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16609

Sigma-Aldrich

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

≥95% (HPLC)

Synonym(s):

5,5′-Dimethyl-BAPTA-AM, MAPTAM

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About This Item

Empirical Formula (Hill Notation):
C36H44N2O18
CAS Number:
147504-94-7
Molecular Weight:
792.74
Beilstein:
8181451
MDL number:
MFCD00036856
UNSPSC Code:
12352108
PubChem Substance ID:
57647583
NACRES:
NA.32

Quality Level

100

Assay

≥95% (HPLC)

solubility

DMSO: soluble

storage temp.

−20°C

SMILES string

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

InChI

1S/C36H44N2O18/c1-23-7-9-29(37(15-33(43)53-19-49-25(3)39)16-34(44)54-20-50-26(4)40)31(13-23)47-11-12-48-32-14-24(2)8-10-30(32)38(17-35(45)55-21-51-27(5)41)18-36(46)56-22-52-28(6)42/h7-10,13-14H,11-12,15-22H2,1-6H3

InChI key

HEOJVQZWOLQUDR-UHFFFAOYSA-N

Other Notes

Membrane-permeable improved derivative of BAPTA; chelators for intracellular calcium incorporated non-disruptively into cells

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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’.

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T Tiffert et al.
The Journal of physiology, 505 ( Pt 2), 403-410 (1998-01-10)
1. A recently developed method of measuring cytoplasmic Ca2+ buffering in intact red cells was applied to re-evaluate the intracellular Ca2+ binding properties of the Ca2+ chelators benz2 and BAPTA. Incorporation of the free chelators was accomplished by incubating the
J M Dubinsky
Neuroscience letters, 150(2), 129-132 (1993-02-19)
In an attempt to probe the relationship between excitotoxicity and increases in intracellular calcium ([Ca2+]i), BAPTA-AM and its analogs were applied to cultured hippocampal neurons. Chelation of [Ca2+]i depressed and prolonged transient responses to glutamate and did not effect elevation
Gurpreet Kaur et al.
Biochemical and biophysical research communications, 450(1), 812-817 (2014-06-24)
We previously showed that increased intracellular calcium can modulate Importin (Imp)β1-dependent nuclear import of SRY-related chromatin remodeling proteins. Here we extend this work to show for the first time that high intracellular calcium inhibits Impα/β1- or Impβ1-dependent nuclear protein import
Wei Song et al.
Neuroscience letters, 589, 104-109 (2015-01-18)
The neuromuscular junction (NMJ) is established through initial contact of motor neuron axon with a skeletal muscle cell and the subsequent synaptic maturation. Previous studies have shown that cyclic AMP (cAMP) enhanced spinal neurons' survival and growth but inhibited synaptogenesis.
Vera Valakh et al.
Neurobiology of disease, 77, 13-25 (2015-03-03)
Nerve injury can lead to axonal regeneration, axonal degeneration, and/or neuronal cell death. Remarkably, the MAP3K dual leucine zipper kinase, DLK, promotes each of these responses, suggesting that DLK is a sensor of axon injury. In Drosophila, mutations in proteins
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