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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
https://doi.org/10.1021/jm970207b
Copyright © 1997 American Chemical Society

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    Abstract

    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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