A metabolomic perspective of melatonin metabolism in the mouse

Endocrinology

Volumn 149, Issue 4, 2008, Pages 1869-1879

  Ma, Xiaochao ^a   Chen, Chi ^a   Krausz, Kristopher W ^a   Idle, Jeffrey R ^b   Gonzalez, Frank J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOMELATONIN; 3 HYDROXYMELATONIN; 5 HYDROXYINDOLEACETALDEHYDE; 6 HYDROXYMELATONIN; 6 HYDROXYMELATONIN GLUCURONIDE; 6 HYDROXYMELATONIN SULFATE; ANTIOXIDANT; BETA GLUCURONIDASE; CYCLIC 6 HYDROXYMELATONIN; CYCLIC MELATONIN; CYCLIC N ACETYLSEROTONIN GLUCURONIDE; CYTOCHROME P450 1A2; DIHYDROXYMELATONIN; GLUCURONIDE; MELATONIN; MELATONIN GLUCURONIDE; N ACETYLSEROTONIN GLUCURONIDE; N ACETYLSEROTONIN SULFATE; N1 ACETYL 5 METHOXYKYNURAMINE; N1 ACETYL N2 FORMYL 5 METHOXYKYNURAMINE; SULFATASE; UNCLASSIFIED DRUG;

ARTICLE; C57BL 6 MOUSE; CONJUGATION; CYP1A2 GENE; GENE; HORMONE METABOLISM; HUMAN; METABOLITE; METABOLOMICS; MOUSE; NONHUMAN; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; SPECIES DIFFERENCE; URINALYSIS;

ANIMALS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 CYP1A2; HUMANS; MASS SPECTROMETRY; MELATONIN; MICE; MICE, INBRED C57BL; MICE, INBRED CBA; SPECIES SPECIFICITY;

EID: 41549100628     PISSN: 00137227     EISSN: 00137227     Source Type: Journal    
DOI: 10.1210/en.2007-1412     Document Type: Article

References (40)

1. Leone RM, Silman RE 1984 Melatonin can be differentially metabolized in the rat to produce N-acetylserotonin in addition to 6-hydroxy-melatonin. Endocrinology 114:1825-1832
2. Young IM, Leone RM, Francis P, Stovell P, Silman RE 1985 Melatonin is metabolized to N-acetyl serotonin and 6-hydroxymelatonin in man. J Clin Endocrinol Metab 60:114-119
3. Kopin IJ, Pare CM, Axelrod J, Weissbach H 1960 6-Hydroxylation, the major metabolic pathway for melatonin. Biochim Biophys Acta 40:377-378
4. Kopin IJ, Pare CM, Axelrod J, Weissbach H 1961 The fate of melatonin in animals. J Biol Chem 236:3072-3075
5. Francis PL, Leone AM, Young IM, Stovell P, Silman RE 1987 Gas chromatographic-mass spectrometric assay for 6-hydroxymelatonin sulfate and 6-hydroxymelatonin glucuronide in urine. Clin Chem 33:453-457
6. Leone AM, Francis PL, Silman RE 1987 The isolation, purification, and characterisation of the principal urinary metabolites of melatonin. J Pineal Res 4:253-266
7. Ma X, Idle JR, Krausz KW, Tan DX, Ceraulo L, Gonzalez FJ 2006 Urinary metabolites and antioxidant products of exogenous melatonin in the mouse. J Pineal Res 40:343-349
8. Skene DJ, Timbers SE, Middleton B, English J, Kopp C, Tobler I, Ioannides C 2006 Mice convert melatonin to 6-sulphatoxymelatonin. Gen Comp Endocrinol 147:371-376
9. Kennaway DJ, Voultsios A, Varcoe TJ, Moyer RW 2002 Melatonin in mice: rhythms, response to light, adrenergic stimulation, and metabolism. Am J Physiol Regul Integr Comp Physiol 282:R358-R365
10. Peniston-Bird JF, Di WL, Street CA, Edwards R, Little JA, Silman RE 1996 An enzyme immunoassay for 6-sulphatoxy-melatonin in human urine. J Pineal Res 20:51-56
11. Chen C, Meng L, Ma X, Krausz KW, Pommier Y, Idle JR, Gonzalez FJ 2006 Urinary metabolite profiling reveals CYP1A2-mediated metabolism of NSC686288 (aminoflavone). J Pharmacol Exp Ther 318:1330-1342
12. Giri S, Idle JR, Chen C, Zabriskie TM, Krausz KW, Gonzalez FJ 2006 A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse. Chem Res Toxicol 19:818-827
13. Giri S, Krausz KW, Idle JR, Gonzalez FJ 2007 The metabolomics of (±)-arecoline 1-oxide in the mouse and its formation by human flavin-containing monooxygenases. Biochem Pharmacol 73:561-573
14. Leone AM, Francis PL, McKenzie-Gray B 1988 Rapid and simple synthesis for the sulphate esters of 6-hydroxy-melatonin and N-acetyl-serotonin. J Pineal Res 5:367-371
15. Liang HC, Li H, McKinnon RA, Duffy JJ, Potter SS, Puga A, Nebert DW 1996 Cyp1a2(-/-) null mutant mice develop normally but show deficient drug metabolism. Proc Natl Acad Sci USA 93:1671-1676
16. Cheung C, Ma X, Krausz KW, Kimura S, Feigenbaum L, Dalton TP, Nebert DW, Idle JR, Gonzalez FJ 2005 Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in mice humanized for CYP1A1 and CYP1A2. Chem Res Toxicol 18:1471-1478
17. Dubois G, Turpin J, Baumann N 1976 p-Nitrocatechol sulfate for arylsulfatase assay: detection of metachromatic leukodystrophy variants. Adv Exp Med Biol 68:233-237
18. Szasz G 1967 Comparison between p-nitrophenyl glucuronide and phenolphthalein glucuronide as substrates in the assay of β-glucuronidase. Clin Chem 13:752-759
19. Ma X, Idle JR, Krausz KW, Gonzalez FJ 2005 Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos 33:489-494
20. Naguib M, Gottumukkala V, Goldstein PA 2007 Melatonin and anesthesia: a clinical perspective. J Pineal Res 42:12-21
21. Suresh Kumar PN, Andrade C, Bhakta SG, Singh NM 2007 Melatonin in schizophrenic outpatients with insomnia: a double-blind, placebo-controlled study. J Clin Psychiatry 68:237-241
22. Mills E, Wu P, Seely D, Guyatt G 2005 Melatonin in the treatment of cancer: a systematic review of randomized controlled trials and meta-analysis. J Pineal Res 39:360-366
23. Weishaupt JH, Bartels C, Polking E, Dietrich J, Rohde G, Poeggeler B, Mertens N, Sperling S, Bohn M, Huther G, Schneider A, Bach A, Siren AL, Hardeland R, Bahr M, Nave KA, Ehrenreich H 2006 Reduced oxidative damage in ALS by high-dose enteral melatonin treatment. J Pineal Res 41: 313-323
24. Ebihara S, Marks T, Hudson DJ, Menaker M 1986 Genetic control of melatonin synthesis in the pineal gland of the mouse. Science 231:491-493
25. von Gall C, Lewy A, Schomerus C, Vivien-Roels B, Pevet P, Korf HW, Stehle JH 2000 Transcription factor dynamics and neuroendocrine signalling in the mouse pineal gland: a comparative analysis of melatonin-deficient C57BL mice and melatonin-proficient C3H mice. Eur J Neurosci 12:964-972
26. Malfatti MA, Kulp KS, Knize MG, Davis C, Massengill JP, Williams S, Nowell S, MacLeod S, Dingley KH, Turteltaub KW, Lang NP, Felton JS 1999 The identification of [2-(14)C]2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine metabolites in humans. Carcinogenesis 20:705-713
27. Fabre G, Combalbert J, Berger Y, Cano JP 1990 Human hepatocytes as a key in vitro model to improve preclinical drug development. Eur J Drug Metab Pharmacokinet 15:165-171
28. Gonzalez FJ 2002 Transgenic models in xenobiotic metabolism and toxicology. Toxicology 181-182:237-239
29. Martignoni M, Groothuis GM, de Kanter R 2006 Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metab Toxicol 2:875-894
30. Yu AM, Idle JR, Byrd LG, Krausz KW, Kupfer A, Gonzalez FJ 2003 Regeneration of serotonin from 5-methoxytryptamine by polymorphic human CYP2D6. Pharmacogenetics 13:173-181
31. Burkhardt S, Reiter RJ, Tan DX, Hardeland R, Cabrera J, Karbownik M 2001 DNA oxidatively damaged by chromium(III) and H(2)O(2) is protected by the antioxidants melatonin, N(1)-acetyl-N(2)-formyl-5- methoxykynuramine, resveratrol and uric acid. Int J Biochem Cell Biol 33:775-783
32. Tan DX, Manchester LC, Burkhardt S, Sainz RM, Mayo JC, Kohen R, Shohami E, Huo YS, Hardeland R, Reiter RJ 2001 N1-acetyl-N2- formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB J 15:2294-2296
33. de Almeida EA, Martinez GR, Klitzke CF, de Medeiros MH, Di Mascio P 2003 Oxidation of melatonin by singlet molecular oxygen [O2(1deltag)] produces N1-acetyl-N2-formyl-5-methoxykynurenine. J Pineal Res 35:131-137
34. Rozov SV, Filatova EV, Orlov AA, Volkova AV, Zhloba AR, Blashko EL, Pozdeyev NV 2003 N1-acetyl-N2-formyl-5-methoxykynuramine is a product of melatonin oxidation in rats. J Pineal Res 35:245-250
35. Silva SO, Rodrigues MR, Carvalho SR, Catalani LH, Campa A, Ximenes VF 2004 Oxidation of melatonin and its catabolites, N1-acetyl- N2-formyl-5-methoxykynuramine and N1-acetyl-5-methoxykynuramine, by activated leukocytes. J Pineal Res 37:171-175
36. Hirata F, Hayaishi O, Tokuyama T, Seno S 1974 In vitro and in vivo formation of two new metabolites of melatonin. J Biol Chem 249:1311-1313
37. Anisimov VN 2003 Effects of exogenous melatonin - a review. Toxicol Pathol 31:589-603
38. Buscemi N, Vandermeer B, Pandya R, Hooton N, Tjosvold L, Hartling L, Baker G, Vohra S, Klassen T 2004 Melatonin for treatment of sleep disorders. Evid Rep Technol Assess (Summ) 1-7
39. Agozzino P, Avellone G, Bongiorno D, Ceraulo L, Filizzola F, Natoli MC, Livrea MA, Tesoriere L 2003 Melatonin: structural characterization of its non-enzymatic mono-oxygenate metabolite. J Pineal Res 35:269-275
40. Tan DX, Manchester LC, Reiter RJ, Plummer BF, Hardies LJ, Weintraub ST, Vijayalaxmi, Shepherd AM 1998 A novel melatonin metabolite, cyclic 3-hydroxymelatonin: a biomarker of in vivo hydroxyl radical generation. Biochem Biophys Res Commun 253:614-620