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Merck

A1076

BAPTA-AM

≥95% (HPLC), powder, intracellular Ca²⁺ store chelator

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C34H40N2O18
CAS Number:
126150-97-8
Molecular Weight:
764.68
NACRES:
NA.77
PubChem Substance ID:
24890502
UNSPSC Code:
12352200
MDL number:
MFCD00036696
Beilstein/REAXYS Number:
7458534
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
200

Key Documents

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Product Name

BAPTA-AM, ≥95% (HPLC)

InChI

1S/C34H40N2O18/c1-23(37)47-19-51-31(41)15-35(16-32(42)52-20-48-24(2)38)27-9-5-7-11-29(27)45-13-14-46-30-12-8-6-10-28(30)36(17-33(43)53-21-49-25(3)39)18-34(44)54-22-50-26(4)40/h5-12H,13-22H2,1-4H3

SMILES string

CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccccc1OCCOc2ccccc2N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O

InChI key

YJIYWYAMZFVECX-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

powder

storage temp.

−20°C

Quality Level

200

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General description

BAPTA-AM inhibits free radical-mediated toxicity, enhances apoptosis in non-neuronal cells and protects neurons from ischemic damage. It regulates ion channels and blocks neuronal Ca2+-activated K+ channel currents. BAPTA-AM maintains intracellular Ca2+ homeostasis.

Application

BAPTA-AM has been used :
  • to reduce the elevation of cleaved caspase-3
  • to block cell death, inhibit ROS (reactive oxygen species) production and inhibit caspase-8 activation
  • to exclude the effect of changes in intracellular Ca2+ ([Ca2+]i) concentration during seizure induction
  • to eliminate the increase of [Ca2+]i induced by 6-hydroxydopamine (6-OHDA)

Biochem/physiol Actions

Selective chelator of intracellular Ca2+ stores.

Other Notes

Membrane-permeable form of BAPTA.

Storage Class

11 - Combustible Solids

wgk

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
SLCF8556
SLBP5439V
120M5022V
SLBH5256V
061M5020V

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BAPTA/AM, an intracellular calcium chelator, induces delayed necrosis by lipoxygenase-mediated free radicals in mouse cortical cultures
Wie MB, et al.
Progress in Neuro-Psychopharmacology & Biological Psychiatry, 25(8), 1641-1659 (2001)
The membrane permeable calcium chelator BAPTA-AM directly blocks human ether a-go-go-related gene potassium channels stably expressed in HEK 293 cells
Tang Q, et al.
Biochemical Pharmacology, 74(11), 1596-1607 (2007)
Glycolysis is essential for chemoresistance induced by transient receptor potential channel C5 in colorectal cancer
Wang T, et al.
BMC Cancer, 18(1), 207-207 (2018)
Hyperactivation of the mammalian degenerin MDEG promotes caspase-8 activation and apoptosis
Pan JA, et al.
The Journal of Biological Chemistry, 288(5), 2952-2963 (2013)
Blockade of RyRs in the ER Attenuates 6-OHDA-induced calcium overload, cellular hypo-excitability and apoptosis in dopaminergic neurons
Huang L, et al.
Frontiers in Cellular Neuroscience, 11, 52-52 (2017)
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