Effect of dopamine, dimethoxyphenylethylamine, papaverine, and related compounds on mitochondrial respiration and complex I activity

Journal of Neurochemistry

Volumn 66, Issue 3, 1996, Pages 1174-1181

  Morikawa, Nami ^a   Nakagawa Hattori, Yuko ^a   Mizuno, Yoshikuni ^a  

^a JUNTENDO UNIVERSITY   (Japan)

Author keywords

Complex I; Dopamine; Mitochondria; Papaverine; Parkinson's disease; Tetrahydroisoquinolines

Indexed keywords

DOPAMINE; HOMOVERATRYLAMINE; LAUDANOSINE; PAPAVERINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); ROTENONE; TETRAHYDROPAPAVERINE;

ANIMAL CELL; ARTICLE; BRAIN MITOCHONDRION; CONTROLLED STUDY; ELECTRON TRANSPORT; ENZYME INHIBITION; MALE; MITOCHONDRIAL RESPIRATION; MOUSE; NEUROTOXICITY; NONHUMAN; OXIDATIVE STRESS; PARKINSON DISEASE; PRIORITY JOURNAL;

ANIMALIA;

EID: 0030051311     PISSN: 00223042     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1471-4159.1996.66031174.x     Document Type: Article

References (67)

1. Albores R., Heafsey E. J., Drucker G., Fields J. Z., and Collins M. A. (1990) Mitochondrial respiratory inhibition by N-methylated beta-carboline derivatives structurally resembling N-methyl-4-phenylpyridine. Proc. Natl. Acad. Sci. USA 87, 9368-9372.
2. Axelrod J., Shofer R., Inscoe J. K., King W M., and Sjoerdsma A. (1958) The fate of papaverine in man and other mammals. J. Pharmacol. Exp. Ther. 124, 9-15.
3. Barbeau A., De Groot J. A., Joly J. G., Tremblay D. R., and Donaldson J. (1963) Urinary excretion of a 3-4-dimethoxyphenyl-ethylamine-like substance in Parkinson's disease. Rev. Can. Biol. 22, 469-472.
4. Barbeau A., Tétreault L., Oliva L., Morazain L., and Cardin L. (1966) Pharmacology of akinesia: investigation on 3,4-dimethoxyphenylethylamine. Nature 209, 719-721.
5. Bradford M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
6. Browning E. T., Groppi V. E., and Kon C. (1973) Papaverine, a potent inhibitor of respiration in C-6 astrocytoma cells. Mol. Pharmacol. 10, 175-181.
7. Chiba K., Trevor A. J., and Castagnoli N. Jr. (1984) Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120, 574-578.
8. Collins M. A., Neafsey E. J., Matsubara K., Cobuzzi R. J. Jr., and Rollema H. (1992) Indo-N-methylated β-carbolinium ions as potential brain-bioactivated neurotoxins. Brain Res. 570, 154-160.
9. Davila J. C., Davis P., and Acosta D. (1991) Changes in glutathione and cellular energy as potential mechanisms of papaverine-induced hepatotoxicity in vitro. Toxicol. Appl. Pharmacol. 109, 28-36.
10. Davis G. C., Williams A. C., Markey S. P , Ebert M. H., Caine E. D., Reichert C. M., and Kopin I. J. (1979) Chronic parkinsonism secondary to intravenous injection of meperidine analogues. Psychiatry Res. 1, 249-254.
11. Dipasquale B , Marini M , and Youl R. J. (1991) Apoptosis and DNA degradation by 1-methyl-4-phenylpyridinium in neurons. Biochem. Biophys. Res. Commun. 181, 1442-1448.
12. Ernst A. M. (1962) Phenomena of the hypokinetic rigid type caused by O-methylation of dopamine in the para-position. Nature 193, 178-179.
13. Errede B., Kamen M. D., Hatefi Y , and Stiggall D. L. (1978) Preparation and properties of complex IV (ferrocytochrome c:oxygen oxidoreductase EC 1.9.3.1), in Methods in Enzymology, Vol. 53 (Fleischer S. and Packer L., eds), pp. 40-47. Academic Press, New York.
14. 2+ release from mitochondria. FEBS Lett. 198, 99-102.
15. Friedhoff A. J. and Furiya K. (1967) 3,4-Dimethoxyphenylacetic acid in urine. Nature 214, 1127-1128.
16. Friedhoff A. J. and Van Winkle E. (1962) Isolation and characterization of a compound from the urine of schizophrenics. Nature 194, 897-898.
17. Friedhoff A. J. and Van Winkle E. (1963) Conversion of dopamine to 3,4-dimethoxyphenylacetic acid in schizophrenic patients. Nature 199, 127-128.
18. Hatefi Y. (1978a) Preparation and properties of NADH:ubiquinone oxidoreductase (complex I), EC 1.6.5.3, in Methods in Enzymology, Vol. 53 (Fleischer S. and Packer L., eds), pp. 11-14. Academic Press, New York.
19. Hatefi Y. (1978b) Preparation and properties of dihydroubiquinone:cytochrome c oxidoreductase (complex III), in Methods in Enzymology, Vol. 53 (Fleischer S. and Packer L., eds), pp. 35-40. Academic Press, New York.
20. Hatefi Y. and Stiggall D. L. (1978) Preparation and properties of succinate:ubiquinone oxidoreductase (complex II), in Methods in Enzymology, Vol. 53 (Fleischer S. and Packer L., eds), pp. 21-27. Academic Press, New York.
21. Hattori N., Tanaka M., Ozawa T., and Mizuno Y. (1991) Immunohistochemical studies on complex I, II, III, and IV of mitochondria in Parkinson's disease. Ann. Neurol. 30, 563-571.
22. Hayakawa M., Hattori K., Sugiyama S., and Ozawa T. (1992) Age-associated oxygen damage and mutations in mitochondrial DNA in human hearts. Biochem. Biophys. Res. Commun. 189, 979-985.
23. + in the substantia nigra: a key to neurotoxicity? Life Sci. 36, 207-212.
24. Javitch J. A., D'Amato R. J., Strittmatter S. M., and Snyder S. H. (1985) Parkinsonism-inducing neurotoxin, N-methyl-4-phenyl1,2,3,6-tetrahydropyridine: uptake of the metabolite N-methyl-4-phenylpyridine by dopamine neurons explains selective toxicity. Proc. Natl. Acad. Sci. USA 82, 2173-2177.
25. Jenner P., Dexter D. T., Sian J., Schapira A. H. V., and Marsden C. G. (1992) Oxidative stress as a cause of nigral cell death in Parkinson's disease and incidental Lewy body disease. Ann. Neurol. 32 (Suppl.), S82-S87.
26. Kowal J. and Hirano Y. (1974) Adrenal cells in tissue culture. The effect of papaverine and Amytal on steroidogenesis, respiration and replication. Arch. Biochem. Biophys. 163, 466-475.
27. Kuehl F. A., Ormond R. E., and Vandenheuvel W. J. A. (1966) Occurrence of 3,4-dimethoxyphenylacetic acid in urines of normal and schizophrenic individuals Nature 211, 606-608.
28. Langston J. W., Ballard P., Tetrud J. W., and Irwin I. (1983) Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219, 979-980.
29. Lesser R. P., Fahn S., Snider S. R., Cote L. J., Isgreen W. P., and Barrett R. E. (1979) Analysis of the clinical problems in parkinsonism and the complications of long-term levodopa therapy. Neurology 29, 1253-1260.
30. Makino Y., Ohta S., Tachikawa O., and Hirobe M. (1988) Presence of tetrahydroisoquinoline and 1-methyl-tetrahydro-isoquinoline in foods: compounds related to Parkinson's disease. Life Sci. 43, 373-378.
31. Markham C. H. and Diamond S. G (1981) Evidence to support early levodopa therapy in Parkinson disease. Neurology 31, 125-131.
32. Maruyama W., Nakahara D., Ota M., Takahashi T., Takahashi A., Nagatsu T., and Naoi M. (1992) N-Methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolmol, in rat brains: in vivo microdialysis study. J. Neurochem. 59, 395-400.
33. Melamed E. (1986) Initiation of levodopa in parkinsonian patients should be delayed until the advanced stages of the disease. Arch. Neurol 43, 402-405.
34. Mena M. A., Pardo B., Casarejos M J., Fahn S., and Garcia de Yébenes J. (1992) Neurotoxicity of levodopa on catecholamine-rich neurons. Mov. Disord. 7, 23-31.
35. Minami M., Takahashi T., Maruyama W., Takahashi A., Dostert P., Nagatsu T., and Naoi M. (1992) Inhibition of tyrosine hydroxylase by R and S enantiomers of salsolinol, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline. J. Neurochem. 58, 2097-2101.
36. Mizuno Y., Sone N., and Saitoh T. (1987a) Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and 1-methyl-4-phenylpyridinium ion on activities of the enzymes in the electron transport system in mouse brain. J. Neurochem 48, 1787-1793.
37. Mizuno Y., Saitoh T., and Sone N. (1987b) Inhibition of mitochondrial alpha-ketoglutarate dehydrogenase by 1-methyl-4-phenylpyridiniura ion. Biochem. Biophys. Res. Commun. 143, 971-976.
38. +) against mitochondria of mouse brain. J. Neurol. Sci. 86, 97-110.
39. Mizuno Y., Ohta S., Tanaka M., Takamiya S., Suzuki K., Sato T., Oya H., Ozawa T., and Kagawa Y. (1989) Deficiencies in complex I subunits of the respiratory chain in Parkinson's disease. Biochem. Biophys. Res. Commun. 163, 1450-1455.
40. Mizuno Y., Matuda S., Yoshino H., Mori H., Hattori N., and Ikebe S. (1994) An immunohistochemical study on α-ketoglutarate dehydrogenase complex in Parkinson's disease. Ann. Neurol 35, 204-210.
41. +) in a ventral mesencephalic-striatal co-culture. Neurosci. Lett. 170, 191-194.
42. Nagatsu T. and Yoshida M. (1988) An endogenous substance of the brain, tetrahydroisoquinoline, produces parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterine in the nigrostriatal regions. Neurosci. Lett. 87, 178-182.
43. Naoi M., Matsuura S., Parvez H., Takahashi T., Hirata Y., Minami M., and Nagatsu T. (1989) Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methyl-isoquinolinium ion by monoamine oxidase. J. Neurochem. 52, 653-655.
44. Nicklas W. J., Vyas I., and Heikkila R. E. (1985) Inhibition of NADH-linked oxidation in brain mitochondria by 1-methyl-4-phenyl-pyridine, a metabolite of the neurotoxin, 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine. Life Sci. 36, 2503-2508.
45. +) destroys cultured mesencephalic dopamine neurons. Biogenic Amines 8, 61-67.
46. +) and tetrahydroisoquinoline derivatives on dopaminergic neurons in ventral mesencephalic-striatal co-culture. Neurodegeneration 3, 33-42.
47. Niwa T., Takeda N., Kaneda N., Hashizume Y., and Nagatsu T (1987) Presence of tetrahydroisoquinoline and 2-methyl-tetrahydroisoquinoline in parkinsonian and normal human brains. Biochem. Biophys. Res. Commun. 144, 1084-1089.
48. Niwa T., Takeda N., Tatematsu A., Matsuura S., Yoshida M., and Nagatsu T. (1988) Migration of tetrahydroisoquinoline, a possible parkinsonian neurotoxin, into monkey brain from blood as proved by gas chromatography-mass spectrometry. J. Chromatogr. 452, 85-91.
49. Niwa T., Yoshizumi H., Tatematsu A., Matsuura S., and Nagatsu T. (1989) Presence of tetrahydroisoquinoline, a parkinsonism-related compound, in foods. J. Chromatogr. 493, 347-352.
50. Ohta S., Kohno M., Makino Y., Tachikawa O., and Hirobe M. (1987) Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline are present in the human brain: relation to Parkinson's disease. Biomed. Res. 8, 453-456.
51. Ozawa K., Seta K., Takeda H., Ando K., Handa H., and Araki C (1966) On the isolation of mitochondria with high respiratory control from rat brain. J. Biochem. (Tokyo) 59, 501-510.
52. Porpaczy Z., Sumegi B , and Alkonyi I. (1987) Interaction between NAD-dependent isocitrate dehydrogenase, α-ketoglutarate dehydrogenase complex, and NADH:ubiquinone oxidoreductase. J. Biol. Chem. 262, 9509-9514.
53. Przedborski S., Jackson-Lewis V., Muthane U., Jiang H , Ferreira M., Naini A. B., and Fahn S. (1993) Chronic levodopa administration alters cerebral mitochondrial respiratory chain activity. Ann. Neurol. 34, 715-723.
54. Przedborski S., Jackson-Lewis V., and Fahn S. (1995) Antiparkinsonian therapies and brain mitochondrial complex I activity. Mov. Disord. 10, 312-317.
55. Ramsay R. R. and Singer T. P. (1986) Energy-dependent uptake of N-methyl-4-phenylpyridinium, the neurotoxic metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, by mitochondria. J Biol. Chem. 261, 7585-7587.
56. Richter C., Park J.-W., and Ames B. N. (1988) Normal oxidative damage to mitochondrial and nuclear DNA is extensive. Proc. Natl. Acad. Sci. USA 85, 6465-6467.
57. Rinne U. K. and Sonninen V. (1967) Urinary excretion of 3,4-dimethoxyphenylethylamine in Parkinson's disease. Nature 216, 489.
58. Ronnov-Jessen V. and Tjernlund A. (1969) Hepatotoxicity due to treatment with papaverine: report of four cases. N. Engl. J. Med. 281, 1333-1335.
59. Sandler M., Carter S. B., Hunter K. R., and Stern G. M. (1973) Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-dopa in man. Nature 241, 439-443.
60. Sayre L. M., Singh M. P., Arora P. K., Wang F., McPeak J., and Hoppel C. L. (1990) Inhibition of mitochondrial respiration by analogues of the dopaminergic neurotoxin 1-methyl-4-phenylpyridinium: structural requirements for accumulation-dependent enhanced inhibitory potency on intact mitochondria. Arch. Biochem. Biophys. 280, 274-283.
61. Schapira A. H. V., Cooper J. M., Dexter D., Jenner P., Clark J. B., and Marsden C. D. (1989) Mitochondrial complex I deficiency in Parkinson's disease. Lancet 1, 1269.
62. Suzuki K., Mizuno Y., and Yoshida M. (1990) Inhibition of mitochondrial respiration by 1,2,3,4-tetrahydroisoquinoline-like endogenous alkaloids in mouse brain. Neurochem. Res. 15, 705-710.
63. Suzuki K., Mizuno Y., Yamauchi Y., Nagatsu T., and Yoshida M. (1992) 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, 219-223.
64. Tanaka M., Sotomatsu A., Kanai H., and Hirai S. (1992) Combined histochemical and biochemical demonstration of nigral vulnerability to lipid peroxidation induced by DOPA and iron. Neurosci. Lett. 140, 42-46.
65. Yonetani T. and Ray G. S. (1965) Studies on cytochrome oxidase. IV. Kinetics of the aerobic oxidation of ferrocytochrome c by cytochrome oxidase. J. Biol. Chem. 240, 3392-3398.
66. Yoshida M., Niwa T., and Nagatsu T. (1990) Parkinsonism in monkeys produced by chronic administration of an endogenous substance of the brain, tetrahydroisoquinoline: the behavioral and biochemical changes. Neurosci. Lett. 119, 109-113.
67. Zhang Y., Marcillat O., Giulvi C., Ernster L., and Davis K. J. A. (1990) The oxidative inactivation of mitochondrial electron transport chain components and ATPase. J. Biol. Chem. 165, 16330-16336.