Ebselen oxide

Names

[ Name ]:
Ebselen oxide

[Synonym ]:
2-Phenyl-1,2-benzoselenazol-3(2H)-one 1-oxide
1,2-Benzisoselenazole-1,3-dione, 2-phenyl
1-oxo-2-phenyl-1λ<sup>4</sup>,2-benzoselenazol-3-one
1,2-Benzisoselenazol-3(2H)-one, 2-phenyl-, 1-oxide

Biological Activity

[Description]:

Ebselen oxide, the selenone analogue of Ebselen, covalently modifies diguanylate cyclase (DGC) to inhibit c-di-GMP-receptor interactions and reduces DGC activity. Ebselen oxide also inhibits alginate production (IC50=14 μM) by Pseudomonas aeruginosa. Ebselen oxide inhibits HDAC1, HDAC3, HDAC4, HDAC5, HDAC6, HDAC7, HDAC8, and HDAC9 (IC50 ranging from 0.2 to 4.7 μM)[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> GPCR/G Protein >> Guanylate Cyclase

[In Vitro]

Ebselen oxide, is a covalent inhibitor of c-di-GMP allosteric binding to I-site containing proteins, diguanylate cyclase (DGC) activity[1]. Ebselen oxide inhibits diguanylate cyclase from synthesizing c-di-GMP. Ebselen oxide exhibits increased potency on HDAC8 (IC50=0.2 μM) in comparison with Ebselen[3].

[References]

[1]. Lieberman OJ, et al. High-throughput screening using the differential radial capillary action of ligand assay identifies ebselen as an inhibitor of diguanylate cyclases. ACS Chem Biol. 2014;9(1):183-192.

[2]. Kim SK, et al. Inhibition of Pseudomonas aeruginosa Alginate Synthesis by Ebselen Oxide and Its Analogues. ACS Infect Dis. 2021;7(6):1713-1726.

[3]. Wang Y, et al. Developing selective histone deacetylases (HDACs) inhibitors through ebselen and analogs. Drug Des Devel Ther. 2017;11:1369-1382. Published 2017 May 2.

Chemical & Physical Properties

[ Boiling Point ]:
277.3±23.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₃H₉NO₂Se

[ Molecular Weight ]:
290.176

[ Flash Point ]:
121.5±22.6 °C

[ Exact Mass ]:
290.979858

[ PSA ]:
37.38000

[ LogP ]:
1.53770

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H331-H373-H410

[ Precautionary Statements ]:
P261-P273-P301 + P310-P311-P501

[ RIDADR ]:
UN 3283 6.1 / PGII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

AMACR amplification in myxofibrosarcomas: a mechanism of overexpression that promotes cell proliferation with therapeutic relevance.

Clin. Cancer Res. 20(23) , 6141-52, (2014)

Myxofibrosarcomas frequently display arm-level gains on 5p. We characterized the pathogenetic and therapeutic relevance of the α-methylacyl coenzyme A racemase (AMACR) at 5p13.3.AMACR mRNA expression ...

AMACR amplification and overexpression in primary imatinib-naïve gastrointestinal stromal tumors: a driver of cell proliferation indicating adverse prognosis.

Oncotarget 5(22) , 11588-603, (2014)

Non-random gains of chromosome 5p have been observed in clinically aggressive gastrointestinal stromal tumors, whereas the driving oncogenes on 5p remain to be characterized. We used an integrative ge...