Cytotoxicity of 17 tetrahydroisoquinoline derivatives in SH-SY5Y human neuroblastoma cells is related to mitochondrial NADH-ubiquinone oxidoreductase inhibition

NeuroToxicology

Volumn 28, Issue 1, 2007, Pages 27-32

  Kotake, Yaichiro ^a,b   Sekiya, Yoko ^a   Okuda, Katsuhiro ^a,c   Ohta, Shigeru ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

^c HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

Dopamine transporter; Lipophilicity; NADH ubiquinone oxidoreductase; Neurotoxicity; Tetrahydroisoquinoline

Indexed keywords

BUTANOL; DOPAMINE TRANSPORTER; MITOCHONDRIAL ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); TETRAHYDROISOQUINOLINE DERIVATIVE; WATER;

ACTIVE TRANSPORT; ANIMAL EXPERIMENT; ARTICLE; CELL DEATH; CORRELATION FUNCTION; CYTOTOXICITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LIPOPHILICITY; MALE; NEUROBLASTOMA CELL; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; RAT;

ANTINEOPLASTIC AGENTS; BRAIN NEOPLASMS; CELL SURVIVAL; CHEMISTRY, PHYSICAL; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; ELECTRON TRANSPORT COMPLEX I; ENZYME INHIBITORS; HUMANS; LIPIDS; MITOCHONDRIA; NEUROBLASTOMA; PARKINSON DISEASE, SECONDARY; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES;

EID: 33846638231     PISSN: 0161813X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuro.2006.06.002     Document Type: Article

References (33)

1. + dependence of the neuronal transport of dopamine. J Neurochem 59 (1992) 1795-1804
2. 3H]GBR 12935 binding in vitro to rat striatal membranes: labeling of the dopamine uptake complex. J Neurochem 48 (1987) 1887-1896
3. Gray N.M., Cheng B.K., Mick S.J., Lair C.M., and Contreras P.C. Phencyclidine-like effects of tetrahydroisoquinolines and related compounds. J Med Chem 32 (1989) 1242-1248
4. Hatefi Y. Preparation and properties of NADH:ubiquinone oxidoreductase (complex I). EC 1.6.5.3. In: Fleischers S., and Packer L. (Eds). Methods in Enzymology 53 (1978), Academic Press, New York, NY 11-14
5. Kawai H., Kotake Y., and Ohta S. Inhibition of dopamine receptors by endogenous amines: binding to striatal receptors and pharmacological effects on locomotor activity. Bioorg Med Chem Lett 10 (2000) 1669-1671
6. Kawai H., Kotake Y., and Ohta S. Dopamine transporter and catechol-O-methyltransferase activities are required for the toxicity of 1-(3′,4′-dihydroxybenzyl)-l,2,3,4-tetrahydroisoquinoline. Chem Res Toxicol 13 (2000) 1294-1301
7. Kawai H., Makino Y., Hirobe M., and Ohta S. Novel endogenous 1,2,3,4-tetrahydroisoquinoline derivatives: uptake by dopamine transporter and activity to induce parkinsonism. J Neurochem 70 (1998) 745-751
8. Kohno M., Ohta S., and Hirobe M. Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline as novel endogenous amines in rat brain. Biochem Biophys Res Commun 140 (1986) 448-454
9. + analogs acting on mitochondria and inducing neuro-degeneration. Curr Med Chem 10 (2003) 2507-2516
10. Kotake Y., Ohta S., Kanazawa I., and Sakurai M. Neurotoxicity of an endogenous brain amine, 1-benzyl-l,2,3,4-tetrahydroisoquinoline in organotypic slice co-culture of mesencephalon and striatum. Neuroscience 117 (2003) 63-70
11. Kotake Y., Taguchi R., Okuda K., Sekiya Y., Tasaki Y., Hirobe M., et al. Neuroprotective effect of 1-methyl-1,2,3,4-tetrahydroisoquinoline on cultured rat mesencephalic neurons in the presence or absence of various neurotoxins. Brain Res 1033 (2005) 143-150
12. Kotake Y., Tasaki Y., Makino Y., Ohta S., and Hirobe M. 1-Benzyl-l,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. J Neurochem 65 (1995) 2633-2638
13. Kotake Y., Yoshida M., Ogawa M., Tasaki Y., Hirobe M., and Ohta S. Chronic administration of 1-benzyl-1,2,3,4-tetrahydroisoquinoline, an endogenous amine in the brain, induces parkinsonism in a primate. Neurosci Lett 217 (1996) 69-71
14. Langston J.W., Ballard P., Tetrad J.W., and Irwin I. Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219 (1983) 979-980
15. Lardy H.A., and Ferguson S.M. Oxidative phosphorylation in mitochondria. Annu Rev Biochem 38 (1969) 991-1034
16. Lowry O.H., Rosebrough N.J., Farr A.L., and Randall R.J. Protein measurement with the Folin phenol reagent. J Biol Chem 193 (1951) 265-275
17. Makino Y., Ohta S., Tasaki Y., Tachikawa O., Kashiwasake M., and Hirobe M. A novel and neurotoxic tetrahydroisoquinoline derivative in vivo: formation of l,3-dimethyl-l,2,3,4-tetrahydroisoquinoline, a condensation product of amphetamines, in brains of rats under chronic ethanol treatment. J Neurochem 55 (1990) 963-969
18. Matsubara K., Senda T., Uezono T., Fukushima S., Ohta S., Igarashi K., et al. Structural significance of azaheterocyclic amines related to Parkinson's disease for dopamine transporter. Eur J Pharmacol 348 (1998) 77-84
19. McNaught K., Carrupt P.A., Altomare C., Cellamare S., Carotti A., Testa B., et al. Isoquinoline derivatives as endogenous neurotoxins in the etiology of Parkinson's disease. Biochem Pharmacol 56 (1998) 921-933
20. McNaught K., Thull U., Carrupt P.A., Altomare C., Cellamare S., Carotti A., et al. Inhibition of complex I by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Biochem Pharmacol 27 (1995) 1903-1911
21. McNaught K., Thull U., Carrupt P.A., Altomare C., Cellamare S., Carotti A., et al. Toxicity to PC12 cells of isoquinoline derivatives structurally related to 1-methyl-4-phenyl-l,2,3,6-tetrahydropyridine. Neurosci Lett 206 (1996) 37-40
22. McNaught K., Thull U., Carrupt P.A., Altomare C., Cellamare S., Carotti A., et al. Effects of isoquinoline derivatives structurally related to 1-methyl-4-phenyl-l,2,3,6-tetrahydropyridine (MPTP) on mitochondrial respiration. Biochem Pharmacol 51 (1996) 1503-1511
23. 3H]dopamine uptake into striatal synaptosomes by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-l,2,3,6-tetrahydropyridine. Biochem Pharmacol 52 (1996) 29-34
24. Mizuno Y., Yoshino H., Ikebe S., Hattori N., Kobayashi T., Shimoda-Matsubayashi S., et al. Mitochondrial dysfunction in Parkinson's disease. Ann Neurol 44 (1998) S99-S109
25. Morikawa N., Naoi M., Maruyama W., Ohta S., Kotake Y., Kawai H., et al. Effects of various tetrahydroisoquinoline derivatives on mitochondrial respiration and the electron transfer complexes. J Neural Transm 105 (1998) 677-688
26. Nagatsu T. Isoquinoline neurotoxins in the brain and Parkinson's disease. Neurosci Res 29 (1997) 99-111
27. Parker Jr. W.D., Boyson S.J., and Parks J.K. Abnormalities of the electron transport chain in idiopathic Parkinson's disease. Ann Neurol 26 (1989) 719-723
28. 1 reductase (complex I) deficiency in Parkinson's disease. J Neurochem 55 (1990) 2142-2145
29. Storch A., Ott S., Hwang Y.I., Ortmann R., Hein A., Frenzel S., et al. Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson's disease: studies using heterologous expression systems of the dopamine transporter. Biochem Pharmacol 63 (2002) 909-920
30. Tasaki Y., Makino Y., Ohta S., and Hirobe M. 1-Methyl-l,2,3,4-tetrahydroisoquinoline, decreasing in 1-methyl-4-phenyl-l,2,3,6-tetrahydropyridine-treated mouse, prevents parkinsonism-like behavior abnormalities. J Neurochem 57 (1991) 1940-1943
31. Tipton K.F., and Singer T.P. Advances in our understanding of the mechanisms of the neurotoxicity of MPTP and related compounds. J Neurochem 61 (1993) 1191-1206
32. Yamato E., Hirakura M., and Sugasawa S. Synthesis of 6,7-dihydroxy-l,2,3,4-tetrahydroisoquinoline derivatives. Tetrahedron 22 Suppl 8 (1966) 129-134
33. Yoshida M., Niwa T., and Nagatsu T. Parkinsonism in monkeys produced by chronic administration of an endogenous substance of the brain, tetrahydroisoquinoline: the behavioral and biochemical changes. Neurosci Lett 119 (1990) 109-113