Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

40843

Sigma-Aldrich

1,2-Bis(2-amino-5-fluorophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl) ester

≥97.0% (HPLC)

Synonym(s):

5,5′-Difluoro-BAPTA-AM

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C34H38F2N2O18
CAS Number:
128255-42-5
Molecular Weight:
800.66
Beilstein/REAXYS Number:
8181644
MDL number:
MFCD00467468
UNSPSC Code:
12352200
PubChem Substance ID:
57650030

assay

≥97.0% (HPLC)

storage temp.

−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

InChI key

ZXXWTKAFGAXGHZ-UHFFFAOYSA-N

Application

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.

Other Notes

19F-NMR calcium indicator

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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

Articles

Sensor Dyes

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service