DL-TBOA

Tocris Bioscience a Bio-Techne Brand

Catalog # 1223

Citations (58)

(1)

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Key Product Details

Description:	Selective non-transportable inhibitor of EAATs
Chemical Name:	DL-threo-β-Benzyloxyaspartic acid
Purity:	≥98% (HPLC)
Molecular Weight:	239.23

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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 (K_i values are 4.4 μM and 3.2 μM respectively). DL-TBOA displays high selectivity for EAATs over ionotropic and metabotropic glutamate receptors. 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.

Licensing Information

Sold for research purposes under license from Suntory Ltd.

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 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.

Select a batch to recalculate based on the batch molecular weight:

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	4.18 mL	20.90 mL	41.80 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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References for DL-TBOA

References are publications that support the biological activity of the product.

Rossi Pre- and postsynaptic effects of glutamate in the frog labyrinth. Neuroscience 2018 PMID: 29913242
Pedraz-Cuesta 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 2015 PMID: 25981639
Shigeri Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J.Neurochem. 2001 PMID: 11677257
Shimamoto Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers. Bioorg.Med.Chem.Lett. 2000 PMID: 11078189
Jabaudon Inhibition of uptake unmasks rapid extracellular turnover of glutamate of nonvesicular origin. Proc.Natl.Acad.Sci.U.S.A. 1999 PMID: 10411944
Shimamoto DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol.Pharmacol. 1998 PMID: 9463476

Citations for DL-TBOA (58)

Showing 1 - 10 of 58 citations Showing All

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Citations are publications that use Bio-Techne products. Selected citations for DL-TBOA include:

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
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
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
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(7):731
PMID: 29955038
Thalman et al. (2018) Synaptic phospholipids as a new target for cortical hyperexcitability and E/I balance in psychiatric disorders. Mol Psychiatry. 23(8):1699
PMID: 29743582
Tchernookova et al. (2018) Activation of retinal glial (M�ller) cells by extracellular ATP induces pronounced increases in extracellular H+ flux. PLoS One. 13:e0190893
PMID: 29466379
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
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
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
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
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
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
Huang et al. (2015) Acidosis-Induced Dysfunction of Cortical GABAergic Neurons through Astrocyte-Related Excitotoxicity. Invest Ophthalmol Vis Sci. 10:e0140324
PMID: 26474076
Falgairolle and O'Donovan (2015) Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons. J Neurosci. 10:e0131430
PMID: 26102354
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
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
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
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
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
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
McCall et al. (2013) Fabrication and application of flexible, multimodal light-emitting devices for wireless optogenetics. Sci Signal. 8:2413
PMID: 24202555
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
Wang et al. (2012) Astrocytes modulate neural network activity by Ca2+-dependent uptake of extracellular K+. PLoS One. 5:ra26
PMID: 22472648
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
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
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
Vandenberg et al. (2011) Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1. Biochem J. 439:333
PMID: 21732909
Maurer et al. (2010) Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant. J Neurosci. 30:11962
PMID: 20826660
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
Biase et al. (2010) Excitability and synaptic communication within the oligodendrocyte lineage. Front Cell Neurosci. 30:3600
PMID: 20219994
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
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
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
Baltan et al. (2008) White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity. Br J Pharmacol. 28:1479
PMID: 18256269
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
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
Bender et al. (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci. 26:4166
PMID: 16624937
Matsui et al. (2006) Effects of ethanol on photoreceptors and visual function in developing zebrafish. J Neurosci. 47:4589
PMID: 17003456
Yang et al. (2005) Behavioral stress enhances hippocampal CA1 long-term depression through the blockade of the glutamate uptake. Neuroscience. 25:4288
PMID: 15858055

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Neuron glia culture

Name: Anonymous

Species: Mouse

Assay Type: In Vitro

Cell Line/Tissue: Mixed neuron-glia

TBOA (100 μM)

Incubate for 24h

PMID: 31257852

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