Oxidation of melatonin by singlet molecular oxygen (O2(1Δg)) produces N1-acetyl-N2-formyl-5-methoxykynurenine

Journal of Pineal Research

Volumn 35, Issue 2, 2003, Pages 131-137

  De Almeida, Eduardo A ^a   Martinez, Glaucia R ^a   Klitzke, Clécio F ^a   De Medeiros, Marisa H G ^a   Di Mascio, Paolo ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Antioxidants; Free radical; Melatonin; N1 acetyl N2 formyl 5 methoxykynurenine; Singlet oxygen

Indexed keywords

ANTIOXIDANT; FREE RADICAL; KYNURENINE; MELATONIN; METHYLENE BLUE; N1 ACETYL N2 FORMYL 5 METHOXYKYNURENINE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOSENSITIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; KYNURAMINE; MASS SPECTROMETRY; MELATONIN; OXIDATION-REDUCTION; SINGLET OXYGEN;

EID: 0042590992     PISSN: 07423098     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-079X.2003.00066.x     Document Type: Article

References (29)

1. TAN DX, CHEN LD, POEGGELER B et al. Melatonin: a potent endogenous hydroxyl radical scavenger. Endocr J 1993; 1:57-60.
2. REITER RJ. Oxidative damage in the central nervous system: protection by melatonin. Prog Neurobiol 1998; 56:359-384.
3. REITER RJ, TAN D-X, MANCHESTER LC et al. Biochemical reactivity of melatonin with reactive oxygen and nitrogen species. Cell Biochem Biophys 2001; 34:237-254.
4. ALLEGRA M, REITER RJ, TAN DX et al. The chemistry of melatonin's interaction with reactive species. J Pineal Res 2003; 34:1-10.
5. MATUSZAK Z, RESZKA KJ, CHIGNELL CF. Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations. Free Rad Biol Med 1997; 23:367-372.
6. ZANG LY, COSMA G, GARDNER H et al. Scavenging of reactive oxygen species by melatonin. Biochim Biophys Acta 1998; 1425:467-477.
7. TAN D-X, MANCHESTER LC, REITER RJ et al. A novel melatonin metabolite, cyclic 3-hydroxymelatonin; a biomarker of in vivo hydroxyl radical generation. Biochem Biophys Res Com 1998; 253:614-620.
8. TURJANSKI AG, LEONIK F, EESTRIN DA et al. Scavenging of NO by melatonin. J Am Chem Soc 2000; 122:10468-10469.
9. TAN D-X, MANCHESTER LC, REITER RJ et al. Melatonin directly scavenges hydrogen peroxide: a potentially new metabolic pathway of melatonin biotransformation. Free Rad Biol Med 2000; 29:1177-1185.
10. CAGNOLI CM, ABATAY C, KHARLANOVA E et al. Melatonin protects neurons from singlet oxygen-induced apoptosis. J Pineal Res 1995; 18:222-226.
11. POEGGELER G, SAARELA S, REITER RJ et al. Melatonin - a highly potent endogenous scavenger and electron donor: new aspects of the oxidation chemistry of this indole assessed in vitro. Ann NY Acad Sci 1994; 739:419-420.
12. ANDRISANO V, BERTUCCI C, BATTAGLIA A et al. Photostability of drugs: photodegradation of melatonin and its determination in commercial formulations. J Phar Biol Anal 2000; 23:15-23.
13. LU J, LAU C, LEE MK et al. Simple and convenient chemiluminescence method for the determination of melatonin. Anal Chim Acta 2002; 455:193-198.
14. 18O-labeled singlet oxygen for mechanistic studies. J Am Chem Soc 2000; 122:10212-10213.
15. DI MASCIO P, SIES H. Quantification of singlet oxygen generated by thermolysis of 3,3′-(1,4-naphthydilene)dipropionate. Monomol and dimol photoemission and effects of 1,4-diazabicyclo[2.2.2.]octane. J Am Chem Soc 1989; 111:2909-2914.
16. INOUE K, MATSUURA T, SAITO I. Mechanism of dye-sensitized photooxidation of triptophanm triptamine, and their derivatives. Singlet oxygen process in competition with type I process. Bull Chem Soc Jpn 1982; 55:2959-2964.
17. FOOTE CS. Definition of type I and type II photosensitized oxidation. Photochem Photobiol 1991; 54:659.
18. PIERLOT C, AUBRY J-M, BRIVIBA K et al. Naphtalene endoperoxides as generators of singlet oxygen in biological media. Methods Enzymol 2000; 319:3-20.
19. COHN M, URBY HC. Oxygen exchange reactions of organic compounds and water. J Am Chem Soc 1938; 60:679-687.
20. BELL RP, MCDOUGALL AO. Hidration equilibria of some aldehydes and ketones. Trans Faraday Soc 1960; 56:1281-1285.
21. BENDER ML, THOMAS RJ. The concurrent and alkaline hydrolysis and isotopic oxygen exchange of a series of p-substituted acetanilides. J Am Chem Soc 1961; 83:4183-4189.
22. FANG X, JIN F, JIN H et al. Reaction of the superoxide radical with the N-centered radical derived from N-acetyltryptophan methyl ester. J Chem Soc Perkin Trans 1998; 2:259-263.
23. 18O-labeled linoleic acid hydroperoxide and monomol light emission measurements. J Am Chem Soc (in press).
24. g)) production in the reaction of linoleic acid hydroperoxide with peroxynitrrite. J Am Chem Soc 2003; 125:4510-4517.
25. PACKER L, SIES H, eds. Singlet oxygen, UV-A, and ozone. Methods Enzymol 2000; 319:682.
26. STONE TW. Kynurenines in the CNS: from endogenous obscurity to therapeutic importance. Prog Neurobiol 2001; 64:185-218.
27. SILVA SO, XIMENES VF, CATALANI LH et al. Myeloperoxidaze-catalyzed oxidation of melatonin by activated neutrophils. Biochem Biophys Res Commun 2000; 279:657-662.
28. CILENTO O. Photobiochemistry in the dark. Photochem Photobiol 1980; 5:199-228.
29. CILENTO O. Generation of eletronically excited triplet species in biochemical system. Pure Appl Chem 1984; 56:1179-1190.