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 / Safety Data Sheet

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Safety Data Sheet: View Safety Data Sheet

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:

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.

Georgieva et al (2013) Conformational ensemble of the sodium-coupled aspartate transporter. Nat Struct Mol Biol 20 215. PMID: 23334289.

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.

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.

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.

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.

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.

Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166. PMID: 16624937.

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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