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A1076

Sigma-Aldrich

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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25 MG
367,00 $

367,00 $


Disponible pour expédition le07 avril 2025Détails


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25 MG
367,00 $

About This Item

Formule empirique (notation de Hill) :
C34H40N2O18
Numéro CAS:
Poids moléculaire :
764.68
Beilstein:
7458534
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

367,00 $


Disponible pour expédition le07 avril 2025Détails


Devis pour commande en gros

Nom du produit

BAPTA-AM, ≥95% (HPLC)

Niveau de qualité

Essai

≥95% (HPLC)

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

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

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

Clé InChI

YJIYWYAMZFVECX-UHFFFAOYSA-N

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Description générale

BAPTA-AM inhibits free radical-mediated toxicity, enhances apoptosis in non-neuronal cells and protects neurons from ischemic damage.[1] It regulates ion channels and blocks neuronal Ca2+-activated K+ channel currents. BAPTA-AM maintains intracellular Ca2+ homeostasis.[2]

Application

BAPTA-AM has been used :
  • to reduce the elevation of cleaved caspase-3[3]
  • to block cell death, inhibit ROS (reactive oxygen species) production and inhibit caspase-8 activation[4]
  • to exclude the effect of changes in intracellular Ca2+ ([Ca2+]i) concentration during seizure induction[5]
  • to eliminate the increase of [Ca2+]i induced by 6-hydroxydopamine (6-OHDA)[6]

Actions biochimiques/physiologiques

Selective chelator of intracellular Ca2+ stores.

Liaison

Membrane-permeable form of BAPTA.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
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)
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)

Articles

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Questions

1–6 of 6 Questions  
  1. What is the typical working concentration for BAPTA-AM, Product A1076?

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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

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

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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