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Synthesis and Pharmacological Characterization of Aminocyclopentanetricarboxylic Acids:  New Tools to Discriminate between Metabotropic Glutamate Receptor Subtypes

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Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, URA 400 CNRS, Université René Descartes-Paris V, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France, and Centre INSERM-CNRS de Pharmacologie-Endocrinologie, UPR 9023, rue de la Cardonille, 34094 Montpellier Cedex 5, France
Cite this: J. Med. Chem. 1997, 40, 19, 3119–3129
Publication Date (Web):September 12, 1997
Copyright © 1997 American Chemical Society

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    The four stereoisomers of 1-aminocyclopentane-1,3,4-tricarboxylic acid {ACPT-I (18) and -II (19), (3R,4R)-III [(−)-20], and (3S,4S)-III [(+)-20]} have been synthesized and evaluated for their effects at glutamate receptors subtypes. ACPTs are ACPD analogues in which a third carboxylic group has been added at position 4 in the cyclopentane ring. None of the ACPT isomers showed a significant effect on ionotropic NMDA, KA, and AMPA receptors. On the other hand, ACPT-II (19) was found to be a general competitive antagonist for metabotropic receptors (mGluRs) and exhibited a similar affinity for mGluR1a (KB = 115 ± 2 μM), mGluR2 (KB = 88 ± 21 μM), and mGluR4a (KB = 77 ± 9 μM), the representative members of group I, II and III mGluRs, respectively. Two other isomers, ACPT-I (18) and (+)-(3S,4S)-ACPT-III [(+)-20], were potent agonists at the group III receptor mGluR4a (EC50 = 7.2 ± 2.3 and 8.8 ± 3.2 μM) and competitive antagonists with low affinity for mGluR1a and mGluR2 (KB > 300 μM). Finally, (−)-(3R,4R)-ACPT-III [(−)-20] was a competitive antagonist with poor but significant affinity for mGluR4a (KB = 220 μM). These results demonstrate that the addition of a third carboxylic group to ACPD can change its activity (from agonist to antagonist) and either increase or decrease its selectivity and/or affinity for the various mGluR subtypes.

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     URA 400 CNRS, Paris.

     Current address:  Unité de Phytopharmacie et des Médiateurs Chimiques, INRA, route de Saint-Cyr, 78026 Versailles, France.


    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.


     UPR 9023 CNRS, Montpellier.

     Abstract published in Advance ACS Abstracts, August 15, 1997.

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