14510

Sigma-Aldrich

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

≥96.0% (HPLC)

Synonym(s):
Ethylenedioxybis(o-phenylenenitrilo)tetraacetic acid, BAPTA
Empirical Formula (Hill Notation):
C22H24N2O10
CAS Number:
Molecular Weight:
476.43
Beilstein/REAXYS Number:
5192406
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥96.0% (HPLC)

fluorescence

λex 251 nm; λem 363 nm (pH 8.0 Highly selective calcium chelating reagent. Suitable for the spectrophotometric monitoring of Ca2+ levels)
λex 274 nm; λem 363 nm (With Calcium)

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

1,2-Bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid is a highly selective calcium chelating reagent. Effect of microinjected calcium-loaded 1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid (CaBAPTA) on cell-to-cell diffusion of carboxyfluorescein has been studied in staminal hairs of Setcreasea purpurea. It is reported to be a metabolite of 1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetra(acetoxymethyl ester) (BAPTA-AM) in rat urine.

Application

1,2-Bis(2-aminophenoxy)ethane-N,N,N′,N′′-tetraacetic acid was used for the spectrophotometric monitoring of Ca2+ levels. It may be used as chelator of cytosolic Ca²+ to investigate the effect of methoxychlor on cytosolic free Ca²+ concentrations and apoptosis in HA59T human hepatoma cells.
Highly selective calcium chelating reagent. Suitable for the spectrophotometric monitoring of Ca2+ levels

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
E B Tucker
Planta, 182(1), 34-38 (1990-08-01)
The effect of microinjected calcium-loaded 1,2-bis(2-aminophenoxy) ethane-N,N,N',N'-tetraacetic acid (CaBAPTA) on cell-to-cell diffusion of carboxyfluorescein (CF) was examined in staminal hairs of S. purpurea Boom. The CaBAPTA was microinjected into the cytoplasm of the staminal hairs either with CF or prior...
Chi-Ting Horng et al.
The Chinese journal of physiology, 58(1), 1-8 (2015-02-18)
Methoxychlor, an organochlorine pesticide, is thought to be an endocrine disrupter that affects Ca²⁺ homeostasis and cell viability in different cell models. This study explored the action of methoxychlor on cytosolic free Ca²⁺ concentrations ([Ca²⁺]i) and apoptosis in HA59T human...
B E Britigan et al.
Biochemical pharmacology, 55(3), 287-295 (1998-03-04)
A role for increases in intracellular calcium (Ca2+) has been suggested in the pathophysiology of various forms of oxidant-mediated cell injury. In recent studies, we found that iron bound to the Pseudomonas aeruginosa siderophore, pyochelin, augments oxidant-mediated endothelial cell injury...
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.
Feng Z and Wenying L.
Journal of Chromatography. B, Biomedical Applications, 878(30), 3052-3058 (2010)
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...

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