Pictet-Spengler condensation of the antiparkinsonian drug L-DOPA with D-glyceraldehyde. Opposite kinetic effects of Fe3+ and Cu2+ ions and possible implications for the origin of therapeutic side effects

Bioorganic and Medicinal Chemistry

Volumn 9, Issue 4, 2001, Pages 923-929

  Manini, Paola ^a   D'Ischia, Marco ^a   Prota, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPARKINSON AGENT; CARBOHYDRATE; COPPER ION; FERRIC ION; FORMALDEHYDE; GLYCERALDEHYDE; LEVODOPA;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTANTIA NIGRA;

ALDEHYDES; ANTIPARKINSON AGENTS; CHELATING AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COPPER; DEUTERIUM OXIDE; GLYCERALDEHYDE; IRON; KINETICS; LEVODOPA; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0035025586     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00309-6     Document Type: Article

References (27)

1. Napolitano A., Pezzella A., Misuraca G., Prota G. Exp. Opin. Ther. Patents. 8:1998;1249.
2. Dunnett S.B., Björklund A. Nature. 399:1999;A32.
3. Yahr M.D. Neurology. 60:1993;11.
4. Cedarbaum, J. M.; Scheilfer, L. S. In Pharmacological Basis of Therapeutics, 18th ed.; Godman L. S., Gilmann A. (Eds.); Macmillan: New York, 1990; Vol. 29, p 537.
5. Fahn, S. In The Scientific Basis for the Treatment of Parkinson's Disease. Olanow C. W., Lieberman A. N., (Eds.), Parthenon: Carnforth, UK, 1992; Vol. 89, p 111.
6. Brossi A., Focella A., Teitel S. Helv. Chim. Acta. 55:1972;15.
7. Daxenbichler M.E., Kleiman R., Weisleder D., VanEtten C.H., Carlson K.D. Tetrahedron Lett. 18:1972;1801.
8. Sandler, M.; Bonham Carter, S.; Hunter, K. R.; Stern, G. M. Nature, 1973, 439.
9. Finch C.E., Cohen D.M. Exp. Neurol. 143:1997;82.
10. Mlakar A., Batna A., Dudda A., Spiteller G. Free Rad. Res. 25:1996;525.
11. Zhang J., Snyder S.H. Proc. Natl. Acad. Sci. U.S.A. 89:1992;9382.
12. McDonald L.J., Moss J. Proc. Natl. Acad. Sci. U.S.A. 90:1993;6238.
13. Marin P., Maus M., Bockaert J., Glowinsky J., Premont J. Biochem. J. 309:1995;891.
14. Dexter D.T., Carayon A., Javoy-Agid F., Agid Y., Wells F.R., Daniel S.E., Lees A.J., Jenner P., Marsden C.D. Brain. 114:1991;1953.
15. Riederer P., Sofic E., Rausch W.D., Schmidt B., Reynolds G.P., Jellinger K., Youdim M.B.H. J. Neurochem. 52:1989;515.
16. Ibañez A.F., Yaculiano G.B., Moltrasio Iglesias G.Y. J. Heterocyclic Chem. 26:1989;907.
17. Ungemach F., Soerens D., Weber R., DiPierro M., Campos O., Mokry P., Cook J.M., Silverton J.V. J. Am. Chem. Soc. 102:1980;6976.
18. 13C NMR Spectroscopy; Chapman and Hall: London/New York, 1987.
19. Brossi A., Focella A., Teitel S. Helv. Chim. Acta. 55:1972;15.
20. Manini P., d'Ischia M., Lanzetta R., Parrilli M., Prota G. Bioorg. Med. Chem. 7:1999;2525.
21. Eliel, E. L., Wilen, S. H., Mander, L. N. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1995, p 115.
22. Collins, P. M., Ferrier, R. J. In Monosaccharides, their Chemistry and their Roles in Natural Products; John Wiley and Sons: New York, 1995, p 115.
23. Gerard C., Chehhal H., Hugel R.P. Polyhedron. 13:1994;591.
24. Walaas E., Walaas O., Haavaldsen S. Arch. Biochem. Biophys. 100:1963;97.
25. Kwik W.L., Purdy E., Stiefel E.I. J. Am. Chem. Soc. 96:1974;1638.
26. Monteiro H.P., Winterbourn C.C. Biochem. Pharmacol. 38:1989;4177.
27. Naoi M., Maruyama W., Niwa T., Nagatsu T. J. Neural Transm. 41:1994;197.