Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules

Molecules, Journal Year: 2023, Volume and Issue: 28(21), P. 7349 - 7349

Published: Oct. 30, 2023

Selenium is an essential trace element in living organisms, and present selenoenzymes with antioxidant activity, like glutathione peroxidase (GPx) thioredoxin reductase (TrxR). The search for small selenium-containing molecules that mimic a strong field of research organic medicinal chemistry. In this review, we review the synthesis bioassays new known organoselenium compounds covering last five years. A detailed description synthetic procedures performed vitro vivo presented, highlighting most active each series.

Language: Английский

---

Solvent effect on the ⁷⁷Se NMR chemical shifts of diphenyl diselenides

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(7), P. 2971 - 2978

Published: Jan. 1, 2024

Herein, we evaluated the solvent effect on 77 Se NMR chemical shifts of diphenyl diselenides. To gain a deeper insight into shift behavior, DFT calculations have been performed.

Language: Английский

---

Synthesis, Reactions, and Antioxidant Properties of Bis(3-amino-1-hydroxybenzyl)diselenide

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3509 - 3522

Published: Feb. 27, 2023

Bis(3-amino-1-hydroxybenzyl)diselenide containing two ortho groups was synthesized from 7-nitro-3H-2,1-benzoxaselenole and in situ generated sodium benzene tellurolate (PhTeNa). One-pot synthesis of 1,3-benzoselenazoles achieved bis(3-amino-1-hydroxybenzyl)diselenide aryl aldehydes using acetic acid as a catalyst. The X-ray crystal structure chloro-substituted benzoselenazole revealed planar with T-shaped geometry around the Se atom. Both natural bond orbital atoms molecules calculations confirmed presence secondary Se···H interactions Se···O benzoselenazoles, respectively. glutathione peroxidase (GPx)-like antioxidant activities all compounds were evaluated thiophenol assay. benzoselenazoles showed better GPx-like activity compared to that diphenyl diselenide ebselen, used references, Based on 77Se{1H} NMR spectroscopy, catalytic cycle for hydrogen peroxide proposed involving selenol, selenosulfide, selenenic intermediates. potency GPx mimics by their vitro antibacterial properties against biofilm formation Bacillus subtilis Pseudomonas aeruginosa. Additionally, molecular docking studies evaluate silico between active sites TsaA LasR-based proteins found

Language: Английский

---

Introduction of Methyl Group in Substituted Isoselenazolones: Catalytic and Mechanistic Study

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4273 - 4285

Published: March 17, 2023

Copper-catalyzed direct selenation of substituted 2-bromo-N-phenylbenzamide substrates with elemental selenium powder provided a series methoxy-substituted isoselenazolones via the C-Se and Se-N bond formations. Phenolic have been obtained by O-demethylation corresponding analogues using boron tribromide. Some structurally characterized X-ray single-crystal analysis. The glutathione peroxidase (GPx)-like antioxidant activity has evaluated both in thiophenol coupled-reductase assays. All showed good GPx-like activities assay. ferric-reducing power phenolic antioxidants also evaluated. best were found to be agents. single electron transfer, hydrogen atom proton-coupled transfer mechanisms for properties all catalysts supported density functional theory calculations. catalytic cycle was proposed one involving diselenide, selenenyl sulfide, selenol, selenenic acid as intermediates 77Se{1H} NMR spectroscopy.

Language: Английский

---

Aminic Organoselenium Compounds as Glutathione Peroxidase Mimics and Inhibitors of Ferroptosis

ChemBioChem, Journal Year: 2024, Volume and Issue: 25(4)

Published: Jan. 31, 2024

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

Language: Английский

---

Glutathione Peroxidase-like Antioxidant Activity of 1,3-Benzoselenazoles: Synthesis and In Silico Molecular Docking Studies as Pancreatic Lipase Inhibitors

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16934 - 16948

Published: Nov. 27, 2023

The synthesis of 1,3-benzoselenazoles was achieved by the reaction corresponding bis[3-amino-N-(p-tolyl)benzamide-2-yl] diselenide, bis[3-amino-N-(4-methoxyphenyl)benzamide-2-yl] and bis[3-amino-N-(4-(dimethylamino)phenyl) benzamide-2-yl] diselenide with aryl aldehydes. continued to exist as planar molecules due presence secondary Se···O interactions revealed single-crystal X-ray analysis. in confirmed using natural bond orbital (NBO) atoms (AIM) calculations. Nucleus-independent chemical shift (NICS) values suggested aromatic character a five-membered benzoselenazole heterocyclic ring. glutathione peroxidase (GPx)-like antioxidant activity all assessed thiophenol assay, exhibiting greater than Ph2Se2 used reference. most active catalyst carrying strong electron-donating group (–NMe2) at ortho-position ring further investigated different concentrations thiophenol, H2O2, for determining their catalytic parameters. Moreover, potential applications against pancreatic lipase (PL) have been identified silico between sites 1LPB protein evaluated molecular docking study.

Language: Английский

---

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

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(9)

Published: Feb. 27, 2024

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

Language: Английский

---

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

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(6), P. 1316 - 1327

Published: Jan. 1, 2023

Phenolic organochalcogen chain-breaking antioxidants, i.e. 6-bromo-8 (hexadecyltellanyl)-3,3-dimethyl-1,5-dihydro-[1,3]dioxepino[5,6-c]pyridin-9-ol and 2-methyl-2,3-dihydrobenzo[b]selenophene-5-ol, have been investigated in a two-phase (chlorobenzene/water) lipid peroxidation model system as potent inhibitors of peroxyl radicals with various co-antioxidants at pH values. The has significant effect on the antioxidant activities phenolic organochalcogens. key mechanism profile was attributed to first oxygen atom transfer from Se/Te atom, followed by hydrogen solvent cage nearby group resulting alkoxyl radical. Finally, regeneration antioxidants could take place presence aqueous-soluble co-antioxidants. Also, aqueous soluble N-acetylcysteine 1-7, both behaved very good radicals. role mild studies system. importance phase catalyst explored inhibition selenium containing using an Fe(II) source. overall pH-dependent organochalcogens depend their ability, relative stability, distribution aqueous/lipid phase.

Language: Английский

---

Can selenenyl sulfides be a substrate of glutathione reductase enzyme? A theoretical insight

RSC Advances, Journal Year: 2024, Volume and Issue: 14(51), P. 37797 - 37802

Published: Jan. 1, 2024

Glutathione reductase (GR) catalyzes the reduction of selenenyl sulfide (RSeSG) to glutathione (GSH) and selenol (RSeH).

Language: Английский

---