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BAPTA/AM

Membrane-permeable form of BAPTA.

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Synonym(s):
BAPTA/AM, 1,2- bis( o-Aminophenoxy)ethane-N,N,Nʹ,Nʹ-tetraacetic Acid Tetra(acetoxymethyl) Ester, 1,2-bis(o-Aminophenoxy)ethane-N,N,Nʹ,Nʹ-tetraacetic Acid Tetra(acetoxymethyl) Ester
Empirical Formula (Hill Notation):
C34H40N2O18
CAS Number:
Molecular Weight:
764.68
MDL number:

Quality Level

assay

≥90% (TLC)

form

solid

reaction suitability

reagent type: chelator

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

light yellow

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

−20°C

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

InChI key

YJIYWYAMZFVECX-UHFFFAOYSA-N

General description

Membrane-permeable form of BAPTA. Can be loaded into a wide variety of cells, where it is hydrolyzed by cytosolic esterases and is trapped intracellularly as the active chelator BAPTA. Prevents cocaine-induced ventricular fibrillations. Induces inactivation of protein kinase C. Also inhibits thapsigargin-induced apoptosis in rat thymocytes.
Membrane-permeable form of BAPTA. Can be loaded into a wide variety of cells, where it is hydrolyzed by cytosolic esterases and is trapped intracellularly as the active chelator BAPTA.Prevents cocaine-induced ventricular fibrillations. Abolishes vitamin D3-induced increase in intracellular Ca2+. Induces inactivation of protein kinase C. Also inhibits thapsigargin-induced apoptosis in rat thymocytes.

Application


  • TRPV1-Dependent Antiproliferative Activity of Dioecious Maclura pomifera Extracts in Estrogen Receptor-Positive Breast Cancer Cell Lines Involves Multiple Apoptotic Pathways.: This study explores how BAPTA/AM, a calcium chelator, contributes to the antiproliferative effects by regulating TRPV1 and apoptotic pathways in breast cancer cells (Rumpa et al., 2024).

  • Mitochondrial calcium uniporter promotes kidney aging in mice through inducing mitochondrial calcium-mediated renal tubular cell senescence.: The research highlights BAPTA/AM′s role in mitigating mitochondrial calcium overload, which is linked to cellular senescence and aging processes in renal cells (Xiong et al., 2024).

  • TRPV3 facilitates lipolysis and attenuates diet-induced obesity via activation of the NRF2/FSP1 signaling axis.: This article discusses the role of BAPTA/AM in the modulation of TRPV3 channels, leading to enhanced lipolysis and protection against obesity through the NRF2/FSP1 pathway (Hu et al., 2024).

  • Inflammation and Acinar Cell Dual-Targeting Nanomedicines for Synergistic Treatment of Acute Pancreatitis via Ca(2+) Homeostasis Regulation and Pancreas Autodigestion Inhibition.: BAPTA/AM is utilized to regulate calcium homeostasis, thereby preventing inflammation and autodigestion in acute pancreatitis treatments (Wang et al., 2024).

  • IP(3)R-Mediated Calcium Release Promotes Ferroptotic Death in SH-SY5Y Neuroblastoma Cells.: This study investigates how BAPTA/AM inhibits IP3R-mediated calcium release, thereby reducing ferroptotic cell death in neuroblastoma cells (Campos et al., 2024).

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot, purge with inert gas and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Bissonnette, M., et al. 1994. Am. J. Physiol.267, G465.
Jiang, S., et al. 1994. Exp. Cell Res.212, 84.
Billman, G.E. 1993. Am. J. Physiol. 265, H1529.
Dieter, P., et al. 1993. Biol. Chem. Hoppe Seyler 374, 171.
Harrison, S.M., and Bers, D.M. 1987. Biochim. Biophys. Acta 925, 133.
Harrison, S.M., and Bers, D.M. 1987. J. Biophys.51, 102A.
Marban, E., et al. 1986. J. Clin. Invest.78, 1185.
Tsien, R.Y. 1981. Nature290, 527.
Tsien, R.Y. 1980. Biochemistry19, 2396.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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