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Molecular Pharmacology

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Rapid CommunicationAccelerated Communication

dl-threo-β-Benzyloxyaspartate, A Potent Blocker of Excitatory Amino Acid Transporters

Keiko Shimamoto, Bruno Lebrun, Yoshimi Yasuda-Kamatani, Masahiro Sakaitani, Yasushi Shigeri, Noboru Yumoto and Terumi Nakajima
Molecular Pharmacology February 1998, 53 (2) 195-201; DOI: https://doi.org/10.1124/mol.53.2.195
Keiko Shimamoto
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Bruno Lebrun
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Yoshimi Yasuda-Kamatani
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Masahiro Sakaitani
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Yasushi Shigeri
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Noboru Yumoto
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Terumi Nakajima
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Abstract

dl-threo-β-Benzyloxyaspartate (dl-TBOA), a novel derivative ofdl-threo-β-hydroxyaspartate, was synthesized and examined as an inhibitor of sodium-dependent glutamate/aspartate (excitatory amino acid) transporters.dl-TBOA inhibited the uptake of [14C]glutamate in COS-1 cells expressing the human excitatory amino acid transporter-1 (EAAT1) (K i = 42 μm) with almost the same potency asdl-threo-β-hydroxyaspartate (K i = 58 μm). With regard to the human excitatory amino acid transporter-2 (EAAT2), the inhibitory effect of dl-TBOA (K i = 5.7 μm) was much more potent than that of dihydrokainate (K i = 79 μm), which is well known as a selective blocker of this subtype. Electrophysiologically, dl-TBOA induced no detectable inward currents in Xenopus laevis oocytes expressing human EAAT1 or EAAT2. However, it significantly reduced the glutamate-induced currents, indicating the prevention of transport. The dose-response curve of glutamate was shifted by addingdl-TBOA without a significant change in the maximum current. The K b values for human EAAT1 and EAAT2 expressed in X. laevis oocytes were 9.0 μm and 116 nm, respectively. These results demonstrated that dl-TBOA is, so far, the most potent competitive blocker of glutamate transporters.dl-TBOA did not show any significant effects on either the ionotropic or metabotropic glutamate receptors. Moreover,dl-TBOA is chemically much more stable than its benzoyl analog, a previously reported blocker of excitatory amino acid transporters; therefore, dl-TBOA should be a useful tool for investigating the physiological roles of transporters.

Footnotes

    • Received October 6, 1997.
    • Accepted November 4, 1997.
  • Send reprint requests to: Dr. Keiko Shimamoto, Suntory Institute for Bioorganic Research, 1–1-1, Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka 618, Japan. E-mail:ldf01705{at}niftyserve.or.jp

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Molecular Pharmacology: 53 (2)
Molecular Pharmacology
Vol. 53, Issue 2
1 Feb 1998
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Rapid CommunicationAccelerated Communication

dl-threo-β-Benzyloxyaspartate, A Potent Blocker of Excitatory Amino Acid Transporters

Keiko Shimamoto, Bruno Lebrun, Yoshimi Yasuda-Kamatani, Masahiro Sakaitani, Yasushi Shigeri, Noboru Yumoto and Terumi Nakajima
Molecular Pharmacology February 1, 1998, 53 (2) 195-201; DOI: https://doi.org/10.1124/mol.53.2.195

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Rapid CommunicationAccelerated Communication

dl-threo-β-Benzyloxyaspartate, A Potent Blocker of Excitatory Amino Acid Transporters

Keiko Shimamoto, Bruno Lebrun, Yoshimi Yasuda-Kamatani, Masahiro Sakaitani, Yasushi Shigeri, Noboru Yumoto and Terumi Nakajima
Molecular Pharmacology February 1, 1998, 53 (2) 195-201; DOI: https://doi.org/10.1124/mol.53.2.195
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