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Description: Potent and selective EAAT1 and EAAT2 blocker
Chemical Name: (3S)-3-[[3-[[4-(Trifluoromethyl)benzoyl]amino]phenyl]methoxy]-L-aspartic acid
Purity: ≥98% (HPLC)
Biological Activity for TFB-TBOA
TFB-TBOA is a potent and selective glial glutamate transporter EAAT1 and EAAT2 inhibitor (IC50 values are 17, 22 and 300 nM for EAAT2, EAAT1 and EAAT3, respectively). Exhibits selectivity for EAAT1 and EAAT2 over EAAT4 and EAAT5, and a wide range of neuronal receptors and transporters. In HEK293 cells expressing human EAAT1, 2, and 3, TFB-TBOA exhibited selectivity for hEAAT1 and hEAAT2 over hEAAT3 (respective IC50 values are 3.6, 10, and 120 nM), while in tsA201 cells expressing rat EAAT4, [3H]-d-Asp uptake was inhibited with an IC50 of 40 nM. Attenuates glutamate-stimulated intracellular Na+ elevation in astrocytes in vitro (IC50 = 43 nM). Induces severe convulsions in vivo.
Compound Libraries for TFB-TBOA
TFB-TBOA is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for TFB-TBOA
| M. Wt | 426.35 |
| Formula | C19H17F3N2O6 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 480439-73-4 |
| PubChem ID | 52941382 |
| InChI Key | LPWONNPEPDHEAI-GJZGRUSLSA-N |
| Smiles | OC([C@@H](N)[C@H](OCC1=CC=CC(NC(C2=CC=C(C(F)(F)F)C=C2)=O)=C1)C(O)=O)=O |
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 Data for TFB-TBOA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 21.32 | 50 |
Preparing Stock Solutions for TFB-TBOA
The following data is based on the product molecular weight 426.35. 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.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 4.69 mL | 23.45 mL | 46.91 mL |
| 2.5 mM | 0.94 mL | 4.69 mL | 9.38 mL |
| 5 mM | 0.47 mL | 2.35 mL | 4.69 mL |
| 25 mM | 0.09 mL | 0.47 mL | 0.94 mL |
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Product Datasheets for TFB-TBOA
References for TFB-TBOA
References are publications that support the biological activity of the product.
Tsukada et al (2005) Effects of a novel glutamate transporter blocker, (2S, 3S)-3-{3-[4-(trifluoromethyl)benzoylamino]benzyloxy}aspartate (TFB-TBOA), on activities of hippocampal neurons. Neuropharmacology 48 479 PMID: 15755476
Shimamoto and Shigeri (2006) Elucidation of glutamate transporter functions using selective inhibitors. CNS Agents Med.Chem. 6 59
Magi et al (2012) Physical and functional interaction of NCX1 and EAAC1 transporters leading to glutamate-enhanced ATP production in brain mitochondria. PLoS One 7 e34015 PMID: 22479505
Bozzo and Chatton (2010) Inhibitory effects of (2S, 3S)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (TFB-TBOA) on the astrocytic sodium responses to glutamate. Brain Res. 1316 PMID: 20026319
Fu et al (2018) Chemoenzymatic synthesis and pharmacological characterization of functionalized aspartate analogues as novel excitatory amino acid transporter inhibitors. J.Med.Chem. 61 7741 PMID: 30011368
If you know of a relevant reference for TFB-TBOA, please let us know.
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Keywords: TFB-TBOA, TFB-TBOA supplier, High, affinity, EAAT1, EAAT2, blockers, EAAT, Excitatory, Amino, Acid, Transporters, GLAST, GLT-1, Glutamate, Monoamine, Neurotransmitter, 2532, Tocris Bioscience
13 Citations for TFB-TBOA
Citations are publications that use Tocris products. Selected citations for TFB-TBOA include:
Belozor et al (2019) Extracellular S100β Disrupts Bergman Glia Morphology and Synaptic Transmission in Cerebellar Purkinje Cells. Brain Sci 9 PMID: 31013844
Zhang et al (2019) Müller Glial Cells Participate in Retinal Waves via Glutamate Transporters and AMPA Receptors. Cell Rep 27 2871 PMID: 31167134
Martinez et al (2020) Loss of excitatory amino acid transporter restraint following chronic intermittent hypoxia contributes to synaptic alterations in nucleus tractus solitarii. J.Neurophysiol. 123 2122 PMID: 32347148
Obba et al (2015) The PRKAA1/AMPKα1 pathway triggers autophagy during CSF1-induced human monocyte differentiation and is a potential target in CMML. Mol Pain 11 1114 PMID: 26029847
Yan et al (2015) PacT. induces acute pain via directly activating toll like receptor 4. Physiol Rep 11 10 PMID: 25868824
Fleischer et al (2015) High-frequency voltage oscillations in cultured astrocytes. PLoS One 3 PMID: 25969464
O'Donnell et al (2016) Transient Oxygen/Glucose Deprivation Causes a Delayed Loss of Mitochondria and Increases Spontaneous Calcium Signaling in Astrocytic Processes. J Neurosci 36 7109 PMID: 27383588
Ivanov et al (2014) Glycolysis and oxidative phosphorylation in neurons and astrocytes during network activity in hippocampal slices. J Cereb Blood Flow Metab 34 397 PMID: 24326389
Chai et al (2017) Neural Circuit-Specialized Astrocytes: Transcriptomic, Proteomic, Morphological, and Functional Evidence. Neuron 95 531 PMID: 28712653
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
Rocchio et al (2019) Gene expression, proteome and calcium signaling alterations in immortalized hippocampal astrocytes from an Alzheimer's disease mouse model. Cell Death Dis 10 24 PMID: 30631041
Canul-Tec (2017) Structure and allosteric inhibition of excitatory amino acid transporter 1. Nature PMID: 28424515
Afzalov et al (2013) Low micromolar Ba(2+) potentiates glutamate transporter current in hippocampal astrocytes. Front Cell Neurosci 7 135 PMID: 24009556
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Literature in this Area
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