Ebselen

Specifications / Handling

More Information
Product Details
Synonyms	2-Phenyl-1,2-benzisoselenazol-3-(2H)-one
Product Type	Chemical
Properties
Formula	C₁₃H₉NOSe
MW	274.2
Merck Index	14: 3486
CAS	60940-34-3
Purity Chemicals	≥98% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO (10mg/ml) or 100% ethanol (5mg/ml).
Identity	Determined by ¹H-NMR.
InChi Key	DYEFUKCXAQOFHX-UHFFFAOYSA-N
Smiles	O=C1N([Se]C2=C1C=CC=C2)C1=CC=CC=C1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Glutathione peroxidase mimetic [1, 4].
Peroxynitrite scavenger [4].
Anti-inflammatory [1, 5-7]
Antioxidant [2, 3, 5].
Protein kinase C (PKC), NADPH, lipoxygenase, COX, NOS, H⁺-ATPase and NADPH oxidase inhibitor [6-9].
Antifungal [9].
Review [10].
Potent IDO-1 inhibitor with Ki 94nM [11].
Inhibitor of HIV-1 capsid C-terminal domain dimerization.
Shown to potentially inhibit the 33.8-kDa Main Protease (Mpro)/3C-like Protease of SARS-CoV-2, consequently inhibiting viral transcription and replication and possibly inhibiting spread of COVID-19.

Product References

A novel biologically active seleno-organic compound--III. Effects of PZ 51 (Ebselen) on glutathione peroxidase and secretory activities of mouse macrophages: M.J. Parnham & S. Kindt; Biochem. Pharmacol. 33, 3247 (1984)
Seleno-organic compounds and the therapy of hydroperoxide-linked pathological conditions: M.J. Parnham & E. Graf; Biochem. Pharmacol. 36, 3095 (1987)
Kinetic mechanism and substrate specificity of glutathione peroxidase activity of ebselen (PZ51): M. Maiorino, et al.; Biochem. Pharmacol. 37, 2267 (1988)
Ebselen as a glutathione peroxidase mimic and as a scavenger of peroxynitrite: H. Sies & H. Masumoto; Adv. Pharmacol.38, 229 (1997)
Ebselen, a glutathione peroxidase mimetic seleno-organic compound, as a multifunctional antioxidant. Implication for inflammation-associated carcinogenesis: Y. Nakamura, et al.; J. Biol. Chem. 277, 2687 (2002)
Molecular actions of ebselen-an antiinflammatory antioxidant: T. Schewe; Gen. Pharmacol. 26, 1153 (1995)
Studies on the anti-inflammatory activity of ebselen. Ebselen interferes with granulocyte oxidative burst by dual inhibition of NADPH oxidase and protein kinase C?: I.A. Cotgreave, et al.; Biochem. Pharmacol. 38, 649 (1989)
Strong inhibition of mammalian lipoxygenases by the antiinflammatory seleno-organic compound ebselen in the absence of glutathione: C. Schewe, et al.; Biochem. Pharmacol. 48, 65 (1994)
Evaluation of the antifungal and plasma membrane H+-ATPase inhibitory action of ebselen and two ebselen analogs in S. cerevisiae cultures: B. Billack, et al.; J. Enzyme Inhib. Med. Chem. 25, 312 (2010)
Ebselen: a thioredoxin reductase-dependent catalyst for alpha-tocopherol quinone reduction: J. Fang, et al.; Toxicol. Appl. Pharmacol. 207, 103 (2005)
The selenazal drug ebselen potently inhibits indoleamine 2,3-dioxygenase by targeting enzyme cysteine residues: A.C. Terentis, et al. Biochem. 49, 591 (2010)
Repurposing ebselen for treatment of multidrug-resistant staphylococcal infections: S. Thangamani, et al.; Nature Sci. Rep. 5, 11596 (2015)
Ebselen, a small-molecule capsid inhibitor of HIV-1 replication: S. Thenin-Houssier, et al.; Antimicrob. Agents Chemother. 60, 2195 (2016)
Screening a Repurposing Library for Inhibitors of Multidrug-Resistant Candida auris Identifies Ebselen as a Repositionable Candidate for Antifungal Drug Development: G. Wall, et al.; Antimicrob. Agents Chemother. 62, e01084 (2018)
Structure of Mpro from COVID-19 virus and discovery of its inhibitors: Z. Jin, et al.; Nature 582, 289 (2020)
A Small Molecule, ACAi-028, with Anti-HIV-1 Activity Targets a Novel Hydrophobic Pocket on HIV-1 Capsid: Antimicrob. Agents Chemother. 65, e01039 (2021)

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