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Merck

A1076

BAPTA-AM

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C34H40N2O18
Numéro CAS:
Poids moléculaire :
764.68
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
7458534

Nom du produit

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

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Catégories apparentées

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.

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.

Other Notes

Membrane-permeable form of BAPTA.

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is BAPTA-AM, Product A1076, and  how is it used?

    BAPTA-AM is a cell-permeant acetoxymethyl ester derivative of BAPTA (Product No. A4926), which is used as a chelator of intracellular Ca2+ stores. The acetoxymethyl ester derivative, which is an ester of the carboxylic acid groups in BAPTA, results in an uncharged molecule which allows it to penetrate cell membranes. Inside the cell, these groups are cleaved by nonspecific esterase activity resulting in the free acid form.

  4. In what solvents is BAPTA-AM, Product A1076, soluble?

    BAPTA-AM is soluble in dimethyl sulfoxide (DMSO) at 25 mg/mL.  It is also soluble in acetonitrile at 0.5 mg/mL.  It is best to use anhydrous DMSO, since it is known that moisture uptake by the DMSO can adversely affect the quality of the BAPTA-AM.  

  5. How would you recommend that I store my BAPTA-AM, Product A1076, solution?

    Stock solutions of 1-10 mM can be prepared in anhydrous DMSO, divided into single-use aliquots, and stored desiccated and frozen at -20°C.

  6. What are the shipping and storage temperatures for BAPTA-AM, Product A1076?

    BAPTA-AM is shipped at ambient temperature.  The recommended storage temperature, once received, is -20 °C.

  7. What is the typical working concentration for BAPTA-AM, Product A1076?

    The typical final working concentrations for cell loading is in the range of 1 to 10 micromolar. It is best to find literature references dealing with your application for more information on the amounts to use.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

M-calpain activation facilitates seizure induced KCC2 down regulation
Wan L, et al.
Frontiers in Molecular Neuroscience, 11, 287-287 (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)
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)
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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