title: Antioxidant properties of (R)-Se-aryl thiazolidine-4-carboselenoate.
abstract: The antioxidant potential of organoselenium compounds has been extensively investigated because oxidative stress is a hallmark of a variety of human diseases. In this study, we report the influence of substituent groups on the antioxidant activity of (R)-Se-aryl thiazolidine-4-carboselenoate (Se-PTC) in several in vitro assays. The amino group in the thiazolidine ring affects the antioxidant activity of the compound. Our data revealed that Se-PTC a had higher radical scavenging efficiency in the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(+)) assays compared to other compounds. In the ferric ion reducing antioxidant power (FRAP) assay, Se-PTC a exhibited ferric-reducing ability at concentrations as low as 5μM. However, this effect was diminished when the amino group was protected with carbamate (Se-PTC d). In the nitric oxide scavenging assay, Se-PTC c presented better NO-scavenging than Se-PTC b. However, Se-PTC a and d did not prevent NO formation at any of the tested concentrations. Se-PTC c decreased the sodium nitroprussate-induced lipid peroxidation in the cortex and hippocampus of mice. In summary, we demonstrate that Se-PTC is a promising antioxidant compound and that the compound's activity is influenced by the amino group and by the characteristics of the arylselenium substituents. Thus, these compounds may be used as synthetic antioxidants that provide protection against oxidative diseases.
authors.affiliation: Faculdade de Agronomia Eliseu Maciel - Departamento de Ciência e Tecnologia dos alimentos, Universidade Federal de Pelotas, UFPel, Pelotas, RS, Brazil.
authors.forename: Francine Novack
authors.initials: FN
authors.lastname: Victoria
authors.forename: Débora Martins
authors.initials: DM
authors.lastname: Martinez
authors.forename: Micheli
authors.initials: M
authors.lastname: Castro
authors.forename: Angela M
authors.initials: AM
authors.lastname: Casaril
authors.forename: Diego
authors.initials: D
authors.lastname: Alves
authors.forename: Eder João
authors.initials: EJ
authors.lastname: Lenardão
authors.forename: Helena Domingues
authors.initials: HD
authors.lastname: Salles
authors.forename: Paulo H
authors.initials: PH
authors.lastname: Schneider
authors.forename: Lucielli
authors.initials: L
authors.lastname: Savegnago
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry / Q000494:pharmacology; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D008297:Male; D051379:Mice; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology*; D010851:Picrates / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000737:chemistry / Q000494:pharmacology; D053778:Thiazolidines / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D016566:Organoselenium Compounds; D010851:Picrates; C568847:Se-phenyl thiazolidine-4-carboselenoate; D013451:Sulfonic Acids; D053778:Thiazolidines; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: Antioxidant; Organoselenium compounds; Selenium; Thiazolidine