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Ebselen

Product Name
Ebselen
CAS No.
60940-34-3
Chemical Name
Ebselen
Synonyms
PZ51;DR-3305;EBSELEN;RP-60931;SPI-1005;CCG-39161;NSC 639762;Ebselen>Ebselen,99%;Harmokisane
CBNumber
CB5301009
Molecular Formula
C13H9NOSe
Formula Weight
274.18
MOL File
60940-34-3.mol
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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.
pka
-0.40±0.20(Predicted)
form 
Crystalline Powder
color 
Yellow to beige
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)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E3520
Product name
Ebselen
Purity
cysteine modifier
Packaging
25mg
Price
$246
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB4300603
Product name
Anti-HA-Tag antibody produced in rabbit
Purity
affinity isolated antibody
Packaging
100μg
Price
$441
Updated
2024/03/01
Sigma-Aldrich
Product number
E3520
Product name
Ebselen
Purity
cysteine modifier
Packaging
100mg
Price
$745
Updated
2024/03/01
TCI Chemical
Product number
E0946
Product name
Ebselen
Purity
>98.0%(GC)
Packaging
25mg
Price
$90
Updated
2024/03/01
TCI Chemical
Product number
E0946
Product name
Ebselen
Purity
>98.0%(GC)
Packaging
100mg
Price
$263
Updated
2024/03/01
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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

antioxidant, lipoxygenase inhibitor, inhibits oxidation of LDL

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

2-Phenyl-1,2-benzoselenazol-3-one acts as an antiinfammatory compounds,, in addition to that it acts as a modulator of KVβ subunits.

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

Ebselen Preparation Products And Raw materials

Raw materials

Preparation Products

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Ebselen Suppliers

Shanghai Rechem science Co., Ltd.
Tel
21-31433387 15618786686
Fax
QQ:1369748377
Email
sales@rechemscience.com
Country
China
ProdList
2972
Advantage
58
Changzhou Chenhong Biotechnology Co., Ltd.
Tel
0519-85788828 13775037613
Email
sales@chemrenpharm.com
Country
China
ProdList
3538
Advantage
58
Wuhan Topule
Tel
+86-02787215551 +86-19945035818
Fax
027-87215551
Email
2936752263@qq.com
Country
China
ProdList
7962
Advantage
58
WUHAN XINXINJIALI BIOTECHNOLOGY Co. LTD.
Tel
027-59223049 15807102573
Fax
027-84666270
Email
lj_xxjlbio@163.com
Country
China
ProdList
277
Advantage
58
Hubei Kele Fine Chemical Co., Ltd
Tel
027-59101668 19945030958
Fax
027-59101668
Email
2881924765@qq.com
Country
China
ProdList
7977
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12990
Advantage
57
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View Lastest Price from Ebselen manufacturers

Wuhan Demeikai Biotechnology Co., Ltd
Product
Ebselen 60940-34-3
Price
US $10.00/Kg/Bag
Min. Order
10g
Purity
99
Supply Ability
1000KG
Release date
2021-12-21
Wuhan Nutra Biotechnology Co.,Ltd
Product
Ebselen 60940-34-3
Price
US $245.00-0.00/g
Min. Order
1ASSAYS
Purity
98%
Supply Ability
10G
Release date
2021-05-24
Shaanxi Dideu Medichem Co. Ltd
Product
Ebselen 60940-34-3
Price
US $5560.00/KG
Min. Order
1KG
Purity
98.0%
Supply Ability
1T
Release date
2020-07-06

60940-34-3, EbselenRelated Search:


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