Multifunctional Antioxidants: Regenerable Radical‐Trapping and Hydroperoxide‐Decomposing Ebselenols

Kumar, Sudhir; Yan, Jiajie; Poon, Jia‐fei; Singh, Vijay Pal; Lu, Xunyu; Ott, Marjam Karlsson; Engman, Lars; Kumar, Sangit

doi:10.1002/ange.201510947

Cited by 26 publications

(6 citation statements)

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“…If the co-antioxidant contained in the aqueous phase can continuously regenerate the antioxidant in the chlorobenzene layer, T inh can be significantly extended. [43][44][45] The R inh was determined as the slope of the line during the inhibited phase of peroxidation (vide infra, Figure 3). The R uninh = 544 μM/h of linoleic acid.…”

Section: Methodsmentioning

confidence: 99%

“…Hence, considerable attention has been paid in the field of regeneration and recycling by the organochalcogen antioxidants world-wide at the expense of easily available co-antioxidants such thiols and ascorbate with an unconventional mechanism. 43 Recently, our group reported ‖multifunctional‖ chain-breaking as well as glutathione peroxidase mimic ebselen derivatives such as ebselenols 44 and ebselenamines 45 acted as the inhibitors of the LPO chain reaction in the presence/absence of aqueous AscOH as co-antioxidant. Herein, we report the systematically effect of pH as well as different co-antioxidants on the chain-breaking antioxidant properties of the best antioxidants 8 and 9 in two phase lipid peroxidation model system.…”

Section: Figure 2 Selected Chain-breaking Antioxidants For Present Workmentioning

confidence: 99%

“…In our previous works on chain-breaking antioxidants, regeneration of antioxidants in two phase lipid peroxidation model system was reported with thiols and AscOH as coantioxidants. 28,38,40,44,45 According to the earlier reported mechanism for quenching of LOO•, the first step would involve O-atom transfer from LOO• to the chalcogen atom. The presence of -OH group will be acted as hydrogen atom donor to the generated alkoxyl radical LO•.…”

Section: Mechanismmentioning

confidence: 99%

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Exploring Chain-Breaking Antioxidants Profile Dependent at Various pH and co-Antioxidants

Kumar

Sharma

Singh

2022

Preprint

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Understanding towards chain-breaking antioxidants as potent inhibitors of lipid peroxyl radicals, high-throughput efforts have been investigated for antioxidant behaviour of 6-bromo-3,3-dimethyl-8 hexadecyltelluro [1,3]dioxepino[5,6-c]pyridin-9-ol and 2-methyl-2,3-dihydrobenzo[b]selenophene-5-ol in the two phase (chlorobenzene/water) lipid peroxidation model system at various pH 1-7 and mild co-antioxidants such as (glutathione, dithiothreitol, ascorbic acid, sodium ascorbate, and potassium hexacyanoferrate(II) trihydrate, sodium metasulfite, and tris(2-carboxyethyl)phosphine hydrochloride). The key chain-breaking mechanism profile was attributed towards the first oxygen transfer atom from the lipid peroxyl radical to the Se/Te atoms and then hydrogen atom transfer from the nearby phenolic group by the alkoxyl radical due to the weak O-H bond dissociation energy in the solvent cage. Finally, the regeneration could take place by the presence of aqueous soluble co-antioxidants that increased the inhibition time of antioxidants more efficiently than α-tocopherol. Tellurium analouge at pH 2-5 in presence of N-acetylcysteine offered better protection for chain-breaking capacity than the selenium analouge. In the presence of aqueous soluble N-acetylcysteine at pH 1-7, both antioxidants in the present study behaved very good inhibitors of lipid peroxyl radicals.

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Section: Methodsmentioning

confidence: 99%

Section: Figure 2 Selected Chain-breaking Antioxidants For Present Workmentioning

confidence: 99%

Section: Mechanismmentioning

confidence: 99%

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Exploring Chain-Breaking Antioxidants Profile Dependent at Various pH and co-Antioxidants

Kumar

Sharma

Singh

2022

Preprint

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“…The authors suggest that such high activity of compound 10 was most likely a result of the hydroxyl group and the selenium center proximity. 30 In 2021, Kumar et al synthesized Nmethyl ebselenamine compounds and then assessed their antioxidant activity (Method A), 19 noting that the excellent GPx-like activity of the obtained derivatives may be related to the close proximity of the -NHMe group and the selenium atom. Of all the compounds, derivative 11 showed the highest antioxidant activity (2.5-fold more active than ebselen 5 and 5-fold more active than α-tocopherol).…”

Section: Modification Of Ebselen Rings a And Bmentioning

confidence: 99%

Organoselenium compounds as antioxidants

Obieziurska‐Fabisiak¹,

Pacuła‐Miszewska²,

Laskowska³

et al. 2022

Arkivoc

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Reactive oxygen species (ROS) are responsible for many of civilization's diseases, including cancer, diabetes, and Alzheimer's disease, decomposition of products in the food industry, and deterioration of physicochemical properties of polymers and nanomaterials. In recent years, several organoselenium compounds have been synthesized and used as peroxide scavengers, which are the source of many antioxidant substances. This review aims to collect and divide the organoselenium compounds obtained in the last twelve years with antioxidant activity, which can prove helpful in a) medicine as supplements preventing diseases caused by oxidative stress, b) as food additives preventing oxidation, or c) in the materials industry as Se-containing nanoparticles and polymers. In addition, the most common methods for determining GPx-like antioxidant activity are presented.

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“…Cells endogenously produce large quantities of ROS under oxidative stress. 18 The Bigger Picture We anticipate that these findings can be extended for the various nanomedicines having movable ability in cell for widely application in the therapeutic field.…”

Section: Introductionmentioning

confidence: 96%