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Merck

A1076

Sigma-Aldrich

BAPTA-AM

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C34H40N2O18
Número de CAS:
Peso molecular:
764.68
Beilstein:
7458534
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77
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Nombre del producto

BAPTA-AM, ≥95% (HPLC)

Nivel de calidad

Ensayo

≥95% (HPLC)

Formulario

powder

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

YJIYWYAMZFVECX-UHFFFAOYSA-N

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Descripción general

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]

Aplicación

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]

Acciones bioquímicas o fisiológicas

Selective chelator of intracellular Ca2+ stores.

Ligadura / enlace

Membrane-permeable form of BAPTA.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Visite la Librería de documentos

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)
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)
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)
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)
M-calpain activation facilitates seizure induced KCC2 down regulation
Wan L, et al.
Frontiers in Molecular Neuroscience, 11, 287-287 (2018)

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Questions

1–6 of 6 Questions  
  1. 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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  2. 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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  3. 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.

      Helpful?

  4. 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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  5. 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.

      Helpful?

  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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