Antioxidant effect of functionalized alkyl-organotellurides: A study in vitro

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 4, 2010, Pages 467-475

  Gay, Bibiana M ^a   Luchese, Cristiane ^a   Nogueira, Cristina W ^a   Wendler, P ^b   MacEdo, Alexandra ^b   Dos Santos, Alcindo A ^c  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Antioxidant; Functionalized alkyl organotellurides; Liver lipid peroxidation; Tellurium

Indexed keywords

2 (BUTYLTELLANYL)ETHYL 2 METHYL 1,3 DIOXOLANE; 4 (BUTYLTELLANYL)BUTAN 2 ONE; 4 (BUTYLTELLANYL)BUTAN 2 ONE OXIME; 4 (BUTYLTELLURO)BUTAN 2 OL; ALPHA TOCOPHEROL; ANTIOXIDANT; EDETATE IRON; NITROPRUSSIDE SODIUM; PORPHOBILINOGEN SYNTHASE; THIOL DERIVATIVE; THIOL OXIDASE; THIOL PEROXIDASE; TROLOX C; UNCLASSIFIED DRUG; ORGANOMETALLIC COMPOUND; OXIDOREDUCTASE; TELLURIUM; THIOL OXIDASE, 47 KDA;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; ENZYME ACTIVITY; IC 50; IN VITRO STUDY; LIPID PEROXIDATION; LIVER HOMOGENATE; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CARBONYLATION; PROTEIN CONTENT; RAT; ANIMAL; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; IC50; LIVER; METABOLISM; STRUCTURE ACTIVITY RELATION;

RATTUS;

ANIMALS; ANTIOXIDANTS; INHIBITORY CONCENTRATION 50; LIPID PEROXIDATION; LIVER; ORGANOMETALLIC COMPOUNDS; OXIDOREDUCTASES ACTING ON SULFUR GROUP DONORS; PORPHOBILINOGEN SYNTHASE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TELLURIUM;

EID: 77954389514     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903257892     Document Type: Article

References (53)

1. Engman L, Kanda T, Gallegos A. Water-soluble organotellurium compounds inhibit thioredoxin reductase and the growth of human cancer cells. Anticancer Drug Des 2000;15:323-330 (Pubitemid 32441347)
2. Nogueira CW, Quinhones EB, Jung EAC, Zeni G, Rocha JBT. Anti-infammatory and antinociceptive activity of diphenyl diselenide. Infamm Res 2003;63:52-56 (Pubitemid 36286702)
3. Cunha LOR, Urano ME, Chagas JR, Almeida PC, Bincoletto C, Tersariol ILS, et al. Tellurium-based cysteine protease inhibitors: evaluation of novel organotellurium (IV) compounds as inhibitors of human cathepsin B. Bioorg Med Chem Lett 2005;15:755-760 (Pubitemid 40143161)
4. Savegnago L, Jesse CR, Pinto LG, Rocha JBT, Barancelli DA, Nogueira CW. Diphenyl diselenide exerts antidepressant-like and anxiolytic-like efects in mice: involvement of l-arginine-nitric oxide-soluble guanylate cyclase pathway in its antidepressant-like action. Pharmacol Biochem Behav 2008;88:418-426 (Pubitemid 350266784)
5. Wöhler F. Ann Chem 1840;35:111.
6. Rooseboom M, Vermeulen NPE, Durgut F: Comparative study on the bioactivation mechanisms and cytotoxicity of Te-phenyl-L-tellurocysteine, Se-phenyl-L-selenocysteine, and S-phenyl-L-cysteine. Chem Res Toxicol 2002;15:1610-1618 (Pubitemid 36008209)
7. Meotti FC, Borges VC, Zeni JBT, Nogueira CW. Potential renal and hepatic toxicity of diphenyl diselenide, diphenyl ditelluride and Ebselen for rats and mice. Toxicol Lett 2003;143:9-16.
8. Nogueira CW, Zeni G, Rocha JBT. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem Rev 2004;104:6255-6285 (Pubitemid 40025738)
9. Engman L, Al-Maharik N, McNaughton M. Tioredoxin reductase and cancer cell growth inhibition by organotellurium compounds that could be selectively incorporated into tumor cells. Bioorg Med Chem 2003;11:5091-5100 (Pubitemid 37352996)
10. Ren X, Xue Y, Zhang K, Liu J, Luo G, Zheng J, et al. A novel dicyclodextrinyl ditelluride compound with antioxidant activity. FEBS Lett 2001;507:377-380 (Pubitemid 33030269)
11. Kanski J, Drake J, Aksenova M. Antioxidant activity of the organotellurium compound 3-[4-(N,N-dimethylamino)benzenetellurenyl] propanesulfonic acid against oxidative stress in synaptosomal membrane systems and neuronal cultures. Brain Res 2001;911:12-21. (Pubitemid 32728234)
12. Ávila DS, Beque MC, Folmer V, Braga AL, Zeni G, Nogueira CW, et al. Diethyl 2-phenyl-2-tellurophenyl vinylphosphonate: an organotellurium compound with low toxicity. Toxicology 2006;224:100-107 (Pubitemid 43912972)
13. Savegnago L, Borges VC, Alves D, Jessé CR, Rocha JBT, Nogueira CW. Evaluation of antioxidant activity and potential toxicity of 1-buthyltelurenyl-2-methylthioheptene. Life Sci 2006;79:1546-1552 (Pubitemid 44301271)
14. Ávila DS, Gubert P, Corte CLD, Alves D, Nogueira CW, Rocha JBT, et al. A biochemical and toxicological study with diethyl 2-phenyl-2-tellurophenyl vinylphosphonate in a sub-chronic intraperitoneal treatment in mice. Life Sci 2007;80:1865-1872 (Pubitemid 46560738)
15. Arteel GE, Sies H. Te biochemistry of selenium and the glutathione system. Environ Toxicol Pharmacol 2001;10:153-158
16. Lecanu L, Greeson J, Papadopoulos V. Beta-amyloid and oxidative stress jointly induce neuronal death, amyloid deposits, gliosis, and memory impairment in the rat brain. Pharmacology 2006;76:19-33. (Pubitemid 41759058)
17. Khan TH, Sultana S. Antioxidant and hepatoprotective potential of Aegle marmelos Correa. against CCl4-induced oxidative stress and early tumor events. J Enzyme Inhib Med Chem 2009;24:320-327
18. Ercan S, Cakmak A, Kosecik M. Total oxidant and antioxidant levels and oxidative stress index levels in children with congenital heart disease. Acta Paediatr 2008;97:86-87
19. Nabben M, Hoeks J. Mitochondrial uncoupling protein 3 and its role in cardiac-and skeletal muscle metabolism. Phys Behav 2008;94:259-269 (Pubitemid 351615421)
20. Augustyniak K, Zavodnik I, Palecz D, Szosland K, Bryszewska M. Te efect of oxidizing agent and diabetes mellitus on the human red blood cell membrane potential. Clin Biochem 1996;29:283-286 (Pubitemid 26142080)
21. Gey KF. Te relationship of antioxidant status and the risk of cancer and cardiovascular disease: a critical evaluation of observational data. In: Nohl H, Esterbauer H, Rice-Evans C, eds. Free Radicals in the Environment, Medicine and Toxicology. London: Richelieu Press, 1994:181-219.
22. Wang BB, Wang J, Zhou SR. Te association of mitochondrial aldehyde dehydrogenase gene (ALDH2) polymorphism with susceptibility to late-onset Alzheimer's disease in Chinese. J Neurol Sci 2008;268:172-175
23. Ayhan-Kilcigil G, Kus C, Coban T, Can-Eke B, Iscan M. Antioxidant and neuroprotective efects of synthesized sintenin derivatives. J Enzyme Inhib Med Chem 2004;19:129-135
24. Yang LX, Zhang LJ, Huang KX, Kun Li X, Hu LH, Wang XY, et al. Antioxidant and neuroprotective efects of synthesized sintenin derivatives. J Enzyme Inhib Med Chem 2009;24:425-431
25. Dos Santos AA, Comasseto JV. β-Butyltellanyl carbonyl compounds: a useful source of masked metal homoenolates. J Braz Chem Soc 2005;16:511-513
26. Comasseto JV, Gariani RA, Princival JL, Dos Santos AA, Zinn FK. Hydrochalcogenation of activated olefnes. Synthesis of functionalized dialkylchalcogenides. Organomet Chem 2008;693:2929-2936
27. Princival JL, Barros SMG, Comasseto J V, Dos Santos AA. β-Butyltelluro-2-butanol: a route to reactive 1,4-dianion intermediates. Tetrahedron Lett 2005;46:4423-4425
28. Dos Santos AA, Ferrarini RS, Princival JL, Comasseto JV. Organotellurides as a source of organometallics: application in the synthesis of (+/-)-frontalin. Tetrahedron Lett 2006;47:8933-8935 (Pubitemid 44711956)
29. Comasseto JV, Dos Santos AA. Organotellurides as precursors of reactive organometallics. Phosphorus Sulfur Silicon Relat Elem 2008;183:939-947
30. Ferrarini RS, Princival JL, Comasseto JV, Dos Santos AA. A concise enantioselective synthesis of (+)-endo-brevicomin accomplished by a tellurium/metal exchange reaction. Braz Chem Soc 2008;19:811-812
31. Wendler EP, Dos Santos AA. Te use of butyl organotellurides in the synthesis of natural bioactive compounds. Synlett 2009:1034-1040
32. Bigdeli MA, Alvi Nikje MM, Jafari S, Heravi MM. Regioselective synthesis of syn-oximes using 3Å molecular sieves in a solventless system. J Chem Res Synop 2002;1:20-21
33. Ohkawa H, Ohishi N, Yagi K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 1979;95:351-358 (Pubitemid 9194347)
34. Yan LJ, Traber MG, Packer L. Spectrophotometric method for determination of carbonyls in oxidatively modifed apolipoprotein B of human low-density lipoproteins. Anal Biochem 1995;228:349-351
35. Levine RL, Garland D, Oliver CN. Determination of carbonyl content in oxidatively modifed proteins. Methods Enzymol 1990;186:464-478 (Pubitemid 20279989)
36. Ellman GL. Tissue sulfhydryl groups. Arch Biochem Biophys 1959;82:70-77
37. Nogueira CW, Borges VC, Zeni G, Rocha JBT. Organochalcogens efects on8-aminolevulinate dehydratase activity from human erythrocytic cells in vitro. Toxicology 2003;191:169-178 (Pubitemid 37329462)
38. Sassa S. Delta aminolevulinic acid dehydratase assay. Enzyme 1982;28:133-145 (Pubitemid 13205206)
39. Barbosa NBV, Rocha JBT, Zeni G, Emanuelli T, Beque MC, Braga AL. Efect of organic selenium on 6-aminolevulinate dehydratase from liver, kidney, and brain of adult rats. Toxicol Appl Pharmacol 1998;149:243-253 (Pubitemid 28202371)
40. Bradford MM. Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding. Anal Biochem 1976;72:248-254
41. 2+-induced lipid peroxidation in the initiation of the mitochondrial permeability transition. Arch Biochem Biophys 2003;414:255-260 (Pubitemid 36627358)
42. Bates JN, Baker MT, Guerra R, Harrison DG. Nitric oxide generation from nitroprusside by vascular tissue: Biochem Pharmacol 1990;42: S157-65.
43. Meotti FC, Stangherlin EC, Zeni G, Nogueira CW, Rocha JBT. Protective role of aryl and alkyl diselenides on lipid peroxidation. Environ Res 2004;94:276-282 (Pubitemid 38328681)
44. Prigol M, Wilhelm EA, Schneider CC, Nogueira CW. Protective efect of unsymmetrical dichalcogenide, a novel antioxidant agent, in vitro and an in vivo model of brain oxidative damage. Chem Biol Interact 2008;176:129-136
45. Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, Milzani A. Protein carbonylation, cellular dysfunction, and disease progression. J Cell Mol Med 2006;10:389-406. (Pubitemid 44870187)
46. Wieslander E, Engman L, Svensjo E, Erlansson M, Johansson U, Linden M, et al. Antioxidative properties of organotellurium compounds in cell system. Biochem Pharmacol 1998;55:573-584 (Pubitemid 28077816)
47. Borges VC, Rocha JBT, Nogueira CW. Efect of diphenyl diselenide, diphenyl ditelluride and ebselen on cerebral Na+, K+-ATPase activity in rats. Toxicology 2005;215:191-197
48. Laden BP, Porter TD. Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. J Lipid Res 2001;42:235-240
49. Chen F, Vallyathan V Castranova V Shi X. Cell apoptosis induced carcinogenic metals. Mol Cell Biochem 2001;221:183-188 (Pubitemid 32910334)
50. Gibson KD, Neuberger A, Scott JJ. Te purifcation and properties of delta-aminolevulinic acid dehydratase. Biochem J 1955;61:618-628
51. Luchese C, Zeni G, Rocha JBT, Nogueira CW, Santos FW. Cadmium inhibits 6-aminolevulinate dehydratase from rat lung in vitro: interaction with chelating and antioxidant agents. Chem Biol Interact 2007;165: 127-137 (Pubitemid 46072797)
52. Souza ACG, Luchese C, Neto JSS, Nogueira CW. Antioxidant efect of a novel class of telluroacetylene compounds: studies in vitro and in vivo. Life Sci 2009;84: 351-357
53. 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;310: 319-414