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Scientific article
English

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

Contributors

Brunner-Guenat, M.; Carrupt, Pierre-Alain; Lisa, G.; Testa, Bernard; Rose, S.; Thomas, K.; Jenner, P.; Ventura, P.

Published in

Journal of pharmacy and pharmacology, vol. 47, no. 10, p. 861-869

Publication date

1995

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

UNIGE 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 ISSN

0022-3573
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Technical informations

Creation

06/08/2010 10:46:39

First validation

06/08/2010 10:46:39

Update

14/03/2023 15:56:16

Status update

14/03/2023 15:56:16

Last indexation

29/10/2024 16:19:48
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