular Weight: 274.18
• MDL number: MFCD00210937
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278417
• NACRES: NA.77

Properties

• product name: Ebselen, cysteine modifier
• 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

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 Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H331,H373,H410
• Precautionary Statements: P260 - P264 - P273 - P301 + P310 - P304 + P340 + P311 - P314
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2
• Storage Class Code: 6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3