Abstract
Organoselenum compounds have been reported to have a wide range of pharmacological properties. Amine-based diselenide, (Z)-N-(4-methylbenzylidene)-1-(2-((2-(1-((E)-4-methyl benzylideneamino)ethyl)phenyl)diselanyl)phenyl)ethanamine ethyl)phenyl) diselanyl) phenyl) ethylimino) methyl)phenol (compound A), and diphenyl diselenide (PhSe)2 were screened for in vitro antioxidant activity. Compound A and (PhSe)2 were tested against sodium nitroprusside (SNP)- and Fe(II)-induced thiobarbituric acid-reactive species (TBARS) in rat brain homogenates. The radical scavenging activity was measured by 1,1-diphenyl-2-picrylhydrazyl assay. Both compounds A and (PhSe)2 decreased Fe(II)- and SNP-stimulated TBARS production in rat brain homogenates. Compound A exhibited the strongest antioxidant activity in the radical scavenging assay, although (PhSe)2, the simplest of the diaryl diselenide, presented no activity. In conclusion, the results of the present investigation indicated that compound A and (PhSe)2 had preventive effects against SNP- and Fe(II)-induced oxidative stress in rat brain homogenates. The amine group in the organic moiety dramatically changed the potency of amine-based diselenide.
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Azbill RD, Mu XJ, BruceKeller AJ, Mattson MP, Springer JE (1997) Impaired mitochondrial function, oxidative stress and altered antioxidant enzyme activities following traumatic spinal cord injury. Brain Res 765:283–290
Halliwell B (2006) Oxidative stress and neurodegeneration: where are we now? J Neurochem 97:1634–1658
Santamaría A, Salvatierra-Sanchez R, Vazquez-Roman B, Santiago-Lopez D, Villeda-Hernandez J, Galvan-Arzates S, Jimenez-Capdeville ME, Ali SF (2003) Protective effects of the antioxidant selenium on quinolinic acid-induced neurotoxicity in rats: in vitro and in vivo studies. J Neurochem 86:479–488
Morrissey PA, O’Brien NM (1998) Dietary antioxidants in health and disease. Int Dairy J 8:463–472
Naziroglu M (2009) Role of selenium on calcium signaling and oxidative stress-induced molecular pathways in epilepsy. Neurochem Res 34:2181–2191
Steinbrenner H, Sies H (2009) Protection against reactive oxygen species by selenoproteins. Biochim Biophys Acta 1790:1478–1485
Nogueira CW, Zeni G, Rocha JBT (2004) Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev 104:6255–6285
Parnham MJ, Graf E (1991) Pharmacology of synthetic organic selenium compounds. Progress in Drug Res 36:9–47
Saito I, Asano T, Sano K, Takakura K, Abe H, Yoshimoto T, Kikuchi H, Ohta T, Ishibashi S (1998) Neuroprotective effect of an antioxidant, ebselen, in patients with delayed neurological deficits after aneurysmal subarachnoid hemorrhage. Neurosurgery 42:269–277
Kondoh S, Nagasawa S, Kawanishi M, Yamaguchi K, Kajimoto S, Ohta T (1999) Effects of ebselen on cerebral ischemia and reperfusion evaluated by microdialysis. Neurological Res 21:682–686
Imai H, Graham DI, Masayasu H, Macrae IM (2003) Antioxidant ebselen reduces oxidative damage in focal cerebral ischemia. Free Radic Biol Med 34:56–63
Wilson SR, Zucker PA, Huang RRC, Spector A (1989) Development of synthetic compound with glutathione peroxidase activity. J Am Chem Soc 111:5936–5939
Chaudiere J, Courtin O, Leclaire J (1992) Glutathione oxidase activity of selenocystamine: a mechanistic study. Biochem Biophys 296:328–336
Rossato JI, Ketzer LA, Centurião FB, Silva SJN, Lüdtke DS, Zeni G, Braga AL, Rubin MA, Rocha JBT (2002) Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain. Neurochem Res 27:297–303
Hassan W, Ibrahim M, Nogueira CW, Braga AL, Mohammad Zai IU, Taube PS, Rocha JBT (2009) Enhancement of iron-catalyzed lipid peroxidation by acidosis in brain homogenate: comparative effect of diphenyl diselenide and ebselen. Brain Res 1258:71–77
Braga AL, Paixão MW, Marin G (2005) Seleno-imine: a new class of versatile, modular N, Se ligands for asymmetric palladium-catalyzed allylic alkylation. Synlett 11:1675–1678
Liu D, Dai Q, Zhang X (2005) A new class of readily available and conformationally rigid phosphino-oxazoline ligands for asymmetric catalysis. Tetrahedron 61:6460–6471
Paulmier C (1986) Synthesis and properties of selenide. In: Baldwin JE (ed) Selenium reagents and intermediates in organic synthesis. Pergamon, Oxford, pp 84–116
Ohkawa H, Ohishi N, Yagi K (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Analytical Biochemistry 95:351–358
Choi CW, Kim SC, Hwang SS, Choi BK, Ahn HJ, Lee MY, Park SH, Kim SK (2002) Antioxidant activity and free radical scavenging capacity between Korean medicinal plants and flavonoids by assay-guided comparison. Plant Sci 153:1161–1168
Talas ZS, Ozdemir I, Yilmaz I, Gok Y, ve Orun I (2008) The investigation of the antioxidative properties of the novel synthetic organoselenium compounds in some rat tissues. Exp Biol Med 233:575–579
Talas ZS, Yilmaz I, Ozdemir I, Ates B, Gok Y, Cetinkaya B (2009) Role of synthesised organoselenium compounds on protection of rat erythrocytes from DMBA-induced oxidative stress. Biol Trace Elem Res 128:167–175
Talas ZS, Bayraktar N, Ozdemir I, Gok Y, Yilmaz I (2009) The effects of synthetic organoselenium compounds on nitric oxide levels in DMBA-induced rat liver. J Environ Biol 30:591–593
Ozdemir I, Talas ZS, Gok Y, Ates B, Yilmaz I (2010) Changes in tyrosine hydroxylase activity, adrenomedullin and total RNA levels by treatment of organoselenium compounds in rat hypothalamus exposed to DMBA. Fresenius Environmental Bulletin 19(4a):664–668
Graf E, Mahoney JR, Bryant RG, Eaton JW (1984) Iron catalyzed hydroxyl radical formation: stringent requirement for free iron coordination site. J Biol Chem 259:3620–3624
Klebanoff SJ, Gally JI, Goldstein IM, Snyderman R (eds) (1992) Oxygen metabolites from phagocytes. Raven, New York, pp 541–588
Arnold WP, Longneeker DE, Epstein RM (1984) Photodegradation of sodium nitroprusside: biologic activity and cyanide release. Anesthesiology 61:254–260
Bates JNMT, Guerra R, Harrison DG (1990) Nitric oxide generation from nitroprusside by vascular tissue. Biochem Pharmacol 42:157–165
Bolanos J, Almeida A (1999) Roles of nitric oxide in brain hypoxia–ischemia. Biochim Biophys Acta 1411:415–436
Ogunmoyole RJBT, Okoronkwo AE, Kade IJ (2009) Altered pH homeostasis modulates the glutathione peroxidase mimics and other antioxidant properties of diphenyl diselenide. Chem Biol Interact 23:106–11
Valko M, Izakovic M, Mazur M, Rhodes CJ, Telser J (2004) Role of oxygen radicals 545 in DNA damage and cancer incidence. Mol Cell Biochem 266:37–56
Acknowledgments
Mohammad Ibrahim is a beneficiary of the TWAS-CNPq doctoral fellowship program. The financial support of TWAS, CNPq, is acknowledged.
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Ibrahim, M., Hassan, W., Deobald, A.M. et al. An Organoselenium Drug with Antioxidant Activity and Free Radical Scavenging Capacity In Vitro. Biol Trace Elem Res 149, 399–404 (2012). https://doi.org/10.1007/s12011-012-9440-7
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DOI: https://doi.org/10.1007/s12011-012-9440-7