An EAAT inhibitor
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DL-TBOA

Item No. 29632

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-3R-(phenylmethoxy)-D-aspartic acid
CAS Number
205309-81-5
Synonyms
  • DL-threo-β-Benzyloxyaspartate
Molecular Formula
C11H13NO5
Formula Weight
239.2
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 100 mMWater: 5mM with warming
SMILES
OC([C@@H](N)[C@@H](C(O)=O)OCC1=CC=CC=C1)=O
InChi Code
InChI=1S/C11H13NO5/c12-8(10(13)14)9(11(15)16)17-6-7-4-2-1-3-5-7/h1-5,8-9H,6,12H2,(H,13,14)(H,15,16)/t8-,9-/m0/s1
InChi Key
BYOBCYXURWDEDS-IUCAKERBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $203

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    10 mg

    $363

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    Product Description

    DL-TBOA is an inhibitor of excitatory amino acid transporters (EAATs), with IC50 values of 67 and 5.5 μM for glutamate uptake in COS-1 cells expressing human EAAT1 and EAAT2, respectively.1 It inhibits inward currents induced by L-aspartate in EAAT4-expressing Xenopus oocytes (Ki = 4.4 μM) and by L-glutamate in EAAT5-expressing oocytes (Ki = 3.2 μM) voltage-clamped at -60 mV.2 In vivo, DL-TBOA (500 μM, intrahippocampal perfusion) increases extracellular aspartate, glutamate, and alanine levels in rat hippocampus.3 Intrahippocampal injection of DL-TBOA increases lesion volume in the rat CA1 region in a dose-dependent manner and induces hyperexcitability, wet-dog shakes, salivation, forelimb myoclonus, limbic seizures, and epileptic EEG discharges at a dose of 25 nmol. DL-TBOA (5 and 10 μg, intrathecal) induces antinociception in the second phase of the formalin test in rats when administered 10 minutes prior to formalin.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shimamoto, K., Lebrun, B., Yasuda-Kamatani, Y., et al. ᴅʟ-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol. Pharmacol. 53(2), 195-201 (1998).

    2. Shigeri, Y., Shimamoto, K., Yasuda-Kamatani, Y., et al. Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J. Neurochem. 79(2), 297-302 (2001).

    3. Montiel, T., Camacho, A., Estrada-Sánchez, A.M., et al. Differential effects of the substrate inhibitor ʟ-trans-pyrrolidine-2,4-dicarboxylate (PDC) and the non-substrate inhibitor ᴅʟ-threo-β-benzyloxyaspartate (ᴅʟ-TBOA) of glutamate transporters on neuronal damage and extracellular amino acid levels in rat brain in vivo. Neuroscience 133(3), 667-678 (2005).

    4. Yaster, M., Guan, X., Petralia, R.S., et al. Effect of inhibition of spinal cord glutamate transporters on inflammatory pain induced by formalin and complete Freund’s adjuvant. Anesthesiology 114(2), 412-423 (2011).