DL-TBOA

Pricing Availability Delivery Time Qty
Cat.No. 1223 - DL-TBOA | C11H13NO5 | CAS No. 205309-81-5
Description: Selective non-transportable inhibitor of EAATs
Chemical Name: DL-threo-β-Benzyloxyaspartic acid
Purity: ≥98% (HPLC)
Datasheet
Citations (36)
Literature

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™.

Licensing Information

Sold for research purposes under license from Suntory Ltd.

Compound Libraries

DL-TBOA is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 23.92 100
water 1.2 5mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 239.23. Batch specific molecular weights may vary from batch to batch due to solvent 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 20.9 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

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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


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View all Glutamate Transporter Inhibitors

Keywords: DL-TBOA, supplier, non-transportable, inhibitors, inhibits, EAATs, EAAT1, EAAT2, EAAT3, EAAT4, EAAT5, Excitatory, Amino, Acid, Transporters, GLAST, GLT-1, Glutamate, Monoamine, Neurotransmitter, Glutamate, Transporters, Tocris Bioscience

36 Citations for DL-TBOA

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

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

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

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

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

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

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

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

Falgairolle and O'Donovan (2015) Pharmacological Investigation of Fluoro-Gold Entry into Spinal Neurons. J Neurosci 10 e0131430 PMID: 26102354

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

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-methyl-D-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


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