- L-(-)-threo-3-Hydroxyaspartic acid
- Dihydrokainic acid
- TFB-TBOA
- WAY 213613
- LDN 212320
- 7-Chlorokynurenic acid sodium salt
| DL-TBOAinhibitor of excitatory amino acid transporters |
Sample solution is provided at 25 µL, 10mM.
Nature.2017 Jan 19;541(7637):417-420.
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Science.2016 Aug 5;353(6299)594-8Nat Nanotechnol.2017 Dec;12(12):1190-1198.Nature Biotechnology.2017 Jun;35(6):569-576Nat Med.2018 Sep 17.Cell.2018 Dec 21. pii: S0092-8674(18)31561-7.Cell.Available online 25 October 2018.Cell.2018 Sep 27. pii: S0092-8674(18)31183-8.Cell.2018 Jun 28;174(1):172-186.e21.Cell.2018 Feb 22;172(5):1007-1021.e17.Cell.2017 Nov 30;171(6):1284-1300.e21.Cell.2017 Aug 17. pii: S0092-8674(17)30869-3.Cell.2017 Jul 13;170(2):312-323Nat Med.2018 Jan 29.Nat Med.2017 Nov;23(11):1342-1351.Cell.2017 Apr 6;169(2):286-300.Cell.2015 Aug 27;162(5):987-1002.Cell.2015 Feb 12;160(4):729-44.Nature Medicine.2017 Apr;23(4):493-500.Cancer Cell.2018 May 14;33(5):905-921.e5.Cancer Cell.2018 Apr 9;33(4):752-769.e8.Cancer Cell.2018 Mar 12;33(3):401-416.e8.Cancer Cell.2017 Aug 14;32(2):253-267.e5.Nat Methods.2018 Jul;15(7):523-526.Cell Stem Cell.2018 May 3;22(5):769-778.e4.Cell Stem Cell.2017 Nov 20. pii: S1934-5909(17)30375-2.Quality Control & MSDS
- View current batch:
- Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
- Datasheet
Chemical structure
| Kinase experiment [1]: | |
Inhibitory activities | DL-threo-b-Benzyloxyaspartate (DL-TBOA) was synthesized and examined as an inhibitor of sodium-dependent glutamate/aspartate (excitatory amino acid) transporters. DL-TBOA inhibited the uptake of glutamate in COS-1 cells expressing the human excitatory amino acid transporter-1 (EAAT1) (Ki=42 mM). With regard to the human excitatory amino acid transporter-2(EAAT2), the Ki of DL-TBOA 5.7 mM. |
| Cell experiment [1]: | |
Cell lines | COS-1 cells |
Preparation method | The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
Reacting condition | Measurements of glutamate uptake in transfected COS-1 cells assey: 37℃ for 12 min. |
Applications | DL-TBOA markedly inhibited glutamate (1 mM) uptake in transfected cells in a dosedependent manner. The subconfluent cells were washed two times with 300 μl of modified phosphate-buffered saline that contained 137 mM NaCl, 2.7 mM KCl, 8.1 mM Na2HPO4, 1.5 mM KH2PO4,1mM MgCl2, 1mM CaCl2, and 10 mM D-glucose, pH 7.4, and preincubated in 300 μl of the same buffer at 37℃ for 12 min. After aspiration of the buffer, cells were incubated with 1 μM L-glutamate in 100 μl of modified phosphate-buffered saline in the absence or presence of DL-TBOAat various concentrations at 37℃ for 12 min. |
| Animal experiment [2]: | |
Animal models | Males Wistar rats |
Dosage form | 500 μM DL-TBOA |
Preparation method | Dissolved in Ringer Krebs medium which containing (in mM): NaCl 118, KCl 4.5, MgSO4 1.18, KH2PO4 1.2, CaCl2 2.5, NaHCO3 25. |
Application | Microdialysis administration of 500μM DL-TBOA into the hippocampus increased 3.4- and nine-fold the extracellular levels of aspartate and glutamate, respectively. |
Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
References: [1]. KEIKO SHIMAMOTO, BRUNO LEBRUN, YOSHIMI YASUDA-KAMATANI, at al. DL-threo-b-Benzyloxyaspartate, A Potent Blocker of Excitatory Amino Acid Transporters. MOLECULAR PHARMACOLOGY, 53:195–201 (1998). [2]. T. MONTIEL,A. CAMACHO,A. M. ESTRADA-S?NCHEZ AND L. MASSIEU. DIFFERENTIAL EFFECTS OF THE SUBSTRATE INHIBITOR L-TRANSPYRROLIDINE-2,4-DICARBOXYLATE (PDC) AND THE NON-SUBSTRATE INHIBITOR DL-THREO-β-BENZYLOXYASPARTATE (DL-TBOA) OF GLUTAMATE TRANSPORTERS ON NEURONAL DAMAGE AND EXTRACELLULAR AMINO ACID LEVELS IN RAT BRAIN IN VIVO. Neuroscience 133 (2005) 667–678. | |
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| Cas No. | 205309-81-5 | SDF | Download SDF |
| Chemical Name | (2S,3S)-2-amino-3-(benzyloxy)succinic acid | ||
| Canonical SMILES | OC([C@H]([C@@H](C(O)=O)N)OCC1=CC=CC=C1)=O | ||
| Formula | C11H13NO5 | M.Wt | 239.23 |
| Solubility | <23.92mg l="" in="" dmso;=""><1.2mg l="" in="" h2o=""> | Storage | Desiccate at -20°C |
| Physical Appearance | White solid | Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
Ki: 42 μM for EAAT1; 5.7 μM for EAAT2
Glutamate acts as an excitatory neurotransmitter in the mammalian central nervous system and a potent neurotoxin. Glutamate transporters also play an important role in maintaining the extracellular glutamate concentration below neurotoxic levels and therefore contribute to the prevention of neuronal damage. DL-TBOA was synthesized and examined as an inhibitor of sodium-dependent glutamate/aspartate transporters(excitatory amino acid transporters).
In vitro: DL-TBOA inhibited the uptake of [14C]glutamate in COS-1 cells overexpressing the human excitatory amino acid transporter-1 (EAAT1) (Ki = 42 μM) with almost the same potency as DL-threo-b-hydroxyaspartate (Ki = 58 μM). With regard to the human excitatory amino acid transporter-2 (EAAT2), the inhibitory effect of DL-TBOA (Ki = 5.7 μM) was much more potent than that of dihydrokainate (Ki = 79 μM), which is well known as a selective blocker of this subtype. [1].
In vivo: Microdialysis administration of 500 μM DL-TBOA into the hippocampus increased 3.4- and nine-fold the extracellular levels of aspartate and glutamate, respectively. Upon stereotaxic administration it induced neuronal damage dose-dependently in CA1 and dentate gyrus, and convulsive behavior. Electroencephalographic recording showed limbic seizures appearance in the hippocampus after DL-TBOA infusion. [2].
Clinical trial: Up to now, DL-TBOA is still in the preclinical development stage.
Reference:[1] Shimamoto K, Lebrun B, Yasuda-Kamatani Y, Sakaitani M, Shigeri Y, Yumoto N, Nakajima T. DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol Pharmacol. 1998 Feb;53(2):195-201.[2] Montiel T, Camacho A, Estrada-Sánchez AM, Massieu L. Differential effects of the substrate inhibitor l-trans-pyrrolidine-2,4-dicarboxylate (PDC) and the non-substrate inhibitor DL-threo-beta-benzyloxyaspartate (DL-TBOA) of glutamate transporters on neuronal damage and extracellular amino acid levels in rat brain in vivo. Neuroscience. 2005;133(3):667-78.
