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  • monoamine oxidase  (2)
  • 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline  (1)
  • Keywords: 1(N)-Amino-4-phenyl-1  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Oxidation of 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine, a 1-amino analog of MPTP, by type A and B monoamine oxidase (1998)
    Springer
    Journal of neural transmission 105 (1998), S. 1253-1264 
    Details
    ISSN: 1435-1463
    Keywords: Keywords: 1(N)-Amino-4-phenyl-1 ; 2 ; 3 ; 6-tetrahydropyridine ; oxidation ; monoamine oxidase ; MPTP ; MPP+ ; human brain synaptosomes.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary. A 1-amino analog of MPTP, 1(N)-amino-4-phenyl-1,2,3,6-tetrahydropyridine, was synthesized and the oxidation was examined using human synaptosomal mitochondria as sources of type A and B monoamine oxidase. An oxidation product, 1-amino-4-phenylpyridinium ion, was quantified by high-performance liquid chromatography-fluorometric detection. The amino analog was a substrate of both type A and B monoamine oxidase and the oxidation depended linearly on the enzyme amount and the reaction time with an optimal pH around 7.5. After the systemic injection of the amino analog in C57/black mice for one week, 1-amino-4-phenylpyridinium ion was detected in the brain. 1(N)-Amino-4-phenyl-1,2,3,6-tetrahydropyridine was proved to be cytotoxic to pheochromocytoma PC12 cells, and it may be a new neurotoxin bioactivated through the oxidation by type A and B monoamine oxidase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s007020050128
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  • 2
    Electronic Resource
    Electronic Resource
    Naturally-occurring isoquinolines perturb monoamine metabolism in the brain: studied by in vivo microdialysis (1993)
    Springer
    Journal of neural transmission 94 (1993), S. 91-102 
    Details
    ISSN: 1435-1463
    Keywords: Tetrahydroisoquinolines ; monoamine oxidase ; catechol-O-methyl-transferase ; monoamines ; rat striatum ; in vivo microdialysis ; Parkinson's disease ; alcoholism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Naturally occurring isoquinolines affected the monoamine metabolism in the rat striatum, as proved by in vivo microdialysis technique. By analysis of monoamines and their metabolites in the dialysate, dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines were found to inhibit monoamine oxidase and catechol-O-methyltransferase activity. 1-Methyl- and 2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline were found to inhibit activity of type A monoamine oxidase most markedly. To compare the structure-activity relationship, corresponding isoquinolines without a catechol structure were also examined. The inhibition by catechol isoquinolines was more manifest than those without a catechol structure. Among latter isoquinolines, N-methyl-isoquinolinium ion was the most potent inhibitor of monoamine oxidase. In addition, catechol isoquinolines increased monoamine levels in the brain. The number and the site of the methyl group are essentially required for the inhibition of monoamine oxidase and a catechol structure for that of catechol-O-methyl-transferase. These results are discussed in relation to possible involvement of these isoquinolines to the clinical features of some neuro-psychiatric diseases, such as alcoholism or in L-DOPA therapy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01245003
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Uptake of a neurotoxin-candidate, (R)-1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline into human dopaminergic neuroblastoma SH-SY5Y cells by dopamine transport system (1994)
    Springer
    Journal of neural transmission 98 (1994), S. 107-118 
    Details
    ISSN: 1435-1463
    Keywords: Uptake ; inhibition ; dopamine transporter ; 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline ; 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline ; 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion ; neuroblastoma SH-SY5Y cells
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Uptake of catechol isoquinolines to dopamine cells was studied using human dopaminergic neuroblastoma SH-SY5Y cells. Only (R)-1,2-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [(R)-1,2-DiMeDHTIQ] was transported by dopamine uptake system, while (S)-1,2-DiMeDHTIQ, (R)- and (S)-1-methyl-6,7-dihydroxy-tetrahydroisoquinoline, and 1,2-dimethyl-6,7-dihydroxyisoquinolinum ion were not. Kinetical study showed that the uptake of (R)-1,2-DiMeDHTIQ followed the Michaelis-Menten equation, and the values of the Michaelis constant and the maximal velocity were obtained to be 102.6 ± 36.9 μM and 66.0 ± 2.8 pmol/min/mg protein. Dopamine was found to inhibit (R-1-DiMeDHTIQ uptake competitively. These results suggest that the selective uptake by dopamine transporter may account for the specific neurotoxicity of (R)-1,2-DiMeDHTIQ to dopamine neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01277014
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    Paper (German National Licenses)
    Fulltext
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