Ebselen

Ebselen 속성

Ebselen MSDS

2-Phenyl-benzo[d]isoselenazol-3-one

Ebselen C화학적 특성, 용도, 생산

개요

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.

화학적 성질

yellow to beige crystalline powder

용도

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.

정의

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.

화학 반응

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.

일반 설명

Ebselen is a sympathomimetic amine.

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.

Ebselen 준비 용품 및 원자재

원자재

준비 용품

Ebselen 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Wuhan Nutra Biotechnology Co.,Ltd	+8617786394783	nutrabiotech@outlook.com	China	300	58
Henan Fengda Chemical Co., Ltd	+86-371-86557731 +86-13613820652	info@fdachem.com	China	16805	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32686	60
Biochempartner	0086-13720134139	candy@biochempartner.com	CHINA	967	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
Shaanxi Dideu Medichem Co. Ltd	+86-029-81148696 +8615536356810	1047@dideu.com	China	3204	58
Antai Fine Chemical Technology Co.,Limited	18503026267	info@antaichem.com	CHINA	9641	58
Zhengzhou Alfa Chemical Co.,Ltd	+8618530059196	sale04@alfachem.cn	China	12568	58

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