Abstract
A new series of multipotent antioxidants (MPAOs), namely Schiff base-1,2,4-triazoles attached to the oxygen-derived free radical scavenging moiety butylated hydroxytoluene (BHT) were designed and subsequently synthesized. The structure-activity relationship (SAR) of the designed antioxidants was established alongside the prediction of activity spectra for substances (PASS). The antioxidant activities of the synthesized compounds 4–10 were tested by the DPPH bioassay. The synthesized compounds 4–10 inhibited stable DPPH free radicals at a level that is 10−4 M more than the well-known standard antioxidant BHT. Compounds 8–10 with para-substituents were less active than compounds 4 and 5 with trimethoxy substituents compared to those with a second BHT moiety (compounds 6 and 7). With an IC50 of 46.13 ± 0.31 µM, compound 6 exhibited the most promising in vitro inhibition at 89%. Therefore, novel MPAOs containing active triazole rings, thioethers, Schiff bases, and BHT moieties are suggested as potential antioxidants for inhibiting oxidative stress processes and scavenging free radicals, hence, this combination of functions is anticipated to play a vital role in repairing cellular damage, preventing various human diseases and in medical therapeutic applications.
Highlights
Regulation of reducing and oxidizing status is critical for the viability of cell organ functions [1].Reactive oxygen species (ROS) have a strong disruptive effect on industrial products, such as oils, plastics and rubbers
The design approach for free radical inhibitors involves gathering the useful features of different antioxidant fragments into a single structure
This approach was implemented to increase the antioxidant activities and other physical properties of the well-known antioxidant (BHT) and identify novel multipotent antioxidants (MPAOs) bearing particular antioxidant fragments that are very important in the introduction of promising MPAO candidates possessing different physical and chemical properties, as illustrated in hydrophilic antioxidants
Summary
Regulation of reducing and oxidizing status is critical for the viability of cell organ functions [1]. Reactive oxygen species (ROS) have a strong disruptive effect on industrial products, such as oils, plastics and rubbers They exist in different forms, such as hydroxyls (HO‚), superoxide anion radicals. Due to its industrial applications, researchers have designed and synthesized a series of BHT derivatives to accelerate the antioxidant discovery process, aiming to expand its applications with a wide range of antioxidant activities to markedly enhance the radical scavenging ability and other physical properties. SAR and rational design approaches were utilized to integrate multiple radical-scavenging activities in designing hybrid compounds with significantly enhanced radical-scavenging capacity. These approaches were verified with PASS training subsets. PASS-predicted antioxidant activities for Schiff base-1,2,4-triazoles bearing BHT moieties were experimentally verified using DPPH assays
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