Studies on the cytochrome p-450 catalyzed ring a-carbon oxidation of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (Mptp)

Chemical Research in Toxicology

Volumn 3, Issue 5, 1990, Pages 423-427

  Ottoboni, Susanne ^a   Carlson, Timothy J ^b   Trager, William F ^b   Castagnoli, Kay ^a   Castagnoli, Neal ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; CYTOCHROME P450;

ANIMAL CELL; ARTICLE; NONHUMAN; OXIDATION; RABBIT; RAT; XENOBIOTIC METABOLISM;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; 1-METHYL-4-PHENYLPYRIDINIUM; ANIMAL; CYTOCHROME P-450 ENZYME SYSTEM; IN VITRO; KINETICS; MICROSOMES, LIVER; MONOAMINE OXIDASE; OXIDATION-REDUCTION; RABBITS; RATS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0025134990     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00017a006     Document Type: Article

References (39)

1. Langston, J. W., Irwin, I., Langston, E. B., and Forno, L. S. (1984) Pargyline prevents MPTP-induced Parkinsonism in primates. Science 225,1480-1482.
2. Chiba, K., Trevor, A., and Castagnoli, N., Jr. (1984) Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun. 120, 574-578.
3. Heikkila, R. E., Manzino, L., Cabbat, F. S., and Duvoisin, R. C. (1985) Studies on the oxidation of the dopaminergic neurotoxin 1- methyl-4-phenyl-l,2,3,6-tetrahydropyridine by monoamine oxidase B. J. Neurochem. 45, 1049-1054.
4. Blaschko, H. (1963) Enzymes, 2nd Ed. 8, 337-351.
5. Ransom, B. R., Kunis, D. M., Irwin, I., and Langston, J. W. (1987) Astrocytes convert the parkinsonism inducing neurotoxin, MPTP, to its active metabolite, MPP+. Neurosci. Lett. 75, 323-328.
6. Di Monte, D., Shinka, T., Sandy, M. S., Castagnoli, N., Jr., and Smith, M. T. (1988) Quantitative analysis of l-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine (MPTP) metabolism in isolated rat hepatocytes. Drug Metab. Dispos. 16, 150-160.
7. Fuller, R. W., Hemrick-Luecke, S. K., Kindt, M. V., and Heikkila, R. E. (1988) Different effects of monoamine oxidase inhibition on MPTP depletion of heart and brain catecholamines in mice. Life Sci. 42, 263-271.
8. Rose, J., and Castagnoli, N., Jr. (1983) The metabolism of tertiary amines. Med. Res. Rev. 3, 73-88.
9. Weissman, J., Trevor, A., Chiba, K., Peterson, L. A., Caldera, P., Castagnoli, N., Jr., and Baillie, T. (1985) Metabolism of the nigrostriatal toxin l-methyl-4-phenyl-l,2,3,6-tetrahydropyridine by liver homogenate fractions. J. Med. Chem. 28, 997-1001.
10. Wu, E., Shinka, T., Caldera-Munoz, P., Yoshizumi, H., Trevor, A., and Castagnoli, N., Jr. (1988) Metabolic studies on the nigrostriatal toxin MPTP and its MAO B generated dihydropyridinium metabolite MPDP+. Chem. Res. Toxicol. 1,186-194.
11. Peterson, L. A., Trevor, A., and Castagnoli, N., Jr. (1987) Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the (S)-nicotine l’(5’)-iminium species. J. Med. Chem. 30, 249-254.
12. Peterson, L. A., and Castagnoli, N., Jr. (1988) Regio- and stereochemical studies on the -carbon oxidation of (S)-nicotine by cytochrome P-450 model systems. J. Med. Chem. 31, 637-640.
13. Johnson, E. A., Wu, E. Y., Rollema, H., Booth, R. G., Castagnoli, N., Jr., and Trevor, A. J. (1989) 1-Methyl-4-phenylpyridinium (MPP+) analogs: in vivo neurotoxicity and inhibition of striatal synaptosomal dopamine uptake. Eur. J. Pharmacol. 166, 65-74.
14. Chiba, K., Peterson, L. A., Castagnoli, K. P., Trevor, A. J., and Castagnoli, N., Jr. (1985) Studies on the molecular mechanism of bioactivation of the selective nigrostriatal toxin l-methyl-4- phenyl-1,2,3,6-tetrahydropyridine. Drug. Metab. Dispos. 13, 342-347.
15. Ottoboni, S., Caldera, P., Trevor, A., and Castagnoli, N., Jr. (1989) Deuterium isotope effect measurements on the interactions of the neurotoxin l-methyl-4-phenyl-l,2,3,6-tetrahydropyridine (MPTP) with monoamine oxidase B. J. Biol. Chem. 264, 13684-13688.
16. Shinka, T., Castagnoli, N., Jr., Wu, E. Y., Hoag, K. P., and Trevor, A. J. (1987) Cation exchange HPLC assay for the nigrostriatal toxicant l-methyl-4-phenyl-l,2,3,6-tetrahydropyridine (MPTP) and its MAO B generated metabolites in brain tissues. J. Chromatogr. Sci. 398, 279-287.
17. Haugen, D. A., and Coon, M. J. (1976) Properties of electrophoretically homogeneous phenobarbital inducible and /3-naphthoflavone inducible forms of liver microsomal cytochrome P-450. J. Biol. Chem. 251, 7929-7939
18. Rettie, A. E., Boberg, M., Rettenmeier, A. W., and Baillie, T. A. (1988) Cytochrome P-450-catalyzed desaturation of valproic acid in vitro. J. Biol. Chem. 263, 13733-13738.
19. Waxman, D. J., and Walsh, C. (1982) Phenobarbital-induced rat liver cytochrome P-450. J. Biol. Chem. 257, 10446-10457.
20. Ardies, C. M., Lasker, J. M., Bioswick, B. P., and Lieber, C. S. (1987) Purification of NADPH:cytochrome c (cytochrome P-450) reductase from hamster liver microsomes by detergent extraction and affinity chromatography. Anal. Biochem. 162, 39-46.
21. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with the Rolin phenol reagent. J. Biol. Chem. 193, 265-275.
22. Omura, T., and Sato, K. (1964) The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378.
23. Wolf, C. R., Seilman, S., Oesch, F., Mayer, R. T., and Burke, M. D. (1986) Multiple forms of cytochrome P-450 related to forms induced marginally by phenobarbital. Biochem. J. 240, 27-33.
24. Bondon, A., Macdonald, T. L., Harris, T. M., and Guengerich, F. P. (1989) Oxidation of cycloalkylamines by cytochrome P-450. Mechanism-based inactivation, adduct formation, ring expansion, and nitrone formation. J. Biol. Chem. 264,1988-1997.
25. Baba, T., Yamade, H., Oguri, K., and Yoshimura, H. (1988) Participation of cytochrome P-450 isozymes in N-demethylation, Nhydroxylation and aromatic hydroxylation of methamphetamine. Xenobiotica 18,475-484.
26. Ziegler, D. M. (1985) in Biological Oxidation of Nitrogen in Organic Molecules—Toxicology, and Pharmacology Gorrod, J. W., and Damani, L. A., Eds. pp 43-52, Ellis Norwood, Chichester, England.
27. Peterson, L. A., Caldera, P., Trevor, A., Chiba, K., and Castagnoli, N., Jr. (1985) Studies on the l-methyl-4-phenyl-2,3-dihydropyridinium species 2,3-MPDP+, the monoamine oxidase catalyzed oxidation product of the nigrostriatal toxin 1-methyl- 4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). J. Med. Chem. 28, 1432-1436.
28. Salach, J. I., Singer, T. P., Castagnoli, N., Jr., and Trevor, A. (1984) Oxidation of the neurotoxic amine l-methyl-4-phenyl- 1,2,3,6-tetrahydropyridine (MPTP) by monoamine oxidases A and B and suicide inactivation of the enzymes by MPTP. Biochem. Biophys. Res. Commun. 125, 831-835.
29. Miwa, G. T., Walsh, J. S., and Lu, A. Y. H. (1984) Kinetic isotope effects on cytochrome P-450-catalyzed oxidation reactions. The oxidative O-dealkylation of 7-ethoxycoumarin. J. Biol. Chem. 259, 3000-3004.
30. Silverman, R. B., and Zieske, P. A. (1986) 1-Phenylcyclobutylamine, the first in a new class of monoamine oxidase inactivators. Further evidence for a radical intermediate. Biochemistry 25, 341-346.
31. Silverman, R. B., and Zieske, P. A. (1985) Mechanism of inactivation of monoamine oxidase by 1-phenylcyclopropylamine. Biochemistry 24, 2128-2138.
32. Guengerich, F. P., and Macdonald, T. L. (1984) Chemical mechanisms of catalysis by cytochromes P-450: A unified view. Acc. Chem. Res. 17, 9-16.
33. Miwa, G. T., Walsh, J. S., Kedderis, G. L., and Hollenberg, P. F. (1983) The use of intramolecular isotope effects to distinguish between deprotonation and hydrogen atom abstraction mechanisms in cytochrome P-450- and peroxidase-catalyzed N-demethylation reactions. J. Biol. Chem. 258, 14445-14449.
34. Dinnocenzo, J. P., and Banach, T. E. (1989) Deprotonation of tertiary amine cation radicals. A direct experimental approach. J. Am. Chem. Soc. 111, 8646-8653.
35. Northrop, D. B. (1975) Steady state analysis of kinetic isotope effects in enzymic reactions. Biochemistry 14, 2644-2651.
36. Korzekwa, K. R., Trager, W. F., and Gillette, J. R. (1989) Theory for the observed isotope effects from enzymatic systems that form multiple products via branched reaction pathways: cytochrome P-450. Biochemistry 28, 9012-9018.
37. Harada, N., Miwa, G. T., Walsh, J. S., and Lu, A. Y. H. (1984) Kinetic isotope effects on cytochrome P-450-catalyzed-oxidation reactions. Evidence for the irreversible formation of an activated oxygen intermediate of cytochrome P-448. J. Biol. Chem. 259, 3005-3010.
38. Subramanyam, B., Rollema, H., Woolf, T., and Castagnoli, N., Jr. (1990) Identification of a potentially neurotoxic pyridinium metabolite of haloperidol in rats. Biochem. Biophys. Res. Commun. 166, 238-244.
39. Niznik, H. B., Tyndale, R. F., Salee, F. R., Gonzalez, F. J., Hardwick, J. P., Inaba, T., and Kalow, W. (1990) The dopamine transporter and cytochrome P450IID1 (debrisoquine 4- hydroxylase) in brain: Resolution and identification of two distinct [3H]GBR-12935 binding proteins. Arch. Biochem. Biophys. 276, 424-432.