1-(2-(2-(2-(1-Aminoethyl)phenyl)diselanyl)phenyl)ethanamine: An amino organoselenium compound with interesting antioxidant profile

• Published in: Toxicology in vitro 2014-06, Vol.28 (4), p.524-530
• Main Authors: Ibrahim, Mohammad, Hassan, Waseem, Anwar, Javed, Deobald, Anna Maria, Kamdem, Jean Paul, Souza, Diogo Onofre, Rocha, Joao Batista Teixeira
• Format: Article
• Language: English
• Subjects: Animals; Antioxidant; Benzene Derivatives - chemistry; Benzene Derivatives - pharmacology; Biphenyl Compounds - chemistry; Brain; Brain - drug effects; DPPH; DTT; Free radical; Hydrogen Peroxide - chemistry; Lipid Peroxidation; Male; Molecular Structure; Organoselenium Compounds - chemistry; Organoselenium Compounds - pharmacology; Phenethylamines - chemistry; Phenethylamines - pharmacology; Picrates - chemistry; Rats; Rats, Wistar; TBARS; tert-Butylhydroperoxide - chemistry; Thiobarbituric Acid Reactive Substances - chemistry; Thiol
• ISSN: 0887-2333; 1879-3177
• DOI: 10.1016/j.tiv.2013.12.010

•Novel organoselenium compounds recently showed promising pharmacological properties.•Synthesis of nontoxic selenium compounds with GPx-mimicking activity of great interest.•New organoselenium synthesized and tested for Initial screening for their antioxidant activities.•Amine-based diselenide have higher antioxidant potential than simple diselenide. Free radical scavenging and antioxidant activities of 1-(2-(2-(2-(1-aminoethyl)phenyl)diselanyl)phenyl)ethanamine (compound A) and diphenyl diselenide (PhSe)2 were examined and compared for inhibition of Fe(II) and sodium nitroprusside (SNP) stimulated lipid peroxidation in rat brain, interaction with 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable free radical and their glutathione peroxidase (GPx) like antioxidant activities with H2O2 or tBuOOH as substrates and with PhSH as thiol co-substrates as well as their ability to oxidize mono- and di-thiols were also evaluated. This study revealed that an amino group in amino diselenide drastically enhances their catalytic activities in the aromatic thiol (PhSH) assay system. Compound A was ∼2-fold more active than (PhSe)2 in both tBuOOH and H2O2 assay systems. In addition, the present results showed that (PhSe)2 exhibited an increased ability to oxidize di-thiols, compound A was not a good substrate for the oxidation of thiol used namely DTT, cystine and DMPS. The antioxidant potency against Fe(II) and SNP-induced brain TBARS were in this order [(compound A); IC50 2μM and 4μM]>[(PhSe)2; IC50 19μM and 27.5μM. Compound A showed DPPH radical-scavenging activity. This study provides in vitro evidence anti-oxidant action of the tested organoselenium compounds, that the nitrogen atom in the organochalcogens can have a profound effect on their antioxidant activity.