Preventative effects of 1,3-dimethyl- and 1,3-dimethyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline on MPTP-induced Parkinson's disease-like symptoms in mice

Brain Research

Volumn 1321, Issue , 2010, Pages 133-142

  Katagiri, Nobuyuki ^a   Chida, Satomi ^b   Abe, Kenji ^b   Nojima, Hiroshi ^b   Kitabatake, Michikazu ^a   Hoshi, Keiko ^a   Horiguchi, Yoshie ^a   Taguchi, Kyoji ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b OHU UNIVERSITY   (Japan)

Author keywords

1,2,3,4 tetrahydroisoquinoline; 1 methyl 4 phenyl 1,2,3,6 tetrahydroprydine; 1 methyl 4 phenylpyridinium ion; Cytotoxicity; Dopamine; Metabolite; Mouse; Parkinson's disease

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; 1,3 DIMETHYL N PROPARGYL 1,2,3,4 TETRAHYDROISOQUINOLINE; SELEGILINE; TETRAHYDROISOQUINOLINE DERIVATIVE; TYROSINE 3 MONOOXYGENASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BEHAVIOR DISORDER; BRADYKINESIA; CELL DEATH; CELL STRAIN; CELL VIABILITY; CIS ISOMER; CONTROLLED STUDY; CORPUS STRIATUM; CYTOTOXICITY; DOPAMINE BLOOD LEVEL; MALE; MOUSE; NEUROPROTECTION; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; SUBSTANTIA NIGRA; TRANS ISOMER;

ANIMALS; BRAIN; HYPOKINESIA; IMMUNOHISTOCHEMISTRY; MICE; NEUROPROTECTIVE AGENTS; PARKINSONIAN DISORDERS; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

MUS;

EID: 77549087710     PISSN: 00068993     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.brainres.2010.01.049     Document Type: Article

References (44)

1. Abe K., Taguchi K., Wasai T., Ren J., Utsunomiya I., Shinohara T., Miyatake T., and Sano T. Stereoselective effect of (R)- and (S)-1-methyl-1, 2, 3, 4-tetrahydroisoquinolines on a mouse model of Parkinson's disease. Brain Res. Bull. 56 (2001) 55-60
2. Abe K., Saitoh T., Horiguchi Y., Utsunomiya I., and Taguchi K. Synthesis and neurotoxicity of tetrahydroisoquinoline derivatives for studying Parkinson's disease. Biol. Pharm. Bull. 28 (2005) 1355-1362
3. Antkiewicz-Michaluk L., Lazarewicz J.W., Patsenka A., Kajta M., Zieminska E., Salinska E., Wasik A., Golembiowska K., and Vetulani J. The mechanism of 1, 2, 3, 4-tetrahydroisoquinolines neuroprotection: the importance of free radicals scavenging properties and inhibition of glutamate-induced excitotoxicity. J. Neurochem. 97 (2006) 846-856
4. Franklin K.B.J., and Paxinos G. The Mouse Brain in Stereotaxic Coordinates (1997), Academic Press, San Diego
5. Gerlach M., Youdim M.B., and Riederer P. Pharmacology of selegiline. Neurology 47 Suppl 3 (1996) S137-S145
6. Hao R., Norgren Jr. R.B., Lau Y.S., and Pfeiffer R.F. Cerebrospinal fluid of Parkinson's disease patients inhibits the growth and function of dopaminergic neurons in culture. Neurology 45 (1995) 138-142
7. Hao R., Ebadi M., and Pfeiffer R.F. Selegiline protects dopaminergic neurons in culture from toxic factor(s) present in the cerebrospinal fluid of patients with Parkinson's disease. Neurosci. Lett. 200 (1995) 77-80
8. Haber H., Collins M., and Melzig M.F. The in vitro formation of 1, 3-dimethyl-1, 2, 3, 4-tetrahydroisoquinoline, a neurotoxic metabolite of amphetamines. Adv. Behav. Biol. 44 (1995) 589-597
9. Imai Y., Soda M., Inoue H., Hattori N., Mizuno Y., and Takahashi R. An unfolded putative transmembrane polypeptide, which can lead to endoplasmic reticulum stress, is a substrate of Parkin. Cell 105 (2001) 891-902
10. Ishiwata K., Koyanagi Y., Abe K., Kawamura K., Taguchi K., Saitoh T., Toda J., Senda M., and Sano T. Evaluation of neurotoxicity of TIQ and MPTP and of parkinsonism-preventing effect of 1-MeTIQ by in vivo measurement of pre-synaptic dopamine transporters and post-synaptic dopamine D(2) receptors in the mouse striatum. J. Neurochem. 79 (2001) 868-876
11. Kanthasamy A.G., Kanthasamy A., Matsumoto R.R., Vu T.Q., and Truong D.D. Neuroprotective effects of the strychnine-insensitive glycine site NMDA antagonist (R)-HA-966 in an experimental model of Parkinson's disease. Brain Res. 759 (1997) 1-8
12. Katagiri N., Abe K., Kitabatake M., Utsunomiya I., Horiguchi Y., Hoshi K., and Taguchi K. Single administration of 1-benzyl-1, 2, 3, 4-tetrahydroisoquinoline increases the extracellular concentration of dopamine in rat striatum. Neuroscience 160 (2009) 820-828
13. Kitabatake M., Nagai J., Abe K., Tsuchiya Y., Ogawa K., Yokoyama T., Mohri K., Taguchi K., and Horiguchi Y. Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives on PC12 cells. Eur. J. Med. Chem. 44 (2009) 4034-4043
14. 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
15. Koshimura I., Imai H., Hidano T., Endo K., Mochizuki H., Kondo T., and Mizuno Y. Dimethoxyphenylethylamine and tetrahydropapaverine are toxic to the nigrostriatal system. Brain Res. 773 (1997) 108-116
16. Kotake Y., Tasaki Y., Makino Y., Ohta S., and Hirobe M. 1-Benzyl-1, 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
17. Kotake Y., Tasaki Y., Hirobe M., and Ohta S. Deprenyl decreases an endogenous parkinsonism-inducing compound, 1-benzyl-1, 2, 3, 4-tetrahydroisoquinoline in mice: in vivo and in vitro studies. Brain Res. 787 (1998) 341-343
18. Kotake Y., Sekiya Y., Okuda K., and Ohta S. Cytotoxicity of 17 tetrahydroisoquinoline derivatives in SH-SY5Y human neuroblastoma cells is related to mitochondrial NADH-ubiquinone oxidoreductase inhibition. Neurotoxicology 28 (2007) 27-32
19. 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
20. Makino Y., Ohta S., Tasaki Y., Tachikawa O., Kashiwasake M., and Hirobe M. A novel and neurotoxic tetrahydroisoquinoline derivative in vivo: formation of 1, 3-dimethyl-1, 2, 3, 4-tetrahydroisoquinoline, a condensation product of amphetamines, in brains of rats under chronic ethanol treatment. J. Neurochem. 55 (1990) 963-969
21. Makino Y., Tasaki Y., Kashiwasake M., Tachikawa O., Ohta S., and Hirobe M. Formation of a novel and neurotoxic tetrahydroisoquinoline derivative, 1, 3-dimethyltetrahydroisoquinoline (1, 3DiMeTIQ), a condensation product of amphetamines and acetaldehyde in vivo. Adv. Behav. Biol. 38A (1990) 325-328
22. Maruyama W., and Naoi M. Neuroprotection by (-)-deprenyl and related compounds. Mech. Ageing Dev. 111 (1999) 189-200
23. McNaught K.S., Thull U., Carrupt P.A., Altomare C., Cellamare S., Carotti A., Testa B., Jenner P., and Marsden C.D. Effects of isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) on mitochondrial respiration. Biochem. Pharmacol. 51 (1996) 1503-1511
24. McNaught K.S., Thull U., Carrupt P.A., Altomare C., Cellamare S., Carotti A., Testa B., Jenner P., and Marsden C.D. Inhibition of [3H]dopamine uptake into striatal synaptosomes by isoquinoline derivatives structurally related to 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine. Biochem. Pharmacol. 52 (1996) 29-34
25. Mizuno Y., Sone N., and Saitoh T. Effects of 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine and 1-methyl-4-phenylpyridinium ion on activities of the enzymes in the electron transport system in mouse brain. J. Neurochem. 48 (1987) 1787-1793
26. Mytilineou C., Radcliffe P., Leonardi E.K., Werner P., and Olanow C.W. l-deprenyl protects mesencephalic dopamine neurons from glutamate receptor-mediated toxicity in vitro. J. Neurochem. 68 (1997) 33-39
27. Nagatsu T., and Yoshida M. An endogenous substance of the brain, tetrahydroisoquinoline, produces parkinsonism in primates with decreased dopamine, tyrosine hydroxylase, and biopterin in the nigrostriatal regions. Neurosci. Lett. 87 (1988) 178-182
28. Nakagawa H., Nihonmatsu N., Ohta S., and Hirobe M. Effects of new endogenous nonprotein amino acids, 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid derivatives, on behavior of mice. Biochem. Biophys. Res. Commun. 225 (1996) 1027-1034
29. Naoi M., Maruyama W., Dostert P., Hashizume Y., Nakahara D., Takahashi T., and Ota M. Dopamine-derived endogenous 1(R), 2(N)-dimethyl-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline, N-methyl-(R)-salsolinol, induced parkinsonism in rat: biochemical, pathological, and behavioral studies. Brain Res. 709 (1996) 285-295
30. Niwa T., Takeda N., Kaneda N., Hashizume Y., and Nagatsu T. Presence of tetrahydroisoquinoline and 2-methyl-tetrahydroquinoline in parkinsonian and normal human brains. Biochem. Biophys. Res. Commun. 144 (1987) 1084-1089
31. Ogawa M., Hirose Y., Ohara S., Ono T., and Watanabe Y. A simple quantitative bradykinesia test in MPTP-treated mice. Res. Commun. Chem. Pathol. Pharmacol. 50 (1985) 435-441
32. Ohta S., Kohno M., Makino Y., Tachikawa O., and Hirobe M. Tetrahydroisoquinoline and 1-methyltetrahydroisoquinoline are present in the human brain: relation to Parkinson's disease. Biomed. Res. 8 (1987) 453-456
33. Parrado J., Absi E., Ayala A., Castaño A., Cano J., and Machado A. The endogenous amine 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline prevents the inhibition of complex I of the respiratory chain produced by MPP+. J. Neurochem. 75 (2000) 65-71
34. Patsenka A., and Antkiewicz-Michaluk L. Inhibition of rodent brain monoamine oxidase and tyrosine hydroxylase by endogenous compounds - 1, 2, 3, 4-tetrahydroisoquinoline alkaloids. Pol. J. Pharmacol. 56 (2004) 727-734
35. Ricaurte G.A., Langston J.W., DeLanney L.E., Irwin I., and Brooks J.D. Dopamine uptake blockers protect against the dopamine depleting effect of 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) in the mouse striatum. Neurosci. Lett. 59 (1985) 259-264
36. Saitoh T., Yamashita A., Abe K., Ogawa K., Kitabatake M., Taguchi K., and Horiguchi Y. Synthesis of chiral 3-methyl- and 3-methyl-N-propargyl-1, 2, 3, 4-tetrahydroisoquinoline and prevention of MPP+-induced cytotoxicity. Med. Chem. 4 (2008) 531-538
37. Shimura H., Schlossmacher M.G., Hattori N., Frosch M.P., Trockenbacher A., Schneider R., Mizuno Y., Kosik K.S., and Selkoe D.J. Ubiquitination of a new form of alpha-synuclein by parkin from human brain: implications for Parkinson's disease. Science 293 (2001) 263-269
38. Shinohara T., Toda J., and Sano T. An improved synthesis of 1, 2, 3, 4-tetrahydroisoquinolines via intramolecular cyclization of N-acyl-N-(aryl)methyl-2-(phenylsulfinyl)ethylamine by Pummerer reaction. Chem. Pharm. Bull. 45 (1997) 813-819
39. Singer T.P., Castagnoli Jr. N., Ramsay R.R., and Trevor A.J. Biochemical events in the development of parkinsonism induced by 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine. J. Neurochem. 49 (1987) 1-8
40. Sjöquist B., and Magnuson E. Analysis of salsolinol and salsoline in biological samples using deuterium-labelled internal standards and gas chromatography-mass spectrometry. J. Chromatogr. 183 (1980) 17-24
41. Sjöquist B., Eriksson A., and Winblad B. Salsolinol and catecholamines in human brain and their relation to alcoholism. Prog. Clin. Biol. Res. 90 (1982) 57-67
42. Sjöquist B., and Ljungquist C. Identification and quantification of 1-carboxysalsolinol and salsolinol in biological samples by gas chromatography-mass spectrometry. J. Chromatogr. 343 (1985) 1-8
43. Tariq M., Khan H.A., Al Moutaery K., and Al Deeb S. Protective effect of quinacrine on striatal dopamine levels in 6-OHDA and MPTP models of Parkinsonism in rodents. Brain Res. Bull. 54 (2001) 77-82
44. Tasaki Y., Makino Y., Ohta S., and Hirobe M. 1-Methyl-1, 2, 3, 4-tetrahydroisoquinoline, decreasing in 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine-treated mouse, prevents parkinsonism-like behavior abnormalities. J. Neurochem. 57 (1991) 1940-1943