Melatonin protects the cytochrome P450 system through a novel antioxidant mechanism

Chemico-Biological Interactions

Volumn 185, Issue 3, 2010, Pages 208-214

  Letelier, María Eugenia ^a   Jara Sandoval, José ^a   Molina Berríos, Alfredo ^a   Faúndez, Mario ^b   Aracena Parks, Paula ^a   Aguilera, Felipe ^a  

^a UNIVERSITY OF CHILE   (Chile)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Antioxidant; Cytochrome P450; Fe3+ ascorbate; Melatonin; Rat liver microsomes; Reactive oxygen species

Indexed keywords

4 NITROANISOLE; CYTOCHROME P450; FERROUS ASCORBATE; GLUCURONOSYLTRANSFERASE; MELATONIN; THIOL PROTEINASE; UNSPECIFIC MONOOXYGENASE; URIDINE TRIPHOSPHATE GLUCOSE 1 PHOSPHATE URIDYLYLTRANSFERASE; ANTIOXIDANT; REACTIVE OXYGEN METABOLITE; SCAVENGER;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DEMETHYLATION; ENDOPLASMIC RETICULUM; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME BINDING; ENZYME SUBSTRATE; LIPID PEROXIDATION; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; RAT; ANIMAL; BIOTRANSFORMATION; ENZYMOLOGY; METABOLISM; OXIDATION REDUCTION REACTION; SPRAGUE DAWLEY RAT;

RATTUS;

ANIMALS; ANTIOXIDANTS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; FREE RADICAL SCAVENGERS; MALE; MELATONIN; MICROSOMES, LIVER; OXIDATION-REDUCTION; RATS; RATS, SPRAGUE-DAWLEY; REACTIVE OXYGEN SPECIES;

EID: 77952301614     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.03.020     Document Type: Article

References (40)

1. Ackermann K., Stehle J.H. Melatonin synthesis in the human pineal gland: advantages, implications, and difficulties. Chronobiol. Int. 2006, 23(1-2):369-379.
2. Ganguly S., Coon S.L., Klein D.C. Control of melatonin synthesis in the mammalian pineal gland: the critical role of serotonin acetylation. Cell Tissue Res. 2002, 309(1):127-137.
3. Simonneaux V., Ribelayga C. Generation of the melatonin endocrine message in mammals: a review of the complex regulation of melatonin synthesis by norepinephrine, peptides, and other pineal transmitters. Pharmacol. Rev. 2003, 55(2):325-395.
4. Delagrange P., Atkinson J., Boutin J.A., Casteilla L., Lesieur D., Misslin R., Pellissier S., Penicaud L., Renard P. Therapeutic perspectives for melatonin agonists and antagonists. J. Neuroendocrinol. 2003, 15(4):442-448.
5. Pandi-Perumal S.R., Zisapel N., Srinivasan V., Cardinali D.P. Melatonin and sleep in aging population. Exp. Gerontol. 2005, 40(12):911-925.
6. Wagner J., Wagner M.L., Hening W.A. Beyond benzodiazepines: alternative pharmacologic agents for the treatment of insomnia. Ann. Pharmacother. 1998, 32(6):680-691.
7. Healy D., Waterhouse J.M. The circadian system and the therapeutics of the affective disorders. Pharmacol. Ther. 1995, 65(2):241-263.
8. Wang J.Z., Wang Z.F. Role of melatonin in Alzheimer-like neurodegeneration. Acta Pharmacol. Sin. 2006, 27(1):41-49.
9. Bruguerolle B., Simon N. Biologic rhythms and Parkinson's disease: a chronopharmacologic approach to considering fluctuations in function. Clin. Neuropharmacol. 2002, 25(4):194-201.
10. Borjigin J., Li X., Snyder S.H. The pineal gland and melatonin: molecular and pharmacologic regulation. Annu. Rev. Pharmacol. Toxicol. 1999, 39:53-65.
11. Tan D.X., Manchester L.C., Terron M.P., Flores L.J., Reiter R.J. One molecule, many derivatives: a never-ending interaction of melatonin with reactive oxygen and nitrogen species?. J. Pineal Res. 2007, 42(1):28-42.
12. Hardeland R. Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine 2005, 27(2):119-130.
13. Reiter R.J., Tan D.X., Maldonado M.D. Melatonin as an antioxidant: physiology versus pharmacology. J. Pineal Res. 2005, 39(2):215-216.
14. Reiter R.J., Tan D.X., Mayo J.C., Sainz R.M., Leon J., Czarnocki Z. Melatonin as an antioxidant: biochemical mechanisms and pathophysiological implications in humans. Acta Biochim. Pol. 2003, 50(4):1129-1146.
15. Zhao F., Liu Z.Q., Wu D. Antioxidative effect of melatonin on DNA and erythrocytes against free-radical-induced oxidation. Chem. Phys. Lipids 2008, 151(2):77-84.
16. Pieri C., Marra M., Moroni F., Recchioni R., Marcheselli F. Melatonin: a peroxyl radical scavenger more effective than vitamin E. Life Sci. 1994, 55(15):271-276.
17. Rodriguez C., Mayo J.C., Sainz R.M., Antolin I., Herrera F., Martin V., Reiter R.J. Regulation of antioxidant enzymes: a significant role for melatonin. J. Pineal Res. 2004, 36(1):1-9.
18. Semak I., Korik E., Antonova M., Wortsman J., Slominski A. Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes. J. Pineal Res. 2008, 45(4):515-523.
19. Ma X., Idle J.R., Krausz K.W., Gonzalez F.J. Metabolism of melatonin by human cytochromes P450. Drug Metab. Dispos. 2005, 33(4):489-494.
20. Singer S.S., Hagedorn J.E., Smith D.M., Williams J.L. The enzymatic basis for the rat liver 6-hydroxymelatonin sulfotransferase activity. J. Pineal Res. 1995, 18(1):49-55.
21. Bondy S.C., Naderi S. Contribution of hepatic cytochrome P450 systems to the generation of reactive oxygen species. Biochem. Pharmacol. 1994, 48(1):155-159.
22. Puntarulo S., Cederbaum A.I. Production of reactive oxygen species by microsomes enriched in specific human cytochrome P450 enzymes. Free Radic. Biol. Med. 1998, 24(7-8):1324-1330.
23. Zangar R.C., Davydov D.R., Verma S. Mechanisms that regulate production of reactive oxygen species by cytochrome P450. Toxicol. Appl. Pharmacol. 2004, 199(3):316-331.
24. Letelier M.E., Lagos F., Faundez M., Miranda D., Montoya M., Aracena-Parks P., Gonzalez-Lira V. Copper modifies liver microsomal UDP-glucuronyltransferase activity through different and opposite mechanisms. Chem. Biol. Interact. 2007, 167(1):1-11.
25. Letelier M.E., Lepe A.M., Faundez M., Salazar J., Marin R., Aracena P., Speisky H. Possible mechanisms underlying copper-induced damage in biological membranes leading to cellular toxicity. Chem. Biol. Interact. 2005, 151(2):71-82.
26. Letelier M.E., Martinez M., Gonzalez-Lira V., Faundez M., Aracena-Parks P. Inhibition of cytosolic glutathione S-transferase activity from rat liver by copper. Chem. Biol. Interact. 2006, 164(1-2):39-48.
27. Letelier M.E., Pimentel A., Pino P., Lepe A.M., Faundez M., Aracena P., Speisky H. Microsomal UDP-glucuronyltransferase in rat liver: oxidative activation. Basic Clin. Pharmacol. Toxicol. 2005, 96(6):480-486.
28. Letelier M.E., Faúndez M., Jara-Sandoval J., Molina-Berríos A., Cortés-Troncoso J., Aracena-Parks P., Marín-Catalán R. Mechanisms underlying the inhibition of the cytochrome P450 system by copper ions. J. Appl. Toxicol. 2009, 29(8):675-702.
29. Letelier M.E., Molina-Berrios A., Cortes-Troncoso J., Jara-Sandoval J., Müller A., Aracena-Parks P. Comparative effects of superoxide anion and hydrogen peroxide on microsomal and cytosolic glutathione S-transferase activities of rat liver. Biol. Trace Elem. Res. 2010, 134(2):203-211.
30. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193(1):265-275.
31. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 1964, 239:2370-2378.
32. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J. Biol. Chem. 1964, 239:2379-2385.
33. Poeggeler B., Thuermann S., Dose A., Schoenke M., Burkhardt S., Hardeland R. Melatonin's unique radical scavenging properties-roles of its functional substituents as revealed by a comparison with its structural analogs. J. Pineal Res. 2002, 33(1):20-30.
34. Crespo A., Turjanski A.G., Estrin D.A. Electronic spectra of indolyl radicals: a time-dependent DFT study. Chem. Phys. Lett. 2002, 365(1-2):15-21.
35. Hoy J.A., Smagghe B.J., Halder P., Hargrove M.S. Covalent heme attachment in Synechocystis hemoglobin is required to prevent ferrous heme dissociation. Protein Sci. 2007, 16(2):250-260.
36. Tesoriere L., Allegra M., D'Arpa D., Butera D., Livrea M.A. Reaction of melatonin with hemoglobin-derived oxoferryl radicals and inhibition of the hydroperoxide-induced hemoglobin denaturation in red blood cells. J. Pineal Res. 2001, 31(2):114-119.
37. Tesoriere L., Avellone G., Ceraulo L., D'Arpa D., Allegra M., Livrea M.A. Oxidation of melatonin by oxoferryl hemoglobin: a mechanistic study. Free Radic. Res. 2001, 35(6):633-642.
38. Xu L.-H., Fushinobu S., Ikeda H., Wakagi T., Shoun H. Crystal structures of cytochrome P450 105P1 from Streptomyces avermitilis: conformational flexibility and histidine ligation state. J. Bacteriol. 2009, 191(4):1211-1219.
39. Chen T.L., Ueng T.H., Chen S.H., Lee P.H., Fan S.Z., Liu C.C. Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br. J. Anaesth. 1995, 74(5):558-562.
40. Sherman D.H., Li S., Yermalitskaya L.V., Kim Y., Smith J.A., Waterman M.R., Podust L.M. The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae. J. Biol. Chem. 2006, 281(36):26289-26297.