Dopamine-derived endogenous 1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, N-methyl-( R)-salsolinol, induced parkinsonism in rat: Biochemical, pathological and behavioral studies

Brain Research

Volumn 709, Issue 2, 1996, Pages 285-295

  Naoi, Makoto ^a   Maruyama, Wakako ^b   Dostert, Philippe ^c   Hashizume, Yoshio ^d   Nakahara, Daiichiro ^e   Takahashi, Tsutomu ^f   Ota, Miyuki ^g  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^b NAGOYA UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^c Pharmacia   (Italy)

^d AICHI MEDICAL UNIVERSITY   (Japan)

^e HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^f KONAN WOMEN'S UNIVERSITY   (Japan)

^g GIFU PREFECTURAL TAJIMI HOSPITAL   (Japan)

Author keywords

1(R); 2(N) Dimethyl 6,7 dihydroxy 1,2,3,4 tetrahydroisoquinoline (N methyl (R) salsolinol); 6,7 Dihydroxyisoquinolinium ion; Animal model; Dopamine; Parkinson's disease; Tyrosine hydroxylase

Indexed keywords

2 METHYLSALSOLINOL; DOPAMINE; NORADRENALIN; SALSOLINOL DERIVATIVE; SEROTONIN; TETRAHYDROISOQUINOLINE; TETRAHYDROISOQUINOLINE DERIVATIVE; TYROSINE 3 MONOOXYGENASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BEHAVIOR; CONTROLLED STUDY; CORPUS STRIATUM; DOPAMINERGIC SYSTEM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOHISTOCHEMISTRY; MALE; NONHUMAN; PARKINSONISM; PRIORITY JOURNAL; RAT; SUBSTANTIA NIGRA;

ANIMALS; BEHAVIOR, ANIMAL; BIOGENIC AMINES; CORPUS STRIATUM; DISEASE MODELS, ANIMAL; INJECTIONS; ISOQUINOLINES; MALE; PARKINSON DISEASE, SECONDARY; RATS; RATS, WISTAR; TETRAHYDROISOQUINOLINES; TYROSINE 3-MONOOXYGENASE;

EID: 0030060483     PISSN: 00068993     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-8993(95)01325-3     Document Type: Article

References (39)

1. Azevedo, I. and Osswald, W., Adrenergic nerve degeneration induced by condensation products of adrenaline and acetaldehyde, Naunyn-Shmiedeberg's Arch. Pharmacol., 300 (1977) 139-144.
2. Bembenek, M.E., Abell, C.W., Chrisey, L.A., Rowadowska, M.D., Gessner, W. and Brossi, A., Inhibition of monoamine oxidase A and B by simple isoquinoline alkaloids: racemic and optically active 1,2,3,4-tetrahydro-3,4-dihydro, and fully aromatic isoquinolines, J. Med. Chem., 33 (1990) 147-152.
3. Brezenoff, H.E. and Cohen, G., Hypothermia following intraventricular injection of a dopamine-derived tetrahydroisoquinoline alkaloid, Neuropharmacology, 12 (1973) 1033-1038.
4. Chiba, K., Trevor, A.J. and Castagnoli, N. Jr., Metabolism of the neurotoxic amine, MPTP, by brain monoamine oxidase, Biochem. Biophys. Res. Commun., 120 (1984) 574-578.
5. Cohen, G., Alkaloid products in the metabolism of alcohol and biogenic amines, Biochem. Pharmacol., 25 (1976) 1123-1128.
6. Collins, M.A., Neafsey, E.J., Matsubara, K., Cobuzzi, R. Jr. and Rollema, H., Indole-N-methylated β-carbolinium ions as potential brain-bioactivated neurotoxins, Brain Res., 570 (1992) 154-160.
7. Costal, B., Naylor, R.J. and Pinder, R.M., Hyperactivity induced by tetrahydroisoquinoline derivatives injected into the nucleus accumbens, Eur. J. Pharmacol., 39 (1976) 153-160.
8. Deng, Y., Maruyama, W., Dostert, P., Takahashi, T., Kawai, M. and Naoi, M., Determination of the (R)- and (S)-enantiomers of salsolinol and N-methylsalsolinol by use of a chiral HPLC column, J. Chromatogr. B., 670 (1995) 47-54.
9. Dostert, P., Strolin Benedetti, M., Bellotti, V., Allievi, C. and Dordain G., Biosynthesis of salsolinol, a tetrahydroisoquinoline alkaloid, in healthy subjects, J. Neural Transm. (GenSect), 81 (1990) 215-223.
10. Klüver, H. and Barrera, E., A method for the combined staining of cells and fibers in the nervous system. J. Neuropathol. Exp. Neurol., 12 (1953) 401-403.
11. Langston, J.W., Irwin, I. and Ricaurte, G.A., Neurotoxins, parkinsonism and Parkinson's disease, Pharmacol. Ther., 32 (1987) 19-49.
12. Liptrot, J., Holdup, D. and Phillipson, O., 1,2,3,4-Tetrahydro-2-methyl-4,6,7-isoquinolinetriol depletes catecholamines in rat brain, J. Neurochem., 61 (1993) 2199-2206.
13. Maruyama, W., Nakahara, D., Ota, M., Takahashi, T., Takahashi, A., Nagatsu, T. and Naoi, M., N-Methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolinol, in rat brains: in vivo microdialysis study, J. Neurochem., 59 (1992) 395-400.
14. Maruyama, W., Nakahara, D., Dostert, P., Hashiguchi, H., Ohta, S., Hirobe, M., Takahashi, A., Nagatsu, T. and Naoi, M., Selective release of serotonin by endogenous alkaloids, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines, (R)- and (S)salsolinol, in the rat striatum; in vivo microdialysis study, Neurosci. Lett., 149 (1993) 115-118.
15. Maruyama, W. and Naoi, M., Inhibition of tyrosine hydroxylase by a dopamine neurotoxin, 1-methyl-4-phenylpyridinium ion: Depletion of allostery to the biopterin cofactor, Life Sci., 55 (1994) 207-212.
16. Maruyama, W., Dostert, P., Matsubara, K. and Naoi, M., N-Methyl(R)salsolinol produces hydroxyl radicals: Involvement to neurotoxicity, Free Radic. Biol. Med., 19 (1995) 67-75.
17. Maruyama, W., Dostert, P. and Naoi, M., Dopamine-derived 1-methyl-6,7-dihydroxyisoquinolines as hydroxyl radical promoters and scavengers in the rat brain: In vivo and in vitro studies, J. Neurochem., 64 (1995) 2635-2643.
18. Minami, M., Takahashi, T., Maruyama, W., Takahashi, A., Dostert, P., Nagatsu, T. and Naoi, M., Inhibition of tyrosine hydroxylase by R and S enantiomers of salsolinol, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, J. Neurochem., 58 (1992) 2097-2101.
19. Mizuno, Y., Saitoh, T. and Sone, N., Inhibition of mitochondrial NADH-ubiquinone oxidoreductase activity by 1-methyl-4-phenylpyridinium ion, Biochem. Biophys. Res. Commun., 143 (1987) 294-299.
20. Myers, R.D. and Oblinger, M.M., Alcohol drinking in the rat induced by acute intracerebral infusion of two tetrahydroisoquinolines and a β-carboline, Drug. Alcohol Depend., 2 (1977) 469-483.
21. Nagatsu, T. and Yoshida, M., An endogenous substance of the brain, tetrahydroisoquinoline, produces parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterin in the nigrostriatal regions, Neurosci. Lett., 87 (1988) 178-182.
22. Naoi, M., Takahashi, T. and Nagatsu, T., Simple assay procedure for tyrosine hydroxylase activity by high-performance liquid chromatography employing coulometric detection with minimal sample preparation, J. Chromatogr., 427 (1988) 229-238.
23. Naoi, M. Maruyama, W. and Dostert, P., Binding of 1,2(N)-dimethyl-6,7-dihydroxyisoquinolinium ion to melanin: effects of ferrous and ferric ion on the binding, Neurosci. Lett., 171 (1994) 9-12.
24. Naoi, M., Maruyama, W., Niwa, T. and Nagatsu, T., Novel toxins and Parkinson's disease: N-methylation and oxidation as metabolic bioactivalion of neurotoxin, J. Neural Transm. (Suppl), 41 (1994) 197-205.
25. Naoi, M., Maruyama, W., Dostert, P., Nakahara, D., Takahashi, T. and Nagatsu, T., Metabolic bioactivation of endogenous isoquinolines as dopaminergic neurotoxins to elicit Parkinson's disease. In I.S. Hanin, M. Yoshida and A. Fisher (Eds.), Alzheimer's and Parkinson's Diseases; Recent Developments, Plenum, New York, 1995, pp. 553-559.
26. Naoi, M., Maruyama W. and Dostert, P., Dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines; oxidation and neurotoxicity, Prog. Brain Res., 106 (1995) 227-239.
27. Naoi, M., Maruyama W., Zhang, J. H., Takahashi, T., Deng, Y. and Dostert, P., Enzymatic oxidation of the dopaminergic neurotoxin, 1(R), 2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, into 1, 2(N)-dimethyl-6,7-dihydroxyisoquinolinium ion, Life Sci., 57 (1995) 1061-1066.
28. Nitta, A., Murase, Y., Furukawa, Y., Hayashi, K., Hasegawa, T. and Nabeshima, T., Memory impairment and neural dysfunction after continuous infusion of anti-nerve growth factor antibody into the septum in adult rats, Neuroscience, 57 (1993) 495-499.
29. Niwa, T., Tekeda, T., Yoshizumi, H., Tatematsu, A., Yoshida, M., Dostert, P., Naoi, M. and Nagatsu, T., Presence of 2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroiso-quinoline and 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, novel endogenous amines, in parkinsonian and normal human brains, Biochem. Biophys. Res. Commun., 177 (1991) 603-609.
30. Ota, A., Maruyama, W., Takahashi, T., Naoi, M. and Nagatsu, T., The effect of a heterocyclic amine, 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole (Trp-P-1), on tyrosine hydroxylase mRNA in PC12h cells, Neurosci. Lett., 154 (1993) 183-186.
31. Paxinos, G. and Watson, C., The Rat Brain in Stereotaxic Coordinates, 2nd Edn., Acad. Press, Sidney, 1986.
32. Riederer, P., Sofic, E., Rausch, W.-D., Schmidt, B., Reynolds, G.D., Jellinger, K. and Youdim, M.B.H., Transition metals, ferritin, glutathione, and ascorbic acid in parkinsonian brains, J. Neurochem., 52 (1989) 515-520.
33. Singer, T.P., Castagnoli, N. Jr., Ramsay, R.R. and Trevor, A.J., Biochemical events in the development of parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, J. Neurochem., 49 (1987) 1-8.
34. Sjöquist, B., Eriksson, A. and Winblad, B., Salsolinol and catecholamines in human brain and their relation to alcoholism, Prog. Clin. Biol. Res., 90 (1982) 57-67.
35. Suzuki, K., Mizuno, Y., Yamauchi, Y., Nagatsu, T. and Yoshida, M., Selective inhibition of complex I by N-methylisoquinolinium ion and N-methyl-1,2,3,4-tetrahydroisoquinoline in isolated mitochondria prepared from mouse brain, J. Neurol. Sci., 109 (1992) 219-223.
36. Takahashi, T., Deng, Y., Maruyama, W., Dostert, P., Kawai, M. and Naoi, M., Uptake of a neurotoxin-candidate, (R)-1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydro-isoquinoline into human dopaminergic neuroblastoma SH-SY5Y cells by dopamine transport system, J. Neural Transm. (GenSect), 98 (1994) 107-118.
37. Teitel, S., O'Brien, J. and Brossi, A., Alkaloids in mammalian tissues, 2. Synthesis of (+) and (-) substituted 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines, J. Med. Chem., 15 (1972) 845-846.
38. Tipton, K.F. and Singer, T.P., Advances in our understanding of the mechanism of the neurotoxicity of MPTP and related compounds, J. Neurochem., 61 (1993) 1191-1206.
39. Whitehouse, P.J., Price, D.L., Struble, R.G., Clark, A.W., Coyle, J.T. and DeLong, M.R., Alzheimer's disease and senile dementia: Loss of neurons in the basal formation, Science, 215 (1982) 1237-1239.