Cleavage of a Peroxide Bond via a Dual Attack by Functional Mimics of Glutathione Peroxidase DOI
Rakesh Kumar, Amirul Islam, Rudra Shankar Pati

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract Nonmetal‐containing peroxidase enzymes, including glutathione (GPx), and peroxiredoxins, control cellular redox levels by catalyzing the reduction of H 2 O . The remarkably higher reactivity GPx enzyme as compared to fully dissociated synthetic selenolate/thiolate molecule is probably due dual‐attack on peroxide bond (HO 1 −O H) enzyme; first one a nucleophilic attack moiety atom second at acidic “parked proton” from Trp or His residue present enzyme's active site, leading facile cleavage O−O bond. Herein, we report two compounds ( ), having selenolate (Se − ) proton donor (imidazolium −COOH group) moieties, which showed excellent GPx‐like activity via combined effect that donates electrons antibonding (σ*) orbital imidazolium carboxylic acid side chain forms strong H‐bonding with facilitates more efficiently. exhibit remarkable ability in protecting Cu(I)‐complex [TpmCu(CH 3 CN)] + 9 against acting sacrificial antioxidant, thereby preventing metal‐mediated ROS production.

Language: Английский

Mechanistic insights into nonlinear effects in copper-catalyzed asymmetric esterification DOI Creative Commons
Xiaotao Zhu, Meirong Huang, Hongli Bao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 4, 2025

Nonlinear effects (NLEs) serve as a widespread tool in the study of asymmetric catalytic reactions. However, due to diversity ligand-metal coordination modes, information obtained solely from linear relationship between ee values ligands and products complex systems is often indirect. Here, we report precise method that directly connects metal complexes products, with purpose determining active species occur systems. Through an in-depth analysis mechanism our previous copper-catalyzed esterification reactions, find intrinsic key (LLCuI) within this traditionally non-linear system. This holds promise powerful for exploration catalysis mechanisms, heralding new avenues understanding application processes.

Language: Английский

Citations

1

Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules DOI Creative Commons
João M. Anghinoni, Paloma T. Birmann, Marcia Juciele da Rocha

et al.

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

Citations

18

Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp2)–H Bond Selenylation of Imidazo[2,1-b]thiazole and Related Structures DOI Creative Commons
Cassio A. O. Moraes,

Rafaely B. C. Santos,

Marcos F. O. Cavalcante

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(42), P. 39535 - 39545

Published: Oct. 12, 2023

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1-b]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, well applicability to imidazopyridine and imidazopyrimidine.

Language: Английский

Citations

11

Naphthalene peri-Diselenide-Based BODIPY Probe for the Detection of Hydrogen Peroxide, tert-Butylhydroperoxide, Hydroxyl Radical, and Peroxynitrite Ion DOI Creative Commons

Babli Chhillar,

Nikhil Sodhi,

Rajni Kadian

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(7), P. 6396 - 6405

Published: Feb. 13, 2025

Dimethoxynaphthalene peri-diselenide-based BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) probe has been synthesized. The demonstrated selectivity and sensitivity for hydrogen peroxide (H2O2) tert-butylhydroperoxide (t-BuOOH), hydroxyl radical (•OH), peroxynitrite ion (ONOO–) detection reversibility upon treatment with glutathione. limits of the were observed to be 0.40 μM H2O2, 0.41 t-BuOOH, 0.95 •OH, 0.46 ONOO–, respectively. A proposed mechanism "turn-on" event suggested corroborated by spectroscopic computational data. It that electron transfer occurred from Se center moiety, followed photoinduced (PET) mechanism.

Language: Английский

Citations

0

Small-molecule organoselenocyanates: Recent developments toward synthesis, anticancer, and antioxidant activities DOI
Md. Badirujjaman, Nikita Pal, Krishna P. Bhabak

et al.

Current Opinion in Chemical Biology, Journal Year: 2023, Volume and Issue: 75, P. 102337 - 102337

Published: June 3, 2023

Language: Английский

Citations

8

Aminic Organoselenium Compounds as Glutathione Peroxidase Mimics and Inhibitors of Ferroptosis DOI

Babli Chhillar,

Rajni Kadian, Manish Kumar

et al.

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

Citations

3

Benzoimidazolyl Organoseleniums: Antioxidant Activity and Catalysts for Selective Iodination of Arenes and Nitro-Michael Reaction DOI
Monojit Batabyal, Deeksha Chaurasia, Priyanka Rani Panda

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14328 - 14340

Published: Sept. 16, 2024

Here, the synthesis and catalytic activities of benzoimidazole-derived organoselenium compounds have been explored. The synthesized bis(2-benzoimidazolyl) diselenide, having increased Lewis acidity on selenium center, outperforms simple phenyl

Language: Английский

Citations

2

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

Babli Chhillar,

Akanksha Sharma,

Shital Rani

et al.

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

Citations

1

Synthesis and glutathione peroxidase (GPx)-like activity of selenocystine (SeC) bioconjugates of biotin and lipoic acid DOI
Shakti K. Maurya, Abhishek Tripathi, Karuthapandi Selvakumar

et al.

Amino Acids, Journal Year: 2023, Volume and Issue: 55(12), P. 1981 - 1989

Published: Nov. 16, 2023

Language: Английский

Citations

2

Can selenenyl sulfides be a substrate of glutathione reductase enzyme? A theoretical insight DOI Creative Commons
Vishnu R. Chari, Raghu Nath Behera

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

Citations

0