Induction of reactive oxygen species by diphenyl diselenide is preceded by changes in cell morphology and permeability in Saccharomyces cerevisiae

References

• Mugesh G, Panda A, Singh HB, Punekar NS, Butcher RJ. Glutathione peroxidase-like antioxidant activity of diaryl diselenides: a mechanistic study. J Am Chem Soc 2011;123:839–850.
   Web of Science ®Google Scholar
• Nogueira CW, Zeni G, Rocha JBT. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev 2004;104:6255–6285.
   PubMed Web of Science ®Google Scholar
• Nogueira CW, Rocha JBT. Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds. Arch Toxicol 2011;85:1313–1359.
   PubMed Web of Science ®Google Scholar
• Gladyshev VN. Selenoproteins and selenoproteomes. Selenium: its molecular biology and role in human health, vol. 9; 2011:109–123.
   Google Scholar
• Hatfield DL, Tsuji PA, Carlson BA, Gladyshev VN. Selenium and selenocysteine: roles in cancer, health, and development. Trends Biochem Sci 2014;39:112–120.
   PubMed Web of Science ®Google Scholar
• Labunskyy VM, Hatfield DL, Gladyshev VN. Selenoproteins: molecular pathways and physiological roles. Physiol Rev 2014;94:739–777.
   PubMed Web of Science ®Google Scholar
• Pillai R, Uyehara-Lock JH, Bellinger FP. Selenium and selenoprotein function in brain disorders. IUBMB Life 2014;66:229–239.
   PubMed Web of Science ®Google Scholar
• Araie H, Shiraiwa Y. Selenium utilization strategy by microalgae. Molecules 2009;14:4880–4891.
   PubMed Web of Science ®Google Scholar
• Kryukov GV, Castellano S, Novoselov SV, Lobanov AV, Zehtab O, Guigo R, Gladyshev VN. Characterization of mammalian selenoproteomes. Science 2003;300:1439–1443.
   PubMed Web of Science ®Google Scholar
• Bartolini D, Piroddi M, Tidei C, Giovagnoli S, Pietrella D, Manevich Y, et al. Reaction kinetics and targeting to cellular glutathione S-transferase of the glutathione peroxidase mimetic PhSeZnCl and its d,l-polylactide microparticle formulation. Free Radic Biol Med 2015;78:56–65.
   PubMed Web of Science ®Google Scholar
• Muller A, Cadenas E, Graf P, Sies H. A novel biologically active seleno-organic compound-I glutathione peroxidase-like activity in vitro and antioxidant capacity of pz 51 (ebselen). Biochem Pharmacol 1984;33:3235–3239.
   PubMed Web of Science ®Google Scholar
• Nogueira CW, Rocha JBT. Diphenyl diselenide a janus-faced molecule. J Braz Chem Soc 2010;21:2055–2071.
   Web of Science ®Google Scholar
• Rosa RM, Moura DJ, Silva ACR, Saffi J, Henriques JAP. Antioxidant activity of diphenyl diselenide prevents the genotoxicity of several mutagens in Chinese hamster V79 cells. Mutat Res 2007;631:44–54.
   PubMed Web of Science ®Google Scholar
• Rosa RM, Roesler R, Braga AL, Saffi J, Henriques JAP. Pharmacology and toxicology of diphenyl diselenide in several biological models. Braz J Med Biol Res 2007;40:1287–1304.
   PubMed Web of Science ®Google Scholar
• Sies H. Ebselen, a seleno organic compound as glutathione peroxidase mimic. Free Radic Biol Med 1993;14:313–323.
   PubMed Web of Science ®Google Scholar
• Santi C, Tidei C, Scalera C, Piroddi M, Galli F. Selenium containing compounds from poison to drug candidates: a review on the GPx-like activity. Curr Chem Biol 2013;7:25–36.
   Google Scholar
• Chanaday NL, De Bem AF, Roth GA. Effect of diphenyl diselenide on the development of experimental autoimmune encephalomyelitis. Neurochem Int 2011;59:1155–1162.
   PubMed Web of Science ®Google Scholar
• Dias GRM, Golombieski RM, Portella RDL, Do Amaral GP, Soares FA, Da Rocha JBT, et al. Diphenyl diselenide modulates gene expression of antioxidant enzymes in the cerebral cortex, hippocampus and striatum of female hypothyroid rats. Neuroendocrinology 2014;100:45–59.
   PubMed Web of Science ®Google Scholar
• Dobrachinski F, Da Silva MH, Tassi CLC, de Carvalho NR, Dias GRM, Golombieski RM, et al. Neuroprotective effect of diphenyl diselenide in an experimental stroke model: maintenance of redox system in mitochondria of brain regions. Neurotox Res 2014;26:317–330.
   PubMed Web of Science ®Google Scholar
• Fiuza TL, Oliveira CS, Costa M, Oliveira VA, Zeni G, Pereira ME. Effectiveness of (PhSe)2 in protect against the HgCl2 toxicity. J Trace Elem Med Biol 2015;29:255–262.
   PubMed Web of Science ®Google Scholar
• Fiuza B, Subelzu N, Calcerrada P, Straliotto MR, Piacenza L, Cassina A, et al. Impact of SIN-1-derived peroxynitrite flux on endothelial cell redox homeostasis and bioenergetics: protective role of diphenyl diselenide via induction of peroxiredoxins. Free Radic Res 2015;49:122–132.
   PubMed Web of Science ®Google Scholar
• Godoi GL, De Oliveira Porciuncula L, Schulz JF, Kaufmann FN, Da Rocha JB, De Souza DOG, et al. Selenium compounds prevent amyloid β-peptide neurotoxicity in rat primary hippocampal neurons. Neurochem Res 2013;38:2359–2363.
   PubMed Web of Science ®Google Scholar
• Hort MA, Straliotto MR, De Oliveira J, Amoedo ND, Da Rocha JBT, Galina A, et al. Diphenyl diselenide protects endothelial cells against oxidized low density lipoprotein-induced injury: involvement of mitocondrial function. Biochimie 2014;105:172–181.
   PubMed Web of Science ®Google Scholar
• Mancini G, De Oliveira J, Hort MA, Moreira ELG, Ribeiro-Do-Valle RM, Rocha JBT, De Bem AF. Diphenyl diselenide differently modulates cardiovascular redox responses in young adult and middle-aged low-density lipoprotein receptor knockout hypercholesterolemic mice. J Pharm Pharmacol 2014;66:387–397.
   PubMed Web of Science ®Google Scholar
• Rupil LL, De Bem AF, Roth GA. Diphenyl diselenide-modulation of macrophage activation: down-regulation of classical and alternative activation markers. Innate Immun 2012;18:627–637.
   PubMed Web of Science ®Google Scholar
• Silvestre F, Danielski LG, Michels M, Florentino D, Vieira A, Souza L, et al. Effects of organoselenium compounds on early and late brain biochemical alterations in sepsis-survivor rats. Neurotox Res 2014;26:382–391.
   PubMed Web of Science ®Google Scholar
• Stefanello ST, Flores Da Rosa EJ, Dobrachinski F, Amaral GP, Rodrigues De Carvalho N, Almeida Da Luz SC, et al. Effect of diselenide administration in thioacetamide-induced acute neurological and hepatic failure in mice. Toxicol Res 2015;4:707–717.
   Web of Science ®Google Scholar
• Zamberlan DC, Arantes LP, Machado ML, Golombieski R, Soares FAA. Diphenyl diselenide suppresses amyloid-β peptide in Caenorhabditis elegans model of Alzheimer’s disease. Neuroscience 2014;278:40–50.
   PubMed Web of Science ®Google Scholar
• Maciel EN, Bolzan RC, Braga AL, Rocha JBT. Diphenyl diselenide and diphenyl ditelluride diferentially afect delta-aminolevulinate dehydratase from liver, kidney, and brain of mice. J Biochem Mol Toxicol 2000;14:310–319.
   PubMed Web of Science ®Google Scholar
• Rosa RM, Sulzbacher K, Picada JN, Roesler R, Saffi J, Brendel M, Henriques JAP. Genotoxicity of diphenyl diselenide in bacteria and yeast. Mutat Res 2004;563:107–115.
   PubMed Web of Science ®Google Scholar
• Rosa RM, Oliveira RB, Saffi J, Braga AL, Roesler R, Dal-Pizzol F, et al. Pro-oxidant action of diphenyl diselenide in the yeast Saccharomyces cerevisiae exposed to ROS-generating conditions. Life Sci 2005;77:2398–2411.
   PubMed Web of Science ®Google Scholar
• Bueno DC, Meinerz DF, Allebrandt J, Waczuk EP, Santos DB, Mariano DOM, Rocha JBT. Cytotoxicity and genotoxicity evaluation of organochalcogens in human leucocytes: a comparative study between ebselen, diphenyl diselenide, and diphenyl ditelluride. Bio Med Res Int 2013;2013:537279. doi: 10.1155/2013/537279
   Web of Science ®Google Scholar
• Rosseti IB, Rocha JBT, Costa MS. Diphenyl diselenide (PhSe)2 inhibits biofilm formation by Candida albicans, increasing both ROS production and membrane permeability. J Trace Elem Med Biol 2015;29:289–295.
   PubMed Web of Science ®Google Scholar
• Tidei C, Piroddi M, Galli F, Santi C. Oxidation of thiols promoted by PhSeZnCl. Tetrahedron Lett 2012;53:232–234.
   Web of Science ®Google Scholar
• Bartolini D, Commodi J, Piroddi M, Incipini L, Sancineto L, Santi C, Galli F. Glutathione S-transferase P expression regulates the Nrf2-dependent response to hermetic diselenides. Free Radic Biol Med 2015;88:466–480.
   PubMed Web of Science ®Google Scholar
• Santi C, Santoro S, Battistelli B, Testaferri L, Tiecco M. Preparation of the first bench-stable phenyl selenolate: an interesting on water nucleophilic reagent. Eur J Org Chem 2008;32:5387–5390.
   Web of Science ®Google Scholar
• Santi C, Battistelli B, Testaferri L, Tiecco M. On-water preparation of phenylselenoesters. Green Chem 2012;14:1277–1280.
   Web of Science ®Google Scholar
• BD FACService Technotes. Customer Focused Solutions, vol. 9; 2004.
   Google Scholar
• Ibrahim M, Muhammada N, Naeem M, Deobald AM, Kamdemb JP, Rocha JBT. In vitro evaluation of glutathione peroxidase (GPx)-like activity and antioxidant properties of an organoselenium compound. Toxicol In Vitro 2015;29:947–952.
   PubMed Web of Science ®Google Scholar
• Machado MS, Villela IV, Moura DJ, Rosa RM, Salvador M, Lopes NP, et al. 3′,3-Ditrifluoromethyldiphenyl diselenide: a new organoselenium compound with interesting antigenotoxic and antimutagenic activities. Mutat Res 2009;673:133–140.
   PubMed Web of Science ®Google Scholar
• Santos DB, Schiar VPP, Ribeiro MCP, Schwab RS, Meinerz DF, Allebrandt J, et al. Genotoxicity of organoselenium compounds in human leukocytes in vitro. Mutat Res 2009;676:21–26.
   PubMed Web of Science ®Google Scholar
• Azad GK, Singh V, Mandal P, Singh P, Golla U, Baranwal S, et al. Ebselen induces reactive oxygen species (ROS)-mediated cytotoxicity in Saccharomyces cerevisiae with inhibition of glutamate dehydrogenase being a target. FEBS Open Bio 2014;4:77–89.
   PubMed Web of Science ®Google Scholar
• Spallholz J. On the nature of selenium toxicity and carcinostatic activity. Free Radic Biol Med 1994;17:46–64.
   Web of Science ®Google Scholar
• Wallenberg M, Olm E, Hebert C, Ornstedt MBJ, Fernandes AP. Selenium compounds are substrates for glutaredoxins: a novel pathway for selenium metabolismo and a potential mechanism for selenium mediated cytotoxicity. Biochem J 2010;429:85–93.
   PubMed Web of Science ®Google Scholar
• Yan L, Spallholz J. Generation of reactive oxygen species from the reaction of selenium compounds with thiols and mammary tumor cells. Biochem Pharmacol 1993;45:429–437.
   PubMed Web of Science ®Google Scholar
• Freitas AS, Prestes AS, Wagner C, Sudati JH, Alves D, Porciuncula LO, et al. Reduction of diphenyl diselenide and analogs by mammalian thioredoxin reductase is independent of their gluthathione peroxidase-like activity: a possible novel pathway for their antioxidant activity. Molecules 2010;15:7699–7714.
   PubMed Web of Science ®Google Scholar
• Zhao R, Holmgren A. A novel antioxidant mechanism of ebselen involving ebselen diselenide, a substrate of mammalian thioredoxin and thioredoxin reductase. J Biol Chem 2002;277:39456–39462.
   PubMed Web of Science ®Google Scholar
• Imlay JA. Pathways of oxidative damage. Annu Rev Microbiol 2003;57:395–418.
   PubMed Web of Science ®Google Scholar
• Barbosa NB, Rocha JBT, Wondracek DC, Perottoni J, Zeni G, Nogueira CW. Diphenyl diselenide reduces temporarily hyperglycemia: possible relationship with oxidative stress. Chem-Biol Interact 2006;16:230–238.
   Web of Science ®Google Scholar
• De Bem AF, Fiuza B, Calcerrada P, Brito PM, Peluffo G, Dinis TCP, et al. Protective effect of diphenyl diselenide against peroxynitrite-mediated endothelial cell death: a comparison with ebselen. Nitric Oxide 2013;31:20–30.
   PubMed Web of Science ®Google Scholar
• Ehren JL, Maher P. Concurrent regulation of the transcription factors Nrf2 and ATF4 mediates the enhancement of glutathione levels by the flavonoid fisetin. Biochem Pharmacol 2013;15:1816–1826.
   Web of Science ®Google Scholar
• Habib E, Linher-Melville K, Lin HX, Singh G. Expression of xCT and activity of system xc- are regulated by NRF2 in human breast cancer cells in response to oxidative stress. Redox Biol 2015;5:33–42.
   PubMed Web of Science ®Google Scholar
• Lushchak VI. Adaptive response to oxidative stress: bacteria, fungi, plants and animals. Comp Biochem Physiol C Toxicol Pharmacol 2011;153:175–190.
   PubMed Web of Science ®Google Scholar
• Rocha JBT, Saraiva RA, Garcia SC, Gravina FS, Nogueira CW. Aminolevulinate dehydratase (ALA-D) as marker protein of intoxication with metals and other pro-oxidant situations. Toxicol Res 2012;85:85–102.
   Web of Science ®Google Scholar
• Abolaji AO, Kamdem JO, Lugokenski TH, Nascimento TK, Waczuk EP, Farombi EO, et al. Involvement of oxidative stress in 4-vinylcyclohexene induced toxicity in Drosophila melanogaster. Free Radic Biol Med 2014;71:99–108.
   PubMed Web of Science ®Google Scholar
• Abolaji AO, Kamdem JP, Lugokenski TH, Farombi EO, Souza DO, Loreto ELS, Rocha JBT. Ovotoxicants 4-vinylcyclohexene 1,2-monoepoxide and 4-vinylcyclohexene diepoxide disrupt redox status and modify different electrophile sensitive target enzymes and genes in Drosophila melanogaster. Redox Biol 2015;5:328–339.
   PubMed Web of Science ®Google Scholar
• Huang Y, Li W, Kong AT. Anti-oxidative stress regulator NF-E2-related factor 2 mediates the adaptive induction of antioxidant and detoxifying enzymes by lipid peroxidation metabolite 4-hydroxynonenal. Cell Biosci 2012;2:1–7.
   PubMed Web of Science ®Google Scholar
• Jin Y, Miao W, Lin X, Pan X, Ye Y, Xu M, Fu Z. Acute exposure to 3-methylcholanthrene induces hepatic oxidative stress via activation of the Nrf2/ARE signaling pathway in mice. Environ Toxicol 2013;29:1399–1408.
   PubMed Web of Science ®Google Scholar