Scientific article
English

Esters of L-dopa: structure-hydrolysis relationships and ability to induce circling behaviour in an experimental model of hemiparkinsonism

Published inJournal of pharmacy and pharmacology, vol. 47, no. 10, p. 861-869
Publication date1995
Abstract

A number of carboxylate esters of L-dopa, some of which are novel, were examined for their physicochemical and biological properties. A few esters of tyrosine and phenylalanine were included for comparison. The compounds displayed great differences in their lipophilicity and stability towards chemical and enzymatic (human plasma) hydrolysis. Within subseries, relationships exist between structural properties and rate constants of chemical or enzymatic hydrolysis. In an experimental model of hemiparkinsonism (circling behaviour in rats), some of the L-dopa esters (the isopropyl, sec-butyl and 2-(tetrahydropyranyl)methyl esters) showed an activity distinctly greater than that of L-dopa, although the difference was not statistically significant.

Keywords
  • Animals
  • Behavior, Animal/*drug effects
  • Chemistry, Physical
  • Disease Models, Animal
  • Esters/chemical synthesis/*chemistry/*pharmacology
  • Humans
  • Hydrolysis
  • Levodopa/*analogs & derivatives/chemistry/*pharmacology
  • Male
  • Parkinson Disease, Secondary/*drug therapy/*physiopathology
  • Physicochemical Phenomena
  • Prodrugs/chemical synthesis/*chemistry/*pharmacology
  • Rats
  • Rats, Wistar
  • Solubility
  • Structure-Activity Relationship
Affiliation entities Not a UNIGE publication
Citation (ISO format)
BRUNNER-GUENAT, M. et al. Esters of L-dopa: structure-hydrolysis relationships and ability to induce circling behaviour in an experimental model of hemiparkinsonism. In: Journal of pharmacy and pharmacology, 1995, vol. 47, n° 10, p. 861–869. doi: 10.1111/j.2042-7158.1995.tb05755.x
Identifiers
Journal ISSN0022-3573
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