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A4926

Sigma-Aldrich

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

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
Beilstein/REAXYS Number:
5192406
MDL number:
MFCD00036255
UNSPSC Code:
12352103
PubChem Substance ID:
57653856
NACRES:
NA.23

Quality Level

200

assay

98%

form

powder

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

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General description

In nature 1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetra acetic acid (BAPTA) is a main metabolic product of BAPTA -AM (BAPTA-tetra(actoxymethyl ester), a neuro protective agent in cerebral ischemia, in rats.BAPTA is an intercellular Ca2+ chelator.

Application

Used to study morphological and signaling events of Ca2+ deficiency.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCF0254
SLBX6598
SLBW9824
SLBS8679
SLBJ9603V

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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
Roger C Hardie
Cell calcium, 38(6), 547-556 (2005-09-06)
In vivo light-induced and basal hydrolysis of phosphatidyl inositol 4,5-bisphosphate (PIP2) by phospholipase C (PLC) were monitored in Drosophila photoreceptors using genetically targeted PIP2-sensitive ion channels (Kir2.1) as electrophysiological biosensors for PIP2. In cells loaded via patch pipettes with varying
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
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
Alexander M Walter et al.
The EMBO journal, 33(15), 1681-1697 (2014-06-07)
The SNARE protein vti1a is proposed to drive fusion of intracellular organelles, but recent data also implicated vti1a in exocytosis. Here we show that vti1a is absent from mature secretory vesicles in adrenal chromaffin cells, but localizes to a compartment
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