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DL-TBOA

Catalog #: 1223
59 Citations 1 Review Datasheet / COA / SDS
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DL-TBOA | CAS No. 205309-81-5 | Glutamate (EAAT) Transporter Inhibitors
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Description: Selective non-transportable inhibitor of EAATs

Chemical Name: DL-threo-β-Benzyloxyaspartic acid

Purity: ≥98%

Product Details
Citations (59)
Reviews (1)
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

DL-TBOA is a competitive, non-transportable blocker of excitatory amino acid transporters (IC50 values are 6 μM, 6 μM and 70 μM, for EAAT2, EAAT3 and EAAT1, respectively). DL-TBOA also inhibits EAAT4 and EAAT5 (Ki values are 4.4 μM and 3.2 μM respectively). DL-TBOA displays high selectivity for EAATs over ionotropic and metabotropic glutamate receptors. In [3H]-d-Asp uptake assays in HEK293 cells expressing human EAAT2, EAAT1 and EAAT3, Ki values are 2.2, 2.9, and 9.3 μM, respectively. In a FLIPR Membrane Potential (FMP) assay, Km values are 0.59, 1.8 and 2.8 μM for human EAAT2, EAAT3 and EAAT1, respectively. DL-TBOA augments SN 38 (Cat. No. 2684) induced colorectal cancer cell death in drug-resistant cell lines. DL-TBOA enhances synaptic activity in the frog labyrinth.

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.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Background References

  1. Interplay between synchronization of multivesicular release and recruitment of additional release sites support short-term facilitation at hippocampal mossy fiber to CA3 pyramidal cells synapses.
    Chamberland S, Evstratova A, Toth K
    J Neurosci, 2014;34(33):11032-47.
  2. Blood glutamate EAAT2-cell grabbing therapy in cerebral ischemia
    M Pérez-Mato, R Iglesias-R, A Vieites-Pr, A Dopico-Lóp, B Argibay, H Fernández-, A da Silva-C, A Pérez-Díaz, C Correa-Paz, A Günther, P Ávila-Góme, M Isabel Loz, A Baumann, J Castillo, T Sobrino, F Campos
    EBioMedicine, 2018;0(0):.
  3. Impaired K(+) binding to glial glutamate transporter EAAT1 in migraine
    P Kovermann, M Hessel, D Kortzak, JC Jen, J Koch, C Fahlke, T Freilinger
    Sci Rep, 2017;7(1):13913.
  4. High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
    Fox JT, Sakamuru S, Huang R
    Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8.
  5. Alterations of gene expression and glutamate clearance in astrocytes derived from an MeCP2-null mouse model of Rett syndrome.
    Okabe Y, Takahashi T, Mitsumasu C, Kosai K, Tanaka E, Matsuishi T
    PLoS ONE, 2012;7(4):e35354.
  6. Up-regulation of GLT1 reverses the deficit in cortically evoked striatal ascorbate efflux in the R6/2 mouse model of Huntington's disease.
    Miller BR, Dorner JL, Bunner KD, Gaither TW, Klein EL, Barton SJ, Rebec GV
    J. Neurochem., 2012;121(4):629-38.
  7. RANTES-mediated control of excitatory amino acid release in mouse spinal cord.
    Di Prisco S, Summa M, Chellakudam V, Rossi PI, Pittaluga A
    J. Neurochem., 2012;121(3):428-37.
  8. Sustained Na+/H+ exchanger activation promotes gliotransmitter release from reactive hippocampal astrocytes following oxygen-glucose deprivation.
    Cengiz P, Kintner D, Chanana V, Yuan H, Akture E, Kendigelen P, Begum G, Fidan E, Uluc K, Ferrazzano P, Sun D
    PLoS ONE, 2014;9(1):e84294.
  9. 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
  10. Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5).
    Shigeri et al.
    J.Neurochem., 2001;79:297
  11. DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters.
    Shimamoto et al.
    Mol.Pharmacol., 1998;53:195
  12. Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers.
    Shimamoto et al.
    Bioorg.Med.Chem.Lett., 2000;10:2407
  13. The glutamate transport inhibitor DL-Threo--Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells.
    Pedraz-Cuesta et al.
    BMC Cancer, 2015;15:411
  14. Pre- and postsynaptic effects of glutamate in the frog labyrinth.
    Rossi et al.
    Neuroscience, 2018;385:198
  15. Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay.
    Jensen and Bräuner-Osborne et al.
    Biochem.Pharmacol., 2004;67:2115

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Citations for DL-TBOA

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

59 Citations: Showing 1 - 10

  1. Differences in glutamate uptake between cortical regions impact neuronal NMDA receptor activation.
    Authors: Romanos Et al.
    Commun Biol  2019;2:127
  2. Pharmacological Dissection of Intrinsic Optical Signal Reveals a Functional Coupling between Synaptic Activity and Astrocytic Volume Transient.
    Authors: Woo Et al.
    Exp Neurobiol  2019;28:30
  3. Role of intraganglionic transmission in the trigeminovascular pathway.
    Authors: Zhang Et al.
    Mol Pain  2019;15:1744806919836570
  4. Novel positive allosteric modulators of glutamate transport have neuroprotective properties in an in vitro excitotoxic model.
    Authors: Falcucci Et al.
    ACS Chem Neurosci  2019;10:3437
  5. Mitochondrial Regulation of the Hippocampal Firing Rate Set Point and Seizure Susceptibility.
    Authors: Styr Et al.
    Neuron  2019;102:1009
  6. Glutamate as a potential "survival factor" in an in vitro model of neuronal hypoxia/reoxygenationinjury: leading role of the Na+/Ca2+ exchanger.
    Authors: Piccirillo Et al.
    Cell Death Dis  2018;9(7):731
  7. Pre- and postsynaptic effects of glutamate in the frog labyrinth.
    Authors: Rossi
    Neuroscience  2018;385:198
  8. Clustered Ca2+ Channels Are Blocked by Synaptic Vesicle Proton Release at Mammalian Auditory Ribbon Synapses.
    Authors: Vincent Et al.
    Cell Rep  2018;25:3451
  9. Synaptic phospholipids as a new target for cortical hyperexcitability and E/I balance in psychiatric disorders.
    Authors: Thalman Et al.
    Mol Psychiatry  2018;23(8):1699
  10. Activation of retinal glial (M�ller) cells by extracellular ATP induces pronounced increases in extracellular H+ flux.
    Authors: Tchernookova Et al.
    PLoS One  2018;13:e0190893
  11. Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters.
    Authors: Lu Et al.
    Neuron  2017;96:73
  12. Human Astrocyte Maturation Captured in 3D Cerebral Cortical Spheroids Derived from Pluripotent Stem Cells.
    Authors: Sloan Et al.
    Neuron  2017;95:779
  13. Transient Opening of the Mitochondrial Permeability Transition Pore Induces Microdomain Calcium Transients in Astrocyte Processes.
    Authors: Agarwal Et al.
    Neuron  2017;93:587
  14. Astrocytes Control Circadian Timekeeping in the Suprachiasmatic Nucleus via Glutamatergic Signaling.
    Authors: Brancaccio Et al.
    Neuron  2017;93:1420
  15. 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
  16. 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
  17. 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
  18. Burst predicting neurons survive an in vitro glutamate injury model of cerebral ischemia.
    Authors: Kuebler Et al.
    J Neurosci  2015;5:17718
  19. Neuron-glia signaling in developing retina mediated by neurotransmitter spillover.
    Authors: Rosa Et al.
    J Neurosci  2015;4
  20. 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
  21. 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
  22. Defective Age-Dependent Metaplasticity in a Mouse Model of Alzheimer's Disease.
    Authors: Megill Et al.
    Nat Protoc  2015;35:11346
  23. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals.
    Authors: Lin Et al.
    Elife  2015;16:5555
  24. The glutamate transport inhibitor DL-Threo--Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells.
    Authors: Pedraz-Cuesta Et al.
    BMC Cancer  2015;15:411
  25. 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
  26. Acidosis-Induced Dysfunction of Cortical GABAergic Neurons through Astrocyte-Related Excitotoxicity.
    Authors: Huang Et al.
    Invest Ophthalmol Vis Sci  2015;10:e0140324
  27. Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons.
    Authors: Falgairolle and O'Donovan
    J Neurosci  2015;10:e0131430
  28. 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
  29. Laser-scanning astrocyte mapping reveals increased glutamate-responsive domain size and disrupted maturation of glutamate uptake following neonatal cortical freeze-lesion.
    Authors: Armbruster Et al.
    Front Cell Neurosci  2014;8:277
  30. Cerebellar modules operate at different frequencies.
    Authors: Zhou Et al.
    Elife  2014;3:e02536
  31. δ-Opioid receptors up-regulate excitatory amino acid transporters in mouse astrocytes.
    Authors: Liang Et al.
    Vision Res  2014;171:5417
  32. Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses.
    Authors: Tse Et al.
    Vision Res  2014;103:63
  33. 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
  34. 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
  35. 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
  36. Fabrication and application of flexible, multimodal light-emitting devices for wireless optogenetics.
    Authors: McCall Et al.
    Sci Signal  2013;8:2413
  37. Impaired glutamate recycling and GluN2B-mediated neuronal calcium overload in mice lacking TGF-β1 in the CNS.
    Authors: Koeglsperger Et al.
    Glia  2013;61:985
  38. Conformational ensemble of the sodium-coupled aspartate transporter.
    Authors: Georgieva Et al.
    Nat Struct Mol Biol  2013;20:215
  39. Synaptic and extrasynaptic plasticity in glutamatergic circuits involving dentate granule cells following chronic N-MthD.-aspartate receptor inhibition.
    Authors: He Et al.
    Int J Mol Sci  2013;109:1535
  40. R.zole and gabapentinoids activate glutamate transporters to facilitate glutamate-induced glutamate release from cultured astrocytes.
    Authors: Yoshizumi Et al.
    Eur J Pharmacol  2012;677:87
  41. Astrocytes modulate neural network activity by Ca2+-dependent uptake of extracellular K+.
    Authors: Wang Et al.
    PLoS One  2012;5:ra26
  42. The mode of retinal presynaptic inhibition switches with light intensity.
    Authors: Ichinose and Lukasiewicz
    J Neurosci  2012;32:4360
  43. Parasynaptic NMDA receptor signaling couples neuronal glutamate transporter function to AMPA receptor synaptic distribution and stability.
    Authors: Jarzylo and Man
    J Neurosci  2012;32:2552
  44. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J  2011;439:333
  45. Morphine potentiates neurodegenerative effects of HIV-1 Tat through actions at μ-opioid receptor-expressing glia.
    Authors: Zou Et al.
    Brain  2011;134:3616
  46. 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
  47. Excitability and synaptic communication within the oligodendrocyte lineage.
    Authors: Biase Et al.
    Front Cell Neurosci  2010;30:3600
  48. Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant.
    Authors: Maurer Et al.
    J Neurosci  2010;30:11962
  49. Inhibition of glutamate transporters couples to Kv4.2 dephosphorylation through activation of extrasynaptic NMDA receptors.
    Authors: Mulholland and Chandler
    PLoS One  2010;165:130
  50. 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
  51. Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition.
    Authors: Costa Et al.
    J Neurosci  2008;28:8040
  52. White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity.
    Authors: Baltan Et al.
    Br J Pharmacol  2008;28:1479
  53. Stimulated efflux of amino acids and glutathione from cultured hippocampal slices by omission of extracellular calcium: likely involvement of connexin hemichannels.
    Authors: Stridh Et al.
    J Biol Chem  2008;283:10347
  54. Neuronal viability is controlled by a functional relation between synaptic and extrasynaptic NMDA receptors.
    Authors: Léveillé Et al.
    FASEB J  2008;22:4258
  55. Somatodendritic release of glutamate regulates synaptic inhibition in cerebellar Purkinje cells via autocrine mGluR1 activation.
    Authors: Duguid Et al.
    J Neurosci  2007;27:12464
  56. Effects of ethanol on photoreceptors and visual function in developing zebrafish.
    Authors: Matsui Et al.
    J Neurosci  2006;47:4589
  57. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci  2006;26:4166
  58. Behavioral stress enhances hippocampal CA1 long-term depression through the blockade of the glutamate uptake.
    Authors: Yang Et al.
    Neuroscience  2005;25:4288

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Slice Electrophysiology
By Anonymous on 04/09/2019
Species: Mouse

Used for slice electrophysiology experiments to inhibit glutamate transport.

Used at 100uM

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