title: Antioxidant properties of diorganoyl diselenides and ditellurides: modulation by organic aryl or naphthyl moiety.
abstract: Diorganoyl dichalcogenide compouds can have antioxidant activity in different in vitro and in vivo models. Here, we have compared the potential antioxidant activity of 1-dinaphthyl diselenide (1-NapSe)(2), 2-dinaphthyl diselenide (2-NapSe)(2), 1-dinaphthyl distelluride (1-NapTe)(2), 2-dinaphthyl ditelluride (2-NapTe)(2) with their well-studied analogs diphenyl diselenide ((PhSe)(2)) and diphenyl telluride ((PhTe)(2)). (PhSe)(2), (PhTe)(2), and naphthalene analogs-inhibited Fe(II)-induced lipid peroxidation, catalytically decomposed hydrogen peroxide and oxidized thiols, such as dithiothreitol (DTT), Cysteine (CYS), dimercaptopropionic acid (DMPS), and thiophenol (PhSH). (PhSe)(2) was the less potent of the tested compounds against Fe(II)-induced lipid peroxidation in brain homogenates and the change in the organic moiety from an aryl to naphthyl group increased considerably the antioxidant potency of diselenide compounds. However, the change from aryl to naphthyl had little effect on the thio-peroxidase-like activity of diorganoyl dichalcogenides. These results suggest that minor changes in the organic moiety of aromatic diselenide compounds can modify profoundly their capacity to inhibit iron-induced lipid peroxidation. The pharmacological properties of organochalcogens are thought to be linked to their capacity of modulating oxidative stress. Consequently, it becomes important to explore the toxicological properties of dinaphthyl diselenides and ditellurides.
authors.affiliation: Programa de Pós-Graduação em Ciências Biológicas-Bioquímica Toxicológica, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria, RS CEP 97105-900, Brazil.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Ibrahim
authors.forename: Waseem
authors.initials: W
authors.lastname: Hassan
authors.forename: Daiane Francine
authors.initials: DF
authors.lastname: Meinerz
authors.forename: Matheus
authors.initials: M
authors.lastname: Dos Santos
authors.forename: Claudia
authors.initials: C
authors.lastname: V Klimaczewski
authors.forename: Anna
authors.initials: A
authors.lastname: M Deobald
authors.forename: Maricilia S
authors.initials: MS
authors.lastname: Costa
authors.forename: Cristina W
authors.initials: CW
authors.lastname: Nogueira
authors.forename: Nilda B V
authors.initials: NB
authors.lastname: Barbosa
authors.forename: Joao B T
authors.initials: JB
authors.lastname: Rocha
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000494:pharmacology*; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D015227:Lipid Peroxidation / Q000187:drug effects; D008297:Male; D009281:Naphthalenes / Q000494:pharmacology*; D009942:Organometallic Compounds / Q000494:pharmacology*; D016566:Organoselenium Compounds / Q000494:pharmacology*; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D009195:Peroxidase / Q000378:metabolism; D010636:Phenols / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D013438:Sulfhydryl Compounds / Q000494:pharmacology; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism
chemical_list: D000975:Antioxidants; D001555:Benzene Derivatives; D009281:Naphthalenes; D009942:Organometallic Compounds; D016566:Organoselenium Compounds; D010636:Phenols; D013438:Sulfhydryl Compounds; D017392:Thiobarbituric Acid Reactive Substances; C503220:diphenyl telluride; C061132:diphenyldiselenide; C042983:thiophenol; D009195:Peroxidase