Catalog Number: 1223
Chemical Name: DL-threo-β-Benzyloxyaspartic acid
Biological Activity
A competitive, non-transportable blocker of excitatory amino acid transporters (IC50 values are 70, 6, and 6 μM for EAAT1, EAAT2 and EAAT3 respectively). Also inhibits EAAT4 and EAAT5 (Ki values are 4.4 and 3.2 μM respectively). Displays high selectivity for EAATs over ionotropic and metabotropic glutamate receptors. Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset™.
Technical Data
  • M.Wt:
    239.23
  • Formula:
    C11H13NO5
  • Solubility:
    Soluble to 100 mM in DMSO and to 5 mM in water with gentle warming
  • Purity:
    >98%
  • Storage:
    Desiccate at -20°C
  • CAS No:
    205309-81-5
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Licensing Caveats:
Sold for research purposes under license from Suntory Ltd.
Background References
  1. Inhibition of uptake unmasks rapid extracellular turnover of glutamate of nonvesicular origin.
    Jabaudon et al.
    Proc.Natl.Acad.Sci.U.S.A., 1999;96:8733
  2. Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5).
    Shigeri et al.
    J.Neurochem., 2001;79:297
  3. DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters.
    Shimamoto et al.
    Mol.Pharmacol., 1998;53:195
  4. Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers.
    Shimamoto et al.
    Bioorg.Med.Chem.Lett., 2000;10:2407
Citations:

The citations listed below are publications that use Tocris products. Selected citations for DL-TBOA include:

36 Citations: Showing 1 - 10
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  1. Colocalization of neurotransmitter transporters on the plasma membrane of the same nerve terminal may reflect cotransmission.
    Authors: Romei Et al.
    Brain Research Bulletin 2016;127:100
  2. Functional changes in glutamate transporters and astrocyte biophysical properties in a rodent model of focal cortical dysplasia.
    Authors: Campbell Et al.
    BMC Cancer 2015;8:425
  3. Repeated cycles of chronic intermittent ethanol exposure increases basal glutamate in the nucleus accumbens of mice without affecting glutamate transport.
    Authors: Griffin Et al.
    Front Pharmacol 2015;6:27
  4. Burst predicting neurons survive an in vitro glutamate injury model of cerebral ischemia.
    Authors: Kuebler Et al.
    J Neurosci 2015;5:17718
  5. Neuron-glia signaling in developing retina mediated by neurotransmitter spillover.
    Authors: Rosa Et al.
    J Neurosci 2015;4
  6. PAR1-activated astrocytes in the nucleus of the solitary tract stimulate adjacent neurons via NMDA receptors.
    Authors: Vance Et al.
    J Neurosci 2015;35:776
  7. Conditional deletion of the glutamate transporter GLT-1 reveals that astrocytic GLT-1 protects against fatal epilepsy while neuronal GLT-1 contributes significantly to glutamate uptake into synaptosomes.
    Authors: Petr Et al.
    Sci Rep 2015;35:5187
  8. Defective Age-Dependent Metaplasticity in a Mouse Model of Alzheimer's Disease.
    Authors: Megill Et al.
    Nat Protoc 2015;35:11346
  9. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals.
    Authors: Lin Et al.
    Elife 2015;16:5555
  10. The glutamate transport inhibitor DL-Threo-β-Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells.
    Authors: Pedraz-Cuesta Et al.
    J Neurosci 2015;15:411
  11. Acidosis-Induced Dysfunction of Cortical GABAergic Neurons through Astrocyte-Related Excitotoxicity.
    Authors: Huang Et al.
    Invest Ophthalmol Vis Sci 2015;10:e0140324
  12. Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons.
    Authors: Falgairolle and O'Donovan
    J Neurosci 2015;10:e0131430
  13. Sustained Na+/H+ exchanger activation promotes gliotransmitter release from reactive hippocampal astrocytes following oxygen-glucose deprivation.
    Authors: Cengiz Et al.
    PLoS One 2014;9:e84294
  14. δ-Opioid receptors up-regulate excitatory amino acid transporters in mouse astrocytes.
    Authors: Liang Et al.
    Vision Res 2014;171:5417
  15. Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses.
    Authors: Tse Et al.
    Vision Res 2014;103:63
  16. Pharmacological inhibitions of glutamate transporters EAAT1 and EAAT2 compromise glutamate transport in photoreceptor to ON-bipolar cell synapses.
    Authors: Tse Et al.
    J Neurophysiol 2014;103:49
  17. Presynaptic Localization and Possible Function of Calcium-Activated Chloride Channel Anoctamin 1 in the Mammalian Retina.
    Authors: Jeon Et al.
    PLoS One 2013;8:e67989
  18. Adenosine triphosphate released from HIV-infected macrophages regulates glutamatergic tone and dendritic spine density on neurons.
    Authors: Tovar-y-Romo Et al.
    J Neuroimmune Pharmacol 2013;8:998
  19. Fabrication and application of flexible, multimodal light-emitting devices for wireless optogenetics.
    Authors: McCall Et al.
    Sci Signal 2013;8:2413
  20. Conformational ensemble of the sodium-coupled aspartate transporter.
    Authors: Georgieva Et al.
    Nat Struct Mol Biol 2013;20:215
  21. Synaptic and extrasynaptic plasticity in glutamatergic circuits involving dentate granule cells following chronic N-methyl-D-aspartate receptor inhibition.
    Authors: He Et al.
    Int J Mol Sci 2013;109:1535
  22. Astrocytes modulate neural network activity by Ca2+-dependent uptake of extracellular K+.
    Authors: Wang Et al.
    PLoS One 2012;5:ra26
  23. The mode of retinal presynaptic inhibition switches with light intensity.
    Authors: Ichinose and Lukasiewicz
    J Neurosci 2012;32:4360
  24. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J 2011;439:333
  25. Morphine potentiates neurodegenerative effects of HIV-1 Tat through actions at μ-opioid receptor-expressing glia.
    Authors: Zou Et al.
    Brain 2011;134:3616
  26. Young age and low temperature, but not female gender delay ATP loss and glutamate release, and protect Purkinje cells during simulated ischemia in cerebellar slices.
    Authors: Mohr Et al.
    Neuropharmacology 2010;58:392
  27. Excitability and synaptic communication within the oligodendrocyte lineage.
    Authors: Biase Et al.
    Front Cell Neurosci 2010;30:3600
  28. Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant.
    Authors: Maurer Et al.
    J Neurosci 2010;30:11962
  29. Inhibition of glutamate transporters couples to Kv4.2 dephosphorylation through activation of extrasynaptic NMDA receptors.
    Authors: Mulholland and Chandler
    PLoS One 2010;165:130
  30. Retrograde intraflagellar transport by cytoplasmic dynein-2 is required for outer segment extension in vertebrate photoreceptors but not arrestin translocation.
    Authors: Krock Et al.
    Invest Ophthalmol Vis Sci 2009;50:5463
  31. Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition.
    Authors: Costa Et al.
    J Neurosci 2008;28:8040
  32. White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity.
    Authors: Baltan Et al.
    Br J Pharmacol 2008;28:1479
  33. Neuronal viability is controlled by a functional relation between synaptic and extrasynaptic NMDA receptors.
    Authors: Léveillé Et al.
    FASEB J 2008;22:4258
  34. Effects of ethanol on photoreceptors and visual function in developing zebrafish.
    Authors: Matsui Et al.
    J Neurosci 2006;47:4589
  35. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci 2006;26:4166
  36. Behavioral stress enhances hippocampal CA1 long-term depression through the blockade of the glutamate uptake.
    Authors: Yang Et al.
    Neuroscience 2005;25:4288
Expand to show all 36 Citations

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