Towards multifunctional antioxidants: synthesis, electrochemistry, in vitro and cell culture evaluation of compounds with ligand/catalytic properties

Abstract

Numerous human diseases are linked to a biochemical condition known as oxidative stress (OS). Antioxidants are therefore becoming increasingly important as potential disease prevention and therapeutic agents. Since OS is a multi-stressor event, agents combining a range of different antioxidant properties, such as redox catalysis and metal binding, might be more effective and selective than mono-functional agents. Selenium derivatives of aniline and pyridine combine redox activity with metal binding properties. These multifunctional agents have a distinct electrochemical profile, and exhibit good catalytic activity in the glutathione peroxidase mimic and metallothionein assays. They also show antioxidant activity in a skin cell model of UVA-induced stress. These compounds might therefore provide the basis for novel agents combining two or more distinct antioxidant properties.

Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms

“…More recently, coordination of sulfur and selenium compounds with metal ions has been proposed as an additional antioxidant mechanism [12,13,15,16]. Collins et al have reported selenium-copper complexes that utilize both metal binding and ROS scavenging in oxidative stress prevention [28]. Our research has demonstrated that metal coordination is required for inhibition of copper-and ironmediated DNA damage by sulfur, oxo-sulfur, and selenium compounds [12,13,15,16].…”

“…However, 2-aniline disulfide showed significantly larger shifts in the copper reduction potential than the corresponding diselenide (-225 mV compared to -50 mV, respectively), and these sulfur-containing compounds did not exhibit GPx activity. Taken together, these results suggest a protective role for selenium compounds through multiple antioxidant mechanisms [28].…”

Synthesis and characterization of 3,5-lutidinyl chalcogen and -dichalcogen compounds: X-ray crystal structure of bis(3,5-dimethyl-2-pyridyl) diselenide and 2,6-bis(selenomethyl)-3,5-lutidine

“…The pyridyl metal chalcogenolates act as better single source precursors of semiconducting materials compared to its alkyl/aryl congeners [4,5]. In biochemistry, selenium derivatives of quinoline and pyridine, because of their superior redox catalytic and metal binding capabilities, act as effective and selective antioxidants when compared with the mono-functional arylselenium compounds [6]. The pyridyl and picolyl chalcogens [7e13] have been known for some time and have been extensively studied.…”

Antioxidant and α-glucosidase inhibitory activities of constituents from Euonymus alatus twigs

“…Oxidative stress is characterized by an excessive increase in the intracellular oxidizing species, such as reactive oxygen species (ROS), which is involved in the loss of antioxidant defense capacity (Collins et al, 2005). It is closely connected with various medical conditions including aging, atherosclerosis, cancer, neurodegenerative disorders, and DM.…”