55038-90-9Relevant academic research and scientific papers
Identification of methionine aminopeptidase 2 as a molecular target of the organoselenium drug ebselen and its derivatives/analogues: Synthesis, inhibitory activity and molecular modeling study
W?glarz-Tomczak, Ewelina,Burda-Grabowska, Ma?gorzata,Giurg, Miros?aw,Mucha, Artur
, p. 5254 - 5259 (2016/11/09)
A collection of twenty-six organoselenium compounds, ebselen and its structural analogues, provided a novel approach for inhibiting the activity of human methionine aminopeptidase 2 (MetAP2). This metalloprotease, being responsible for the removal of the amino-terminal methionine from newly synthesized proteins, plays a key role in angiogenesis, which is essential for the progression of diseases, including solid tumor cancers. In this work, we discovered that ebselen, a synthetic organoselenium drug molecule with anti-inflammatory, anti-oxidant and cytoprotective activity, inhibits one of the main enzymes in the tumor progression pathway. Using three-step synthesis, we obtained twenty-five ebselen derivatives/analogues, ten of which are new, and tested their inhibitory activity toward three neutral aminopeptidases (MetAP2, alanine and leucine aminopeptidases). All of the tested compounds proved to be selective, slow-binding inhibitors of MetAP2. Similarly to ebselen, most of its analogues exhibited a moderate potency (IC50= 1–12 μM). Moreover, we identified three strong inhibitors that bind favorably to the enzyme with the half maximal inhibitory concentration in the submicromolar range.
Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides
Pietka-Ottlik, Magdalena,Potaczek, Piotr,Piasecki, Egbert,Mlochowski, Jacek
, p. 8214 - 8228 (2011/03/19)
Various N-substituted benzisoselenazol-3(2H)-ones and their non-seleniumcontaining analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol- 3(2H)-ones-diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses.
Nucleophilic cleavage of selenaheterocyclic ring in benzisoselenazol-3(2H)- ones and 1,3,2-benzodiselenazoles
Lisiak,Mlochowski,Palus
, p. 1403 - 1411 (2008/09/17)
The reactions of cyclic selenenamides: benzisoselenazol-3(2H)-ones and 1,3,2-benzo-diselenazoles 3 with living cell nucleophiles such as water and thiols were investigated. Both of them caused Se-N bond cleavage. The thiolysis of 1 led to selenosulphides
Aromatic and Azaaromatic Diselenides, Benzisoselenazolones and Related Compounds as Immunomodulators Active in Humans: Synthesis and Properties
Mlochowski, Jacek,Kloc, Krystian,Syper, Ludwik,Inglot, Anna D.,Piasecki, Egbert
, p. 1239 - 1244 (2007/10/02)
Convenient syntheses of aryl diselenides 2, 1,2-benzisoselenazol-3(2H)-ones 4 and their 1-oxides 7 are reported.Reductive conversions of these compounds to bis(2-carbamoyl)phenyl diselenides 5 and oxidative cyclization of 5 to 1,2-benzisoselenazol-3(2H)-one 1-oxides 7 as the methods for the synthesis of these compounds are reported.Their ability to induce cytokines, such as TNF and IFN-γ, in human peripheral blood leucocyte cultures is described. - Key Words: 1,2-benzisoselenazol-3(2H)-ones/ Cytokine inducers/ Diselenides/ Interferon-gamma/ Tumor necrosis factor
SYNTHESE DE DERIVES OXO DE LA BENZOSELENAZINE-1,3
Mbuyi, M.,Christiaens, L.,Renson, M.
, p. 395 - 404 (2007/10/02)
Synthesis of 1,3-benzoselenazine derivatives is attempted via cyclization of o-methylselenobenzoylformamidines, via ring-expansion of 1,2-benzisoselenazolin-3-ones and via N-ethoxycarbonyl o-bromoselenobenzaldimine. This research succeeded in the synthesi
LITHIUM DISELENIDE IN APROTIC MEDIUM - A CONVENIENT REAGENT FOR SYNTHESIS OF ORGANIC DISELENIDES
Syper, Ludwik,Mlochowski, Jacek
, p. 6119 - 6130 (2007/10/02)
The reduction of selenium with lithium in THF in the presence of diphenylacetylene as a catalyst afforded lithium diselenide, which reacted with electrophiles giving alkyl or aryl diselenides 1 - 3 and selenides 4, as by-products.The useful method for preparation of diselenides based on this reaction was elaborated.
