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40843

Sigma-Aldrich

1,2-Bis-(2-amino-5-fluorphenoxy)-ethan-N,N,N′,N′-tetraessigsäure-tetrakis-(acetoxymethyl)-ester

≥97.0% (HPLC)

Synonym(e):

5,5′-Difluor-BAPTA-AM

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About This Item

Empirische Formel (Hill-System):
C34H38F2N2O18
CAS-Nummer:
128255-42-5
Molekulargewicht:
800.66
Beilstein:
8181644
MDL-Nummer:
MFCD00467468
UNSPSC-Code:
12352200
PubChem Substanz-ID:
57650030

Assay

≥97.0% (HPLC)

Lagertemp.

−20°C

SMILES String

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccc(F)cc1OCCOc2cc(F)ccc2N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O

InChI

1S/C34H38F2N2O18/c1-21(39)49-17-53-31(43)13-37(14-32(44)54-18-50-22(2)40)27-7-5-25(35)11-29(27)47-9-10-48-30-12-26(36)6-8-28(30)38(15-33(45)55-19-51-23(3)41)16-34(46)56-20-52-24(4)42/h5-8,11-12H,9-10,13-20H2,1-4H3

InChIKey

ZXXWTKAFGAXGHZ-UHFFFAOYSA-N

Anwendung

1,2-Bis(2-amino-5-fluorophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl) ester (5,5′-Difluoro-BAPTA-AM, 5FBAPTA-AM), a calcium chelator, may be used to modulate calcium levels and flow within cells to study calcium homeostasis and cell signaling.

Sonstige Hinweise

19F-NMR Calcium Indikator

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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G A Smith et al.
Proceedings of the National Academy of Sciences of the United States of America, 80(23), 7178-7182 (1983-12-01)
Symmetrically substituted difluoro derivatives of 1,2-bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (nFBAPTA) show large 19F NMR chemical shifts on chelating divalent cations. The complexes of Ca2+ with 4FBAPTA and 5FBAPTA show fast and slow exchange behavior, respectively, and the chemical shift or the areas
E Marban et al.
Circulation research, 66(5), 1255-1267 (1990-05-01)
Calcium has been implicated as a mediator of cell injury in ischemia and reperfusion, but direct measurements of Ca2+ are required to refine this idea. We used nuclear magnetic resonance spectroscopy and the Ca2+ indicator 5F-BAPTA to measure [Ca2+]i in
J M Boeynaems et al.
European journal of pharmacology, 233(1), 13-20 (1993-03-16)
Our observation that loading of bovine aortic endothelial cells with quin 2 or 1,2-bis(O-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA) enhances their release of prostacyclin (PGI2) has been studied in detail. The action of the acetoxymethyl ester (AM) of BAPTA (BAPTA-AM) was biphasic: at
H L Kirschenlohr et al.
The Biochemical journal, 293 ( Pt 2), 407-411 (1993-07-15)
A new n.m.r. indicator, 1,2-bis-(2-[1-(hydroxycarbony)ethyl- (hydroxycarbonylmethyl)]amino-5-fluorophenoxy)ethane (DiMe-5FBAPTA), with a higher affinity for calcium (apparent Kd 46 nM, pH 7.2, 30 degrees C) than the parent 5FBAPTA chelator (Kd 537 nM, pH 7.1, 30 degrees C) has been used to measure
Jiao Zhang et al.
Development, growth & differentiation, 53(5), 679-696 (2011-06-16)
During the early blastula period of zebrafish embryos, the outermost blastomeres begin to undergo a significant thinning in the apical/basolateral dimension to form the first distinct cellular domain of the embryo, the enveloping layer (EVL). During this shape transformation, only

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