Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress

Biochemical Pharmacology

Volumn 60, Issue 4, 2000, Pages 471-478

  Dubuisson, Marlène L N ^a   Wergifosse, Bertrand De ^a   Trouet, André ^a   Baguet, Fernand ^a   Marchand Brynaert, Jacqueline ^a   Rees, Jean François ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Antioxidant; Coelenterazine; Hepatocytes; Imidazolopyrazinone; Lipid peroxidation; Tert butyl hydroperoxide

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; BUTYLCRESOL; METHYL COELENTERAZINE; PROBUCOL; TERT BUTYL HYDROPEROXIDE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; TROLOX C; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CELL PROTECTION; CELL SURVIVAL; CONTROLLED STUDY; CYTOTOXICITY; LIPID PEROXIDATION; LIVER CELL; MALE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT;

EID: 0034664190     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(00)00359-2     Document Type: Article

References (43)

1. Thompson E.M., Rees J.F. Origins of luciferins Ecology of bioluminescence in marine fishes . Hochachka P.W., Mommsen T.P. Biochemistry and Molecular Biology of Fishes. Vol. 4:1994;435-466 Elsevier Science, Amsterdam.
2. Shimomura O. Presence of coelenterazine in non-bioluminescent marine organisms. Comp Biochem Physiol. 86B:1987;361-363.
3. Suzuki N., Ogawa K., Yoda B., Nomoto T., Inaba H., Goto T. Chemiluminescent detection of active oxygen species, singlet molecular oxygen and superoxide, using Cypridina luciferin analogs. Nippon Suisan Gakkaishi. 57:1991;1711-1715.
4. Rees J.F., de Wergifosse B., Noiset O., Dubuisson M., Janssens B., Thompson E.M. The origins of marine bioluminescence Turning oxygen defence mechanisms into deep-sea communication tools . J Exp Biol. 201:1998;1211-1221.
5. Poli G, Liver damage due to free radicals. Free Radicals in Medicine. The British Council: 604-620, 1993.
6. Chance B., Sies H., Boveris A. Hydroperoxide metabolism in mammalian organs. Physiol Rev. 59:1979;527-605.
7. Inoue S., Sugiara S., Kakoi H., Hashizume K., Goto T., Iio H. Squid bioluminescence II. Isolation from Watasenia scintillans and synthesis of 2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one. Chem Lett. 1975:1975;141-144.
8. Seglen P.O. Preparation of isolated rat liver cells. Methods Cell Biol. 13:1976;29-83.
9. Wey H.E., Pyron L., Woolery M. Essential fatty acid deficiency in cultured human keratinocytes attenuates toxicity due to lipid peroxidation. Toxicol Appl Pharmacol. 120:1993;72-79.
10. Günther T., Vormann J., Höllriegl V. Effects of magnesium and iron on lipid peroxidation in cultured hepatocytes. Mol Cell Biochem. 144:1995;141-145.
11. Tseng T.H., Wang C.J., Kao E.S., Chu H.Y. Hibiscus procatechuic acid protects against oxidative damage induced by tert-butylhydroperoxide in rat primary hepatocytes. Chem Biol Interact. 101:1996;137-148.
12. 2+-mediated vulnerability of immature cerebellar granule cells to ischemia. Free Radic Biol Med. 25:1998;793-802.
13. Fernandes E.R., Carvalho F.D., Remiao F.G., Bastos M.L., Pinto M.M., Gottlieb O.R. Hepatoprotective activity of xanthones and xanthonolignoids against tert-butylhydroperoxide-induced toxicity in isolated rat hepatocytes - comparison with silybin. Pharm Res. 12:1995;1756-1760.
14. Hwang J.M., Tseng T.H., Hsieh Y.S., Chou F.P., Wang C.J., Chu C.Y. Inhibitory effect of atractylon on tert-butyl hydroperoxide induced DNA damage and hepatic toxicity in rat hepatocytes. Arch Toxicol. 70:1996;640-644.
15. Miguez M.P., Amundi I., Sainz-Pardo L.A., Lindros K.O. Hepatoprotective mechanism of silymarin No evidence for involvement of cytochrome P450 2E1 . Chem Biol Interact. 91:1994;51-63.
16. Carini R., Comoglio A., Albano E., Poli G. Lipid peroxidation and irreversible damage in the rat hepatocyte model. Protection by the silybin-phospholipid complex IdB 1016. Biochem Pharmacol. 43:1992;2111-2115.
17. Masaki N., Kyle M.E., Farber J.L. tert-Butyl hydroperoxide kills cultured hepatocytes by peroxidizing membrane lipids. Arch Biochem Biophys. 269:1989;390-399.
18. Masaki N., Kyle M.E., Serroni A., Farber J.L. Mitochondrial damage as a mechanism of cell injury in the killing of cultured hepatocytes by tert-butyl hydroperoxide. Arch Biochem Biophys. 270:1989;672-680.
19. Rush G.F., Gorski J.R., Ripple M.G., Sowinski J., Bugelski P., Hewitt W.R. Organic hydroperoxyde-induced lipid peroxidation and cell death in isolated hepatocytes. Toxicol Appl Pharmacol. 78:1985;473-483.
20. Minotti G. tert-Butyl hydroperoxide-dependent microsomal release of iron and lipid peroxidation. Arch Biochem Biophys. 273:1989;137-143.
21. Davies M.J. Detection of peroxyl and alkoxyl radicals produced by reaction of hydroperoxides with rat liver microsomal fractions. Biochem J. 257:1989;603-606.
22. Thornalley P.J., Trotta R.J., Stern A. Free radical involvement in the oxidative phenomena induced by tert-butyl hydroperoxide in erythrocytes. Biochim Biophys Act. 759:1983;16-22.
23. Nakayama T., Hori K., Terazawa K., Kawakishi S. Comparison of the cytotoxicity of different hydroperoxides to V79 cells. Free Radic Res Commun. 14:1991;173-178.
24. Lu A.Y. NADPH-dependent cytochrome P540 reductase. Arinç E., Schenkman J.B., Hodgson E. Molecular Aspects of Monooxygenase and Bioactivation of Toxic Compounds. 1991;135-147 Plenum Press, NY.
25. Dean R.T., Hunt J.V., Grant A.J., Yamamoto Y., Niki E. Free radical damage to proteins The influence of the relative localization of radical generation, antioxidants, and target proteins . Free Radic Biol Med. 11:1991;161-168.
26. Pike C.J., Ramezan-Arab N., Cotman C.W. β-amiloid neurotoxicity in vitro Evidence of oxidative stress but no protection by antioxidants . J Neurochem. 69:1997;1601-1611.
27. Roberts C.P., Murphy A.A., Santanam N., Parthasarathy S. Regulation of monocyte to macrophage differentiation by antiglucocorticoids and antioxidants. Am J Obstet Gynecol. 179:1998;354-362.
28. Kaneko T., Kaji K., Matsuo M. Protection of linoleic acid hydroperoxide-induced cytotoxicity by phenolic antioxidants. Free Radic Biol Med. 16:1994;405-409.
29. Massey K., Burton K.P. Free radical damage in neonatal rat cardiac myocyte cultures Effects of α-tocopherol, Trolox, and phytol . Free Radic Biol Med. 8:1990;449-458.
30. Sugiyama H, Fung KP and Wu TW, Purpurogallin as an antioxidant protector of human erythrocytes against lysis by peroxyl radicals. Life Sci 53: PL 39-43, 1993.
31. Wu T.W., Hashimoto N., Wu J., Carey D., Li R.K., Mickle D.A., Weisel R.D. The cytoprotective effect of Trolox demonstrated with three types of human cells. Biochem Cell Biol. 68:1990;1189-1194.
32. Lambert C.R., Black H.S., Truscott T.G. Reactivity of butylated hydroxytoluene. Free Radic Biol Med. 21:1996;395-400.
33. Ross L., Barclay C., Vinqvist M.R. Membrane peroxidation Inhibiting effects of water-soluble antioxidants on phospholipids of different charge types . Free Radic Biol Med. 16:1994;779-788.
34. Decker D.E., Vroegop S.M., Buxser S.E. Inhibition of oxidative insult in cultured cells by a novel 6-chromanol-containing antioxidant. Biochem Pharmacol. 50:1995;1063-1070.
35. Castle L., Perkins M.J. Inhibition kinetics of chain-breaking phenolic antioxidants in SDS micelles. Evidence that intermicellar diffusion may be rate-limiting for hydrophobic inhibitors such as alpha-tocopherol. J Am Chem Soc. 108:1986;6381-6382.
36. Kendall J.M., Dormer R.L., Campbell A.K. Targeting aequorin to the endoplasmic reticulum of living cells. Biochem Biophys Res Com. 189:1992;1008-1016.
37. Kendall J.M., Badminton M.N. Aequora victoria bioluminescence moves into an exciting new area. TIBTECH. 16:1998;216-224.
38. Suzuki N., Suetsuna K., Mashiko S., Yoda B., Nomoto T., Toya Y., Inaba H., Goto T. Reaction rates for the chemiluminescence of Cypridina luciferin analogues with superoxide A quenching experiment with superoxide dismutase . Agric Biol Chem. 55:1991;157-160.
39. Tarpey M.M., White C.R., Suarez E., Richardson G., Radi R., Freeman B.A. Chemiluminescent detection of oxidants in vascular tissue. Lucigenin but not coelenterazine enhances superoxide formation. Circ Res. 84:1999;1203-1211.
40. Tampo Y., Tsukamoto M., Yonaha M. The antioxidant action of 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-α]pyrazin-3-one (MCLA), a chemiluminescence probe to detect superoxide anions. FEBS Lett. 430:1998;348-435.
41. Testa B., Jenner P. Inhibitors of cytochrome P-450s and their mechanism of action. Drug Metab Rev. 12:1981;1-117.
42. Minotti G., Borrello S., Palombini G., Galeotti T. Cytochrome P-450 deficiency and resistance to t-butyl hydroperoxide of hepatoma microsomal lipid peroxidation. Biochim Biophys Acta. 876:1986;220-225.
43. Hiroya K., Murakami Y., Shimizu T., Hatano M., Ortiz de Montellano P.R. Differential roles of Glu318 and Thr319 in cytochrome P450 1A2 catalysis supported by NADPH-cytochrome P450 reductase and tert-butyl hydroperoxide. Arch Biochem Biophys. 310:1994;397-401.