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Reagentes e instrumentos para imunologia, biologia celular e biologia molecular.

DL-TBOA [205309-81-5]

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Referência HY-107522-10mg

Tamanho : 10mg

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Marca : MedChemExpress

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Description

DL-TBOA is a potent non-transportable inhibitor of excitatory amino acid transporters with IC₅₀s of 70 μM, 6 μM and 6 μM for excitatory amino acid transporter-1 (EAAT1), EAAT2 and EAAT3, respectively. DL-TBOA inhibits the uptake of [¹⁴C]glutamate in COS-1 cells expressing the human EAAT1 and EAAT2 with K_i valuesof 42 μM and 5.7 μM, respectively. DL-TBOA blocks EAAT4 and EAAT5 in a competitive manner with K_i values of 4.4 μM and 3.2 μM, respectively^[1]^[2]^[3].

IC₅₀ & Target

EAAT1

EAAT2

EAAT3

Cellular Effect

Cell Line	Type	Value	Description	References
COS-1	IC₅₀	>1000 μM Compound: D-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1	[PMID: 11078189]
COS-1	IC₅₀	>1 mM Compound: D-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1	[PMID: 11078189]
COS-1	IC₅₀	134 μM Compound: L-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3	[PMID: 11078189]
COS-1	IC₅₀	161 μM Compound: D-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3	[PMID: 11078189]
COS-1	IC₅₀	164 μM Compound: L-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2	[PMID: 11078189]
COS-1	IC₅₀	21 μM Compound: D-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3	[PMID: 11078189]
COS-1	IC₅₀	221 μM Compound: D-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2	[PMID: 11078189]
COS-1	IC₅₀	23 μM Compound: L-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1	[PMID: 11078189]
COS-1	IC₅₀	3.8 μM Compound: L-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2	[PMID: 11078189]
COS-1	IC₅₀	637 μM Compound: D-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1	[PMID: 11078189]
COS-1	IC₅₀	64 μM Compound: D-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 2	[PMID: 11078189]
COS-1	IC₅₀	7 μM Compound: L-TBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 3	[PMID: 11078189]
COS-1	IC₅₀	7 μM Compound: L-TBOA	Inhibition of [14C]glutamate uptake at human EAAT3 expressed in african green monkey COS1 cells Inhibition of [14C]glutamate uptake at human EAAT3 expressed in african green monkey COS1 cells	[PMID: 18650095]
COS-1	IC₅₀	817 μM Compound: L-EBOA	Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1 Concentration required for blocking [14C]glutamate uptake in COS-1 cells expressing human Excitatory amino acid transporter 1	[PMID: 11078189]
HEK293	IC₅₀	0.96 μM Compound: TBOA	Inhibition of [3H]-D-Asp uptake at human EAAT2 expressed in HEK293 cells measured after 3 mins by TopCount method Inhibition of [3H]-D-Asp uptake at human EAAT2 expressed in HEK293 cells measured after 3 mins by TopCount method	[PMID: 27636002]
HEK293	IC₅₀	1.6 μM Compound: TBOA	Inhibition of [3H]-D-Asp uptake at human EAAT1 expressed in HEK293 cells measured after 3 mins by TopCount method Inhibition of [3H]-D-Asp uptake at human EAAT1 expressed in HEK293 cells measured after 3 mins by TopCount method	[PMID: 27636002]
HEK293	IC₅₀	3.7 μM Compound: TBOA	Inhibition of [3H]-D-Asp uptake at human EAAT3 expressed in HEK293 cells measured after 3 mins by TopCount method Inhibition of [3H]-D-Asp uptake at human EAAT3 expressed in HEK293 cells measured after 3 mins by TopCount method	[PMID: 27636002]
MDCK	IC₅₀	1.3 μM Compound: L-TBOA	Glutamate uptake inhibition assay on glutamate transporters (excitatory amino acid transporters EAAT2) stably expressed on MDCK cells before U.V radiation Glutamate uptake inhibition assay on glutamate transporters (excitatory amino acid transporters EAAT2) stably expressed on MDCK cells before U.V radiation	[PMID: 12617931]

In Vitro

DL-TBOA (70-350 μM; 48 hours; HCT116 and LoVo cell lines) treatment concentration-dependently enhances SN38-induced loss of viability. DL-TBOA reversed Oxaliplatin-induced loss of viability^[4].
DL-TBOA (350 μM; 24 hours; HCT116 and LoVo cell lines) treatment decreases p53 induction by SN38 and oxaliplatin^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[4]

Cell Line:	HCT116 and LoVo cell lines
Concentration:	70 μM, 350 μM
Incubation Time:	48 hours
Result:	Enhanced SN38-induced, and counteracted Oxaliplatin-induced, cell death.

Cell Viability Assay^[4]

Cell Line:	HCT116 and LoVo cell lines
Concentration:	350 μM
Incubation Time:	24 hours
Result:	p53 induction by SN38 and oxaliplatin was decreased.

In Vivo

DL-TBOA (10 nmol; i.c.v., rats) significantly facilitates the expression of naloxone-precipitated somatic signs and conditioned place aversion^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Male Sprague-Dawley rats (180-250 g)^[5]
Dosage:	1 nmol, 3 nmol, 10 nmol
Administration:	Intracerebroventricularly injection (i.c.v.)
Result:	Dose dependently facilitated various somatic signs induced by Naloxone (0.1 mg/kg).

Masse moléculaire

239.23

Formule

C₁₁H₁₃NO₅

CAS No.

205309-81-5

Appearance

Solid

Color

White to off-white

SMILES

OC([C@@H](N)[C@@H](C(O)=O)OCC1=CC=CC=C1)=O

Livraison

Room temperature in continental US; may vary elsewhere.

Stockage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Solvant et solubilité

In Vitro:

DMSO : 200 mg/mL (836.02 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H₂O : 5 mg/mL (20.90 mM; ultrasonic and warming and heat to 60°C)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	4.1801 mL	20.9004 mL	41.8008 mL
5 mM	0.8360 mL	4.1801 mL	8.3602 mL
10 mM	0.4180 mL	2.0900 mL	4.1801 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 5 mg/mL (20.90 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 5 mg/mL (20.90 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 5 mg/mL (20.90 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL Corn oil, and mix evenly.

Pureté et documentation

Purity: 99.54%

Fiche technique (279 KB) SDS (393 KB)

COA (249 KB) HNMR (170 KB) LCMS (89 KB)

Instruction de manipulation (2659 KB)

Références

[1]. Shimamoto K, et al. DL-threo-beta-benzyloxyaspartate, a potent blocker of excitatory amino acid transporters. Mol Pharmacol. 1998 Feb;53(2):195-201. [Content Brief]

[2]. Jabaudon D, et al. Inhibition of uptake unmasks rapid extracellular turnover of glutamate of nonvesicular origin. Proc Natl Acad Sci U S A. 1999 Jul 20;96(15):8733-8. [Content Brief]

[3]. Shigeri Y, et al. Effects of threo-beta-hydroxyaspartate derivatives on excitatory amino acid transporters (EAAT4 and EAAT5). J Neurochem. 2001 Oct;79(2):297-302. [Content Brief]

[4]. Pedraz-Cuesta E, et al. The glutamate transport inhibitor DL-Threo-β-Benzyloxyaspartic acid (DL-TBOA) differentially affects SN38- and oxaliplatin-induced death of drug-resistant colorectal cancer cells. BMC Cancer. 2015 May 16;15:411. [Content Brief]

[5]. Yumiko Sekiya, et al. Facilitation of morphine withdrawal symptoms and morphine-induced conditioned place preference by a glutamate transporter inhibitor DL-threo-beta-benzyloxyaspartate in rats. Eur J Pharmacol. 2004 Feb 6;485(1-3):201-10. [Content Brief]

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Referência HY-107522-10mg

Contactar o distribuidor local :

Marca : MedChemExpress

Contactar o distribuidor local :

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