Evaluation of the oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) to toxic pyridinium cations by monoamine oxidase (MAO) enzymes and its use to search for new MAO inhibitors and protective agents

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 6, 2012, Pages 810-817

  Herraiz, Tomás ^a  

^a INSTITUTE OF FOOD SCIENCE   (Spain)

Author keywords

carboline; 1 methyl 4 phenyl 1,2,3,6 tetrahydropyridine (MPTP); 5 nitroindazole; menadione (2 methyl 1,4 naphtoquinone); Monoamine oxidase (MAO); MPP+; Neurotoxins; Parkinson's disease; Pyridinium cation; Tobacco smoke

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; 1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 2,3 DIHYDRO 1 METHYL 4 PHENYLPYRIDINIUM; 5 NITROINDAZOLE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; BETA CARBOLINE; CLORGYLINE; MONOAMINE OXIDASE B INHIBITOR; SELEGILINE; TOBACCO SMOKE; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFECT; DRUG MECHANISM; DRUG SCREENING; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; 1-METHYL-4-PHENYLPYRIDINIUM; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLORGYLINE; ENZYME ASSAYS; HARMINE; HUMANS; INDAZOLES; ISOENZYMES; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; PYRIDINIUM COMPOUNDS; RECOMBINANT PROTEINS; SELEGILINE; SMOKE; TOBACCO; VITAMIN K 3;

NICOTIANA TABACUM;

EID: 84870575182     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.616946     Document Type: Article

References (50)

1. Youdim MB, Edmondson D, Tipton KF. The therapeutic potential of monoamine oxidase inhibitors. Nat Rev Neurosci 2006;7:295-309.
2. Cohen G, Farooqui R, Kesler N. Parkinson disease: a new link between monoamine oxidase and mitochondrial electron flow. Proc Natl Acad Sci USA 1997;94:4890-4894.
3. Vindis C, Séguélas MH, Bianchi P, Parini A, Cambon C. Monoamine oxidase B induces ERK-dependent cell mitogenesis by hydrogen peroxide generation. Biochem Biophys Res Commun 2000;271:181-185.
4. Siddiqui A, Mallajosyula JK, Rane A, Andersen JK. Ability to delay neuropathological events associated with astrocytic MAO-B increase in a Parkinsonian mouse model: implications for early intervention on disease progression. Neurobiol Dis 2010;40:444-448.
5. Youdim MB, Lavie L. Selective MAO-A and B inhibitors, radical scavengers and nitric oxide synthase inhibitors in Parkinson's disease. Life Sci 1994;55:2077-2082.
6. Mallajosyula JK, Kaur D, Chinta SJ, Rajagopalan S, Rane A, Nicholls DG et al. MAO-B elevation in mouse brain astrocytes results in Parkinson's pathology. PLoS ONE 2008;3:e1616.
7. Drechsel DA, Patel M. Role of reactive oxygen species in the neurotoxicity of environmental agents implicated in Parkinson's disease. Free Radic Biol Med 2008;44:1873-1886.
8. Langston JW, Ballard P, Tetrud JW, Irwin I. Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis. Science 1983;219:979-980.
9. Jackson-Lewis V, Przedborski S. Protocol for the MPTP mouse model of Parkinson's disease. Nat Protoc 2007;2:141-151.
10. Langston JW, Irwin I, Langston EB, Forno LS. 1-Methyl-4- phenylpyridinium ion (MPP+): identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci Lett 1984;48:87-92.
11. Herraiz T, Guillén H, Galisteo J. N-methyltetrahydro-β- carboline analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxin are oxidized to neurotoxic β-carbolinium cations by heme peroxidases. Biochem Biophys Res Commun 2007;356:118-123.
12. Thomas B, Saravanan KS, Mohanakumar KP. In vitro and in vivo evidences that antioxidant action contributes to the neuroprotective effects of the neuronal nitric oxide synthase and monoamine oxidase-B inhibitor, 7-nitroindazole. Neurochem Int 2008;52:990-1001.
13. Seet RC, Lee CY, Lim EC, Tan JJ, Quek AM, Chong WL et al. Oxidative damage in Parkinson disease: Measurement using accurate biomarkers. Free Radic Biol Med 2010;48:560-566.
14. González-Polo RA, Soler G, Rodríguezmartín A, Morán JM, Fuentes JM. Protection against MPP+ neurotoxicity in cerebellar granule cells by antioxidants. Cell Biol Int 2004;28:373-380.
15. Herraiz T, Guillén H, Arán VJ, Idle JR, Gonzalez FJ. Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated β-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6. Toxicol Appl Pharmacol 2006;216:387-398.
16. Hauptmann N, Grimsby J, Shih JC, Cadenas E. The metabolism of tyramine by monoamine oxidase A/B causes oxidative damage to mitochondrial DNA. Arch Biochem Biophys 1996;335:295-304.
17. Heikkila RE, Manzino L, Cabbat FS, Duvoisin RC. Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl- 1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature 1984;311:467-469.
18. Sonsalla PK, Wong LY, Winnik B, Buckley B. The antiepileptic drug zonisamide inhibits MAO-B and attenuates MPTP toxicity in mice: clinical relevance. Exp Neurol 2010;221:329-334.
19. Herraiz T, Arán VJ, Guillén H. Nitroindazole compounds inhibit the oxidative activation of 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyridine (MPTP) neurotoxin to neurotoxic pyridinium cations by human monoamine oxidase (MAO). Free Radic Res 2009;43:975-984.
20. Reznichenko L, Kalfon L, Amit T, Youdim MB, Mandel SA. Low dosage of rasagiline and epigallocatechin gallate synergistically restored the nigrostriatal axis in MPTP-induced parkinsonism. Neurodegener Dis 2010;7:219-231.
21. Bolasco A, Carradori S, Fioravanti R. Focusing on new monoamine oxidase inhibitors. Expert Opin Ther Pat 2010;20:909-939.
22. Desideri N, Bolasco A, Fioravanti R, Monaco LP, Orallo F, Yáñez M et al. Homoisoflavonoids: natural scaffolds with potent and selective monoamine oxidase-B inhibition properties. J Med Chem 2011;54:2155-2164.
23. Chimenti F, Secci D, Bolasco A, Chimenti P, Granese A, Carradori S et al. Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors. Bioorg Med Chem 2010;18:5063-5070.
24. Deeb O, Alfalah S, Clare BW. QSAR of aromatic substances: MAO inhibitory activity of xanthone derivatives. J Enzyme Inhib Med Chem 2007;22:277-286.
25. Dar A, Khan KM, Ateeq HS, Khan S, Rahat S, Perveen S et al. Inhibition of monoamine oxidase-A activity in rat brain by synthetic hydrazines: structure-activity relationship (SAR). J Enzyme Inhib Med Chem 2005;20:269-274.
26. Pisani L, Muncipinto G, Miscioscia TF, Nicolotti O, Leonetti F, Catto M et al. Discovery of a novel class of potent coumarin monoamine oxidase B inhibitors: development and biopharmacological profiling of 7-[(3-chlorobenzyl) oxy]-4-[(methylamino)methyl]- 2H-chromen-2-one methanesulfonate (NW-1772) as a highly potent, selective, reversible, and orally active monoamine oxidase B inhibitor. J Med Chem 2009;52:6685-6706.
27. Zhou M, Panchuk-Voloshina N. A one-step fluorometric method for the continuous measurement of monoamine oxidase activity. Anal Biochem 1997;253:169-174.
28. Albers AE, Rawls KA, Chang CJ. Activity-based fluorescent reporters for monoamine oxidases in living cells. Chem Commun (Camb) 2007;44:4647-4649.
29. Yan Z, Caldwell GW, Zhao B, Reitz AB. A high-throughput monoamine oxidase inhibition assay using liquid chromatography with tandem mass spectrometry. Rapid Commun Mass Spectrom 2004;18:834-840.
30. Herraiz T, Chaparro C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants. J Chromatogr A 2006;1120:237-243.
31. Hu K, Zhang L, Li X, Zhao S. Rapid screening of monoamine oxidase B inhibitors in natural extracts by capillary electrophoresis after enzymatic reaction at capillary inlet. J Chromatogr B Analyt Technol Biomed Life Sci 2010;878:3156-3160.
32. Shinka T, Castagnoli N Jr, Wu EY, Hoag MK, Trevor AJ. Cationexchange high-performance liquid chromatography assay for the nigrostriatal toxicant 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine and its monoamine oxidase B generated metabolites in brain tissues. J Chromatogr 1987;398:279-287.
33. Herraiz T, Guillén H. Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors. Food Chem Toxicol 2011;49:1773-1781.
34. Herraiz T, Chaparro C. Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors. Biochem Biophys Res Commun 2005;326:378-386.
35. Herraiz T, Chaparro C. Human monoamine oxidase enzyme inhibition by coffee and β-carbolines norharman and harman isolated from coffee. Life Sci 2006;78:795-802.
36. Di Monte DA, Wu EY, Irwin I, Delanney LE, Langston JW. Biotransformation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in primary cultures of mouse astrocytes. J Pharmacol Exp Ther 1991;258:594-600.
37. Heikkila RE, Kindt MV, Sonsalla PK, Giovanni A, Youngster SK, McKeown KA et al. Importance of monoamine oxidase A in the bioactivation of neurotoxic analogs of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine. Proc Natl Acad Sci USA 1988;85:6172-6176.
38. Youngster SK, McKeown KA, Jin YZ, Ramsay RR, Heikkila RE, Singer TP. Oxidation of analogs of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine by monoamine oxidases A and B and the inhibition of monoamine oxidases by the oxidation products. J Neurochem 1989;53:1837-1842.
39. Wernicke C, Hellmann J, Zieba B, Kuter K, Ossowska K, Frenzel M et al. 9-Methyl-β-carboline has restorative effects in an animal model of Parkinson's disease. Pharmacol Rep 2010;62:35-53.
40. Kim DH, Jang YY, Han ES, Lee CS. Protective effect of harmaline and harmalol against dopamine- and 6-hydroxydopamineinduced oxidative damage of brain mitochondria and synaptosomes, and viability loss of PC12 cells. Eur J Neurosci 2001;13:1861-1872.
41. Cheng Y, Prusoff WH. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099-3108.
42. Fowler JS, Volkow ND, Wang GJ, Pappas N, Logan J, MacGregor R et al. Inhibition of monoamine oxidase B in the brains of smokers. Nature 1996;379:733-736.
43. Fowler JS, Logan J, Wang GJ, Volkow ND. Monoamine oxidase and cigarette smoking. Neurotoxicology 2003;24:75-82.
44. Pryor WA. Cigarette smoke radicals and the role of free radicals in chemical carcinogenicity. Environ Health Perspect 1997;105 Suppl 4:875-882.
45. Nolen WA, Hoencamp E, Bouvy PF, Haffmans PM. Reversible monoamine oxidase-A inhibitors in resistant major depression. Clin Neuropharmacol 1993;16 Suppl 2:S69-S76.
46. Castagnoli K, Palmer S, Anderson A, Bueters T, Castagnoli N Jr. The neuronal nitric oxide synthase inhibitor 7-nitroindazole also inhibits the monoamine oxidase-B-catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine. Chem Res Toxicol 1997;10:364-368.
47. Herraiz T. β-Carboline alkaloids.(2008) In Gilbert, J., Şenyuva, HZ., eds. Bioactive Compounds in Foods. UK: Blackwell, Oxford,199-218.
48. Kim H, Sablin SO, Ramsay RR. Inhibition of monoamine oxidase A by β-carboline derivatives. Arch Biochem Biophys 1997;337:137-142.
49. Krueger MJ, Mazouz F, Ramsay RR, Milcent R, Singer TP. Dramatic species differences in the susceptibility of monoamine oxidase B to a group of powerful inhibitors. Biochem Biophys Res Commun 1995;206:556-562.
50. Novaroli L, Daina A, Favre E, Bravo J, Carotti A, Leonetti F et al. Impact of species-dependent differences on screening, design, and development of MAO B inhibitors. J Med Chem 2006;49:6264-6272.