Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors.

Research output: Contribution to journalJournal articleResearchpeer-review

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Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors. / Rasmussen, Julie; Storgaard, Morten; Pickering, Darryl S; Bunch, Lennart.

In: ChemMedChem, Vol. 6, No. 3, 07.03.2011, p. 498-504.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Rasmussen, J, Storgaard, M, Pickering, DS & Bunch, L 2011, 'Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors.', ChemMedChem, vol. 6, no. 3, pp. 498-504. https://doi.org/10.1002/cmdc.201000543

APA

Rasmussen, J., Storgaard, M., Pickering, D. S., & Bunch, L. (2011). Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors. ChemMedChem, 6(3), 498-504. https://doi.org/10.1002/cmdc.201000543

Vancouver

Rasmussen J, Storgaard M, Pickering DS, Bunch L. Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors. ChemMedChem. 2011 Mar 7;6(3):498-504. https://doi.org/10.1002/cmdc.201000543

Author

Rasmussen, Julie ; Storgaard, Morten ; Pickering, Darryl S ; Bunch, Lennart. / Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors. In: ChemMedChem. 2011 ; Vol. 6, No. 3. pp. 498-504.

Bibtex

@article{1e0aa610bf91448a830c7dc8592e7e7c,
title = "Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors.",
abstract = "In this paper we describe the rational design, synthesis and pharmacological evaluation of two new stereoisomeric (S)-glutamate (Glu) analogues. The rational design was based on hybrid structures of the natural product kainic acid, a synthetic analogue CPAA and the high-affinity Glu analogue SYM2081. Pharmacological evaluation of the two stereoisomers revealed that one stereoisomer showed a subtype selectivity profile with low micromolar affinity for GluK1 and GluK3 and a 10- to 15-fold lower affinity for GluK2. The other stereoisomer displayed full selectivity for the KA over AMPA and NMDA receptors (GluK1-3: 0.39, 0.51 and 0.099¿µM, respectively).",
author = "Julie Rasmussen and Morten Storgaard and Pickering, {Darryl S} and Lennart Bunch",
year = "2011",
month = "3",
day = "7",
doi = "10.1002/cmdc.201000543",
language = "English",
volume = "6",
pages = "498--504",
journal = "ChemMedChem",
issn = "1860-7179",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "3",

}

RIS

TY - JOUR

T1 - Rational Design, Synthesis and Pharmacological Evaluation of the (2R)- and (2S)-Stereoisomers of 3-(2-Carboxypyrrolidinyl)-2-methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors.

AU - Rasmussen, Julie

AU - Storgaard, Morten

AU - Pickering, Darryl S

AU - Bunch, Lennart

PY - 2011/3/7

Y1 - 2011/3/7

N2 - In this paper we describe the rational design, synthesis and pharmacological evaluation of two new stereoisomeric (S)-glutamate (Glu) analogues. The rational design was based on hybrid structures of the natural product kainic acid, a synthetic analogue CPAA and the high-affinity Glu analogue SYM2081. Pharmacological evaluation of the two stereoisomers revealed that one stereoisomer showed a subtype selectivity profile with low micromolar affinity for GluK1 and GluK3 and a 10- to 15-fold lower affinity for GluK2. The other stereoisomer displayed full selectivity for the KA over AMPA and NMDA receptors (GluK1-3: 0.39, 0.51 and 0.099¿µM, respectively).

AB - In this paper we describe the rational design, synthesis and pharmacological evaluation of two new stereoisomeric (S)-glutamate (Glu) analogues. The rational design was based on hybrid structures of the natural product kainic acid, a synthetic analogue CPAA and the high-affinity Glu analogue SYM2081. Pharmacological evaluation of the two stereoisomers revealed that one stereoisomer showed a subtype selectivity profile with low micromolar affinity for GluK1 and GluK3 and a 10- to 15-fold lower affinity for GluK2. The other stereoisomer displayed full selectivity for the KA over AMPA and NMDA receptors (GluK1-3: 0.39, 0.51 and 0.099¿µM, respectively).

U2 - 10.1002/cmdc.201000543

DO - 10.1002/cmdc.201000543

M3 - Journal article

C2 - 21268287

VL - 6

SP - 498

EP - 504

JO - ChemMedChem

JF - ChemMedChem

SN - 1860-7179

IS - 3

ER -

ID: 32927619