Oxidation of melatonin and its catabolites, N1-acetyl-N 2-formyl-5-methoxykynuramine and N1-acetyl-5- methoxykynuramine, by activated leukocytes

Journal of Pineal Research

Volumn 37, Issue 3, 2004, Pages 171-175

  Silva, Sueli O ^a   Rodrigues, Maria R ^a   Carvalho, Sandra R Q ^a,b   Catalani, Luiz H ^a   Campa, Ana ^a   Ximenes, Valdecir F ^c  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b STATE UNIVERSITY OF LONDRINA   (Brazil)

^c SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Melatonin; Mononuclear cells; Myeloperoxidase; N1 acetyl 5 methoxykynuramine (AMK); N1 acetyl N2 formyl 5 methoxykynuramine (AFMK); Neutrophils

Indexed keywords

ACETONITRILE; HYDROGEN PEROXIDE; KYNURAMINE; LIPOPOLYSACCHARIDE; MELATONIN; MYELOPEROXIDASE; N1 ACETYL 5 METHOXYKYNURAMINE; N1 ACETYL N2 FORMYL 5 METHOXYKYNURAMINE; PHORBOL 13 ACETATE 12 MYRISTATE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL STIMULATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LEUKOCYTE ACTIVATION; NEUTROPHIL; OXIDATION; PERIPHERAL BLOOD MONONUCLEAR CELL; REVERSED PHASE LIQUID CHROMATOGRAPHY;

CATALASE; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYDROGEN PEROXIDE; KINETICS; KYNURAMINE; LEUKOCYTES; LIPOPOLYSACCHARIDES; MELATONIN; NEUTROPHIL ACTIVATION; OXIDATION-REDUCTION; PEROXIDASE; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPEROXIDE DISMUTASE; TETRADECANOYLPHORBOL ACETATE;

EID: 4644244154     PISSN: 07423098     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1600-079X.2004.00149.x     Document Type: Article

References (19)

1. SENER G, JAHOVIC N, TOSUN O et al. Melatonin ameliorates ionizing radiation-induced oxidative organ damage in rats. Life Sci 2003; 74:563-572.
2. TAN DX, POEGGELER B, REITER RJ et al. The pineal hormone melatonin inhibits DNA-adduct formation induced by the chemical carcinogen safrole in vivo. Cancer Lett 1993; 70:65-71.
3. DELLEGAR SM, MURPHY SA, BOURNE AE et al. Identification of the factors affecting the rate of deactivation of hypochlorous acid by melatonin. Biochem Biophys Res Commun 1999; 257:431-439.
4. TAN DX, CHEN LD, POEGGELER LC et al. Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocrine J 1993; 1:57-60.
5. BLANCHARD B, POMPON D, DUCROCQ C. Nitrosation of melatonin by nitric oxide and peroxynitrite. J Pineal Res 2000; 29:184-192.
6. GITTO E, KARBOWNIK M, REITER RJ et al. Effects of melatonin treatment in septic newborns. Pediatr Res 2001; 50:756-760.
7. GITTO E. REITER RJ, AMODIO A et al. Early indicators of chronic lung disease in preterm infants with respiratory distress syndrome and their inhibition by melatonin. J Pineal Res 2004; 36:250-255.
8. TAN DX, MANCHESTER LC, BURKHARDT S et al. N1-acetyl-N2-formyl-5- methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB J 2001; 15:2294-2296.
9. RESSMEYER AR, MAYO JC, ZELOSKO V et al. Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction. Redox Rep 2003; 8:205-213.
10. KELLY RW, AMATO F, SEAMARK RF. N-acetyl-5-methoxy kynurenamine, a brain metabolite of melatonin, is a potent inhibitor of prostaglandin biosynthesis. Biochem Biophys Res Commun 1984; 121:372-379.
11. SILVA SO, XIMENES VF, CATALANI LH et al. Myeloperoxidase-catalyzed oxidation of melatonin by activated neutrophils. Biochem Biophys Res Commun 2000; 279:657-662.
12. RODRIGUES MR, RODRIGUEZ D, CATALANI LH et al. Interferon-gamma independent oxidation of melatonin by macrophages. J Pineal Res 2003; 34:69-74.
13. Rozov SV, FILATOVA EV, ORLOV AA et al. N1-acetyl-N2-formyl-5- methoxykynuramine is a product of melatonin oxidation in rats. J Pineal Res 2003; 35:245-250.
14. HIRATA F, HAYAISHI O, TOKUYAMA T et al. In vitro and in vivo formation of two new metabolites of melatonin. J Biol Chem 1974; 249:1311-1313.
15. BOYUM A. Isolation of lymphocytes, granulocytes and macrophages. Scand J Immunol 1976; 5:9-15.
16. ALMEIDA EA, KLITZKE CF, MARTINEZ GR, MEDEIROS MH, DI MASCIO P. Synthesis of internal labeled standards of melatonin and its metabolite N1-acetyl-N2-formyl-5-methoxykynuramine for their quantification using an on-line liquid chromatography-electrospray tandem mass spectrometry system. J Pineal Res 2004; 36:64-71.
17. SIBELIUS U, HATTAR K, HOFFMANN S et al. Distinct pathways of lipopolysaccharide priming of human neutrophil respiratory burst: role of lipid mediator synthesis and sensitivity to interleukin-10. Crit Care Med 2002; 30:2306-2312.
18. STIBOROVA M, MIKSANOVA M, HAVLICEK V et al. Mechanism of peroxidase-mediated oxidation of carcinogenic o-anisidine and its binding to DNA. Mutat Res 2002; 500:49-66
19. O'BRIEN PJ. Peroxidases. Chem Biol Interact 2000; 129:113-139.