Occurrence and distribution of salsolinol-like compound, 1-acetyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (ADTIQ) in Parkinsonian brains

Journal of Neural Transmission

Volumn 119, Issue 4, 2012, Pages 435-441

  Deng, Yulin ^a   Zhang, Yongqian ^a   Li, Yujuan ^a   Xiao, Shengyuan ^a   Song, Dewei ^a   Qing, Hong ^a   Li, Qin ^a   Rajput, Ali H ^b  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

1 Acetyl 6,7 dihydroxy 1,2,3,4 tetrahydroisoquinoline; Dopamine; Human brain tissues; Methylglyoxal; Parkinson's disease

Indexed keywords

1 ACETYL 6,7 DIHYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; DOPAMINE; METHYLGLYOXAL; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BRAIN LEVEL; BRAIN TISSUE; CAUDATE NUCLEUS; CEREBELLUM; CONTROLLED STUDY; FRONTAL CORTEX; FROZEN SECTION; HUMAN; HUMAN TISSUE; PARKINSON DISEASE; PRIORITY JOURNAL; PUTAMEN; SUBSTANTIA NIGRA;

AGED; AGED, 80 AND OVER; ANALYSIS OF VARIANCE; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOPAMINE; FEMALE; HUMANS; MALE; MASS SPECTROMETRY; MIDDLE AGED; PARKINSONIAN DISORDERS; POSTMORTEM CHANGES; PYRUVALDEHYDE; TETRAHYDROISOQUINOLINES;

EID: 84863423974     PISSN: 03009564     EISSN: 14351463     Source Type: Journal    
DOI: 10.1007/s00702-011-0724-4     Document Type: Article

References (23)

1. Antkiewicz-Michaluk L, Romañska I, Papla I, Michaluk J, Bakalarz M, Vetulani J, Krygowska-Wajs A, Szczudlik A (2000) Neurochemical changes induced by acute and chronic administration of 1, 2, 3, 4-tetrahydroisoquinoline and salsolinol in dopaminergic structures of rat brain. Neuroscience 96:59-64
2. Davis GC, Williams AC, Markey SP, Ebert MH, Caine ED, Reichert CM, Kopin IJ (1979) Chronic parkinsonism secondary to intravenous injection of meperidine analogues. Psychiatry Res 1:249-254
3. Deng Y, Yu PH (1999) Assessment of deamination of aminoacetone, an endogenous substrate for semicarbazide-sensitive amine oxidase. Anal Biochem 270:97-102
4. Deng Y, Maruyama W, Kawai M, Dostert P, Yamamura H, Takahashi T, Naoi M (1997) Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair highperformance liquid chromatography using β-cyclodextrin as a chiral mobile phase additive. J Chromatogr B 689:313-320
5. Gerlach M, Koutsilieri E, Riederer P (1998) N-Methyl-(R)-salsolinol and its relevance to Parkinson's disease. Lancet 351:850-851
6. Hornykiewies O, Kish SJ (1986) Biochemical pathology of Parkinson's disease. Adv Neurol 45:19-34
7. Langston JW, Ballard P, Tetrud JW, Irwin I (1983) Chronic parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219:979-980
8. Langston JW, Irwin I, Langston EB, Forno LS (1984) 1-Methyl-4- phenylpyridinium ion (MPP+): identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci Lett 48:87-92
9. Meng QH, Lu JX, Randall E, Adeli K, Krahn J (2010) Increased plasma methylglyoxal level and inflammation are associated with diabetic nephropathy. Clin Biochem 43:780-780
10. Minami C, Deng Y, Maruyama W, Takahashi T, Kawai M, Nakahara D, Naoi M (1998) Generation of reactive oxygen species accounts for cytotoxicity of an endogenous dopaminergic neurotoxin (R)-N-methylsalsolinol, to differentiated dopaminergic SH-SY5Y cells. J Neural Transm 105:397-405
11. Naoi M, Maruyama W (1999) N-methyl-(R)-salsolinol, a dopamine neurotoxin, in Parkinson's disease. Adv Neurol 46:259-264
12. Naoi M, Maruyama W, Zhang JH, Takahashi T, Deng Y, Dostert P (1995) Enzymatic oxidation of the dopaminergic neurotoxin, 1 (R), 2(N)-dimethyl-6, 7-dihydroxy-l, 2, 3, 4-tetrahydroisoquinoline, into 1, 2(N)-dimethyl-6, 7-dihydroxyisoquinolinium ion. Life Sci 57:1061-1066
13. Naoi M, Maruyama W, Dostert P, Kohda K, Kaiya T (1996) A novel enzyme enantio-selectively synthesizes (R)salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl(R)salsolinol. Neurosci Lett 212:183-186
14. +-like neurotoxin, 1, 2-dimethyl-6, 7-dihydroxyisoquinolinium ion, in the substantia nigra of human brains. Neurosci Lett 235:81-84
15. Naoi M, Maruyama W, Kasamatsu T, Dostert P (1998a) Oxidation of N-methyl(R)salsolinol: involvement to neurotoxicity and neuroprotection by endogenous catechol isoquinolines. J Neural Transm Suppl 52:125-138
16. Naoi M, Maruyama W, Nakao N, Ibi T, Sahashi K, Benedetti MS (1998b) (R) Salsolinol N-methyltransferase activity increases in parkinsonian lymphocytes. Ann Neurol 43:212-216
17. Rajput AH (2001) Environmental toxins accelerate Parkinson's disease onset. Neurology 56:4-5
18. +. Biochem Biophys Res Commun 134:743-748
19. Richard JP (1984) Acid-base catalysis of the elimination and isomerization reactions of triose phosphates. J Am Chem Soc 106:4926-4936
20. Teitel S, O'brien J, Brossi A (1972) Alkaloids in mammalian tissues. 2. Synthesis of (+)-and (-)-1-substituted-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinolines. J Med Chem 15:845-846
21. Vander Jagt DL (2008) Methylglyoxal, diabetes mellitus and diabetic complications. Drug Metab Drug Interact 23:93-124
22. Yang LB, Lindholm K, Yan R, Citron M, Xia W, Yang X, Beach T, Sue L, Wong P, Price D, Li R, Shen Y (2003) Elevated betasecretase expression and enzymatic activity detected in sporadic Alzheimer disease. Nat Med 9:3-4
23. Zhang Y, Wang L, Mu X, Duan J, Zhu Y, Qing H, Li Y, Xiao S, Deng Y (2011) Assessment of salsolinol N-methyltransferase activity in rat peripheral lymphocytes by liquid chromatography-electrospray time-of-flight mass spectrometry. Anal Bioanal Chem 399:351-354