Glutathione peroxidase-like functions of 1,2-diselenane-4,5-diol and its amphiphilic derivatives: Switchable catalytic cycles depending on peroxide substrates.

Bioorganic & Medicinal Chemistry
Kenta AraiMichio Iwaoka

Abstract

Amphiphilic derivatives of (±)-trans-1,2-diselenane-4,5-diol (DSTox) decorated with long alkyl chains or aromatic substituents via ester linkages were applied as glutathione peroxidase (GPx)-like catalysts. The reduction of H2O2 with the diselenide catalysts was accelerated through a GPx-like catalytic cycle, in which the diselenide (Se-Se) bond was reduced to the diselenolate form ([Se-,Se-]) by coexisting dithiothreitol, and the generated highly active [Se-,Se-] subsequently reduced H2O2 to H2O retrieving the original Se-Se form. In the lipid peroxidation of lecithin/cholesterol liposomes induced by 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH), on the other hand, the Se-Se form directly reduced lipid peroxide (LOOH) to the corresponding alcohol (LOH), inhibiting the radical chain reaction, to exert the antioxidative effect. Thus, the two GPx-like catalytic cycles can be switched depending on the peroxide substrates. Furthermore, hydrophilic compounds with no or short alkyl groups (C3) showed high antioxidative activities for the catalytic reduction of H2O2, while lipophilic compounds with long alkyl chains (C6-C14) or aromatic substituents were more effective antioxidants against lipid peroxidation. In addition, these...Continue Reading

References

Jun 1, 1979·Analytical Biochemistry·H OhkawaK Yagi
Oct 1, 1987·Annals of Internal Medicine·C E CrossD Harman
May 15, 1973·FEBS Letters·L FloheH H Schock
Apr 11, 2007·Biochemistry·Joris BeldDonald Hilvert
Oct 17, 2007·Biological Chemistry·Marcus ConradGeorg W Bornkamm
Aug 1, 2008·Chemistry : a European Journal·Krishna P Bhabak, Govindasamy Mugesh
Apr 21, 2009·Biochimica Et Biophysica Acta·Stefano ToppoMatilde Maiorino
Aug 10, 2010·Accounts of Chemical Research·Krishna P Bhabak, Govindasamy Mugesh
Oct 23, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniel PlanoCarmen Sanmartín
Dec 3, 2010·Chemical Society Reviews·Xin HuangJiacong Shen
Dec 4, 2012·Biochimica Et Biophysica Acta·Regina Brigelius-Flohé, Matilde Maiorino
Dec 25, 2012·International Journal of Molecular Sciences·Bidur BhandaryHan-Jung Chae
Oct 15, 2013·Angewandte Chemie·John C LukeshRonald T Raines
Sep 23, 2014·European Journal of Medicinal Chemistry·Vanessa NascimentoAntonio L Braga
Apr 18, 2015·Chembiochem : a European Journal of Chemical Biology·Michio IwaokaK Indira Priyadarsini
Jun 6, 2015·European Journal of Medicinal Chemistry·Laura L Romero-HernándezJosé G Fernández-Bolaños
Jul 23, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Michio IwaokaKavirayani Indira Priyadarsini
Jul 30, 2015·Organic & Biomolecular Chemistry·Debasish Bhowmick, Govindasamy Mugesh
Mar 8, 2016·International Journal of Molecular Sciences·Hafiz Maher Ali ZeeshanHan-Jung Chae
Nov 16, 2016·Future Medicinal Chemistry·Azucena MarsetJosé G Fernández-Bolaños
Mar 2, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kenta AraiMichio Iwaoka
Dec 3, 2017·Chembiochem : a European Journal of Chemical Biology·Kenta AraiMichio Iwaoka
Nov 25, 2015·Toxicology Research·Prachi VermaK Indira Priyadarsini
Jan 16, 2020·Antioxidants·Ana Carolina RuberteCarmen Sanmartín

❮ Previous
Next ❯

Citations

Mar 5, 2021·Chemistry, an Asian Journal·Aditya UpadhyaySangit Kumar
Jul 4, 2021·European Journal of Medicinal Chemistry·Hongyan ChuaiMinhang Xin
Oct 1, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Aditya UpadhyaySangit Kumar

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.