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Chemical Compound Review

TOPA     (2S)-2-amino-3-(2,4,5- trihydroxyphenyl)pro...

Synonyms: L-Hydroxydopa, Hydroxy-L-dopa, Lopac-H-2380, AG-E-68020, CHEMBL1256516, ...
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Disease relevance of L-Hydroxydopa


Psychiatry related information on L-Hydroxydopa


High impact information on L-Hydroxydopa


Chemical compound and disease context of L-Hydroxydopa

  • The growth inhibitory effect of 6-hydroxydopa, a cytotoxic analog of L-dopa, was studied in melanotic and amelanotic Cloudman melanoma, mouse fibroblast L929 and Chinese hamster ovary cells [1].
  • Moreover, the possible protective effects of GM1 were assessed following exposure of cultured cerebellar granule cells and dopaminergic mesencephalic neurons to different doses of 6-OH-DOPA, a metabolite of the dopamine pathway which has excitotoxic properties and has been hypothesized to participate in the pathology of Parkinson's disease [12].

Biological context of L-Hydroxydopa

  • Although 6-hydroxydopa has been implicated in neurotoxicity, the data presented suggest that this compound has a functional role at an enzyme active site [7].
  • Similar modifications in the development of central noradrenergic neurons were found in the offspring of rats which had received 6-hydroxydopa at 16 days of gestation [13].
  • Neonatal treatment with 6-hydroxydopa produced a significant increase only in Bmax in beta 1-adrenoceptors without changing Bmax and KD in beta 2-receptors. "Up' regulation in the density of beta 2-type of adrenoceptors seems to be caused by the 6-hydroxydopa-induced sympathetic lesion [14].
  • Increased water consumption developed the fourth day for those surviving toxic levels of 6-OH-DOPA given subcutaneously as compared with controls [15].

Anatomical context of L-Hydroxydopa


Associations of L-Hydroxydopa with other chemical compounds


Gene context of L-Hydroxydopa


Analytical, diagnostic and therapeutic context of L-Hydroxydopa


  1. Selective toxicity of 6-hydroxydopa for melanoma cells. Wick, M.M., Byers, L., Ratliff, J. J. Invest. Dermatol. (1979) [Pubmed]
  2. Excitotoxicity of L-dopa and 6-OH-dopa: implications for Parkinson's and Huntington's diseases. Olney, J.W., Zorumski, C.F., Stewart, G.R., Price, M.T., Wang, G.J., Labruyere, J. Exp. Neurol. (1990) [Pubmed]
  3. Opiate-enhanced toxicity and noradrenergic sprouting in rats treated with 6-hydroxydopa. Harston, C.T., Clark, M.B., Hardin, J.C., Kostrzewa, R.M. Eur. J. Pharmacol. (1981) [Pubmed]
  4. Hypersensitivity of cardiac beta-adrenergic receptors after neonatal treatment of rats with 6-hydroxydopa. Nomura, Y., Kajiyama, H., Segawa, T. Eur. J. Pharmacol. (1980) [Pubmed]
  5. Neonatal 6-hydroxydopa, but not DSP-4, elevates brainstem monoamines and impairs inhibitory avoidance learning in developing rats. Cornwell-Jones, C.A., Decker, M.W., Chang, J.W., Cole, B., Goltz, K.M., Tran, T., McGaugh, J.L. Brain Res. (1989) [Pubmed]
  6. Effects of 6-hydroxydopa and 5,6-dihydroxytryptophan treatment on spontaneous motor activity and brain monoamines in mice. Segawa, T., Sakamoto, K., Naitoh, F. Jpn. J. Pharmacol. (1975) [Pubmed]
  7. A new redox cofactor in eukaryotic enzymes: 6-hydroxydopa at the active site of bovine serum amine oxidase. Janes, S.M., Mu, D., Wemmer, D., Smith, A.J., Kaur, S., Maltby, D., Burlingame, A.L., Klinman, J.P. Science (1990) [Pubmed]
  8. Skin conductance activity after intraventricular administration of 6-hydroxydopa in rats. Yamamoto, K., Hoshino, T., Takahashi, Y., Kaneko, H., Ozawa, N. Biol. Psychiatry (1991) [Pubmed]
  9. Inhibition of copper amine oxidase by haloamines: a killer product mechanism. Medda, R., Padiglia, A., Pedersen, J.Z., Agrò, A.F., Rotilio, G., Floris, G. Biochemistry (1997) [Pubmed]
  10. Studies on the formation of 6-hydroxydopamine in mouse brain after administration of 2,4,5-trihydroxyphenylalanine (6-hydroxyDOPA). Evans, J.M., Cohen, G. J. Neurochem. (1989) [Pubmed]
  11. Tryptamine as substrate and inhibitor of lentil seedling copper amine oxidase. Medda, R., Padiglia, A., Finazzi Agrò, A., Pedersen, J.Z., Lorrai, A., Floris, G. Eur. J. Biochem. (1997) [Pubmed]
  12. Gangliosides and neurotrophic factors in neurodegenerative diseases: from experimental findings to clinical perspectives. Fusco, M., Vantini, G., Schiavo, N., Zanotti, A., Zanoni, R., Facci, L., Skaper, S.D. Ann. N. Y. Acad. Sci. (1993) [Pubmed]
  13. Differential effect of various 6-hydroxydopa treatments on the development of central and peripheral noradrenergic neurons. Jaim-Etcheverry, G., Zieher, L.M. Eur. J. Pharmacol. (1977) [Pubmed]
  14. The increase of cardiac beta 1-subtype of beta-adrenergic receptors in adult rats following neonatal 6-hydroxydopa treatment. Kajiyama, H., Obara, K., Nomura, Y., Segawa, T. Eur. J. Pharmacol. (1982) [Pubmed]
  15. Short- and long-term effects of graduated doses of DL-6-OH-DOPA upon marsh mice. Bischoff, F., Bryson, G. Res. Commun. Chem. Pathol. Pharmacol. (1979) [Pubmed]
  16. 6-hydroxydopa during development of central adrenergic neurons produces different long-term changes in rat brain noradrenaline. Zieher, L.M., Jaim-Etcheverry, G. Brain Res. (1975) [Pubmed]
  17. Excitotoxins L-beta-oxalyl-amino-alanine (L-BOAA) and 3,4,6-trihydroxyphenylalanine (6-OH-DOPA) inhibit [3H] alpha-amino-3- hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) binding in human hippocampus. Künig, G., Hartmann, J., Niedermeyer, B., Deckert, J., Ransmayr, G., Heinsen, H., Beckmann, H., Riederer, P. Neurosci. Lett. (1994) [Pubmed]
  18. Loss of nerve cell bodies in caudal locus coeruleus following treatment of neonates with 6-hydroxydopa. Clark, M.B., King, J.C., Kostrzewa, R.M. Neurosci. Lett. (1979) [Pubmed]
  19. Parallel changes in brain flunitrazepam binding and density of noradrenergic innervation. Medina, J.H., Novas, M.L. Eur. J. Pharmacol. (1983) [Pubmed]
  20. The relationship of benzodiazepine binding sites to the norepinephrine projection in the hypothalamus of the adult rat. Harary, N., Kellogg, C. Brain Res. (1989) [Pubmed]
  21. Specific detection of quinoproteins by redox-cycling staining. Paz, M.A., Flückiger, R., Boak, A., Kagan, H.M., Gallop, P.M. J. Biol. Chem. (1991) [Pubmed]
  22. An investigation of bovine serum amine oxidase active site stoichiometry: evidence for an aminotransferase mechanism involving two carbonyl cofactors per enzyme dimer. Janes, S.M., Klinman, J.P. Biochemistry (1991) [Pubmed]
  23. Differential effects of metal ligands on synaptic membrane glutamate binding and uptake systems. Michaelis, E.K., Belieu, R.M., Grubbs, R.D., Michaelis, M.L., Chang, H.H. Neurochem. Res. (1982) [Pubmed]
  24. Amine oxidases from Aspergillus niger: identification of a novel flavin-dependent enzyme. Schilling, B., Lerch, K. Biochim. Biophys. Acta (1995) [Pubmed]
  25. Choline acetyltransferase activity increases in the brain stem of rats treated at birth with 6-hydroxydopa. Jaim-Etcheverry, G., Teitelman, G., Zieher, L.M. Brain Res. (1975) [Pubmed]
  26. Production of 6-hydroxydopa by human tyrosinase. Hansson, C., Rorsman, H., Rosengren, E., Wittbjer, A. Acta Derm. Venereol. (1985) [Pubmed]
  27. TRH-induced behavioral arousal in developing rats pretreated with 6-hydroxydopa. Nomura, Y., Oki, K. Pharmacol. Biochem. Behav. (1980) [Pubmed]
  28. Studies on the mechanism of sprouting of noradrenergic terminals in rat and mouse cerebellum after neonatal 6-hydroxydopa. Kostrezewa, R.M., Klara, J.W., Robertson, J., Walker, L.C. Brain Res. Bull. (1978) [Pubmed]
  29. The influence of central chemical sympathectomy and reserpine on peripheral effects of noradrenaline and cyclic AMP dibutyrate injected into the cerebral ventricles. Brus, R., Herman, Z.S., Dzikowski, A., Zabawska, J. Arch. Immunol. Ther. Exp. (Warsz.) (1976) [Pubmed]
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