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Ebselen

CAS No.60940-34-3
Chemical Name:Ebselen
CBNumber:CB5301009
Molecular Formula:C13H9NOSe
Formula Weight:274.18
MOL File:60940-34-3.mol

Ebselen Property

Melting point 176-182 °C
Boiling point 402.8±28.0 °C(Predicted)
storage temp. 2-8°C
solubility Soluble in ethanol, methanol, acetone, acetonitrile.
form Crystalline Powder
pka -0.40±0.20(Predicted)
color Yellow to beige
biological source rabbit
Merck 14,3486
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey DYEFUKCXAQOFHX-UHFFFAOYSA-N
CAS DataBase Reference 60940-34-3(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 40X2P7DPGH
UNSPSC Code 12352203
NACRES NA.77

Safety

Hazard Codes :T,N,Xi
Risk Statements :23/25-33-50/53-36/37/38
Safety Statements :20/21-28-45-60-61-28A-36/37-26
RIDADR :UN 3283 6.1/PG 3
WGK Germany :3
RTECS :DE4140750
HazardClass :6.1
PackingGroup :III
HS Code :29310099

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301+H331-H373-H410
Precautionary statements P260-P264-P273-P301+P310-P304+P340+P311-P314

Ebselen Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: E3520
Product name : Ebselen
Purity: cysteine modifier
Packaging: 25MG
Price: ₹17969.5
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: SAB4300603
Product name : Anti-HA-Tag antibody produced in rabbit
Purity: affinity isolated antibody
Packaging: 100μG
Price: ₹48029.7
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: E3520
Product name : Ebselen
Purity: cysteine modifier
Packaging: 100MG
Price: ₹58076.13
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: E0946
Product name : Ebselen
Purity: min. 98.0 %
Packaging: 25MG
Price: ₹5700
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: E0946
Product name : Ebselen
Purity: min. 98.0 %
Packaging: 100MG
Price: ₹14500
Updated: 2022/05/26
Buy: Buy

Ebselen Chemical Properties,Usage,Production

Description Ebselen is one of the selenium-containing anti-inflammatory drugs.In 2003, Rocha and co-workers identified diselenides as a new class of antiinflammatory agents.In 2014, Nogueira and co-workers reported the synthesis and anti-inflammatory activity of salicyclic-based diselenides and selenocynates.Recently, Wilhelm and co-workers identified 4-phenylselenyl-7-chloroquinoline 270 as a potent antiinflammatory compound.
Chemical Properties yellow to beige crystalline powder
Uses 2-Phenyl-1,2-benzoselenazol-3-one acts as an antiinfammatory compounds,, in addition to that it acts as a modulator of KVβ subunits.
Uses Ebselen is a lipid-soluble organoselenium compound. Numerous in vivo experiments have demonstrated that ebselen is able to inhibit both vasospasm and tissue damage in cerebral stroke/ischemia animal models (i.e. rat, mice, guinea pig and dog).For example, ebselen has been shown to provide significant protection against ischemic damage in both gray and white matter, and in the ventral posterior nucleus of rodent brains.Additionally, administration of ebselen in gerbils significantly reduces neuronal death induced by ischemia and reperfusion in the hippocampal CA1 region.It has been reported that ebselen inhibits inositol monophosphatase and acts as a safe treatment for bipolar disorder.
The optimal GPx-like activity of ebselen was observed at neutral or nearphysiological pH (7.4), and the activity of ebselen was barely detected in acidic medium.During ischemia, brain pH falls rapidly within the first 5 min from 7.0 to 6.2, which is not optimal for ebselen's GPx-like activity.Meanwhile, since ebselen has shown promising activity in the treatment of stroke, it seems that GPx-like activity of ebselen in the brain may not occur.Thus, the enzymatic reduction of ebselen by TrxR might be the main contribution to its antioxidant property during ischemia. Unlike inorganic and aliphatic selenium compounds, ebselen does not liberate the selenium moiety, which remains within the ring structure. Subsequent metabolism involves methylation, glucuronidation and hydroxylation. Additionally, ebselen could also inhibit enzymes such as lipoxygenases, nitric oxide synthases, nitrogen oxides, protein kinase C and H1/K1-ATPase.
Besides the relationship with redox systems, another neuroprotective mechanism of ebselen is involved in controlling the expression of gaminobutyric acid shunt enzymes to supply the tricarboxylic acid cycle, and significantly inhibiting acetylcholinesterase activity,demonstrating its engagement in the metabolic system.
Uses antioxidant, lipoxygenase inhibitor, inhibits oxidation of LDL
Definition ChEBI: A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.
Reactions Ebselen is a substrate for mammalian TrxR and can be converted to ebselen selenol by consuming NADPH.The reduction reaction acts with an apparent KM value of 2.5 mM and a kcat of 588 min-1. Oxidants such as H2O2 react with ebselen selenol to produce ebselen selenenic acid (EbSeOH), and spontaneously produce H2O and ebselen to form a redox cycling mechanism for ebselen.
Upon the addition of Trx to TrxR, NADPH and ebselen, the reaction rate increases several-fold. This may be achieved by a very fast oxidation of reduced Trx by ebselen at a reaction rate constant42107 M1 s1.This rate is orders of magnitude faster than the reaction of reduced Trx with a substrate such as insulin disulfides. Thus, ebselen can compete with disulfide substrates for the reduction by Trx. These results indicate that ebselen can serve as a mediator in the redox environment via the Trx system.
General Description Ebselen is a sympathomimetic amine.
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.
Clinical Use Ebselen and its analogs have also been shown to be inhibitors of Bacillus anthracis TrxR. The ebselen analogs displayed antibacterial activity on Bacillus subtilis, S. aureus, Bacillus cereus and M. tuberculosis. There existed a high resistance barrier for the bacteria to develop ebselen-resistant strains and isolating resistant mutants was found to be difficult and, ultimately, unsuccessful.28 The reason for the difficulty of developing ebselen-resistant bacteria may be because ebselen has exerted a multiple drug-target mechanism, although the exact mechanism is not yet known. In addition to the thioredoxin and GSH systems, ebselen has been reported to have some other potential targets in bacteria, which may help it to overcome the bacterial drug resistance. Ebselen was identified as an inhibitor of diguanylate cyclases by a high-throughput screening in another study by covalent binding to Cys residues.29 This may block the cyclic-di-GMP signaling pathway, regulating biofilm formation, flagella-mediated motility in Pseudomonas aeruginosa, and thus its pathogenesis. Ebselen was identified as an inhibitor of the cysteine protease domain (CPD) in the Clostridium difficile major virulence factor toxin B (TcdB) by another high-throughput screening study.
A CPD can bind with one or two ebselen molecules with a covalent modification probably occurring at the active site Cys. The treatment of ebselen blocked the toxic effects of TcdB and the pathology of C. difficile infection in mice.30 Another study also indicated that ebselen is a potent inhibitor of the M. tuberculosis Ag85 complex by binding covalently to a Cys residue (C209) located near the Ag85C active site, which is central to the synthesis of major components of the inner and outer leaflets of the mycobacterial outer membrane.
storage Room temperature
References 1) Schewe et al. (1995), Molecular actions of ebselen – an anti-inflammatory antioxidant; Gen. Pharmacol., 26 1153 2) Parnham et al. (2000), Ebselen: prospective therapy for cerebral ischaemia; Expert. Opin. Investig. Drugs, 9 607 3) Masumoto et al. (1996), Kinetic study of the reaction of ebselen with peroxynitite; FEBS Lett., 398 179 4) Nakamura et al. (2002), Ebselen, a glutathione peroxidase mimetic seleno-organic compound, as a multifunctional antioxidant. Implication for inflammation-associated carcinogenesis; J. Biol. Chem., 277 2687