Butane-2,3-dionethiosemicarbazone: An oxime with antioxidant properties

Chemico-Biological Interactions

Volumn 177, Issue 2, 2009, Pages 153-160

  Puntel, Gustavo Orione ^a   de Carvalho, Nelson Rodrigues ^a   Gubert, Priscila ^a   Palma, Aline Schwertner ^a   Corte, Cristiane Lenz Dalla ^a   Ávila, Daiana Silva ^a   Pereira, Maria Ester ^a   Carratu, Vanessa Santana ^b   Bresolin, Leandro ^c   da Rocha, João Batista Teixeira ^a   Soares, Félix A Antunes ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF RIO GRANDE   (Brazil)

^c UNIVERSIDADE FEDERAL DO ACRE   (Brazil)

Author keywords

Antioxidant; Butane 2,3 dionethiosemicarbazone oxime; Reactive species

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 1,10 PHENANTHROLINE; ANTIOXIDANT; BUTANE 2,3 DIONETHIOSEMICARBAZONE; DEOXYRIBOSE; DIHYDROXYBENZOATE; FERROUS ION; HYDROGEN PEROXIDE; HYDROXYBENZOIC ACID; HYDROXYL RADICAL; MALONIC ACID; NITRIC OXIDE; OXIME; PORPHOBILINOGEN SYNTHASE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; THIOL; THIOSEMICARBAZONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; AUTOOXIDATION; CARBOHYDRATE METABOLISM; CONTROLLED STUDY; DIHYDROXYLATION; FENTON REACTION; IRON CHELATION; LIPID BRAIN LEVEL; LIPID LIVER LEVEL; LIPID PEROXIDATION; MALE; MOLECULAR INTERACTION; MOUSE; NONHUMAN; SUPERNATANT; SWISS WEBSTER MOUSE;

MUS;

EID: 84984565118     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.09.028     Document Type: Article

References (48)

1. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine. 4th ed. (2006), Oxford University Press, Oxford
2. Gutteridge J.M.C., and Halliwell B. Antioxidants in Nutrition, Health and Disease (1994), Oxford University Press, New York pp. 111-123
3. Halliwell B. Oxidative stress and neurodegeneration: were are we now?. J. Neurochem. 97 (2006) 1634-1658
4. Augusto O., Bonini M.G., Amanso A.M., Linares E., Santos C.C., and Menezes S.L. Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology. Free Radic. Biol. Med. 32 (2002) 841-859
5. Chain A.C., Chow C.K., and Chiu D. Interaction of antioxidants and their implication in genetic anemia. Proc. Soc. Exp. Biol. Med. (1999) 274-282
6. Banerjee B.D., Seth V., Bhattacharya A., Pasha S.T., and Chakraborty A.K. Biochemical effects of some pesticides on lipid peroxidation and free-radical scavengers. Toxicol. Lett. 107 (1999) 33-47
7. Gultekin F., Ozturk M., and Akdogan M. The effect of organophosphate insecticide chlorpyrifos-ethyl on lipid peroxidation and antioxidant enzymes (in vitro). Arch. Toxicol. 74 (2000) 533-568
8. Gupta R.C., Milatovic D., and Dettbarn W.D. Depletion of energy metabolites following acetylcholinesterase inhibitor-induced sattus epilepticus: protection by antioxidants. Neurotoxicology 22 (2001) 271-282
9. Silva A.P., Meotti F.C., Santos A.R.S., and Farina M. Lactational exposure to malathion inhibits brain acetylcholinesterase in mice. Neurotoxicology 27 (2006) 1101-1105
10. Silva A.P., Farina M., Franco J.L., Dafre A.L., Kassa J., and Kuca C. Temporal effects of newly developed oximes (K027, K048) on malathion-induced acetylcholinesterase inhibition and lipid peroxidation in mouse prefrontal cortex. Neurotoxicology 29 (2008) 184-189
11. Fortunato J.J., Feier G., Vitali A.M., Petronilho F.C., Dal-Pizzol F., and Quevedo J. Malathion induced oxidative stress in rat brain regions. Neurochem. Res. 31 (2006) 671-678
12. Verma R.S. Chlorpyrifos-induced alterations in levels of thiobarbituric acid reactive substances and glutathione in rat brain. Indian J. Exp. Biol. 39 (2001) 174-177
13. Abdollahi M., Ranjbar A., Shadnia S., Nikfar S., and Rezaie A. Pesticides and oxidative stress: a review. Med. Sci. Monit. 10 6 (2004) 141-147
14. Worek F., Thiermann H., Szinicz L., and Eyer P. Kinetic analysis of interactions between human acetylcholineserase, structurally different organophosphorus compounds and oximes. Biochem. Pharmacol. 68 (2004) 2237-2248
15. Puntel G.O., Gubert P., Peres G.L., Bresolin L., Rocha J.B.T., Pereira M.E., Carratu V.S., and Soares F.A.A. Antioxidant properties of oxime 3-(phenylhydrazono) butan-2-one. Arch. Toxicol. 82 (2008) 755-762
16. Puntel R.L., Nogueira C.W., and Rocha J.B.T. Krebs cycle intermediates modulate thiobarbituric acid reactive species (TBARS) production in rat brain in vitro. Neurochem. Res. 30 (2005) 225-235
17. Puntel R.L., Nogueira C.W., and Rocha J.B.T. N-methyl-d-aspartate receptors are involved in the quinolinic acid, but not in the malonate pro-oxidative activity in vitro. Neurochem. Res. 30 (2005) 417-424
18. Folmer V., Soares J.C.M., Gabriel D., and Rocha J.B.T. A high fat diet inhibits δ-aminolevulinate dehydratase and increases lipid peroxidation in mice (Mus musculus). J. Nutr. 133 7 (2003) 2165-2170
19. Perottoni J., Meotti F.C., Folmer V., Pivetta L., Nogueira C.W., Zeni G., and Rocha J.B.T. Ebselen and diphenyl diselenide do not change the inhibitory effect of lead acetate on delta-aminolevulinate dehidratase. Environ. Toxicol. Pharmacol. 19 (2005) 239-248
20. Singh N.P., McCoy M.T., Tice R.R., and Schneider E.A. Simple technique for quantification of low levels of DNA damage in individual cells. Exp. Cell Res. 175 (1988) 184-191
21. 15N]nitrate in biological fluids. Anal. Biochem. 126 (1981) 131-138
22. Marcocci L., Maguire J.J., Droy-Lefaix M.T., and Packer L. The nitric oxide-scavenging properties of Ginkgo biloba extract EGb 761. Biochem. Biophys. Res. Commun. 201 (1994) 748-755
23. Choi C.W., Kim S.C., Hwang S.S., Choi B.K., Ahn H.J., Lee M.Y., Park S.H., and Kim S.K. Antioxidant activity and free radical scavenging capacity between Korean medicinal plants and flavonoids by assay-guided comparison. Plant Sci. 153 (2002) 1161-1168
24. Gutteridge J.M.C. Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA. Biochem. J. 243 3 (1987) 709-714
25. Halliwell B., and Gutteridge J.M.C. Formation of a thiobarbituric-acid-reactive substance from deoxyribose in the presence of iron salts: the role of superoxide and hydroxyl radicals. FEBS Lett. 128 (1981) 347-352
26. Gutteridge J.M.C. Thiobarbituric acid-reactivity following iron-dependent free-radical damage to amino acids and carbohydrates. FEBS Lett. 128 (1981) 343-346
27. Bucber J.R., Tien M., Morehouse L.A., and Aust S.D. Redox cycling and lipid peroxidation: the central role of iron chelates. Fundam. Appl. Toxicol. 3 (1983) 222-226
28. 2+-dependent lipid peroxidation. Free Radic. Biol. Med. 3 (1987) 379-387
29. Ohkawa H., Ohishi N., and Yagi K. Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal. Biochem. 95 (1979) 351-358
30. Hissin P.J., and Hilf R. A fluorimetric method for determination of oxidized and reduced glutathione in tissues. Anal. Biochem. 74 (1976) 214-226
31. Sassa S. Delta-aminolevulinic acid dehydratase assay. Enzyme 28 (1982) 133-145
32. Lowry O.H., Rosebrough N.J., Farr A.L., and Randall R.J. Protein measurement with the folin phenol reagent. Biol. Chem. 193 (1951) 265-275
33. Halliwell B., and Gutteridge J.M.C. Oxygen toxicity, oxygen radicals, transition metals and disease. Biochem. J. 219 (1984) 1-14
34. Miller D.M., Buettner G.R., and Aust S.D. Transition metals as catalysts of "autoxidation" reactions. Free Radic. Biol. Med. 8 (1990) 95-108
35. Welch K.D., Davis T.Z., Van Eden M.E., and Aust S.D. Deleterious iron-mediated oxidation of biomolecules. Free Radic. Biol. Med. 32 7 (2002) 577-583
36. Molina-Holgado F., Hider R.C., Gaeta A., Williams R., and Francis P. Metal ions and neurodegeneration. Biometals 20 (2007) 639-654
37. Ong W.Y., and Halliwell B. Iron, atherosclerosis, and neurodegeneration: a key role for cholesterol in promoting iron-dependent oxidative damage?. Ann. N. Y. Acad. Sci. 1012 (2004) 51-64
38. Ryan T.P., Miller D.M., and Aust S.D. The role of metals in the enzymatic and nonenzymatic oxidation of epinephrine. J. Biochem. Toxicol. 8 (1993) 33-39
39. Bermejo E., Castiñeiras A., Garcia-Santos I., and West D.X. Structural and coordinative variability in zinc(ii), cadmium(ii), and mercury(ii) complexes of 2-pyridineformamide 3-hexamethyleneiminylthiosemicarbazone. Z. Anorg. Allg. Chem. 630 (2004) 1096-1109
40. Huheey J.E., Keiter E.A., and Keiter R.L. Inorganic Chemistry: Principles of Structure and Reactivity. 4th ed. (1993), Harper Collins College Publishers, NY
41. Georgieva I., Trendafilova N., Rodrigues-Santiago L., and Sodupe M. Coordination properties of the oxime analogue of glycine to Cu(II). J. Phys. Chem. A 109 (2005) 5668-5676
42. Puntel R.L., Roos D.H., Paixão M.W., Braga A.L., Zeni G., Nogueira C.W., and Rocha J.B.T. Oxalate modulates thiobarbituric acid reactive species (TBARS) production in supernatants of homogenates from rat brain, liver and kidney: effect of diphenyl diselenide and diphenyl ditelluride. Chem. Biol. Interact. 165 (2007) 87-98
43. Bates J.N., Baker M.T., Guerra D., and Harrison G. Nitric oxide generation from nitroprusside by vascular tissue. Evidence that reduction of the nitroprusside anion and cyanide loss is required. Biochem. Pharmacol. 42 (1991) S157-S165
44. Darley-Usmar V.M., Wiseman H., and Halliwell B. Nitric oxide and oxigen radicals: a question of balance. FEBS Lett. 369 (1995) 131-135
45. Rao D.N., Elguindi S., and O'Brien P.J. Reductive metabolism of nitroprusside in rat hepatocytes and human erythrocytes. Arch. Biochem. Biophys. 286 (1991) 30-37
46. Roncaroli F., Van Eldik R., and Olabe J.A. Release of NO from reduced nitroprusside ion iron-dinitrosyl formation and NO-disproportionation reactions. Inorg. Chem. 44 (2005) 2781-2790
47. Sakurada K., Matsubara K., Shimizu K., Shiono H., Seto Y., Tsuge K., Yoshino M., Sakai I., Mukoyama H., and Takatori T. Pralidoxime iodide (2-PAM) penetrates across the blood-brain barrier. Neurochem. Res. 28 (2003) 1401-1407
48. Arena J.M. Poisoning, Toxicology, Symptoms, Treatments. 4th ed. (1979), Springfield Ill, Charles C. Thomas p. 133