DL-TBOA

Name: DL-TBOA
Brand: Tocris Bioscience
SKU: 1223
Rating: 5 (1 reviews)

Tocris Bioscience, part of Bio-Techne | Catalog # 1223

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Citations (262)

COA / SDS

Selective non-transportable inhibitor of EAATs

Key Product Details

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

View Full Technical Details for DL-TBOA

Technical Data
Citations / Reviews (1)

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. In [³H]-d-Asp uptake assays in HEK293 cells expressing human EAAT2, EAAT1 and EAAT3, K_i values are 2.2, 2.9, and 9.3 μM, respectively. In a FLIPR Membrane Potential (FMP) assay, K_m 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 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
Jensen and Bräuner-Osborne Pharmacological characterization of human excitatory amino acid transporters EAAT1, EAAT2 and EAAT3 in a fluorescence-based membrane potential assay. Biochem.Pharmacol. 2004 PMID: 15135308
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
Shimamoto Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers. Bioorg.Med.Chem.Lett. 2000 PMID: 11078189
Shimamoto DL-threo-β-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol.Pharmacol. 1998 PMID: 9463476
Shigeri Effects of threo-β-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J.Neurochem. 2001 PMID: 11677257
Jabaudon Inhibition of uptake unmasks rapid extracellular turnover of glutamate of nonvesicular origin. Proc.Natl.Acad.Sci.U.S.A. 1999 PMID: 10411944