title: 1-(2-(2-(2-(1-Aminoethyl)phenyl)diselanyl)phenyl)ethanamine: an amino organoselenium compound with interesting antioxidant profile.
abstract: 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 2 μM and 4 μM]>[(PhSe)2; IC50 19 μM and 27.5 μM. 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.
authors.affiliation: Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria CEP 97105-900, RS, Brazil; Department of Chemistry, Abdul Wali Khan University, Mardan 23200, Khyber Pakhtunkhwa, Pakistan; Departamento de Bioquímica, Instituto de Ciências Básica da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS CEP 90035-003, Brazil. Electronic address: Ibrahim189@yahoo.com.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Ibrahim
authors.affiliation: Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria CEP 97105-900, RS, Brazil; Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Khyber Pakhtunkhwa, Pakistan.
authors.forename: Waseem
authors.initials: W
authors.lastname: Hassan
authors.affiliation: Department of Biochemistry, Abdul Wali Khan University, Mardan 23200, Khyber Pakhtunkhwa, Pakistan.
authors.forename: Javed
authors.initials: J
authors.lastname: Anwar
authors.affiliation: Universidade de São Paulo, Instituto de Física de São Carlos, Avenida João Dagnone, 1100 Jardim Santa Angelina, 13563120 São Carlos, SP, Brazil.
authors.forename: Anna Maria
authors.initials: AM
authors.lastname: Deobald
authors.affiliation: Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria CEP 97105-900, RS, Brazil; Departamento de Bioquímica, Instituto de Ciências Básica da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS CEP 90035-003, Brazil.
authors.forename: Jean Paul
authors.initials: JP
authors.lastname: Kamdem
authors.affiliation: Departamento de Bioquímica, Instituto de Ciências Básica da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS CEP 90035-003, Brazil.
authors.forename: Diogo Onofre
authors.initials: DO
authors.lastname: Souza
authors.affiliation: Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria CEP 97105-900, RS, Brazil. Electronic address: jbtrocha@pesquisador.cnpq.br.
authors.forename: Joao Batista Teixeira
authors.initials: JB
authors.lastname: Rocha
mesh_terms: D000818:Animals; D001555:Benzene Derivatives / Q000737:chemistry / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D001921:Brain / Q000187:drug effects; D006861:Hydrogen Peroxide / Q000737:chemistry; D015227:Lipid Peroxidation; D008297:Male; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology*; D010627:Phenethylamines / Q000737:chemistry* / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D017392:Thiobarbituric Acid Reactive Substances / Q000737:chemistry; D020122:tert-Butylhydroperoxide / Q000737:chemistry
chemical_list: C000598829:1-(2-(2-(2-(1-aminoethyl)phenyl)diselanyl)phenyl)ethanamine; D001555:Benzene Derivatives; D001713:Biphenyl Compounds; D016566:Organoselenium Compounds; D010627:Phenethylamines; D010851:Picrates; D017392:Thiobarbituric Acid Reactive Substances; C061132:diphenyldiselenide; D020122:tert-Butylhydroperoxide; D006861:Hydrogen Peroxide; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: Antioxidant; Brain; DPPH; DTT; Free radical; TBARS; Thiol