Oxidation of 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine, a 1-amino analog of MPTP, by type A and B monoamine oxidase

Journal of Neural Transmission

Volumn 105, Issue 10-12, 1998, Pages 1253-1264

  Umeda, M ^a   Aoyama, S ^a   Kaiya, T ^a   Kohda, K ^a   Maruyama, W ^b   Naoi, M ^c,d,e  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY   (Japan)

^c NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^d Institute of Applied Biochemistry   (Japan)

^e Institute of Applied Biochemistry   (Japan)

Author keywords

1(N) amino 4 phenyl 1,2,3,6 tetrahydropyridine; Human brain synaptosomes; Monoamine oxidase; MPP+; MPTP; Oxidation

Indexed keywords

1 AMINO 4 PHENYL 1,2,3,6 TETRAHYDROPYRIDINE; 3 PIPERIDEINE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; PARGYLINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL STRAIN; CONTROLLED STUDY; CYTOTOXICITY; FLUOROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MITOCHONDRION; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; RAT; REACTION TIME; SYNAPTOSOME;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; ANIMALS; HUMANS; MALE; MICE; MICE, INBRED C57BL; MITOCHONDRIA; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; OXIDATION-REDUCTION; PC12 CELLS; RATS; SYNAPTOSOMES;

EID: 0032444278     PISSN: 03009564     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007020050128     Document Type: Article

References (31)

1. Asano S, Yokoyama Y, Kohda K (1997) Growth inhibition of cultured human leukemia cells by 3-aminothymidine and its analog. Anticancer Res 17: 823-826
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein using the principle of protein dye binding. Anal Biochem 72: 248-254
3. Chiba K, Trevor A, Catagnoli N Jr (1984) Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem Biophys Res Commun 120: 574-578
4. Cohen G, Pasik P, Cohen B, Leist A, Mytilineou C, Jahr MV (1984) Pargyline and deprenyl prevent the neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in monkey. Eur J Pharmacol 106: 209-210
5. Gray E, Whittaker V (1962) The isolation of nerve endings from brain; an electron-microscopic study of cell fragments derived by homogenization and centrifugation. J Anat 96: 79-87
6. Heikkila RE, Manzino L, Cabbat FS, Duvoisin RC (1985) Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and several of its analogues on the dopaminergic nigrostriatal pathway in mice. Neurosci Lett 58: 133-137
7. +) in the pathogenesis of Parkinson's disease. Brain Res 575: 285-298
8. Kindt MV, Youngster SK, Sonsalla PK, Duvoisin RC, Heikkila RE (1988) Role for monoamine oxidase-A (MAO-A) in the bioactivation and nigrostriatal dopaminergic neurotoxicity of the MPTP analog, 2′ Me-MPTP. Eur J Pharmacol 146: 313-318
9. Kohda K, Yasuda M, Ukai H, Baba K, Yamagata Y, Kawazoe Y (1989) Synthesis and properties of N-aminoguanine. Tetrahedron 45: 6367-6374
10. Kohda K, Baba K, Kawazoe Y (1990) Electrophilic amination of guanine derivatives. Mechanism for formation of 8-aminoguanosine derivatives. Tetrahedron 46: 1531-1540
11. Kohda K, Kobayashi I, Itano K, Asano S, Kawazoe Y (1993) Syntheses and properties of N-aminopyrimidines. Tetrahedron 49: 3947-3958
12. +, to clonal pheochromocytoma PC12 cells. Chem Res Toxicol (in press)
13. Kraml M (1965) A rapid microfluorometric determination of monoamine oxidase. Biochem Pharmacol 14: 1684-1686
14. Langston JW, Ballard P, Tetrud JW, Irwin I (1983) Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219: 979-980
15. Maret G, Testa B, Jenner P, Tyar E, Carrupt PA (1990) The MPTP assay: MAO activates tetrahydrophyridine derivatives to toxins causing parkinsonism. Drug Met Rev 22: 291-332
16. Maruyama W, Dostert P, Matsubara K, Naoi M (1995) N-Methyl(R)salsolinol produces hydroxyl radicals: involvement to neurotoxicity. Free Radic Biol Med 19: 67-75
17. Maruyama W, Naoi M, Kasamatsu T, Hashizume Y, Takahashi T, Kohda K, Dostert P (1997a) An endogenous dopamineric neurotoxin, N-methyl-(R)salsolinol, induces 1264 M. Umeda et al.: Oxidation of an amino analog of MPTP by type A and B MAO DNA damage in human dopaminergic neuroblastoma SH-SY5Y cells. J Neurochem 69: 322-329
18. Maruyama W, Strolin Benedetti M, Takahashi T, Naoi M (1997b) A neurotoxin N-methyl(R)salsolinol induces apoptotic cell death in differentiated human dopaminergic neuroblastoma SH-SY5Y cells. Neurosci Lett 232: 147-150
19. Naoi M, Nagatsu T (1986) Inhibition of monoamine oxidase by 3,4-dihydroxyphenylserine. J Neurochem 47: 604-607
20. Naoi M, Takahashi T, Nagatsu T (1987) A fluorometric determination of N-methyl-4-phenylpyridinium ion, using high-performance liquid chromatography. Anal Biochem 162: 540-545
21. Naoi M, Maruyama W, Dostert P, Hashizume Y (1997) N-Methyl-(R)Salsolinol as a dopaminergic neurotoxin: from an animal model to an early marker of Parkinson's disease. J Neural Transm [Suppl] 50: 89-105
22. Naoi M, Maruyama W, Kasamatsu T, Dostert P (1998) Oxidation of N-methyl(R)salsolinol: involvement to neurotoxicity and neuroprotection by endogenous catechol isoquinolines. J Neural Transm [Suppl] 52: 125-138
23. +. J Neural Transm [GenSect] 89: 139-145
24. Riachi NJ, Arora PK, Sayre LM, Harik SI (1988) Potent neurotoxic fluorinated 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs as potential probes in models of Parkinson's disease. J Neurochem 50: 1319-1321
25. +-analogues and related charged species. J Med Chem 33: 2221-2230
26. Saga T, Kaiya T, Asano S, Kohda K (1996) Electrophilic amination of adenines. Formation and characteristics of N-aminoadenines. Nucleosides & Nucleotides 15: 219-233
27. Scudiero DA, Shoemaker RH, Paull KD, Monks A, Tierney S, Nofziger TH, Currens MJ, Seniff D, Boyd MR (1988) Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res 48: 4827-4833
28. Tipton K, Singer TP (1993) Advances in our understanding of the mechanism of the neurotoxicity of MPTP and related compounds. J Neurochem 61: 1191-1206
29. Youdim MBH, Heldman E, Pollard HB, Fleming P, McHugh E (1986) Contrasting monoamine oxidase activity and tyramine induced catecholamine release in PC12 and chromaffin cells. Neuroscience 19: 1311-1318
30. Youngster SK, Sonsalla PK, Sieber B-A, Heikkila RE (1989) Structure-activity study of the mechanism of 1-methyl-1,2,3,6-tetrahydropyridien (MPTP)-induced neurotoxicity. I. J Evaluation of the biological activity of MPTP analogs. J Pharmacol Exp Ther 249: 820-829
31. Zang L-Y, Misra HP (1992) EPR kinetic studies of superoxide radicals generated during the autoxidation of 1-methyl-4-phenyl-2,3-dihydroxypyridinium, a bioactivated intermediate of Parkinsonism-inducing neurotoxin, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J Biol Chem 267: 23601-23608