104473-83-8

104473-83-8 structure

Name: Ebselen oxide
Chemical Name: 1-Oxide-2-phenyl-1,2-benzisoselenazol-3(2H)-one Ebselen selenoxide
CAS Number: 104473-83-8
Molecular Formula: C₁₃H₉NO₂Se
Molecular Weight: 290.176
Catalog: Signaling Pathways GPCR/G Protein Guanylate Cyclase
Create Date: 2017-10-25 16:56:20
Modify Date: 2024-01-11 18:34:05
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].

Name	1-Oxide-2-phenyl-1,2-benzisoselenazol-3(2H)-one Ebselen selenoxide
Synonyms	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

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.

106663-84-7

~77%

104473-83-8

Literature: Mlochowski, Jacek; Kloc, Krystian; Syper, Ludwik; Inglot, Anna D.; Piasecki, Egbert Liebigs Annalen der Chemie, 1993 , # 12 p. 1239 - 1244

60940-34-3

~71%

104473-83-8

Literature: Fisher, Hartmut; Dereu, Norbert Bulletin des Societes Chimiques Belges, 1987 , vol. 96, # 10 p. 757 - 768

60940-34-3

70-18-8

104473-83-8

101562-89-4

Literature: Daiber, Andreas; Zou, Ming-Hui; Bachschmid, Markus; Ullrich, Volker Biochemical Pharmacology, 2000 , vol. 59, # 2 p. 153 - 160