DL-TBOA

Cat. No. 1223

DL-TBOA C11H13NO5 [205309-81-5]

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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™.

Licensing Information

Sold for research purposes under license from Suntory Ltd.

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

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 (2000) Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers. Bioorg.Med.Chem.Lett. 10 2407. PMID: 11078189.

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.

Shimamoto et al (1998) DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol.Pharmacol. 53 195. PMID: 9463476.

If you know of a relevant reference for this product please let us know.

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

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.

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

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.

Huang et al (2015) Acidosis-Induced Dysfunction of Cortical GABAergic Neurons through Astrocyte-Related Excitotoxicity. Invest Ophthalmol Vis Sci 10 e0140324. PMID: 26474076.

Kuebler et al (2015) Burst predicting neurons survive an in vitro glutamate injury model of cerebral ischemia. J Neurosci 5 17718. PMID: 26648112.

Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Elife 16 5555. PMID: 25768340.

Megill et al (2015) Defective Age-Dependent Metaplasticity in a Mouse Model of Alzheimer's Disease. Nat Protoc 35 11346. PMID: 26269641.

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.

Rosa et al (2015) Neuron-glia signaling in developing retina mediated by neurotransmitter spillover. J Neurosci 4. PMID: 26274565.

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.

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.

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.

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.

McCall et al (2013) Fabrication and application of flexible, multimodal light-emitting devices for wireless optogenetics. Sci Signal 8 2413. PMID: 24202555.

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.

Ichinose and Lukasiewicz (2012) The mode of retinal presynaptic inhibition switches with light intensity. J Neurosci 32 4360. PMID: 22457487.

Wang et al (2012) Astrocytes modulate neural network activity by Ca2+-dependent uptake of extracellular K+. PLoS One 5 ra26. PMID: 22472648.

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.

Biase et al (2010) Excitability and synaptic communication within the oligodendrocyte lineage. Front Cell Neurosci 30 3600. PMID: 20219994.

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.

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.

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.

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.

Do you know of a great paper that uses DL-TBOA from Tocris? If so please let us know.show all ▼show less ▲

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

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