Identification of sulfhydryl-containing proteins and further evaluation of the selenium-tagged redox homeostasis-regulating proteins DOI Creative Commons
Zhongyao Jiang,

Yue Tang,

Jun Lu

et al.

Redox Biology, Journal Year: 2023, Volume and Issue: 69, P. 102969 - 102969

Published: Nov. 27, 2023

Chemoproteomic profiling of sulfhydryl-containing proteins has consistently been an attractive research hotspot. However, there remains a dearth probes that are specifically designed for proteins, possessing sufficient reactivity, specificity, distinctive isotopic signature, as well efficient labeling and evaluation capabilities implicated in the regulation redox homeostasis. Here, specific selenium-containing (Se-probes) this work displayed high specificity reactivity toward cysteine thiols on small molecules, peptides purified showed very good competitive effect gel-ABPP. We identified more than 6000 candidate proteins. In TOP-ABPP, we investigated peptide labeled by Se-probes, which revealed distinct envelope pattern selenium both primary secondary mass spectra. This unique can provide compelling evidence identifying regulatory other target peptides. Furthermore, our examiation post-translational modification (PTMs) site residues oxidation PTMs was predominantly observed. anticipate Se-probes will enable broader deeper proteome-wide ideal tool focusing regulate homeostasis advance development innovative selenium-based pharmaceuticals.

Language: Английский

Organoselenium compounds in medicinal chemistry DOI
Carola Gallo‐Rodriguez, Juan B. Rodríguez

ChemMedChem, Journal Year: 2024, Volume and Issue: 19(17)

Published: May 23, 2024

Abstract The chemical and biological interest in this element the molecules bearing selenium has been exponentially growing over years. Selenium, formerly designated as a toxin, becomes vital trace for life that appears selenocysteine its dimeric form, selenocystine, active sites of selenoproteins, which catalyze wide variety reactions, including detoxification reactive oxygen species modulation redox activities. From point view drug developments, organoselenium drugs are isosteres sulfur‐containing oxygen‐containing with advantage presence atom confers antioxidant properties high lipophilicity, would increase cell membrane permeation leading to better oral bioavailability. This statement is paramount relevance considering big number clinically employed compounds sulfur or atoms their structures nucleosides carbohydrates. Thus, article we have focused on relevant features application medicinal chemistry. With increasing chemistry, attempted highlight most significant published data subject, mainly concentrating analysis last In consequence, recent advances pharmacological discussed.

Language: Английский

Citations

11
Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides DOI
Peng‐Fei Huang,

Jia-Le Fu,

Zhi-Gang Quan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Language: Английский

Citations

0
Green and efficient choline hydroxide-promoted C(sp3)-H selenation of arylacetamides at room temperature DOI
Jun-Bo Wang,

Yu Guan,

Bo-Xuan Huo

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 567, P. 114452 - 114452

Published: Aug. 15, 2024

Language: Английский

Citations

1
Highly Electrophilic Intermediates in the Bypass Mechanism of Glutathione Peroxidase: Synthesis, Reactivity, and Structures of Selenocysteine‐Derived Cyclic Selenenyl Amides DOI Creative Commons
Ryosuke Masuda,

Takafumi Karasaki,

Shohei Sase

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(71)

Published: Sept. 22, 2023

Selenocysteine (Sec)-derived cyclic selenenyl amides, formed by the intramolecular cyclization of Sec selenenic acids (Sec-SeOHs), have been postulated to function as protective forms in bypass mechanism glutathione peroxidase (GPx). However, their chemical properties not experimentally elucidated proteins or small-molecule systems. Recently, we reported first nuclear magnetic resonance observation Sec-SeOHs and corresponding amides using selenopeptide model systems incorporated a molecular cradle. Herein, elucidate structures reactivities Sec-derived amides. The crystal reactions toward cysteine thiol 1,3-diketone-type probe indicated highly electrophilic character This suggests that they can serve only suppress inactivation GPx but also intermediates selenoproteins.

Language: Английский

Citations

3
Should ebselen be considered for the treatment of mercury intoxication? A minireview DOI
Nilda Vargas Barbosa, Michael Aschner, Alexey A. Tinkov

et al.

Toxicology Mechanisms and Methods, Journal Year: 2023, Volume and Issue: 34(1), P. 1 - 12

Published: Sept. 20, 2023

AbstractMercury is a ubiquitous environmental contaminant and can be found in inorganic (Hg0, Hg+ Hg2+) organic forms (chiefly CH3Hg+ or MeHg+). The main route of human, mammals bird exposure occurs via predatory fish ingestion. Occupational to Hg0 (and also occur; furthermore, gold mining areas the Hg high. toxicity electrophilic (E+Hg) mediated by disruption thiol (-SH)- selenol (-SeH)-containing proteins. therapeutic approaches treat methylmercury (MeHg+), Hg2+ are limited. Here we discuss potential use ebselen as agent lower body burden man. Ebselen safe drug for humans has been tested clinical trials (for instance, brain ischemia, noise-induce hearing loss, diabetes complications, bipolar disorders) at doses varying from 400 3600 mg per day. Two with moderate severe COVID approved. metabolized an intermediate -SeH (selenol) functional group, which greater affinity than available thiol-containing agents. Accordingly, observed vitro rodent models vivo, exhibited protective effects against MeHg+, indicating its MeHg+ overexposure. combined molecules (e.g. N-acetylcysteine enaramide)) commented, because they have synergistic MeHg+.Keywords: Mercury intoxicationebselenmercury exposureseleniummercury antagonism Disclosure statementNo conflict interest was reported author(s).Additional informationFundingThis work financially supported Brazilian developmental agencies: FAPERGS/CNPq 12/2014-PRONEX: n◦ 16/2551-0000, CAPES/PROEX [n◦ 23038.004173/2019-93; 0493/2019; n◦88882.182125/2018-01; 88882.182123/2018-01], INCT-EN: National Institute Science Technology Cerebral Diseases, Excitotoxicity, Neuroprotection (NVB., JBTR). MA part grant Environmental Health Sciences (NIEHS) R01ES07331. Marcelo Farina's research funded grants Council Scientific Technological Development (CNPq) [research 405426/2021-6, 302952/2018-7 404666/2018-3]. AAT Ministry Higher Education Russian Federation 0856-2020-0008. Education, Project No. FENZ-2023-0004.

Language: Английский

Citations

2
A selenoureido-iminoglycolipid transported by zeolitic-imidazolate framework nanoparticles: a novel antioxidant therapeutic approach DOI Creative Commons
Fátima Guerrero, Andrés Carmona,

Victoria Vidal

et al.

Nanoscale Horizons, Journal Year: 2023, Volume and Issue: 8(12), P. 1700 - 1710

Published: Jan. 1, 2023

The controlled encapsulation of a Se-containing glycomimetic into zeolitic-imidazolate framework-8 nanoparticles resulted in an effective antioxidant nanoplatform (DSeU@ZIF8), which allowed protecting endothelial cells from oxidative stress damage.

Language: Английский

Citations

2
Three-Component Syntheses of Functionalized Selenocyanates DOI
Yu. V. Ostapiuk, Andreas Schmidt, Oksana V. Barabash

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 10, 2024

Abstract A metal-free Meerwein-type arylation protocol of α,β-unsaturated compounds is reported. 4-Aryl-3-selenocyanatobutan-2-ones, methyl 3-aryl-2-selenocyanatopropanoates, 3-aryl-2-selenocyanatopropanenitriles, and 1-aryl-2-phenyl-2-selenocyanatoethanes were prepared by a selenocyanatoarylation reaction from easily available arenediazonium tetrafluoroborates, potassium selenocyanate, vinyl ketone, acrylate, acrylonitrile, or styrene, respectively, in 39–84% yields. The proceeds smoothly quickly under mild conditions. can be scaled to the gram scale. mechanism for this proposed.

Language: Английский

Citations

0
Selenium and small molecules: a symbiotic partnership DOI
Cristina Morán-Serradilla, Carmen Sanmartín, Arun Sharma

et al.

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 217 - 232

Published: Nov. 1, 2024

Language: Английский

Citations

0
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

1
Identification of sulfhydryl-containing proteins and further evaluation of the selenium-tagged redox homeostasis-regulating proteins DOI Creative Commons
Zhongyao Jiang,

Yue Tang,

Jun Lu

et al.

Redox Biology, Journal Year: 2023, Volume and Issue: 69, P. 102969 - 102969

Published: Nov. 27, 2023

Chemoproteomic profiling of sulfhydryl-containing proteins has consistently been an attractive research hotspot. However, there remains a dearth probes that are specifically designed for proteins, possessing sufficient reactivity, specificity, distinctive isotopic signature, as well efficient labeling and evaluation capabilities implicated in the regulation redox homeostasis. Here, specific selenium-containing (Se-probes) this work displayed high specificity reactivity toward cysteine thiols on small molecules, peptides purified showed very good competitive effect gel-ABPP. We identified more than 6000 candidate proteins. In TOP-ABPP, we investigated peptide labeled by Se-probes, which revealed distinct envelope pattern selenium both primary secondary mass spectra. This unique can provide compelling evidence identifying regulatory other target peptides. Furthermore, our examiation post-translational modification (PTMs) site residues oxidation PTMs was predominantly observed. anticipate Se-probes will enable broader deeper proteome-wide ideal tool focusing regulate homeostasis advance development innovative selenium-based pharmaceuticals.

Language: Английский

Citations

1