The strong inhibition of triosephosphate isomerase by the natural β-carbolines may explain their neurotoxic actions

Neuroscience

Volumn 127, Issue 2, 2004, Pages 443-453

  Bonnet, R ^a   Pavlovic, S ^a   Lehmann, J ^b   Rommelspacher, H ^a  

^a Psychiatric Clinic   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

carboline; carbolines; carbolinium ion; AD; adenosine triphosphate; Alzheimer disease; ATP; BC; BC+; CHAPS; neurodegeneration; neurotoxin; Parkinson's disease; triosephosphate isomerase

Indexed keywords

2,9 DIMETHYL BETA CARBOLINE; BETA CARBOLINE DERIVATIVE; TRIOSEPHOSPHATE ISOMERASE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN; CATTLE; CLINICAL FEATURE; CLINICAL OBSERVATION; CONTROLLED STUDY; DISEASE COURSE; DISEASE SEVERITY; ENZYME DEFICIENCY; ENZYME INHIBITION; EXTRAPYRAMIDAL SYNDROME; INHIBITION KINETICS; INJECTION; NERVE DEGENERATION; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN ISOLATION; SUBSTANTIA NIGRA;

ANIMALS; BINDING, COMPETITIVE; BRAIN CHEMISTRY; CARBOLINES; CATTLE; CELL LINE; CELL MEMBRANE; CELL RESPIRATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ENERGY METABOLISM; FEMALE; GLYCOLYSIS; MPTP POISONING; NERVE DEGENERATION; NEURONS; NEUROTOXINS; RADIOLIGAND ASSAY; SUBCELLULAR FRACTIONS; SUBSTANTIA NIGRA; TRIOSE-PHOSPHATE ISOMERASE; TRITIUM;

EID: 3242703231     PISSN: 03064522     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuroscience.2004.05.002     Document Type: Article

References (41)

1. Airaksinen M.M., Kari I. β-carbolines, psychoactive compounds in the mammalian body Part i. Occurrence, origins, and metabolism. Med Biol. 59:1981;21-34
2. Bonini N.M. Chaperoning brain degeneration. Proc Natl Acad Sci USA. 99:(suppl 4):2002;16407-16411
3. Collins M.A., Neafsey E.J., Matsubara K., Cobuzzi R.J., Rollema H. Indole-N-methylated β-carbolinium ions as potential brain-bioactivated toxins. Brain Res. 507:1992;154-160
4. Collins M.A., Neafsey E.J., Cheng B.Y., Hurley-Gius K., Ung-Chhun N., Pronger D.A., Christensen M.A., Hurley-Gius D. Endogenous analogs of MPTP Indoleamine derived tetrahydro-β-carbolines as potential causative factors in parkinson's disease. Adv Neurol. 45:1986;179-185
5. Crosby A.H. Disruption of cellular transport A common cause of neurodegeneration? Lancet Neurol. 2:2003;311-316
6. Daner W., Przedborski S. Parkinson's disease Mechanisms and models. Neuron. 39:2003;889-909
7. Drucker G., Raikoff K., Neafsey E.J., Collins M.A. Dopamine uptake inhibitory capacities of beta-carboline and 3,4-dihydro-beta-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) oxidation products. Brain Res. 509:1990;125-133
8. Esnouf M.P., Harris R.P., McVittie J.D. Triosephosphate isomerase from chicken and rabbit muscle. Methods Enzymol. 89:(Pt D):1982;579-583
9. Fekkes D., Tuiten A., Bom I., Pepplinkhuizen L. Tryptophan A precursor for the endogenous synthesis of norharman in man. Neurosci Lett. 303:2001;145-148
10. Gearhart D.A., Neafsey E.J., Collins M.A. Phenylethanolamine-N- methyltransferase has β-carboline 2N-methyltransferase activity Hypothetical relevance to parkinson's disease. Neurochem Int. 40:2002;611-620
11. 3H]β-carboline) binding proteins from rat liver. J Chromatogr B. 784:2003;155-168
12. 3H]β- carboline) binds reversibly and with high affinity to a specific binding site in rat liver. Neurochem Res. 18:1993;1029-1031
13. Heydari A.R., Conrad C.C., Richardson A.J. Expression of heat shock genes in hepatocytes is affected by age and food restriction in rats. J Nutr. 125:1995;410-418
14. Ho B.T., Gardner P.M., Walker K.E. Inhibition of MAO by β-carbolinium halides. J Pharm Sci. 62:1973;36-39
15. Hollán S, Fodor E, Horanyi M, et al. (1997) Decrease in non-bilayer forming lipid composition of lymphocytes in triosephosphate isomerase (TPI) deficiency. Blood 94:10,362-10,366.
16. Honecker H., Rommelspacher H. Tetrahydronorharman (tetrahydro-β- carboline) a physiologically occurring compound of indole metabolism. Naunyn Schmiedebergs Arch Pharmacol. 305:1978;135-141
17. Jamora C., Dennert G., Lee A.S. Inhibition of tumor progression by suppression of stress protein GRP 78/BiP induction in fibrosarcoma B/C IOME. Proc Natl Acad Sci USA. 93:1996;7690-7694
18. Kannan K., Jain S.K. Oxidative stress and apoptosis. Pathophysiology. 7:2000;153-163
19. Katayama T., Imaizumi K., Sato N., et al. Presenilin-1 mutations downregulate the signalling pathway of the unfolded protein response. Nat Cell Biol. 1:1999;479-483
20. Kitamura Y., Nomura Y. Stress proteins and glial function Possible therapeutic targets for neurodegenerative disorders. Pharmacol Ther. 97:2003;35-53
21. Kuhn W., Mueller T., Grosse H., Rommelspacher H. Elevated levels of harman and norharman in cerebrospinal fluid of Parkinsonian patients. J Neural Transm. 103:1996;1435-1440
22. Lehmann J., Heineke D. Indole, 12 Mitteilung-β-Carboline aus Lactonen Zur synthese von liganden am norharman-rezeptor. Arch Pharm (Weinheim). 327:1994;715-720
23. Martinus R.D., Ryan M.T., Naylor D.J., Herd S.M., Hoogenraad N.J., Hoj P.B. Role of chaperones in the biogenesis and maintenance of the mitochondrion. FASEB J. 9:1995;371-378
24. Matsubara K., Collins M.A., Akane A., Ikebuchi L., Neafsey E.J., Kagawa M., Shiono H. Potential bioactivated neurotoxicants, N-methylated β-carbolinium ions, are present in human brain. Brain Res. 610:1993;90-96
25. McGeer P.L., McGeer E.G. The inflammatory response system of brain Implications for therapy of alzheimer and other neurodegenerative diseases. Brain Res Rev. 21:1995;195-218
26. Mühlbauer E, Rommelspacher H (2004) Glucose-regulated stress proteins (GRPs) and alcohol. In: Comprehensive handbook of alcohol-related pathology (Preedy VR, Watson RR, eds), London: Academic Press, in press
27. + cause nigrostriatal toxicity after substantia nigra injections in rats. Brain Res. 675:1995;279-288
28. Orosz F., Wagner G., Liliom K., Kovacs J., Baroti K., Horanyi M., Farkas T., Hollán S., Ovadi J. Enhanced association of mutant triosephosphate isomerase to red cell membranes and to brain microtubules. Proc Natl Acad Sci USA. 97:2000;1026-1031
29. 3H]β-carboline) binding sites in rat brain. J Chem Neuroanat. 3:1990;19-24
30. 3H]beta- carboline) in the rat brain. Eur J Pharmacol. 147:1988;163-171
31. Sällström Baum S., Hill R., Rommelspacher H. Harman-induced changes of extracellular concentrations of neurotransmitters in the nucleus accumbens of rats. Eur J Pharmacol. 314:1996;75-82
32. Schneider A.S. Triosephosphate isomerase deficiency Historical perspectives and molecular aspects. Baillieres Clin Hematol. 13:2000;119-140
33. Sigimura T., Wakabayashi K., Ohgaki H., Takayama S., Nagao M., Esumi H. Heterocyclic amines in cooked food Unavoidable xenobiotics. Princess Takamatsu Symp. 21:1990;279-288
34. Smith P.K., Krohn R.I., Hermanson G.T., Mallia A.K., Gartner F.H., Provenzano M.D., Fujimoto E.K., Goeke N.M., Olson B.J., Klenk D.C. Measurement of protein using bicinchoninic acid. Anal Biochem. 150:1985;76-85
35. Southwood C.M., Garbern J., Jiang W., Gow A. The unfolded protein response modulates disease severity in Pelizaeus-Merzbacher disease. Neuron. 36:2002;585-596
36. Stamer K., Vogel R., Thies E., Mandelkow E., Mandelkow E.M. Tau blocks traffic of organelles, neurofilaments, and APP vesicles in neurons and enhances oxidative stress. J Cell Biol. 156:2002;1051-1063
37. 3H]β-carboline) to the ethanol-inducible cytochrome P450 2E1 in rat liver. Biochem Pharmacol. 57:1999;511-520
38. Susilo R., Rommelspacher H. Formation of a β-carboline (1,2,3,4-tetrahydro-1-methyl-β-carboline-1-carboxylic acid) following intracerebroventricular injection of tryptamine and pyruvic acid. Naunyn Schmiedebergs Arch Pharmacol. 335:1987;70-76
39. Susilo R., Rommelspacher H. Formation of 1-methyl-β-carbolines in rats from their possible carboxylic acid precursor. Naunyn Schmiedebergs Arch Pharmacol. 337:1988;566-571
40. Uezono T., Maruyama W., Matsubara K., Naoi M., Shimizu K., Saito O., Ogawa K., Mizukami H., Hayase N., Shiono H. Norharman, an indoleamine-derived β-carboline, but not trp-P-2, a γ-carboline, induces apoptotic cell death in human neuroblastoma SH-SY5Y cells. J Neural Transm. 108:2001;943-953
41. Zhang J., Burnell J.C., Dumaual N., Bosron W.F. Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther. 290:1999;314-318