BAPTA-AM Chemical Properties

Melting point:

86-90°C

Boiling point:

796.1±60.0 °C(Predicted)

Density 

1.350±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in chloroform, dimethyl sulfoxide

form 

powder

pka

1.69±0.50(Predicted)

color 

White

λmax

287 nm

BRN 

7458534

Stability:

Light Sensitive

Biological Applications

Calcium indicators; treating cancer,chronic bacterial infection,glaucoma,ocular hypertension,HIV-associated conditions,infectious diseases,neurodegenerative disorders,neurological conditions,psychiatric conditions

InChIKey

YJIYWYAMZFVECX-UHFFFAOYSA-N

CAS DataBase Reference

126150-97-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-10-21

HS Code 

2921490090

MSDS

• Language:English Provider:SigmaAldrich

BAPTA-AM Usage And Synthesis

Description

BAPTA-AM is a selective, membrane-permeable calcium chelator.

Description

BAPTA-AM (126150-97-8) is a selective cell permeable Ca2+ chelator. It is a widely used intracellular calcium sponge.1,2 Rapidly taken up by cells where it is irreversibly hydrolyzed to BAPTA by intracellular esterases. Pretreatment of cells with BAPTA-AM inhibits thapsigargin-induced responses.3

Chemical Properties

Off-White to Light Yellow Solid

Uses

A membrane-permeable form of BAPTA;Selective chelator of intracellular Ca2+ stores.

Uses

BAPTA is membrane-impermeable calcium chelator that binds extracellular calcium ions (Kd = 0.11 μM), with selectivity over magnesium ions or protons. BAPTA and its derivatives can also be used as calcium indicators, since the absorption maximum for BAPTA changes when it is complexed with calcium (absorption maxima free/complexed = 254/274 nm, emission maxima free/complexed = 363/363 nm). BAPTA AM is a cell permeable analog of BAPTA that binds calcium only after the acetoxymethyl group is removed by cytoplasmic esterases. It is commonly used at 10-100 μM to evaluate the role of intracellular calcium in cell signaling. It can also be used in animals. BAPTA AM also inhibits voltage-gated potassium (Kv) channels, including Kv1.3, Kv1.5, and Kv11.1 (Ki = 1.45, 1.23, and 1.30 μM, respectively).

Uses

A cell permeable derivative of BAPTA which is widely used as an intracellular calcium sponge. Fluorescence: max. Abs. 287nm; e x 10-3: 5.9

Uses

BAPTA-AM is a lipophilic diester of BAPTA used for inhibition of proteolytic activities of certain metalloproteinases, calpain and TACE. Fluorescence: max. Abs. 287nm; e x 10-3: 5.9

Definition

ChEBI: 2-[N-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]anilino]acetic acid acetyloxymethyl ester is an alpha-amino acid ester.

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.

reaction suitability

reagent type: chelator

Biological Activity

Selective calcium chelator that is the cell-permeable analog of BAPTA (Cat No. 2786 ). Blocks hK v 1.5, hERG and hK v 1.3 channels (K i values are 1.23, 1.30 and 1.45 μ M respectively). Displays antithrombotic activity in vitro .

Biochem/physiol Actions

Selective chelator of intracellular Ca2+ stores.

storage

-20°C

References

1) Smith et al. (1992), Cytosolic calcium as a second messenger for collagen-induced platelet responses; Biochem. J., 288 925 2) Yoshida et al. (1993), Role of calcium ion in induction of apoptosis by etoposide in human leukemia HL-60 cells; Biochem. Biophys. Res. Commun., 196 927 3) Jiang et al. (1994), Intracellular Ca2+ signals activate apoptosis in thymocytes: studies using the Ca(2+)-ATPase inhibitor thapsigargin; Exp. Cell Res., 212 84

BAPTA-AM(126150-97-8)Related Product Information

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