Irreversible inhibition of mitochondrial complex I by 7-(2-aminoethyl)- 3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (DHBT-1): A putative nigral endotoxin of relevance to Parkinson's disease

Journal of Neurochemistry

Volumn 69, Issue 4, 1997, Pages 1530-1541

  Li, Hong ^a   Dryhurst, Glenn ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Complex I; Cysteinyldopamine; Dopamine; Mitochondria; Parkinson's disease

Indexed keywords

ASCORBIC ACID; CATALASE; CYSTEINE; DOPAMINE; DOPAMINE DERIVATIVE; ENDOTOXIN; MITOCHONDRIAL ENZYME; SUPEROXIDE DISMUTASE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DEGENERATIVE DISEASE; DOPAMINERGIC NERVE CELL; ENZYME INHIBITION; MALE; MOTOR DYSFUNCTION; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; RAT; SUBSTANTIA NIGRA;

ANIMALIA; PARKINSONIA;

EID: 0030886119     PISSN: 00223042     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1471-4159.1997.69041530.x     Document Type: Article

References (71)

1. Barbeau A. (1983) Etiology of Parkinson's disease: a research strategy. Can. J. Neurol. Sci. 11, 24-28.
2. Barbeau A. (1984) Manganese and extrapyramidal disorders. Neurotoxicology 5, 13-36.
3. Barbeau A., Roy M., Paris S., Cloutier T., Plasse L., and Poirier J. (1985) Ecogenetics of Parkinson's disease: 4-hydroxylation of debrisoquine. Lancet i, 1213-1216.
4. Benecke R., Strumper P., and Weiss H. (1993) Electron transfer complexes I and IV of platelets are abnormal in Parkinson's disease but normal in Parkinson-plus syndromes. Brain 116, 1451-1455.
5. Bernard P. A. and Cockrell R. S. (1979) The respiration of brain mitochondria and its regulation by monovalent cation transport. Biochim. Biophys. Acta 548, 173-186.
6. Bindoff L. A., Birch-Machin M. A., Cartlidge N. E. F., Parker W. D., and Turnbull D. M. (1991) Respiratory chain abnormalities in skeletal muscle from patients with Parkinson's disease. J. Neurol. Sci. 104, 203-208.
7. Blin O., Desnuelle C., Rascol O., Borg M., Paul H. P. S., Azulay J. P., Billé F., Figarella D., Coulom F., Pellissier J. F., Montastrue J. L., Chatel M., and Serratrice G. (1994) Mitochondrial respiratory failure in skeletal muscle from patients with Parkinson's disease and multiple system atrophy. J. Neurol. Sci. 125, 95-101.
8. Carstam R., Brinck C., Hindemith-Augustsson A., Rorsman H., and Rosengren E. (1991) The neuromelanin of the human substantia nigra. Biochim. Biophys. Acta 1097, 152-160.
9. Chandra S. V. and Shukla G. S. (1981) Concentration of striatal catecholamines in rats given manganese chloride through drinking water. J. Neurochem. 36, 683-687.
10. Cheng F.-C., Kuo J.-S., Ghia L.-C., and Dryhurst G. (1996) Elevated 5-S-cysteinyldopamine/homovanillic acid ratio and reduced homovanillic acid in cerebrospinal fluid: possible markers for and potential insights into the pathoetiology of Parkinson's disease. J. Neural Transm. 103, 433-446.
11. Cleeter M. W. J., Cooper J. M., and Schapira A. H. V. (1992) Irreversible inhibition of mitochondrial complex I by 1-methyl-4-phenylpyridinium: evidence for free radical involvement. J. Neurochem. 58, 786-789.
12. Dexter D. T., Carter C. J., Wells F. R., Javoy-Agid F., Agid Y., Lees A., Jenner P., and Marsden C. D. (1989) Basal lipid peroxidation in substantia nigra is increased in Parkinson's disease. J. Neurochem. 52, 381-389.
13. Dexter D. T., Sian J., Jenner P., and Marsden C. D. (1993) Implications of alterations in trace element levels in brain in Parkinson's disease and other neurological disorders affecting the basal ganglia. Adv. Neurol. 60, 273-281.
14. Dexter D. T., Holley A. E., Flitter W. D., Slater T. F., Wells F. R., Daniel S. E., Lees A. J., Jenner P., and Marsden C. D. (1994a) Increased levels of lipid hydroperoxides in the parkinsonian substantia nigra: an HPLC and ESR study. Mov. Disord. 9, 92-97.
15. Dexter D. T., Sian J., Rose S., Hindmarsh J. G., Mann V. M., Cooper J. M., Wells F. R., Daniel S. E., Lees A. J., Schapira A. H. V., Jenner P., and Marsden C. D. (1994b) Indices of oxidative stress and mitochondrial function in individuals with incidental Lewy body disease. Ann. Neurol 35, 38-44.
16. Ferraro T. N., Golden G. T., DeMattei M., Hare T. A., and Fariello R. G. (1986) Effect of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) on levels of glutathione in the extrapyramidal system of the mouse. Neuropharmacology 25, 1071-1074.
17. Fornstedt B., Brun A., Rosengren E., and Carlsson A. (1989) The apparent autoxidation rate of catechols in dopamine-rich regions of human brains increases with the degree of depigmentation of substantia nigra. J. Neural Transm. Park. Dis. Dement. Sect. 1, 279-295.
18. Golbe L. I. (1990) The genetics of Parkinson's disease: a reconsideration. Neurology 40(Suppl. 3), 7-14.
19. Golbe L. I., Di Iorio G., Bonavita V., Miller D. C., and Duvoisin R. C. (1990) A large kindred with autosomal dominant Parkinson's disease. Ann. Neurol. 27, 276-282.
20. Graham D. G. (1978) Oxidation pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol. Pharmacol. 14, 633-643.
21. +) induces NADH-dependent superoxide formation, and enhances NADH-dependent lipid peroxidation in bovine heart submitochondrial particles. Biochem. Biophys. Res. Commun. 170, 1049-1055.
22. Hastings T. G. (1995) Enzymatic oxidation of dopamine: the role of prostaglandin H synthase. J. Neurochem. 64, 919-924.
23. Hirsch E. C., Graybiel A. M., and Agid Y. (1988) Melanized dopaminergic neurons are differentially susceptible to degeneration in Parkinson's disease. Nature 334, 345-348.
24. Ikebe S., Tanaka M., and Ozawa T. (1995) Point mutations of mitochondrial genome in Parkinson's disease. Brain Res. Mol. Brain Res. 28, 281-295.
25. Johnson W. G., Hodge S. E., and Duvoisin R. (1990) Twin studies and the genetics of Parkinson's disease - a reappraisal. Mov. Disord. 5, 187-194.
26. Kastner A., Hirsch E. C., Lejeune O., Javoy-Agid F., Roscol O., and Agid Y. (1992) Is the vulnerability of neurons in the substantia nigra of patients with Parkinson's disease related to their neuromelanin content? J. Neurochem. 59, 1080-1089.
27. Kinemuchi H., Fowler C. J., and Tipton K. F. (1987) The neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its relevance to Parkinson's disease. Neurochem. Int. 11, 359-373.
28. Liccione J. J. and Maines M. D. (1988) Selective vulnerability of glutathione metabolism and cellular defense mechanisms in rat striatum to manganese. J. Pharmacol. Exp. Ther. 247, 156-161.
29. Liu R.-M., Hu H., Robinson T. W., and Forman H. J. (1996) Increased γ-glutamylcysteine synthetase and γ-glutamyl transpeptidase activities enhance resistance of rat lung epithelial L2 cells to quinone toxicity. Am. J. Respir. Cell Mol. Biol. 14, 192-197.
30. Lowry O. H., Rosebrough N. J., Farr A. L., and Randall R. J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
31. Mann D. M. A. and Yates P. O. (1983) Possible role of neuromelanin in the pathogenesis of Parkinson's disease. Mech. Ageing Dev. 21, 193-203.
32. Marsden C. D. (1987) Parkinson's disease in twins. J. Neurol. Neurosurg. Psychiatry 50, 105-106.
33. Martilla R. J., Kaprio J., Koskenvuo M., and Rinne U. K. (1988) Parkinson's disease in a nationwide twin cohort. Neurology 38, 1217-1219.
34. Meister A. (1988) Glutathione metabolism and its selective modification. J. Biol. Chem. 263, 17205-17208.
35. Meister A. and Anderson M. E. (1983) Glutathione. Annu. Rev. Biochem. 52, 711-760.
36. Mizuno Y., Ohta S., Tanaka M., Takamiya S., Suzuki K., Sata 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.
37. Mytilineou C., Werner P., Molinari S., DiRocco A., Cohen G., and Yahr M. D. (1994) Impaired oxidative decarboxylation of pyruvate in fibroblasts from patients with Parkinson's disease. J. Neural Transm. 8, 223-228.
38. Naruta Y. and Maruyama K. (1992) 1. Tributyl(3-methyl-2-butenyl) tin. 2. Ubiquinone-I. Org. Synth. 71, 118-132.
39. Odh G., Carstam R., Paulson J., Wittbjer A., Rosengren E., and Rorsman H. (1994) Neuromelanin of the human substantia nigra: a mixed-type melanin. J. Neurochem. 62, 2030-2036.
40. Parker W. D., Boyson S. J., and Parks J. K. (1989) Electron transport chain abnormalities in idiopathic Parkinson's disease. Ann. Neurol. 26, 719-723.
41. Perry T. L. and Yong V. W. (1986) Idiopathic Parkinson's disease, progressive supranuclear palsy and glutathione metabolism in the substantia nigra of patients. Neurosci. Lett. 67, 269-274.
42. Ramsey 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.
43. +) and its analogs with the rote-none-piericidin binding site of NADH dehydrogenase. J. Neurochem. 56, 1184-1190.
44. Raps S. P., Lai J. C. K., Hertz L., and Cooper A. J. L. (1989) Glutathione is present in high concentrations in cultured astrocytes but not in cultured neurons. Brain Res. 493, 398-401.
45. Riederer P., Sofic E., Rausch W. D., Schmidt B., Reynolds G., Jellinger K., and Youdim M. B. H. (1989) Transition metals, ferritin, glutathione, and ascorbic acid in parkinsonian brain. J. Neurochem. 52, 515-520.
46. Rodgers A. D. and Curzon G. (1975) Melanin formation by human brain in vitro. J. Neurochem. 24, 1123-1129.
47. Ross H. R., Romrell L. J., and Kaye G. I. (1995) Histology. A Text and Atlas, chapter 11, p. 282. Williams and Wilkins, Baltimore.
48. Sagara J., Miura K., and Bannai S. (1993) Maintenance of neuronal glutathione by glial cells. J. Neurochem. 61, 1672-1676.
49. Sagara J., Makino N., and Bannai S. (1996) Glutathione efflux from cultured astrocytes. J. Neurochem. 66, 1876-1881.
50. Sanchez-Ramos A. and Ames B. N. (1994) A marker of oxyradical-mediated DNA damage (8-hydroxy-2-deoxyguanosine) is increased in the nigrostriatum of Parkinson's disease brain. Neurodegeneration 3, 197-204.
51. Schapira A. H. V., Cooper J., Dexter D., Clark J. B., Jenner P., and Marsden C. D. (1990a) Mitochondrial complex I deficiency in Parkinson's disease. J. Neurochem. 54, 823-827.
52. 1 reductase (complex I) deficiency in Parkinson's disease. J. Neurochem. 55, 2142-2145.
53. Shaw C. A., Pasqualotto B. A., and Curry K. (1996) Glutathione-induced sodium currents in neocortex. Neuroreport 7, 1149-1152.
54. Sheehan J. P., Swerdlow R. H., Parker W. D., Miller S. W., Davis R. E., and Tuttle J. B. (1997) Altered calcium homeostasis in cells transformed by mitochondria from individuals with Parkinson's disease. J. Neurochem. 68, 1221-1233.
55. Shen X.-M. and Dryhurst G. (1996) Further insights into the influence of L-cysteine on the oxidation chemistry of dopamine: reaction pathways of potential relevance to Parkinson's disease. Chem. Res. Toxicol. 9, 751-763.
56. Shen X.-M., Zhang F., and Dryhurst G. (1997) Oxidation of dopamine in the presence of cysteine: characterization of new toxic products. Chem. Res. Toxicol. 10, 147-155.
57. Shoffner J. M., Watts R. L., Juncos J. L., Torroni A., and Wallace D. C. (1991) Mitochondrial oxidative phosphorylation defects in Parkinson's disease. Ann. Neurol 30, 332-339.
58. Sian J., Dexter D., Lees A., Daniel S., Agid Y., Javoy-Agid F., Jenner P., and Marsden C. D. (1994a) Alterations in glutathione levels in Parkinson's disease and other neurodegenerative disorders affecting the basal ganglia. Ann. Neurol. 36, 348-355.
59. Sian J., Dexter D. T., Lees A. J., Daniel S., Jenner P., and Marsden C. D. (1994b) Glutathione-related enzymes in brain in Parkinson's disease. Ann. Neurol. 36, 356-361.
60. Slivka A., Mytilineou C., and Cohen G. (1987) Histochemical evaluation of glutathione in brain. Brain Res. 409, 275-284.
61. Sofic E., Lange K. W., Jellinger K., and Riederer P. (1992) Reduced and oxidized glutathione in the substantia nigra of patients with Parkinson's disease. Neurosci. Lett. 142, 128-130.
62. Steventon G. B., Heafield M. T. E., Waring R. H., and Williams A.C. (1989) Xenobiotic metabolism in Parkinson's disease. Neurology 39, 883-887.
63. Swerdlow R. H., Parks J. K., Miller S. W., Tuttle J. B., Trimmer P. A., Sheehan J. P., Bennett J. P., Davis R. E., and Parker W. D. (1996) Origin and functional consequences of the complex I defect in Parkinson's disease. Ann. Neurol. 40, 663-671.
64. Tanner C. M., Chen B., Wang W., Peng M., Liu Z., Liang X., Kao L.-C., Gilley D. W., Goetz C. G., and Schoenberg B. S. (1989) Environmental factors and Parkinson's disease. Neurology 39, 660-664.
65. Van Woert M. H. and Ambani L. M. (1974) Biochemistry of neuromelanin. Adv. Neurol. 5, 215-223.
66. Wakamatsu K., Ito S., and Nagatsu T. (1991) Cysteinyldopamine is not incorporated into neuromelanin. Neurosci. Lett. 131, 57-60.
67. Ward C. D., Duvoisin R. C., Ince S. E., Nutt J. D., Eldridge R., and Clane D. B. (1983) Parkinson's disease in 65 pairs of twins and in a set of quadruplets. Neurology 33, 815-824.
68. Waring R. H., Sturman S. G., Smith M. C. G., Steventon G. B., Heafield M. T. E., and Williams A.C. (1989) S-Methylation in motoneuron disease and Parkinson's disease. Lancet i, 356-357.
69. Yong V. W., Perry T. L., and Krisman A. A. (1985) Depletion of glutathione in brainstem of mice caused by N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is prevented by antioxidant pretreatment. Neurosci. Lett. 63, 56-60.
70. Zhang F. and Dryhurst G. (1994) Effects of L-cysteine on the oxidation chemistry of dopamine: new reaction pathways of potential relevance to idiopathic Parkinson's disease. J. Med. Chem. 37, 1084-1098.
71. Zhang F. and Dryhurst G. (1995) Influence of glutathione on the oxidation chemistry of the catecholaminergic neurotransmitter dopamine. J. Electroanal. Chem. 398, 117-128.