Synthesis and antioxidant activities of N-thiophenyl ebselenamines: a 77Se{1H} NMR mechanistic study

Kumar, Manish; Singh, Vijay Pal

doi:10.1039/d2nj01225a

Cited by 9 publications

(28 citation statements)

References 111 publications

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“…Probably, organochalcogen chain-breaking antioxidants rapidly oxidized from their divalent to the tetravalent state and acted as poor radical quenchers. 28–30,38,39,42–44 The resulting tetravalent state would be considered as retarders of peroxidation rather than inhibitors due to high water solubility. In the regeneration study of antioxidants, co-antioxidants were responsible for the reduction of the tetravalent state of organochalcogen antioxidants and for always keeping the antioxidants in their active divalent state.…”

Section: Resultsmentioning

confidence: 99%

“…If the co-antioxidants contained in the aqueous phase could continuously regenerate the antioxidants in the chlorobenzene layer, T inh could be significantly extended. 42–44 It was also possible that co-antioxidants present in the aqueous phase of the peroxidation model could affect the solubility of the antioxidants 8 and 9 at the aqueous/lipid interphase due to the changes in the p K a values.…”

Section: Resultsmentioning

confidence: 99%

“…28,30,38,40,43,44 The pH-dependent co-antioxidant behavior on the regeneration of phenolic organochalcogen antioxidants has not been explored. According to earlier reports, 43,44,47 an unconventional mechanism has been proposed involving the initial O-atom transfer from LOO˙ to the Te atom in antioxidant 8 , resulting in telluroxide intermediate I and an alkoxyl radical (LO˙) in a solvent cage (Scheme 3). The generated LO˙ could abstract the H-atom from the nearby OH group in the solvent cage, leading to a phenoxyl radical/telluroxide intermediate II and the corresponding alcohols (LOH).…”

Section: Mechanismmentioning

confidence: 99%

“…In previous works on chain-breaking antioxidants, regeneration of antioxidant activity following the well-known mechanism of quenching chain-carrying LOO˙ by HAT or PCET in a two-phase lipid peroxidation model system was reported with thiols and AscOH as co-antioxidants. 28,30,38,40,43,44 The pH-dependent co-antioxidant behavior on the regeneration of phenolic organochalcogen antioxidants has not been explored. According to earlier reports, 43,44,47 an unconventional mechanism has been proposed involving the initial O-atom transfer from LOO˙ to the Te atom in antioxidant 8 , resulting in telluroxide intermediate I and an alkoxyl radical (LO˙) in a solvent cage (Scheme 3).…”

Section: Mechanismmentioning

confidence: 99%

“…chain-breaking antioxidants as well as glutathione peroxidase (GPx) mimics such as ebselenols 43 and ebselenamines have been explored. 44…”

Section: Introductionmentioning

confidence: 99%

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Modulation of the chain-breaking antioxidant activity of phenolic organochalcogens with various co-antioxidants at various pH values

2023

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Mechanismmentioning

confidence: 99%

Section: Mechanismmentioning

confidence: 99%

“…chain-breaking antioxidants as well as glutathione peroxidase (GPx) mimics such as ebselenols 43 and ebselenamines have been explored. 44…”

Section: Introductionmentioning

confidence: 99%

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Modulation of the chain-breaking antioxidant activity of phenolic organochalcogens with various co-antioxidants at various pH values

2023

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Aminic Organoselenium Compounds as Glutathione Peroxidase Mimics and Inhibitors of Ferroptosis

Chhillar,

Kadian,

Kumar

et al. 2024

ChemBioChem

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The synthesis of diarylamine‐based organoselenium compounds via the nucleophilic substitution reactions has been described. Symmetrical monoselenides and diselenides were conveniently synthesized by the reduction of their corresponding selenocyanates using sodium borohydride. Selenocyanates were obtained from 2‐chloro acetamides by the nucleophilic displacement with potassium selenocyanate. Selenides were synthesized by treating the 2‐chloro acetamides with in situ generated sodium butyl selenolate as nucleophile. Further, the newly synthesized organoselenium compounds were evaluated for their glutathione peroxidase (GPx)‐like activity in thiophenol assay. This study revealed that the methoxy‐substituted organoselenium compounds showed significant effect on the GPx‐like activity. The catalytic parameters for the most efficient catalysts were also determined. The anti‐ferroptotic activity for all GPx‐mimics evaluated in a 4−OH‐tamoxifen (TAM) inducible GPx4 knockout cell line using liproxstatin as standard.

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Synthesis of bis‐Naphthol based Organoselenium Antioxidants as Efficient Inhibitors against Biofilms

Chhillar,

Sharma,

Rani

et al. 2024

ChemistrySelect

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In the present study, synthesis of bis‐naphthol based organoselenium compounds has been described. The synthetic strategy involves electrophilic aromatic addition of alkyl/aryl selenium species at the electron rich center of 2,7‐dihydroxynaphthalene. The reaction with electrophilic selenylating reagents in situ generated by potassium persulphate and diselenides produced desired selenides. Synthesized compounds were studied for their glutathione peroxidase (GPx)‐like antioxidant activities using thiophenol assay. It was observed that all compounds exhibited greater GPx‐like antioxidant activity than diphenyl diselenide used as reference. Further, these GPx mimics were introduced for their antibacterial properties against biofilm formation by Bacillus subtilis and Pseudomonas aeruginosa. To support experimental details, molecular docking studies were also performed to elucidate in silico interactions between the active sites of proteins TsaA and LasR found in Bacillus subtilis and Pseudomonas aeruginosa, respectively. The minimum inhibitory concentration assay was performed for all the antioxidants against Bacillus subtilis and Pseudomonas aeruginosa. Additionally, hemolytic assay has also been carried out to check the impact on red blood cells. Cytotoxicity assessments of antioxidants have also been carried using MTT assay.

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Synthesis and antioxidant activities of N-thiophenyl ebselenamines: a ⁷⁷Se{¹H} NMR mechanistic study

Abstract: The step-by-step redox process of bis-[2-phenyl-1,2-benzisoselenazol-3(2H)-one-7-yl]diazene i.e. azo-bis-ebselen in the presence of PhSH and H2O2 was reported by using 77Se{1H} NMR spectroscopy. The synthesis of N-thiophenyl ebselenamines as well as...

Cited by 9 publications

References 111 publications

Modulation of the chain-breaking antioxidant activity of phenolic organochalcogens with various co-antioxidants at various pH values

Modulation of the chain-breaking antioxidant activity of phenolic organochalcogens with various co-antioxidants at various pH values

Aminic Organoselenium Compounds as Glutathione Peroxidase Mimics and Inhibitors of Ferroptosis

Synthesis of bis‐Naphthol based Organoselenium Antioxidants as Efficient Inhibitors against Biofilms

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