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A4926

1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid

Name: 1,2-Bis(2-Aminophenoxy)ethane-<I>N,N,N′,N′</I>-tetraacetic acid
Brand: ALDRICH

98%

Synonym(s):

2,2′-(Ethylenedioxy)dianiline-N,N,N′,N′-tetraacetic acid, BAPTA, Ethylenedioxybis(o-phenylenenitrilo)tetraacetic acid

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₄N₂O₁₀

CAS Number:

85233-19-8

Molecular Weight:

476.43

UNSPSC Code:

12352103

NACRES:

NA.23

PubChem Substance ID:

57653856

MDL number:

MFCD00036255

Beilstein/REAXYS Number:

5192406

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Properties

assay

98%

form

powder

density

±1.494 g/cm³ at 25 °C (Predicted)

storage temp.

2-8°C

SMILES string

OC(=O)CN(CC(O)=O)c1ccccc1OCCOc2ccccc2N(CC(O)=O)CC(O)=O

InChI

1S/C22H24N2O10/c25-19(26)11-23(12-20(27)28)15-5-1-3-7-17(15)33-9-10-34-18-8-4-2-6-16(18)24(13-21(29)30)14-22(31)32/h1-8H,9-14H2,(H,25,26)(H,27,28)(H,29,30)(H,31,32)

InChI key

FTEDXVNDVHYDQW-UHFFFAOYSA-N

Description

General description

1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid (BAPTA) is a high-affinity, fast-acting calcium chelator for precise intracellular Ca²⁺ regulation. Its rapid binding kinetics and strong selectivity for Ca²⁺ make it essential for investigating calcium-dependent processes in neuronal and cellular research. BAPTA and its membrane-permeable derivative, BAPTA-AM, allow controlled manipulation of Ca²⁺ dynamics, facilitating studies on calcium signaling, neuroprotection, and cell signaling pathways.

Application

The product can be used in various R&D applications such as:

Neuroscience: Used to suppress intracellular Ca²⁺ overload, reduce neuronal apoptosis, and preserve electrophysiological function in injury models, demonstrating strong neuroprotective action.

Pharmacology: Enables precise buffering of intracellular Ca²⁺ levels, allowing researchers to distinguish Ca²⁺‑ dependent drug effects and dissect therapeutic signaling mechanisms.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Articles

Sensor Dyes

Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.

感应染料

一氧化氮 (NO) 是神经元、内皮细胞和免疫系统中的信号转运分子。

Determination of 1,2-bis (2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA free acid) in rat plasma, urine and feces by liquid chromatography with UV and tandem mass spectrometric detection.

Zheng Feng et al.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878(30), 3052-3058 (2010-10-23)

BAPTA free acid was identified as the main metabolic product of 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetra(actoxymethyl ester) (BAPTA-AM), a neuroprotective agent in cerebral ischemia, in rats. In this paper, liquid chromatography-ultraviolet (LC-UV) and mass spectrometry/mass spectrometry (LC-MS/MS) methods were employed for the

Calcium rubies: a family of red-emitting functionalizable indicators suitable for two-photon Ca2+ imaging.

Mayeul Collot et al.

Journal of the American Chemical Society, 134(36), 14923-14931 (2012-07-24)

We designed Calcium Rubies, a family of functionalizable BAPTA-based red-fluorescent calcium (Ca(2+)) indicators as new tools for biological Ca(2+) imaging. The specificity of this Ca(2+)-indicator family is its side arm, attached on the ethylene glycol bridge that allows coupling the

1,2-bis(2-Aminophenoxy)ethane-N,N,N',N'-tetraacetic acid induces caspase-mediated apoptosis and reactive oxygen species-mediated necrosis in cultured cortical neurons.

K S Han et al.

Journal of neurochemistry, 78(2), 230-239 (2001-07-20)

Sustained alteration in [Ca(2+)]i triggers neuronal death. We examined morphological and signaling events of Ca(2+)-deficiency-induced neuronal death. Cortical cell cultures exposed to 20 microM 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA-AM), an intracellular calcium chelator, underwent neuronal apoptosis within 12 h that was evident

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Global Trade Item Number

SKU	GTIN
A4926-1G	04061833375235
A4926-250MG	04061833375242
A4926-5G	04061833425930