2,9-Dimethyl-β-carbolinium, a neurotoxin occurring in human brain, is a potent inducer of apoptosis as 1-methyl-4-phenylpyridinium

Neuroscience

Volumn 139, Issue 4, 2006, Pages 1525-1537

  Pavlovic, S ^a   Schulze, G ^a   Wernicke, C ^a   Bonnet, R ^a   Gille, G ^b   Badiali, L ^a   Kaminska, A ^c   Lorenc Koci, E ^d   Ossowska, K ^d   Rommelspacher, H ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^c MEDICAL UNIVERSITY OF WARSAW   (Poland)

^d POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

carboline; endogenous neurotoxins; MPP+; neuro 2A; rat; synthetic neurotoxins

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; 2,9 DIMETHYL BETA CARBOLINIUM; BETA CARBOLINE; CASPASE 3; CASPASE 7; DOPAMINE; GLUTATHIONE; NEUROTOXIN; NITROGEN; NORADRENALIN; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); SEROTONIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CELL DEATH; CONTROLLED STUDY; CORPUS STRIATUM; CYTOMETRY; DOPAMINERGIC NERVE CELL; ELECTRON MICROSCOPY; ENZYME ACTIVATION; FLUORESCENCE ACTIVATED CELL SORTING; INCUBATION TIME; MEMBRANE POTENTIAL; METABOLITE; METHYLATION; MITOCHONDRIAL MEMBRANE; MOUSE; NERVE DEGENERATION; NEUROBLASTOMA CELL; NEUROTOXICITY; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; SUBSTANTIA NIGRA;

1-METHYL-4-PHENYLPYRIDINIUM; ANIMALS; APOPTOSIS; CARBOLINES; CASPASES; CELL LINE, TUMOR; CELL SURVIVAL; DOPAMINE; DOSE-RESPONSE RELATIONSHIP, DRUG; FLOW CYTOMETRY; HUMANS; MICE; MICROSCOPY, ELECTRON; NEUROBLASTOMA; NEUROTOXINS; RATS; RATS, WISTAR; REACTIVE OXYGEN SPECIES; TIME FACTORS;

EID: 33646137553     PISSN: 03064522     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuroscience.2006.01.018     Document Type: Article

References (41)

1. Albores R., Neafsey E.J., Drucker G., Fields J.Z., and Collins M.A. Mitochondrial respiratory inhibition by N-methylated beta-carboline derivatives structurally resembling N-methyl-4-phenyl-pyridine. Proc Natl Acad Sci U S A 87 (1990) 9368-9372
2. Banki K., Hutter E., Colombo E., Gonchoroff N.J., and Perl A. Glutathione levels and sensitivity to apoptosis are regulated by changes in transaldolase expression. J Biol Chem 271 (1996) 32994-33001
3. Banki K., Hutter E., Gonchoroff N.J., and Perl A. Elevation of mitochondrial transmembrane potential and reactive oxygen intermediates levels are early events and occur independently from activation of caspases in Fas signaling. J Immunol 162 (1999) 1466-1479
4. Bonnet R., Pavlovic S., Lehmann J., and Rommelspacher H. The strong inhibition of triosephosphate isomerase by the natural β-carbolines may explain their neurotoxic actions. Neuroscience 127 (2004) 443-453
5. Brookes P.S., Yoon Y., Robotham J.L., Anders M.W., and Sheu S.-S. Calcium, ATP, and ROS. a mitochondrial love-hate triangle. Am J Physiol Cell Physiol 287 (2004) C817-C833
6. Cadenas E., Boveris A., Ragan C.I., and Soppani A.O. Production of superoxide radicals and hydrogen peroxide by NADH-ubiquinone reductase and ubiquinol-cytochrome c reductase from beef-heart mitochondria. Arch Biochem Biophys 180 (1977) 248-257
7. + as environmental neurotoxins. In: Storch A., and Collins M.A. (Eds). Neurotoxic factors in Parkinson's disease and related disorders (2000), Kluwer Academic, New York 115-130
8. Collins M.A., Neafsey E.J., Matsubara K., Cobuzzi R.J., and Rollema H. Indole-N-methylated β-carbolinium ions as potential brain-bioactivated toxins. Brain Res 505 (1992) 154-160
9. Costantini P., Chernyak B.V., Petronilli V., and Bernardi P. Modulation of the mitochondrial permeability transition pore by pyridine nucleotides and dithiol oxidation at two separate sites. J Biol Chem 271 (1996) 6746-6751
10. Davis G., Williams A., Markey S., Ebert M., Caine E., Reichert C., and Kopin I. Chronic parkinsonism secondary to intravenous injection of meperidine analogues. Psychiatry Res 1 (1979) 249-254
11. Dawson T.M., and Dawson V.L. Molecular pathways of neurodegeneration in Parkinson's disease. Science 302 (2003) 819-822
12. Duvall E., Wyllie A.H., and Morris R.G. Macrophage recognition of cells undergoing programmed cell death (apoptosis). Immunology 56 (1985) 351-358
13. Gearhart D.A., Neafsey E.J., and Collins M.A. Phenylethanolamine-N-methyltransferase has β-carboline 2N-methyltransferase activity. hypothetical relevance to Parkinson's disease. Neurochem Int 40 (2002) 611-620
14. Hardman J.G., and Limbird L.E. Goodman and Gilman's the pharmacological basis of therapeutics. 9th edition (1996), McGraw-Hill, New York
15. Haeberlein S.L.B. Mitochondrial function in apoptotic neuronal cell death. Neurochem Res 29 (2004) 521-530
16. Hayer-Zillgen M., Brüss M., and Bönisch H. Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol 136 (2002) 829-836
17. Ho B.T., Gardner P.M., and Walker K.E. Inhibition of MAO by β-carbolinium halides. J Pharmacol Sci 62 (1973) 36-39
18. Korte A., Köchling J., Badiali L., Eckert C., Andreae J., Geilen W., Kebelmann C., Taube T., Wu S., Henze G., and Seeger K. Expression analysis and characterization of alternatively spliced transcripts of human IL-7Rα chain encoding two truncated receptor proteins in relapsed childhood all. Cytokine 12 (2000) 1597-1608
19. Kuhn W., Müller T.H., Grosse H., and Rommelspacher H. Elevated levels of harman and norharman in cerebrospinal fluid of parkinsonian patients. J Neural Transm 103 (1996) 1435-1440
20. Langston J.W., Ballard P., Tetrud J.W., and Irwin I. Chronic parkinsonism in humans due to a product of meperidine analog synthesis. Science 219 (1983) 979-980
21. Li N., Ragheb K., Lawler G., Sturgis J., Rajwa B., Melendez J.A., and Robinson J.P. Mitochondrial complex 1 inhibitor rotenone induces apoptosis through enhancing mitochondrial reactive oxygen species production. J Biol Chem 278 (2003) 8516-8525
22. Matsubara K., Collins M.A., Akane A., Ikebuchi J., Neafsey E.J., Kagawa M., and Shiono H. Potential bioactivated neurotoxicants, N-methylated β-carbolinium ions, are present in human brain. Brain Res 610 (1993) 90-96
23. + analogs, in the lumbar cerebrospinal fluid of patients with Parkinson's disease. Neurology 45 (1995) 2240-2245
24. Merad-Boudia M., Santiard-Baron N.A., Saille C., and Ceballos-Picot I. Mitochondrial impairment as an early event in the process of apoptosis induced by glutathione depletion in neuronal cells. relevance to Parkinson's disease. Biochem Pharmacol 56 (1998) 645-655
25. Nagatsu T. Amine-related neurotoxins in Parkinson's disease. past, present, and future. Neurotoxicol Teratol 24 (2002) 565-569
26. Neafsey E.J., Albores R., Gearhart D., Kindel G., Raikoff K., Tamayo F., and Collins M.A. Methyl-β-carbolinium analogs of MPP+ cause nigrostriatal toxicity after substantia nigra injections in rats. Brain Res 675 (1995) 279-288
27. Paxinos C., and Watson C. The rat brain in stereotaxic coordinates (1985), Academic Press, London
28. Perl A., Gergely P., Puskas P., and Banki K. Metabolic switches of T-cell activation and apoptosis. Antioxid Redox Signal 4 (2002) 427-442
29. Perl A., Gergely Jr. P., Nagy G., Koncz A., and Banki K. Mitochondrial hyperpolarization. a checkpoint of T-cell life, death and autoimmunity. Trends Immunol 25 (2004) 360-367
30. Ramsay R.R., Krueger M.J., Youngster S.K., Gluck M.R., Casida J.E., and Singer T.P. Interaction of 1-methyl-4-phenylpyridinium ion (MPP+) and its analogs with the rotenone/piericidin binding site of NADH dehydrogenase. J Neurochem 56 (1991) 1184-1190
31. Ramsay R.R., and Singer T.P. Relation of superoxide generation and lipid peroxidation to the inhibition of NADH-Q oxidoreductase by rotenone, piericidin A, and MPP+. Biochem Biophys Res Commun 30 (1992) 47-92
32. Ramsay R.R., Youngster S.K., Nicklas W.J., McKeown K.A., Jin Y.Z., Heikkila R.E., and Singer T.P. Structural dependence of the inhibition of mitochondrial respiration and of NADH oxidase by 1-methyl-4-phenylpyridinium (MPP+) analogs and their energized accumulation by mitochondria. Proc Natl Acad Sci U S A 86 (1989) 9168-9172
33. Rommelspacher H., Meier-Henco M., Smolka M., and Kloft C. The levels of norharman are high enough after smoking to affect monoamineoxidase B in platelets. Eur J Pharmacol 441 (2002) 115-125
34. Sigimura T., Wakabayashi K., Ohgaki H., Takayama S., Nagao M., and Esumi H. Heterocyclic amines in cooked food. unavoidable xenobiotics. Princess Takamatsu Symp 21 (1990) 279-288
35. Spijkerman R., van der Eijnden R., van de Mheen D., Bongers I., and Fekkes D. The impact of smoking and drinking on plasma levels of norharman. Eur Neuropsychopharmacol 12 (2002) 61-71
36. Starkov A.A., and Fiskum G. Regulation of brain mitochondrial H2O2 production by membrane potential and NAD(P)H redox state. J Neurochem 86 (2003) 1101-1107
37. Storch A., Hwang Y.-I., Gearhart D.A., Beach W., Neafsey E.J., Collins M.A., and Schwarz J. Dopamine transporter-mediated cytotoxicity of β-carbolinium derivatives related to Parkinson's disease. relationship to transporter-dependent uptake. J Neurochem 89 (2004) 685-694
38. Tan S., Sagara Y., Liu Y., Maher P., and Schubert D. The regulation of reactive oxygen species production during programmed cell death. J Cell Biol 141 (1998) 1423-1432
39. Uezono T., Maruyama W., Matsubara K., Naoi M., Shimizu K., Saito O., Ogawa K., Misukami H., Hayase N., and Shiono H. Norharman, an indoleamine-derived β-carboline, but not trp-P-2, a β-carboline, induces apoptotic cell death in human neuroblastoma SH-SY5Y cells. J Neural Transm 108 (2001) 943-953
40. Vermes I., Haanen C., and Reutelingsperger C. Flow cytometry of apoptotic cell death. J Immunol Methods 243 (2000) 167-190
41. m-Dependent and -independent production of reactive oxygen species by rat brain mitochondria. J Neurochem 79 (2001) 266-277