Drug treatment of Parkinson's disease. Time for phase II

Biochemical Pharmacology

Volumn 59, Issue 9, 2000, Pages 1023-1031

  Drukarch, Benjamin ^a   Van Muiswinkel, Freek L ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Glutathione S transferase; Neuroprotection; Parkinson's disease; Phase II biotransformation; Quinone; Quinone reductase

Indexed keywords

ANETHOLE TRITHIONE; ANTIOXIDANT; ASCORBIC ACID; DIHYDROLIPOATE; DOPAMINE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; NEUROMELANIN; OLTIPRAZ; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); THIOCTIC ACID;

AUTOOXIDATION; DOPAMINE METABOLISM; DOPAMINERGIC NERVE CELL; ENZYME ACTIVATION; HUMAN; NERVE DEGENERATION; NEUROPROTECTION; OXIDATIVE STRESS; PARKINSON DISEASE; PRIORITY JOURNAL; REVIEW; SUBSTANTIA NIGRA;

EID: 0033954833     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00340-8     Document Type: Article

References (74)

1. Hagan J.J., Middlemiss D.N., Sharpe P.C., Poste G.H. Parkinson's disease Prospects for improved drug therapy . Trends Pharmacol Sci. 18:1997;156-163.
2. Agid Y. Levodopa Is toxicity a myth? Neurology. 50:1998;858-863.
3. Dunnett S.B., Bjorklund A. Prospects for new restorative and neuroprotective treatments in Parkinson's disease. Nature. 399:(Suppl):1999;A32-A39.
4. Olanow C.W., Jenner P., Brooks D. Dopamine agonists and neuroprotection in Parkinson's disease. Ann Neurol. 44:(Suppl):1998;S167-S174.
5. Ebadi M., Srinivasan S.K., Baxi M.D. Oxidative stress and antioxidant therapy in Parkinson's disease. Prog Neurobiol. 48:1996;1-19.
6. Gash D.M., Zhang Z.M., Gerhardt G. Neuroprotective and neurorestorative properties of GDNF. Ann Neurol. 44:(Suppl):1998;S121-S125.
7. Sian J., Gerlach M., Youdim M.B.H., Riederer P. Parkinson's disease A major hypokinetic basal ganglia disorder . J Neural Transm. 106:1999;443-476.
8. Jenner P., Olanow C.W. Understanding cell death in Parkinson's disease. Ann Neurol. 44:(Suppl):1998;S72-S84.
9. Fahn S., Cohen G. The oxidant stress hypothesis in Parkinson's disease Evidence supporting it . Ann Neurol. 32:1992;804-812.
10. DATATOP A multicenter controlled clinical trial in early Parkinson's disease . Arch Neurol. 46:1989;1052-1060.
11. Rescigno A., Rinaldi A.C., Sanjust E. Some aspects of tyrosine secondary metabolism. Biochem Pharmacol. 56:1998;1089-1096.
12. Stokes A.H., Hastings T.G., Vrana K.E. Cytotoxic and genotoxic potential of dopamine. J Neurosci Res. 55:1999;659-665.
13. Hastings T.G. Enzymatic oxidation of dopamine The role of prostaglandin H synthase . J Neurochem. 64:1995;919-924.
14. Xu Y., Stokes A.H., Freeman W.M., Kumer S.C., Vogt B.A., Vrana K.E. Tyrosinase mRNA is expressed in human substantia nigra. Mol Brain Res. 45:1997;159-162.
15. Mattammal M.B., Strong R., Lakshmi V.M., Chung H.D., Stephenson A.H. Prostaglandin H synthetase-mediated metabolism of dopamine Implication for Parkinson's disease . J Neurochem. 64:1995;1645-1654.
16. Bindoli A., Rigobello M.P., Deeble D.J. Biochemical and toxicological properties of the oxidation products of catecholamines. Free Radic Biol Med. 13:1992;391-405.
17. Graham D.G. Oxidative pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol Pharmacol. 14:1978;633-643.
18. Smythies J., Galzigna L. The oxidative metabolism of catecholamines in the brain A review . Biochim Biophys Acta. 1380:1998;159-162.
19. D'Ischia M., Prota G. Biosynthesis, structure, and function of neuromelanin and its relation to Parkinson's disease A critical update . Pigment Cell Res. 10:1997;370-376.
20. Carstam R., Brinck C., Hindemith-Augustsson A., Rorsman H., Rosengren E. The neuromelanin of the human substantia nigra. Biochim Biophys Acta. 1097:1991;152-160.
21. Palumbo A., D'Ischia M., Misuraca G., De Martino L., Prota G. Iron- and peroxide-dependent conjugation of dopamine with cysteine Oxidative routes to the novel brain metabolite 5-S-cysteinyldopamine . Biochim Biophys Acta. 1245:1995;255-261.
22. Hirsch E., Graybiel A.M., Agid Y.A. Melanized dopaminergic neurons are differentially susceptible to degeneration in Parkinson's disease. Nature. 334:1988;345-348.
23. Muthane U., Yasha T.C., Shankar S.K. Low numbers and no loss of melanized nigral neurons with increasing age in normal human brains in India. Ann Neurol. 43:1998;283-287.
24. Wang W., Ballatori N. Endogenous glutathione conjugates Occurrence and biological functions . Pharmacol Rev. 50:1998;335-355.
25. Spencer P.E., Jenner P., Daniel S.E., Lees A.J., Marsden C.D., Halliwell B. Conjugates of catecholamines with cysteine and GSH in Parkinson's disease Possible mechanisms of formation involving reactive oxygen species . J Neurochem. 71:1998;2112-2122.
26. Li H., Shen X.-M., Dryhurst G. Brain mitochondria catalyze the oxidation of 7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (DHBT-1) to intermediates that irreversibly inhibit complex I and scavenge glutathione Potential relevance to the pathogenesis of Parkinson's disease . J Neurochem. 71:1998;2049-2062.
27. Segura-Aguilar J. Peroxidase activity of liver microsomal vitamin D 25-hydroxylase and cytochrome P450 1A2 catalyzes 25-hydroxylation of vitamin D3 and oxidation of dopamine to aminochrome. Biochem Mol Med. 58:1996;122-129.
28. Segura-Aguilar J., Metodiewa D., Welch C.J. Metabolic activation of dopamine o-quinones to o-semiquinone by NADPH cytochrome P450 reductase may play an important role in oxidative stress and apoptotic effects. Biochim Biophys Acta. 1381:1998;1-6.
29. Baez S., Linderson Y., Segura-Aguilar J. Superoxide dismutase and catalase enhance autoxidation during one-electron reduction of aminochrome by NADPH-cytochrome P-450 reductase. Biochem Mol Med. 54:1995;12-18.
30. Meister A., Anderson M.E. Glutathione. Annu Rev Biochem. 52:1983;711-760.
31. Ravindranath V., Anandatheerthavarada H.K., Shankar S.K. NADPH cytochrome P-450 reductase in rat, mouse and human brain. Biochem Pharmacol. 39:1990;1013-1018.
32. Bernhardt R., Cytochrome P. 450 Structure, function, and generation of reactive oxygen species . Rev Physiol Biochem Pharmacol. 127:1996;137-221.
33. Meyer U.A. Overview of enzymes of drug metabolism. J Pharmacokinet Biopharm. 24:1996;449-459.
34. Wilkinson J. IV, Clapper M.L. Detoxication enzymes and chemoprevention. Proc Soc Exp Biol Med. 216:1997;192-200.
35. Lind C., Hochstein P., Ernster L. DT-diaphorase as a quinone reductase A cellular control device against semiquinone and superoxide radical formation . Arch Biochem Biophys. 216:1982;178-185.
36. 3+-induced neurotoxicity of dopamine Prevention of quinone-derived oxygen toxicity by DT diaphorase and superoxide dismutase . Chem Biol Interact. 72:1989;309-324.
37. Cadenas E. Antioxidant and prooxidant functions of DT-diaphorase in quinone metabolism. Biochem Pharmacol. 49:1995;127-140.
38. Cadenas E., Hochstein P., Ernster L. Pro- and antioxidant functions of quinones and quinone reductases in mammalian cells. Adv Enzymol. 65:1992;97-146.
39. Zhang P., Damier P., Hirsch E.C., Agid Y., Ceballos-Picot I., Sinet P.M., Nicole A., Laurent M., Javoy-Agid F. Preferential expression of superoxide dismutase messenger RNA in melanized neurons in human mesencephalon. Neuroscience. 55:1993;167-175.
40. Baez S., Segura-Aguilar J., Widersten M., Johansson A.-S., Mannervik B. Glutathione transferases catalyse the detoxication of oxidized metabolites (o-quinones) of catecholamines and may serve as an antioxidant system preventing degenerative cellular processes. Biochem J. 324:1997;25-28.
41. Hansson L.O., Bolton-Grob R., Massoud T., Mannervik B. Evolution of differential substrate specificities in Mu class glutathione transferases probed by DNA shuffling. J Mol Biol. 287:1999;265-276.
42. Segura-Aguilar J., Baez S., Widersten M., Welch C.J., Mannervik B. Human class Mu glutathione transferases, in particular isoenzyme M2-2, catalyze detoxication of the dopamine metabolite aminochrome. J Biol Chem. 272:1997;5727-5731.
43. Murphy T.H., So A.P., Vincent S.R. Histochemical detection of quinone reductase activity in situ using LY 83583 reduction and oxidation. J Neurochem. 70:1998;2156-2164.
44. Schultzberg M., Segura-Aguilar J., Lind C. Distribution of DT diaphorase in the rat brain Biochemical and immunohistochemical studies . Neuroscience. 27:1988;763-776.
45. Menegon A., Board P.G., Blackburn A.C., Mellick G.D., Le Couteur D.G. Parkinson's disease, pesticides, and glutathione transferase polymorphisms. Lancet. 352:1998;1344-1346.
46. Stroombergen M.C.M.J., Waring R.H., Bennett P., Williams A.C. Determination of the GSTM1 gene deletion frequency in Parkinson's disease by allele specific PCR. Parkinsonism Relat Disord. 2:1996;151-154.
47. Sian J., Dexter D.T., Lees A.J., Daniel S., Jenner P., Marsden C.D. Glutathione-related enzymes in brain in Parkinson's disease. Ann Neurol. 36:1994;356-361.
48. Begleiter A., Leith M.K., Curphey T.J., Doherty G.P. Induction of DT-diaphorase in cancer chemoprevention and chemotherapy. Oncol Res. 9:1997;371-382.
49. Prestera T., Holtzclaw W.D., Zhang Y., Talalay P. Chemical and molecular regulation of enzymes that detoxify carcinogens. Proc Natl Acad Sci USA. 90:1993;2965-2969.
50. Primiano T., Sutter T., Kensler T.W. Antioxidant-inducible genes. Adv Pharmacol. 38:1997;293-328.
51. Prochaska H.J., De Long M.J., Talalay P. On the mechanisms of induction of cancer-protective enzymes A unifying proposal . Proc Natl Acad Sci USA. 82:1985;8232-8236.
52. Wang W., Liu L.Q., Higuchi C.M., Chen H. Induction of NADPH, quinone reductase by dietary phytoestrogens in colonic Colo205 cells. Biochem Pharmacol. 56:1998;189-195.
53. Zhang Y., Talalay P., Cho C.-G., Posner G.H. A major inducer of anticarcinogenic protective enzymes from broccoli Isolation and elucidation of structure . Proc Natl Acad Sci USA. 89:1992;2399-2403.
54. Van Lieshout E.M.M., Tiemessen D.M., Roelofs H.M.J., Peters W.H.M. Nonsteroidal anti-inflammatory drugs enhance glutathione S-transferase theta levels in rat colon. Biochim Biophys Acta. 1381:1998;305-311.
55. Jaiswal A.K. Antioxidant response element. Biochem Pharmacol. 48:1994;439-444.
56. Ahlgren-Beckendorf J.A., Reising A.M., Schander M.A., Herdler J.W., Johnson J.A. Coordinate regulation of NAD(P)H:quinone oxidoreductase and glutathione-S-transferases in primary cultures of rat neurons and glia Role of the antioxidant/electrophile responsive element . Glia. 25:1999;131-142.
57. Ansher S.S., Dolan P., Bueding E. Biochemical effects of dithiolthiones. Food Chem Toxicol. 24:1986;405-415.
58. Christen M.-O. Anethole dithiolethione Biochemical considerations . Methods Enzymol. 252:1995;316-323.
59. O'Dwyer P.J., Szarka C.E., Yao K.-S., Halbherr T.C., Pfeiffer G.R., Green F., Gallo J.M., Brennan J., Frucht H., Goosenberg E.B., Hamilton T.C., Litwin S., Balshem A.M., Engstrom P.F., Clapper M.L. Modulation of gene expression in subjects at risk for colorectal cancer by the chemopreventive dithiolethione oltipraz. J Clin Invest. 98:1996;1210-1217.
60. De Long M.J., Dolan P., Santamaria A.B., Bueding E. 1,2-Dithiol-3-thione analogs Effects on NAD(P)H:quinone reductase and glutathione levels in murine hepatoma cells . Carcinogenesis. 7:1986;977-980.
61. Egner P.A., Kensler T.W., Prestera T., Talalay P., Libby A.H., Joyner H.H., Curphey T.J. Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones. Carcinogenesis. 15:1994;177-181.
62. Maxuitenko Y.Y., Libby A.H., Joyner H.H., Curphey T.J., MacMillan D.L., Kensler T.W., Roebuck B.D. Identification of dithiolethiones with better chemopreventive properties than oltipraz. Carcinogenesis. 19:1998;1609-1615.
63. Khanna S., Sen C.K., Roy S., Christen M.-O., Packer L. Protective effects of anethole dithiolethione against oxidative stress-induced cytotoxicity in human Jurkat T cells. Biochem Pharmacol. 56:1998;61-69.
64. Antras-Ferry E., Maheo K., Chevanne A., Dubos M.-P., Morel F., Guillouzo A., Cillard P., Cillard J. Oltipraz stimulates the transcription of the manganese superoxide dismutase gene in rat hepatocytes. Carcinogenesis. 18:1997;2113-2117.
65. Sen C.K., Traber K.E., Packer L. Inhibition of NF-κB activation in human T-cell lines by anetholdithiolthione. Biochem Biophys Res Commun. 218:1996;148-153.
66. Primiano T., Kensler T.W., Kuppusamy P., Zweier J.L., Sutter T. Induction of hepatic heme oxygenase-1 and ferritin in rats by cancer chemopreventive dithiolethiones. Carcinogenesis. 17:1996;2291-2296.
67. Dringen R., Hamprecht B., Drukarch B. Anethole dithiolethione, a putative neuroprotectant, increases intracellular and extracellular glutathione levels during starvation of cultured astroglial cells. Naunyn Schmiedebergs Arch Pharmacol. 358:1998;616-622.
68. Drukarch B., Schepens E., Stoof J.C., Langeveld C.H. Anethole dithiolethione prevents oxidative damage in glutathione-depleted astrocytes. Eur J Pharmacol. 329:1997;259-262.
69. Duffy S., So A., Murphy T.H. Activation of endogenous antioxidant defenses in neuronal cells prevents free radical-mediated damage. J Neurochem. 71:1998;69-77.
70. Packer L., Tritschler H.J., Wessel K. Neuroprotection by the metabolic antioxidant α-lipoic acid. Free Radic Biol Med. 22:1997;359-378.
71. Packer L., Witt E.H., Tritschler H.J. Alpha-lipoic acid as a biological antioxidant. Free Radic Biol Med. 19:1995;227-250.
72. Sen C.K. Redox signaling and the emerging therapeutic potential of thiol antioxidants. Biochem Pharmacol. 55:1998;1747-1758.
73. Traber K., Packer L. Quantitation of anethole dithiolthione using high performance liquid chromatography with electrochemical detection. Methods Enzymol. 299:1999;300-306.
74. Brooks D.J. The early diagnosis of Parkinson's disease. Ann Neurol. 44:(Suppl):1998;S10-S18.