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Submit ReviewDL-TBOA
Description: Selective non-transportable inhibitor of EAATs
Chemical Name: DL-threo-β-Benzyloxyaspartic acid
Purity: ≥98% (HPLC)
Biological Activity for DL-TBOA
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.
Compound Libraries for DL-TBOA
DL-TBOA is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for DL-TBOA
| M. Wt | 239.23 |
| Formula | C11H13NO5 |
| Storage | Desiccate at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 205309-81-5 |
| PubChem ID | 90479771 |
| InChI Key | CSEZCYBVEGIYNG-MFBWXLJUSA-N |
| Smiles | [H][C@@](OCC1=CC=CC=C1)(C(O)=O)[C@@]([H])(C(O)=O)N.[H][C@](OCC2=CC=CC=C2)(C(O)=O)[C@]([H])(C(O)=O)N |
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.
Solubility Data for DL-TBOA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 23.92 | 100 | |
| water | 1.2 | 5 with gentle warming |
Preparing Stock Solutions for DL-TBOA
The following data is based on the product molecular weight 239.23. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 4.18 mL | 20.9 mL | 41.8 mL |
| 5 mM | 0.84 mL | 4.18 mL | 8.36 mL |
| 10 mM | 0.42 mL | 2.09 mL | 4.18 mL |
| 50 mM | 0.08 mL | 0.42 mL | 0.84 mL |
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Product Datasheets for DL-TBOA
References for DL-TBOA
References are publications that support the biological activity of the product.
Jabaudon et al (1999) Inhibition of uptake unmasks rapid extracellular turnover of glutamate of nonvesicular origin. Proc.Natl.Acad.Sci.U.S.A. 96 8733 PMID: 10411944
Shigeri et al (2001) Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J.Neurochem. 79 297 PMID: 11677257
Shimamoto et al (1998) DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol.Pharmacol. 53 195 PMID: 9463476
Shimamoto et al (2000) Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers. Bioorg.Med.Chem.Lett. 10 2407 PMID: 11078189
Pedraz-Cuesta et al (2015) The glutamate transport inhibitor DL-Threo--Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells. BMC Cancer 15 411 PMID: 25981639
Rossi et al (2018) Pre- and postsynaptic effects of glutamate in the frog labyrinth. Neuroscience 385 198 PMID: 29913242
Jensen and Bräuner-Osborne et al (2004) Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay. Biochem.Pharmacol. 67 2115 PMID: 15135308
If you know of a relevant reference for DL-TBOA, please let us know.
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Keywords: DL-TBOA, DL-TBOA supplier, non-transportable, inhibitors, inhibits, EAATs, EAAT1, EAAT2, EAAT3, EAAT4, EAAT5, Excitatory, Amino, Acid, Transporters, GLAST, GLT-1, Glutamate, Monoamine, Neurotransmitter, 1223, Tocris Bioscience
58 Citations for DL-TBOA
Citations are publications that use Tocris products. Selected citations for DL-TBOA include:
Koeglsperger et al (2013) Impaired glutamate recycling and GluN2B-mediated neuronal calcium overload in mice lacking TGF-β1 in the CNS. Glia 61 985 PMID: 23536313
Mulholland and Chandler (2010) Inhibition of glutamate transporters couples to Kv4.2 dephosphorylation through activation of extrasynaptic NMDA receptors. PLoS One 165 130 PMID: 19850106
Yang et al (2005) Behavioral stress enhances hippocampal CA1 long-term depression through the blockade of the glutamate uptake. Neuroscience 25 4288 PMID: 15858055
Romei et al (2016) Colocalization of neurotransmitter transporters on the plasma membrane of the same nerve terminal may reflect cotransmission. Brain Research Bulletin 127 100 PMID: 27565422
Campbell et al (2015) Functional changes in glutamate transporters and astrocyte biophysical properties in a rodent model of focal cortical dysplasia. BMC Cancer 8 425 PMID: 25565960
Pedraz-Cuesta et al (2015) The glutamate transport inhibitor DL-Threo-β-Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells. J Neurosci 15 411 PMID: 25981639
Petr et al (2015) 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. Sci Rep 35 5187 PMID: 25834045
Kuebler et al (2015) Burst predicting neurons survive an in vitro glutamate injury model of cerebral ischemia. J Neurosci 5 17718 PMID: 26648112
Vance et al (2015) PAR1-activated astrocytes in the nucleus of the solitary tract stimulate adjacent neurons via NMDA receptors. J Neurosci 35 776 PMID: 25589770
Megill et al (2015) Defective Age-Dependent Metaplasticity in a Mouse Model of Alzheimer's Disease. Nat Protoc 35 11346 PMID: 26269641
Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Elife 16 5555 PMID: 25768340
Rosa et al (2015) Neuron-glia signaling in developing retina mediated by neurotransmitter spillover. J Neurosci 4 PMID: 26274565
Huang et al (2015) Acidosis-Induced Dysfunction of Cortical GABAergic Neurons through Astrocyte-Related Excitotoxicity. Invest Ophthalmol Vis Sci 10 e0140324 PMID: 26474076
Mohr et al (2010) 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. Neuropharmacology 58 392 PMID: 19825379
Maurer et al (2010) Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant. J Neurosci 30 11962 PMID: 20826660
Matsui et al (2006) Effects of ethanol on photoreceptors and visual function in developing zebrafish. J Neurosci 47 4589 PMID: 17003456
Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166 PMID: 16624937
Styr et al (2019) Mitochondrial Regulation of the Hippocampal Firing Rate Set Point and Seizure Susceptibility. Neuron 102 1009 PMID: 31047779
Romanos et al (2019) Differences in glutamate uptake between cortical regions impact neuronal NMDA receptor activation. Commun Biol 2 127 PMID: 30963115
Armbruster et al (2014) Laser-scanning astrocyte mapping reveals increased glutamate-responsive domain size and disrupted maturation of glutamate uptake following neonatal cortical freeze-lesion. Front Cell Neurosci 8 277 PMID: 25249939
Zhou et al (2014) Cerebellar modules operate at different frequencies. Elife 3 e02536 PMID: 24843004
Wang et al (2012) Astrocytes modulate neural network activity by Ca2+-dependent uptake of extracellular K+. PLoS One 5 ra26 PMID: 22472648
Biase et al (2010) Excitability and synaptic communication within the oligodendrocyte lineage. Front Cell Neurosci 30 3600 PMID: 20219994
Duguid et al (2007) Somatodendritic release of glutamate regulates synaptic inhibition in cerebellar Purkinje cells via autocrine mGluR1 activation. J Neurosci 27 12464 PMID: 18003824
Falcucci et al (2019) Novel positive allosteric modulators of glutamate transport have neuroprotective properties in an in vitro excitotoxic model. ACS Chem Neurosci 10 3437 PMID: 31257852
Stridh et al (2008) Stimulated efflux of amino acids and glutathione from cultured hippocampal slices by omission of extracellular calcium: likely involvement of connexin hemichannels. J Biol Chem 283 10347 PMID: 18272524
Griffin et al (2015) Repeated cycles of chronic intermittent ethanol exposure increases basal glutamate in the nucleus accumbens of mice without affecting glutamate transport. Front Pharmacol 6 27 PMID: 25755641
Cengiz et al (2014) Sustained Na+/H+ exchanger activation promotes gliotransmitter release from reactive hippocampal astrocytes following oxygen-glucose deprivation. PLoS One 9 e84294 PMID: 24392123
McCall et al (2013) Fabrication and application of flexible, multimodal light-emitting devices for wireless optogenetics. Sci Signal 8 2413 PMID: 24202555
He et al (2013) Synaptic and extrasynaptic plasticity in glutamatergic circuits involving dentate granule cells following chronic N-MthD.-aspartate receptor inhibition. Int J Mol Sci 109 1535 PMID: 23255721
Vandenberg et al (2011) Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1. Biochem J 439 333 PMID: 21732909
Zou et al (2011) Morphine potentiates neurodegenerative effects of HIV-1 Tat through actions at μ-opioid receptor-expressing glia. Brain 134 3616 PMID: 22102648
Baltan et al (2008) White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity. Br J Pharmacol 28 1479 PMID: 18256269
Costa et al (2008) Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition. J Neurosci 28 8040 PMID: 18685029
Léveillé et al (2008) Neuronal viability is controlled by a functional relation between synaptic and extrasynaptic NMDA receptors. FASEB J 22 4258 PMID: 18711223
Tchernookova et al (2018) Activation of retinal glial (Müller) cells by extracellular ATP induces pronounced increases in extracellular H+ flux. PLoS One 13 e0190893 PMID: 29466379
Pedraz-Cuesta et al (2015) The glutamate transport inhibitor DL-Threo--Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells. BMC Cancer 15 411 PMID: 25981639
Liang et al (2014) δ-Opioid receptors up-regulate excitatory amino acid transporters in mouse astrocytes. Vision Res 171 5417 PMID: 25052197
Tse et al (2014) Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses. Vision Res 103 63 PMID: 24972005
Tse et al (2014) Pharmacological inhibitions of glutamate transporters EAAT1 and EAAT2 compromise glutamate transport in photoreceptor to ON-bipolar cell synapses. J Neurophysiol 103 49 PMID: 25152321
Tovar-y-Romo et al (2013) Adenosine triphosphate released from HIV-infected macrophages regulates glutamatergic tone and dendritic spine density on neurons. J Neuroimmune Pharmacol 8 998 PMID: 23686368
Jeon et al (2013) Presynaptic Localization and Possible Function of Calcium-Activated Chloride Channel Anoctamin 1 in the Mammalian Retina. PLoS One 8 e67989 PMID: 23840801
Georgieva et al (2013) Conformational ensemble of the sodium-coupled aspartate transporter. Nat Struct Mol Biol 20 215 PMID: 23334289
Falgairolle and O'Donovan (2015) Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons. J Neurosci 10 e0131430 PMID: 26102354
Yoshizumi et al (2012) R.zole and gabapentinoids activate glutamate transporters to facilitate glutamate-induced glutamate release from cultured astrocytes. Eur J Pharmacol 677 87 PMID: 22206816
Krock et al (2009) Retrograde intraflagellar transport by cytoplasmic dynein-2 is required for outer segment extension in vertebrate photoreceptors but not arrestin translocation. Invest Ophthalmol Vis Sci 50 5463 PMID: 19474410
Woo et al (2019) Pharmacological Dissection of Intrinsic Optical Signal Reveals a Functional Coupling between Synaptic Activity and Astrocytic Volume Transient. Exp Neurobiol 28 30 PMID: 30853822
Zhang et al (2019) Role of intraganglionic transmission in the trigeminovascular pathway. Mol Pain 15 1744806919836570 PMID: 30784351
Ichinose and Lukasiewicz (2012) The mode of retinal presynaptic inhibition switches with light intensity. J Neurosci 32 4360 PMID: 22457487
Jarzylo and Man (2012) Parasynaptic NMDA receptor signaling couples neuronal glutamate transporter function to AMPA receptor synaptic distribution and stability. J Neurosci 32 2552 PMID: 22396428
Brancaccio et al (2017) Astrocytes Control Circadian Timekeeping in the Suprachiasmatic Nucleus via Glutamatergic Signaling. Neuron 93 1420 PMID: 28285822
Agarwal et al (2017) Transient Opening of the Mitochondrial Permeability Transition Pore Induces Microdomain Calcium Transients in Astrocyte Processes. Neuron 93 587 PMID: 28132831
Lu et al (2017) Slow AMPAR Synaptic Transmission Is Determined by Stargazin and Glutamate Transporters. Neuron 96 73 PMID: 28919175
Sloan et al (2017) Human Astrocyte Maturation Captured in 3D Cerebral Cortical Spheroids Derived from Pluripotent Stem Cells. Neuron 95 779 PMID: 28817799
Vincent et al (2018) Clustered Ca2+ Channels Are Blocked by Synaptic Vesicle Proton Release at Mammalian Auditory Ribbon Synapses. Cell Rep 25 3451 PMID: 30566869
Rossi (2018) Pre- and postsynaptic effects of glutamate in the frog labyrinth. Neuroscience 385 198 PMID: 29913242
Thalman et al (2018) Synaptic phospholipids as a new target for cortical hyperexcitability and E/I balance in psychiatric disorders. Mol Psychiatry 23 1699 PMID: 29743582
Piccirillo et al (2018) Glutamate as a potential "survival factor" in an in vitro model of neuronal hypoxia/reoxygenationinjury: leading role of the Na+/Ca2+ exchanger. Cell Death Dis 9 731 PMID: 29955038
Do you know of a great paper that uses DL-TBOA from Tocris? Please let us know.
Reviews for DL-TBOA
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Neuron glia culture.
By
Anonymous on 07/12/2020
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Mixed neuron-glia
TBOA (100 μM)
Incubate for 24h
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