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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Nov 14

PMID 37959771

Authors

Joao M Anghinoni

Paloma T Birmann

Marcia J da Rocha

Caroline S Gomes

Michael J Davies

Cesar A Bruning

Lucielli Savegnago

Eder J Lenardao

Affiliations

Soon will be listed here.

Abstract

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

Citing Articles

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Synthesis of Selenium-Decorated -Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions.

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References

Kumar M, Chhillar B, Yadav M, Sagar P, Singhal N, Gates P . Catalytic and highly regenerable aminic organoselenium antioxidants with cytoprotective effects. Org Biomol Chem. 2021; 19(9):2015-2022. DOI: 10.1039/d0ob02368j. View

Plano D, Moreno E, Font M, Encio I, Antonio Palop J, Sanmartin C . Synthesis and in vitro anticancer activities of some selenadiazole derivatives. Arch Pharm (Weinheim). 2010; 343(11-12):680-91. DOI: 10.1002/ardp.201000014. View

Frizon T, Cararo J, Saba S, Dal-Pont G, Michels M, Braga H . Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress. Oxid Med Cell Longev. 2020; 2020:5417024. PMC: 7275203. DOI: 10.1155/2020/5417024. View

Kalyanaraman B, Darley-Usmar V, Davies K, Dennery P, Forman H, Grisham M . Measuring reactive oxygen and nitrogen species with fluorescent probes: challenges and limitations. Free Radic Biol Med. 2011; 52(1):1-6. PMC: 3911769. DOI: 10.1016/j.freeradbiomed.2011.09.030. View

Storkey C, Pattison D, Ignasiak M, Schiesser C, Davies M . Kinetics of reaction of peroxynitrite with selenium- and sulfur-containing compounds: Absolute rate constants and assessment of biological significance. Free Radic Biol Med. 2015; 89:1049-56. DOI: 10.1016/j.freeradbiomed.2015.10.424. View

Domingues M, Casaril A, Birmann P, Lourenco D, Vieira B, Begnini K . Selanylimidazopyridine Prevents Lipopolysaccharide-Induced Depressive-Like Behavior in Mice by Targeting Neurotrophins and Inflammatory/Oxidative Mediators. Front Neurosci. 2018; 12:486. PMC: 6060445. DOI: 10.3389/fnins.2018.00486. View

Steinbrenner H, Speckmann B, Klotz L . Selenoproteins: Antioxidant selenoenzymes and beyond. Arch Biochem Biophys. 2016; 595:113-9. DOI: 10.1016/j.abb.2015.06.024. View

Pinheiro A, Busatto F, Schaefer B, Tomasini P, Nunes I, Machado T . Synthesis, characterization, antioxidant potential, and cytotoxicity screening of new Cu(II) complexes with 4-(arylchalcogenyl)-1H-pyrazoles ligands. J Inorg Biochem. 2022; 237:112013. DOI: 10.1016/j.jinorgbio.2022.112013. View

de Freitas Couto S, Araujo S, Bortolotto V, Poetini M, Pinheiro F, Musachio E . 7-chloro-4-(phenylselanyl) quinoline prevents dopamine depletion in a Drosophila melanogaster model of Parkinson's-like disease. J Trace Elem Med Biol. 2018; 54:232-243. DOI: 10.1016/j.jtemb.2018.10.015. View

10.

Hartwig de Oliveira D, Sousa F, Birmann P, Pesarico A, Alves D, Jacob R . Evaluation of antioxidant activity and toxicity of sulfur- or selenium-containing 4-(arylchalcogenyl)-1-pyrazoles. Can J Physiol Pharmacol. 2020; 98(7):441-448. DOI: 10.1139/cjpp-2019-0356. View

11.

Mailahn D, Iarocz L, Nobre P, Perin G, Sinott A, Pesarico A . A greener protocol for the synthesis of phosphorochalcogenoates: Antioxidant and free radical scavenging activities. Eur J Med Chem. 2020; 213:113052. DOI: 10.1016/j.ejmech.2020.113052. View

12.

Villalpando-Rodriguez G, Gibson S . Reactive Oxygen Species (ROS) Regulates Different Types of Cell Death by Acting as a Rheostat. Oxid Med Cell Longev. 2021; 2021:9912436. PMC: 8380163. DOI: 10.1155/2021/9912436. View

13.

Carroll L, Pattison D, Fu S, Schiesser C, Davies M, Hawkins C . Reactivity of selenium-containing compounds with myeloperoxidase-derived chlorinating oxidants: Second-order rate constants and implications for biological damage. Free Radic Biol Med. 2015; 84:279-288. DOI: 10.1016/j.freeradbiomed.2015.03.029. View

14.

Wang X, Li C, Huan Y, Cao H, Sun S, Lei L . Diphenyl diselenide ameliorates diabetic nephropathy in streptozotocin-induced diabetic rats via suppressing oxidative stress and inflammation. Chem Biol Interact. 2021; 338:109427. DOI: 10.1016/j.cbi.2021.109427. View

15.

Sies H, Jones D . Reactive oxygen species (ROS) as pleiotropic physiological signalling agents. Nat Rev Mol Cell Biol. 2020; 21(7):363-383. DOI: 10.1038/s41580-020-0230-3. View

16.

Carroll L, Gardiner K, Ignasiak M, Holmehave J, Shimodaira S, Breitenbach T . Interaction kinetics of selenium-containing compounds with oxidants. Free Radic Biol Med. 2020; 155:58-68. DOI: 10.1016/j.freeradbiomed.2020.05.007. View

17.

He X, Nie Y, Zhong M, Li S, Li X, Guo Y . New organoselenides (NSAIDs-Se derivatives) as potential anticancer agents: Synthesis, biological evaluation and in silico calculations. Eur J Med Chem. 2021; 218:113384. DOI: 10.1016/j.ejmech.2021.113384. View

18.

Ng H, Leo C, OSullivan K, Alexander S, Davies M, Schiesser C . 1,4-Anhydro-4-seleno-d-talitol (SeTal) protects endothelial function in the mouse aorta by scavenging superoxide radicals under conditions of acute oxidative stress. Biochem Pharmacol. 2016; 128:34-45. DOI: 10.1016/j.bcp.2016.12.019. View

19.

Gall J, Alves A, Carraro Junior L, Rech T, Dos Santos Neto J, Alves D . Insights into serotonergic and antioxidant mechanisms involved in antidepressant-like action of 2-phenyl-3-(phenylselanyl)benzofuran in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2020; 102:109956. DOI: 10.1016/j.pnpbp.2020.109956. View

20.

Nogueira C, Barbosa N, Rocha J . Toxicology and pharmacology of synthetic organoselenium compounds: an update. Arch Toxicol. 2021; 95(4):1179-1226. PMC: 8012418. DOI: 10.1007/s00204-021-03003-5. View