Chemical modification of the mitochondrial complex I inhibitor 1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline: Synthesis and evaluation of N-alkanoyl derivatives

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 55, Issue 7-8, 2000, Pages 620-630

  Bringmann, Gerhard ^a   Feineis, Doris ^a   God, Ralf ^a   Brückner, Ralph ^a   Protzen, Jens Achim ^a   Blank, Michael ^a   Peters, Karl ^b   Peters, Eva Maria ^b   Janetzky, Bernd ^c   Reichmann, Heinz ^c  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

^c UNIVERSITY HOSPITAL CARL GUSTAV CARUS   (Germany)

Author keywords

1 Trichloromethyl 1,2,3,4 tetrahydro carboline; Chloral Derived Tetrahydro carbolines; Mi tochondrial Respiration

Indexed keywords

1 TRICHLOROMETHYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITOR; HYDROPHOBICITY; MITOCHONDRION; NICOTINAMIDE ADENINE DINUCLEOTIDE; RAT; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE);

EID: 0033836175     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2000-7-822     Document Type: Article

References (33)

1. +. Proc. Natl. Acad. Sci. USA 87, 9368-9372.
2. Bringmann G. and Hille A. (1990), 1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline - a potential chloral-derived indol alkaloid in man. Arch. Pharm. 323, 567-569.
3. Bringmann G., Brückner R., Mössner R., Feineis D., Heils A. and Lesch K.-P. (2000a), Effect of 1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline (TaClo) on human serotonergic cells. Neurochem. Res. 25, 837-843.
4. Bringmann G., Feineis D., Brückner R., Blank M., Peters K., Peters E.-M., Reichmann H., Janetzky B., Grote C., Clement H.-W. and Wesemann W. (2000b), Bromal-derived tetrahydro-β-carbolines as neurotoxic agents: chemistry, impairment of the dopamine metabolism, and inhibitory effects on mitochondrial respiration. Bioorg. Med. Chem. 8, 1467-1478.
5. Bringmann G., Feineis D., God R., Fähr S., Wesemann W., Clement H.-W., Grote C., Kolasiewicz W., Sontag K.-H., Heim C., Sontag T. A., Reichmann H., Janetzky B., Rausch W.-D., Abdel-mohsen M., Koutsilieri E., Götz M. E., Gsell W., Zielke B. and Riederer P. (1996), Neurotoxic effects on the dopaminergic system induced by TaClo (1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline), a potential mammalian alkaloid: in vivo and in vitro studies. Biogenic Amines 12, 83-102.
6. Bringmann G., Feineis D., Grote C., God R., Clement H.-W., Sontag K.-H., Janetzky B., Reichmann H., Rausch W.-D., Riederer P. and Wesemann W. (1998), Highly halogenated tetrahydro-β-carbolines as a new class of dopaminergic neurotoxins. In: Pharmacology of Endogenous Neurotoxins - A Handbook (Moser A., ed.). Birkhäuser, Boston, Basel, Berlin, pp. 151-169.
7. Bringmann G., God R., Fähr S., Feineis D., Fornadi F. and Fornadi K. (1999), Identification of the dopaminergic neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline in human blood after intake of the hypnotic chloral hydrate. Anal. Biochem. 270, 167-175.
8. Bringmann G., God R., Feineis D., Janetzky B. and Reichmann H. (1995), TaClo as a neurotoxic lead: improved synthesis, stereochemical analysis, and inhibition of the mitochondrial respiratory chain. J. Neural Transm. 46 [Suppl.], 245-254.
9. El Tayar N., Marston A., Bechalany A., Hostettmann K. and Testa B. (1989), Use of centrifugal partition chromatography for assessing partition coefficients in various solvent systems. J. Chromatogr. 469, 91-99.
10. +. Arch. Biochem. Biophys. 294, 539-543.
11. Gerlach M., Xiao A.-Y., Heim C., Lan J., God R., Feineis D., Bringmann G., Riederer P. and Sontag K.-H. (1998), 1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline increases extracellular serotonin and stimulates hydroxyl radical production in rats. Neurosci. Lett. 257, 17-20.
12. Grote C., Clement H.-W., Wesemann W., Bringmann G., Feineis D., Riederer P. and Sontag K.-H. (1995), Biochemical lesions of the nigrostriatal system by TaClo (1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline) and derivatives. J. Neural Transm. 46 [Suppl.], 265-273.
13. Janetzky B., Gille G., Abdel-mohsen M., God R., Rausch W.-D., Bringmann G. and Reichmann H. (1999), Effects of highly halogenated β-carbolines on dopaminergic cells in culture and mitochondrial respiration. Drug Dev. Res. 46, 51-56.
14. Janetzky B., God R., Bringmann G. and Reichmann H. (1995), 1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline, a new inhibitor of complex I. J. Neural Transm. 46 [Suppl.], 265-273.
15. Janetzky B., Hauck S., Youdim M. B., Riederer P., Jellinger K., Pantucek F., Zöchling R., Boissl K. W. and Reichmann H. (1994), Unaltered aconitase activity, but decreased complex I activity in substantia nigra pars compacta of patients with Parkinson's disease. Neurosci. Lett. 169, 126-128.
16. Keller E. (1990), SCHAKAL 88. A FORTRAN Program for the Graphic Representation of Molecules and Crystallographic Models. Kristallographisches Institut der Universität Freiburg, Germany.
17. Lestienne P., Nelson J., Riederer P., Jellinger K. and Reichmann H. (1990), Normal mitochondrial genome in brain from patients with Parkinson's disease and complex I defect [published erratum appeared in J. Neurochem. (1991) 56, 1457]. J. Neurochem. 55, 1810-1812.
18. McNaught K. S. P., Thull U., Carrupt P. A., Altomare C., Cellamare S., Carotti A., Testa B., Jenner P. and Marsden C. D. (1995), Inhibition of complex I by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Biochem. Pharmacol. 50, 1903-1911.
19. Miyoshi H. (1998). Structure-activity relationships of some complex I inhibitors. Biochem. Biophys. Acta 1364, 236-244.
20. Mizuno Y., Saitoh T. and Sone N. (1987), Inhibition of mitochondrial NADH-ubiquinone oxidoreductase activity by 1-methyl-4-phenylpyridinium ion. Biochem. Biophys. Res. Commun. 143, 294-299.
21. Morikawa N., Naoi, M., Maruyama W., Ohta S., Kotake Y., Kawai H., Niwa T., Dostert P. and Mizuno Y. (1998), Effects of various tetrahydroisoquinoline derivatives on mitochondrial respiration and the electron transport complexes. J. Neural Transm. 105, 677-688.
22. Nicklas W. J., Vyas I. and Heikkila R. E. (1985), Inhibition of NADH-linked oxidation in brain mitochondria by 1-methyl-4-phenyl-pyridine, a metabolite of the neurotoxin, 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine. Life Sci. 36, 2503-2508.
23. Peters K., Peters E.-M., von Schnering H. G., Bringmann G. and God R. (1995), 2-Trifluoroacetyl-1-methyl-1,2,3,4-tetrahydro-β-carboline, a gaschromatographically useful derivative of the mammalian alkaloid eleagnine. Z. Naturforsch. 50b, 1564-1565.
24. Ramsay R. R. and Singer T. P. (1986), Energy-dependent uptake of N-methyl-4-phenylpyridinium, the toxic metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, by mitochondria. J. Biol. Chem. 261, 7585-7587.
25. Rausch W.-D., Abdel-mohsen M., Koutsilieri E., Chan W. W. and Bringmann G. (1995), Studies of the potentially endogenous toxin TaClo (1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline) in neuronal and glial cell cultures. J. Neural Transm. 46 [Suppl.], 255-263.
26. Schapira A. H. V. (1998). Human complex I defects in neurodegenerative diseases. Biochim. Biophys. Acta 1364, 261-270.
27. Schapira A. H. V., Cooper J. M., Dexter D., Clark, J. B., Jenner P. and Marsden C. D. (1990), Mitochondrial complex I deficiency in Parkinson's disease. J. Neurochem. 54, 823-827.
28. Sheldrick G. M. (1990). Program Package SHELXTL-PLUS, Release 4.1., Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA.
29. Siemens (1996). P4 X-ray Program System, Analytical X-ray Instruments Inc., Madison, Wisconsin 53719, USA.
30. Slacanin I., Marston A. and Hostettmann K. (1989), Modifications to a high-speed counter-current chromatograph for improved separation capability. J. Chromatogr. 482, 234-239.
31. Sontag K.-H., Heim C., Sontag T. A., Kolasiewicz W., Clement H.-W., Grote C., Wesemann W., Janetzky B., Reichmann H., Feineis D., God R., Bringmann G., Rausch W.-D., Abdel-mohsen M., Abdel-moneim M., Chan W. W., Koutsilieri E., Zielke B., Götz M., Gsell W. and Riederer P. (1996), Progressive neurodegeneration of the dopaminergic system and inhibition of the complex I induced by the chloral-derived tetrahydro-β-carboline TaClo. In: The Basal Ganglia V (Ohye C., Kimura M. and McKenzie J. S., eds.). Plenum Press, New York and London, pp. 387-394.
32. Suzuki K., Mizuno Y. and Yoshida M. (1990), Inhibition of mitochondrial respiration by 1,2,3,4-tetrahydroisoquinoline-like endogenous alkaloids in mouse brain. Neurochem. Res. 15, 705-710.
33. Vallat P., El Tayar N., Testa B., Slacanin I., Marston A. and Hostettmann K. (1990), Centrifugal counter-current chromatography, a promising means of measuring partition coefficients. J. Chromatogr. 504, 411-419.