Antioxidant properties of (R)-Se-aryl thiazolidine-4-carboselenoate

• Published in: Chemico-biological interactions 2013-09, Vol.205 (2), p.100-107
• Main Authors: Victoria, Francine Novack, Martinez, Débora Martins, Castro, Micheli, Casaril, Angela M., Alves, Diego, Lenardão, Eder João, Salles, Helena Domingues, Schneider, Paulo H., Savegnago, Lucielli
• Format: Article
• Language: English
• Subjects: Animals; Antioxidant; antioxidant activity; antioxidants; Antioxidants - chemistry; Antioxidants - pharmacology; Benzothiazoles - chemistry; Benzothiazoles - pharmacology; Biphenyl Compounds - chemistry; Biphenyl Compounds - pharmacology; Brain - drug effects; Brain - metabolism; cortex; Free Radical Scavengers - chemistry; Free Radical Scavengers - pharmacology; hippocampus; human diseases; Humans; in vitro studies; lipid peroxidation; Lipid Peroxidation - drug effects; Male; Mice; nitric oxide; Organoselenium compounds; Organoselenium Compounds - chemistry; Organoselenium Compounds - pharmacology; oxidative stress; Picrates - chemistry; Picrates - pharmacology; Selenium; sodium; Structure-Activity Relationship; Sulfonic Acids - chemistry; Sulfonic Acids - pharmacology; Thiazolidine; Thiazolidines - chemistry; Thiazolidines - pharmacology
• ISSN: 0009-2797; 1872-7786
• DOI: 10.1016/j.cbi.2013.06.019

•(R)-Se-aryl thiazolidine-4-carboselenoate (Se-PTC) is a promising antioxidant compound.•Antioxidant activity of Se-PTC is influenced by the amino group.•Antioxidant activity of Se-PTC is altered by the characteristics of the substituents of the arylselenium moiety. 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.