Melatonin and its derivatives cyclic 3-hydroxymelatonin, N1-acetyl-N2-formyl-5-methoxykynuramine and 6-methoxymelatonin reduce oxidative DNA damage induced by Fenton reagents

Journal of Pineal Research

Volumn 34, Issue 3, 2003, Pages 178-184

  López Burillo, Silvia ^a   Tan, Dun Xian ^b   Rodriguez Gallego, Vergelina ^c   Manchester, Lucien C ^b   Mayo, Juan Carlos ^b   Sainz, Rosa Maria ^b   Reiter, Russel J ^b  

^a UNIVERSITY OF VALLADOLID   (Spain)

^b UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

^c CIEMAT   (Spain)

Author keywords

6 methoxymelatonin; 8 hydroxydeoxyguanosine; Chromium; Cyclic 3 hydroxymelatonin; Hydroxyl radical; Melatonin; N1 acetyl N2 formyl 5 methoxykynuramine

Indexed keywords

6 METHOXYMELATONIN; 8 HYDROXYDEOXYGUANOSINE; ACETONITRILE; BIOLOGICAL MARKER; CHROMIUM; CHROMIUM CHLORIDE; CYCLIC 3 HYDROXYMELATONIN; DNA; HYDROGEN PEROXIDE; HYDROXYL RADICAL; MELATONIN; MELATONIN DERIVATIVE; METHANOL; N1 ACETYL N2 FORMYL 5 METHOXYKYNURAMINE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; DNA DAMAGE; FENTON REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; OXIDATIVE STRESS; REACTION ANALYSIS;

EID: 0037378276     PISSN: 07423098     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-079X.2003.00025.x     Document Type: Article

References (48)

1. HALLIWELL B. Effect of diet on cancer development: is oxidative DNA damage a biomarker? Free Radical Biol Med 2002; 32:968-974.
2. KASAI H. Analysis of a form of oxidative DNA damage, 8-hydroxy-2′-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis. Mutat Res 1997; 387:146-163.
3. RODRIGUEZ H, JURADO J, LAVAL J, DIZDAROGLU M. Comparison of the levels of 8-hydroxyguanine in DNA as measured by gas chromatography mass spectrometry following hydrolysis of DNA by Escherichia coli Fpg protein or formic acid. Nucleic Acids Res 2000; 28:75-99.
4. ANDERSON RA. Nutritional role of chromium in glucose and lipid metabolism of humans. In: Metal Ions in Biology and Medicine. COLLERY P, ed., JOHN LIBBEY, London, 1990; pp. 315-319.
5. SNOW ET. A possible roll for chromium(III) in genotoxicity. Environ Health Perspect 1991; 92:75-81.
6. SINGH J, CARLISLE DL, PRITCHARD DE, PATERNO SR. Chromium-induced genotoxicity and apoptosis. Oncol Rep 1998; 5:1307-1318.
7. TSOU TC, CHEN CL, LIU TY, YANG JL. Induction of 8-hydroxydeoxygunosine in DNA by chromium(III) plus hydrogen peroxide and its prevention by scavengers. Carcinogenesis 1996; 17:103-108.
8. CHEN KC, CHAHILL DS, KASAI S, NISHIMURA S, LOEB LA. 8-hydroxydeoxyhguanosine, an abundant form of oxidative DNA damage, causes G → T and A → C substitution. J Biol Chem 1996; 267:166-172.
9. MANCHESTER LC, POEGGELER B, ALVARES FL, OGDEN GB, REITER RJ. Melatonin immunoreactivity in the photosynthetic prokaryote, Rhodospirillum rubrum: implications for an ancient antioxidant system. Cell Mol Biol Res 1995; 41:391-395.
10. REITER RJ, TAN DX, MANCHESTER LC, CALVO JR, Antioxidative capacity of melatonin. In: Handbook of Antioxidants, 2nd edn. CADENAS E, PACKER L eds, Marcel Dekker, NY, 2002; pp. 565-613.
11. TAN DX, CHEN LD, POEGGELER B, MANCHESTER LC, REITER RJ. Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocr J 1993; 1:57-60.
12. REITER RJ, MELCHIORRI D, SEWERNYK E et al. A review of the evidence supporting melatonin's role as an antioxidant. J Pineal Res 1995; 18:1-11.
13. REITER RJ, TANG L, GARCIA JJ, MUNOZ-HOYOS A. Pharmacological actions of melatonin in oxygen radical patho-physiology. Life Sci 1997; 60:2255-2271.
14. REITER RJ, TAN DX, KIM SJ, QI W. Melatonin as a pharmacological agent against oxidative damage to lipids and DNA. Proc West Pharmacol Soc 1998; 41:229-236.
15. 2: protection by melatonin and related molecules. J Pineal Res 2000; 29:54-61.
16. 2-formyl-5-methoxykynuramine, resveratrol, and uric acid. Int J Biochem Cell Biol 2001; 33:775-783.
17. TAN DX, MANCHESTER LC, REITER RJ, QI WB, KARBOWNIK M, CALVO JR. Significance of melatonin in antioxidative defense system: reactions and products. Biol Signals Recept 2000; 9:137-159.
18. SEEGAR H, MECK AO, LIPPERT TH. Effect of melatonin and metabolites on copper-mediated oxidation of low density lipoproteins. Br J Clin Pharmacol 1997; 44:283-284.
19. TAN DX, MANCHESTER LC, REITER RJ et al. Melatonin directly scavenges hydrogen peroxide: a potentially new metabolic pathway of melatonin biotransformation. Free Radical Biol Med 2000; 29:1177-1185.
20. TAN DX, MANCHESTER LC, REITER RJ et al. A novel melatonin metabolite, cyclic 3-hydroxymelatonin: a biomarker of in vivo hydroxyl radical generation. Biochem Biophys Res Commun 1998; 253:614-620.
21. LI XJ, ZHANG LM, GU J, ZHANG AZ, SUN FY. Melatonin decreases production of hydroxyl radical during ischemia-reperfusion. Acta Pharmacol Sin 1997; 18:394-396.
22. STASICA AP, ULANSKI P, ROSIAK JM. Melatonin as a hydroxyl radical scavenger. J Pineal Res 1998; 25:65-66.
23. ZANG LY, COSMA H, GARDNER H, VALLYNATHAN V. Scavenging of reactive oxygen species by melatonin. Biochem Biophys Acta 1998; 1425:469-477.
24. LIVREA MA, TESORIERE L, TAN DX, REITER RJ. Radical and reactive intermediate-scavenging properties of melatonin in pure chemical systems. In: Handbook of Antioxydants, 2nd edn. CADENAS E, PARKER L eds, Marcel Dekker, New York, 2002; pp. 615-631.
25. POEGGELER B, THUERMAN S, DOSE A, SCHOENKE M, BURKHARDT S, HARDELAND R. Melatonin's unique radical scavenging properties-roles of its functional substituents as revealed by comparison with its structural analogs. J Pineal Res 2002; 33:20-30.
26. COSTA EJ, LOPES RH, LAMY-FREUND MT. Permeability of pure lipid bilayers to melatonin. J Pineal Res 1995; 19:123-126.
27. SHIDA CS, CASTRUCCI AM, LAMY-FREUND MT. High melatonin solubility in aqueous medium. J Pineal Res 1994; 16:198-201.
28. MENEDEZ-PELAEZ A, REITER RJ, GUERRERO JM, PUIG-DOMINGO M, HOWES K. Sexual dimorphism in N-acetiltransferase activity, hydroxyindol-O-methyltransferase activity and melatonin content in the harderian gland of Syrian hamsters: changes following gonadectomy. Proc Soc Exp Biol Med 1988; 187:287-291.
29. OKATANI Y, OKAMOTO K, HAYASI K, WAKATSUKI A, TUMURA S, SAGARA Y. Maternal-fetal transfer of melatonin in pregnant women near term. J Pineal Res 1998; 25:129-134.
30. CONTI A, CONCONI S, HERTENS E, SKWARLO-SONTA K, MARCOUSKA M, MAESTRONI GJM. Melatonin synthesis in mouse and human bone marrow. J Pineal Res 2000; 28:193-202.
31. TAN DX, MANCHESTER LC, REITER RJ, QI W, HANES MA, FARLEY NJ. High physiological levels of melatonin in the bile of mammals. Life Sci 1999; 65:2523-2529.
32. POEGGELER B, REITER RJ, TAN DX, CHEN LD, MANCHESTER LC. Melatonin, hydroxyl radical-mediated oxidative damage and aging: a hypothesis. J Pineal Res 1993; 14:151-168.
33. MENENDEZ-PELAEZ A, POEGGELER B, REITER RJ, BARLOW-WALDEN L, PABLOS MI, TAN DX. Nuclear localization of melatonin in different mammalian tissues: immunocytochemical and radioimmunoassay evidence. J Cell Biochem 1993; 53:373-382.
34. MENENDEZ-PELAEZ A, REITER RJ. Distribution of melatonin in mammalian tissues: reactive importance of nuclear verses cytosolic localization. J Pineal Res 1993; 15:59-69.
35. REITER RJ, TAN DX, MANCHESTER LC, QI W. Biochemical reactivity of melatonin with reactive oxygen and nitrogen species: a review of the evidence. Cell Biochem Biophys 2001; 34:237-256.
36. TAN DX, MANCHESTER LC, REITER RJ, PLUMER BF. Cyclic 3-hydroxymelatonin: a metabolite generated as a result of hydroxyl radical scavenging. Biol Signals Recept 1999; 8:70-74.
37. 2 formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB J 2001; 15:2294-2296.
38. ANTILLA S. Biological effects of occupational and environmental exposure to chromium. In: Metal Ions in Biology and Medicine. COLLERY P, ed., John Libbey, London, 1990; pp. 315-319.
39. LEONARD A, LAWERYS RR. Carcinogenicity and mutagenicity of chromium. Mutat Res 1980:76:227-239.
40. DE FLORA S, BANASCO M, SERRA D, ZANACCHI P. Genotoxicity of chromium compounds: a review. Mutat Res 1990; 238:99-112.
41. CEDERBAUM AI, QURESHI A. Role of catalase and hydroxyl radicals in the oxidation of methanol by rat liver microsomes. Biochem Pharmacol 1982; 31:329-335.
42. SUTHANTHIRAN M, SOLOMON SD, WILLIAMS PS, RUBIN AL, NOVOGRODSKY A, STENZEL KH. Hydroxyl radical scavengers inhibit human natural killer cell activity. Nature 1984; 307:276-278.
43. RAHHAL S, RICHTER HW. Reaction of hydroxyl radicals with the ferrous and ferric iron chelates of diethylenetriamine-N,N,N′,N″,N″-pentaacetate. Free Radic Res Commun 1989; 6:369-377.
44. WINK DA, WINK CB, NIMS RW, FORD PC. Oxidizing intermediates generated in Fenton reagents: kinetic arguments against the intermediacy of the hydroxyl radical. Environ Health Perspect 1994; 102(Suppl. 3): 11-15.
45. PARMAR P, LIMSON J, NYOKONG T, DAYA S. Melatonin protects against copper-mediated free radical damage. J Pineal Res 2002; 32:237-242.
46. CABRERA J, BURKHARDT S, TAN DX, MANCHESTER LC, KARBOWNIK M, REITER RJ. Autoxidation and toxicant-induced oxidation of lipid and DNA in monkey liver: reduction of molecular damage by melatonin. Pharmacol Toxicol 2001; 89:225-230.
47. ALLEGRA M, REITER RJ, TAN DX, GENTILE C, TESORIERE L, LIBREA MA. The chemistry of melatonin's interaction with reactive species. J Pineal Res 34:1-10.
48. LIMSON J, NYOKONG T, DAYA S. The interaction of melatonin and its precursors with aluminum, cadmium, cooper, iron, lead and zinc: an adsorptive voltametric study. J Pineal Res 1998; 24:15-21.