Organochalcogens effects on δ-aminolevulinate dehydratase activity from human erythrocytic cells in vitro

Toxicology

Volumn 191, Issue 2-3, 2003, Pages 169-178

  Nogueira, C W ^a   Borges, V C ^a   Zeni, G ^a   Rocha, J B T ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Diphenyl diselenide; Diphenyl ditelluride; Ebselen and toxicity; ALA D

Indexed keywords

CHALCOGEN; CYSTEINE; DIPHENYL DISELENIDE; DIPHENYL DITELLURIDE; DITHIOTHREITOL; EBSELEN; PHENYL GROUP; PORPHOBILINOGEN SYNTHASE; REDUCING AGENT; THIOL; THIOL DERIVATIVE; THIOL GROUP; UNCLASSIFIED DRUG; ZINC CHLORIDE; ANTIOXIDANT; BENZENE DERIVATIVE; DIPHENYL DISULFIDE; DIPHENYLDITELLURIDE; DISULFIDE; GLUTATHIONE TRANSFERASE; ORGANOMETALLIC COMPOUND; ORGANOSELENIUM DERIVATIVE; PYRROLE DERIVATIVE; ZINC;

ARTICLE; ENZYME ACTIVITY; ERYTHROCYTE; HUMAN; HUMAN EXPERIMENT; IN VITRO STUDY; INCUBATION TIME; INHIBITION KINETICS; NORMAL HUMAN; PRIORITY JOURNAL; BLOOD; DRUG ANTAGONISM; DRUG EFFECT; DRUG INTERACTION; ENZYMOLOGY; METABOLISM;

ANTIOXIDANTS; AZOLES; BENZENE DERIVATIVES; CYSTEINE; DISULFIDES; DITHIOTHREITOL; DRUG INTERACTIONS; ERYTHROCYTES; GLUTATHIONE TRANSFERASE; HUMANS; ORGANOMETALLIC COMPOUNDS; ORGANOSELENIUM COMPOUNDS; PORPHOBILINOGEN SYNTHASE; ZINC;

EID: 0142056982     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0300-483X(03)00250-6     Document Type: Article

References (63)

1. Barbosa N.B.V., Rocha J.B.T., Zeni G., Emanuelli T., Beque M.C., Braga A.L. Effect of organic forms of selenium on δ-aminolevulinate dehydratase from liver, kidney and brain of adult rats. Toxicol. Appl. Pharmacol. 149:1998;243-253.
2. Bechara E.J.H., Medeiros M.H.G., Monteiro H.P., Hermes-Lima M., Pereira B., Demasi M., Costa C.A., Adballa D.S.P., Onuki J., Wendel C.M.A., Masci P.D. A free radical hypothesis of lead poisoning and inborn porphyrias associated with 5-aminolevulinic acid overload. Quim. Nova. 16:1993;385-392.
3. Berlin A., Schaller K.H. European Standardized Method for the determination of δ-aminolevulinic acid dehydratase activity in blood. Z. Klin. Chem. Klin. Biochem. 1974;389-390.
4. Bock A., Forchammer J.H., Leinfelder W., Sawers G., Vepreck B., Zinnia F. Selenocysteine: the 21st amino acid. Mol. Microbiol. 5:1991;515-520.
5. Bolzan R.C., Folmer V., Farina M., Zeni G., Nogueira C.W., Rocha J.B.T., Emanuelli T. Aminolevulinate dehydratase inhibition by phenyl selenoacetylene: effect of reaction with hydrogen peroxide. Pharmacol. Toxicol. 90:2002;214-219.
6. Braga A.L., Zeni G., Andrade L.H., Silveira C.C. Stereoconservative formation and reactivity of δ-chalcogen-functionalized vinylithium compounds from bromo-vinilyc chalcogens. Synlett. 5:1997;595-596.
7. Chasteen T.G., Bentley R. Biomethylation of selenium and tellurium: microorganisms and plants. Chem. Rev. 103:2003;1-25.
8. Clark R.F., Strukle E., Willians S.R., Manoguerra A.S. Selenium poisoning from a nutritional supplement. JAMA. 275:1996;1087-1088.
9. Comasseto J.V., Ling L.W., Petragnani N., Stefani H.A. Vinylic selenides and tellurides - preparation, reactivity and synthetic compounds. Synthesis. 4:1997;373-403.
10. Daiber A., Zhou M., Bachscmid M., Ullrich V. Ebselen as a peroxynitrite scavanger in vitro and ex vivo. Biochem. Pharmacol. 59:2000;153-160.
11. Duydu Y., Suzen H.S., Aydin A., Cander O., Uysal H., Isimer A., Vural N. Correlation between lead exposure indicators and sister chromatid exchange (SCE) frequencies in lymphocytes from inorganic lead exposed workers. Arch. Environ. Contam. Toxicol. 41:2001;241-246.
12. Emanuelli T., Rocha J.B.T., Pereira M.E., Porciuncula L.O., Morsch V.M., Martins A.F., Souza D.O.G. Effect of mercuric chloride intoxication and dimercaprol treatment on δ-aminolevulinic acid dehydratase from brain, liver and kidney of adult mice. Pharmacol. Toxicol. 79:1996;136-143.
13. Emanuelli T., Pagel F.W., Alves L.B., Regner A., Souza D.O. Inhibition of adenylate cyclase activity by 5-aminolevulinic acid in rat and human brain. Neurochem. Int. 38:2001;213-218.
14. Engman L. Expedient synthesis of Ebselen and related compounds. J. Org. Chem. 54:1989;2964-2966.
15. Engman L., Stern D., Cotgreave I.A., Andersson C.M. Thiol peroxidase activity of diaryl ditellurides as determined by a HNMR method. J. Am. Chem. Soc. 114:1992;9737-9743.
16. Engman L., Persson J., Vessman K., Ekstrom M., Berglund M., Andersson C.M. Organotellurium compounds as efficient retards of lipid peroxidation in methanol. Free Radical Bio. Med. 19:1995;441-452.
17. Farina M., Folmer V., Bolzan R.C., Andrade L.H., Zeni G., Braga A.L., Rocha J.B.T. Selenoxides inhibit δ-aminolevulinate dehydratase. Toxicol. Lett. 119:2001;27-37.
18. Farina M., Barbosa N.B.V., Nogueira C.W., Folmer V., Zeni G., Andrade L.H., Braga L.A., Rocha J.B.T. Reaction of diphenyl diselenide with hydrogen peroxide and inhibition of δ-aminolevulinate dehydratase from rat liver and cucumber leaves. Braz. J. Med. Biol. Res. 35:2002;623-631.
19. Fernández-Cuartero B., Rebollar J.L., Batlle A., Salamanca R.E. Delta aminolevulinate dehydratase (ALA-D) activity in human and experimental diabetes mellitus. Int. J. Biochem. Cell Biol. 31:1999;479-488.
20. Folmer V., Soares J.C.M., Rocha J.B.T. Oxidative stress in mice is dependent on the free glucose content of the diet. IJBCB. 34:2002;1279-1285.
21. Fujita H., Orh Y., Sano S. Evidence of increased synthesis of δ-aminolevulinate acid dehydratase in experimental lead-poisoning. Biochim. Biophys. Acta. 678:1981;39-50.
22. Gasmi A., Garnier R., Galliot-Guilley M., Gaudillat C., Quartenoud B., Buisine A., Djebbar D. Acute selenium poisoning. Vet. Hum. Toxicol. 39:1997;304-308.
23. Goeger D.E., Ganther H.E. Oxidation of dimethyl selenide to dimethyl selenoxide by microsomes from rat liver and flavin-containing monooxygenase from pig liver. Arch. Biochem. Biophys. 310:1994;448-451.
24. Goering P.L. Lead-protein interactions as a basis for lead toxicity. Neurotoxicology. 14:1993;45-60.
25. Goering P.L., Mistry P., Fowler B.A. A low-molecular-weight lead-binding protein in brain attenuates lead inhibition of delta-aminolevulininic-acid dehydratase - comparison with a renal lead-binding protein. J. Pharmacol. Exp. Ther. 237:1986;220-225.
26. Gupta N., Porter T.D. Garlic and garlic-derived compounds inhibit human squalene monooxygenase. J. Nutr. 131:2001;1662-1667.
27. Gupta N., Porter T.D. Inhibition of human squalene monooxygenase by selenium compounds. J. Biochem. Mol. Toxicol. 16:2002;18-23.
28. Jacques-Silva M.C., Nogueira C.W., Broch L.C., Rocha J.B.T. Diphenyl diselenide and ascorbic acid changes deposition of selenium and ascorbic acid in brain of mice. Pharmacol. Toxicol. 88:2001;119-125.
29. Laden P.B., Porter T.D. Inhibition of human squalene monooxygenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. J. Lipid Res. 42:2001;235-240.
30. Lech T. Suicide by sodium tetraoxoselenate (VI) poisoning. Forensic Sci. Int. 130:2002;44-48.
31. Maciel E.N., Bolzan R.C., Braga A.L., Rocha J.B.T. Diphenyl diselenide and diphenyl ditelluride differentially affect δ-aminolevulinate dehydratase from liver, kidney, and brain of mice. J. Biochem. Mol. Toxicol. 14:2000;310-319.
32. Marino J.P., McClure M.S., Holub D.P., Comasseto J.V., Tucci F.C. Stereocontrolled synthesis of (-)-macrolactin A. J. Am. Chem. Soc. 8:2002;1664-1668.
33. Meotti F.C., Borges V.C., Zeni G., Rocha J.B.T., Nogueira C.W. Potential renal and hepatic toxicity of diphenyl diselenide, diphenyl ditelluride and Ebselen for rats and mice. Toxicol. Lett. 143:2003;9-16.
34. Meredith P.A., Moore M.R., Goldberg A. Erythrocyte ALA dehydratase activity and blood protoporfhyrin concentrations as indices of lead exposure and altered haem biosynthesis. Clin. Sci. Mol. Med. 56:1979;61-69.
35. Mugesh G., du Mont W.W., Sies H. Chemistry of biologically important organoselenium compounds. Chem. Rev. 101:2001;2125-2179.
36. Müller A., Gabriel H., Sies H. A novel biologically active selenoorganic compound-IV. Protective glutathione-dependent effect of PZ51 (Ebselen) against ADP-Fe induced lipid peroxidation in isolated hepatocytes. Biochem. Pharmacol. 34:1985;1185-1189.
37. Nogueira, C.W., Maciel, E.M., Zeni, G., Graça, D., Rocha, J.B.T., 2001a. Biochemical toxicology of simple diorganoyl chalcogenides. ECSOC Eletronic Conference on Synthetic Organic Chemistry. Available from http://www.mdpi.net/ecsoc-5/d0013 .
38. Nogueira C.W., Rotta L.N., Perry M.L., Souza D.O., Rocha J.B.T. Diphenyl diselenide and diphenyl ditelluride affect the rat glutamatergic system in vitro and in vivo. Brain Res. 906:2001;157-163.
39. Nogueira C.W., Rotta L.N., Zeni G., Souza D.O., Rocha J.B.T. Exposure to Ebselen changes glutamate uptake and release by rat brain synaptosomes. Neurochem. Res. 3:2002;283-288.
40. Nogueira C.W., Soares F.A., Nascimento P.C., Muller D., Rocha J.B.T. 2,3-Dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid increase mercury and cadmium-induced inhibition of δ-aminolevulinate dehydratase. Toxicology. 184:2003;85-95.
41. Nogueira C.W., Quinhones E.B., Jung E.A.C., Zeni G., Rocha J.B.T. Anti-inflammatory and antinociceptive activity of diphenyl diselenide. Inflamm. Res. 52:(2):2003;56-63.
42. Oskarsson A. Effects of perinatal treatment with lead and dissulfiram on ALA-D activity in blood, liver and kidney and urinary ALA excretion in rats. Pharmacol. Toxicol. 64:1989;344-348.
43. Pande M., Flora S.J.S. Lead induced oxidative damage and its response to combined administration of alfa-lipoic acid and succimers in rats. Toxicology. 177:2002;187-196.
44. Pappas J.B., Ahlquist J.T., Allen E.M., Banner J.W. Oral dimercaptosuccinic acid and ongoing exposure to lead: effects on heme synthesis and lead distribution in a rat model. Toxicol. Appl. Pharmacol. 133:1995;121-129.
45. Parnham M.J., Graf E. Pharmacology of synthetic organic selenium compounds. Prog. Drug Res. 36:1991;9-47.
46. Paulmier C. Selenoorganic functional groups. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis. first ed. 1986;25-51 Pergamon press, Oxford, England.
47. Pires J.B., Miekeley N., Donangelo C.M. Calcium supplementation during lactation blunts erythrocyte lead levels and delta-aminolevulinic acid dehydratase zinc-reactivation in women non-exposed to lead and with marginal calcium intakes. Toxicology. 175:2002;247-255.
48. Polo C.F., Afonso S.G., Navone N.M., Rossetti M.V., Battle A.M. Zinc aminolevulinic acid dehydratase reactivation index as a tool for diagnosis of lead exposure. Ecotoxicol. Environ. Saf. 32:1995;267-272.
49. Rodrigues A.L., Bellinaso M.L., Dick T. Effect of some metal-ions on blood and liver delta-aminolevulinate dehydratase of Pimelodus-Maculatus (Pisces, Pimelodidae). Comp. Biochem. Physiol. 94:1989;65-69.
50. Rodrigues A.L.S., Rocha J.B.T., Pereira M.E., Souza D.O. Delta aminolevulinic acid dehydratase activity in weanling and adult rats exposed to lead acetate. Environ. Contam. Tox. 57:1996;47-53.
51. Rocha J.B.T., Pereira M.E., Emanuelli T., Christofari R.S., Souza D.O. Effect of treatment with mercury chloride and lead acetate during the second stage of rapid postnatal brain growth on delta-aminolevulinic acid dehydratase (ALA-D) activity in brain, liver kidney and blood of suckling rats. Toxicology. 100:1995;27-37.
52. Rossato J.I., Ketzer L.A., Centurião F.B., Silva S.J.N., Lüdtke D.S., Zeni G., Braga A.L., Rubin M.A., Rocha J.B.T. Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain. Neurochem. Res. 3:2002;297-303.
53. Rossato J.I., Zeni G., Mello C.F., Rubin M.A., Rocha J.B.T. Ebselen blocks the quinolinic acid-induced production of thiobarbituric acid reactive species but does not prevent the behavioral alterations produced by intra-striatal quinolinic acid administration in the rat. Neurosci. Lett. 3:2002;137-141.
54. Rotruck J.T., Pope A.L., Ganther H.E., Swanson A.B., Hafeman D.G., Hoestra W.G. Selenium: biochemical role as a component of glutathione peroxidase. Science. 179:1973;558-560.
55. Saito I., Asano T., Sano K., Takakura H., Abe T., Yoshimoto H., Kikuchi T., Ohta Y. Ishibashi. Neuroprotective effect of an antioxidant, Ebselen, in patients with delayed neurological deficits after aneurysmal subarachnoid hemorrhage. Neurosurgery. 42:1998;269-277.
56. Taylor A. Biochemistry of tellurium. Biol. Trace Elem. Res. 55:1996;231-239.
57. Tinggi U. Essentiality and toxicity of selenium and its status in Australia: a review. Toxicol. Lett. 137:2003;103-110.
58. Tsukamoto I., Yoshinaga T., Sano S. The role of zinc with special reference to the essential thiol groups in delta-aminolevulinic acid dehydratase of bovine liver. Biochim. Biophys. Acta. 570:1979;167-178.
59. Tsukamoto I., Yoshinaga T., Sano S. Zinc and cysteine residues in the active site of bovine liver delta-aminolevulinic acid dehydratase. Int. J. Biochem. 12:1980;751-756.
60. Ursini F., Maiorino M., Valente M., Ferri K., Gregolin C. Purification of pig liver of a protein which protects liposomes from peroxidative degradation and exhibits glutathione peroxidase activity on phosphatidylcholine hydroperoxidase. Biochem. Biophys. Acta. 710:1982;197-211.
61. Vieira V.L.P., Rocha J.B.T., Schetinger M.R.C., Morsch V.M., Rodrigues S.R., Tuerlinckz S.M., Bohrer D., Nascimento P.C. Effect of aluminum on δ-aminolevulinic acid dehydratase from mouse blood. Toxicol. Lett. 17:2000;45-52.
62. Zeni G., Panatieri R.B., Lissner E., Menezes P.H., Braga A.L., Stefani H.A. Synthesis of polyacetylenic acids isolated from Heisteria Acuminata. Org. Lett. 6:2001;819-821.
63. Wendel A., Fausel M., Safayi H., Otter R. A novel biologically active seleno-organic compound-II. Activity of PZ 51 in relation to glutathione peroxidase. Biochem. Pharmacol. 33:1984;3241-3245.