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BAPTA-AM

BAPTA-AM structure

CAS No:
126150-97-8
Formula:
C34H40N2O18
Chemical Name:
BAPTA-AM
Synonyms:
BAPTA-AM;1,2-BIS(2-AMINOPHENOXY)ETHANE-N,N,N,N-TETRAACETIC ACID ACETOXYMETHYL ESTER;1,2-BIS (2-AMINOPHENOXY)ETHANE-N,N,N',N'-TETRAACETIC ACID, TETRAACETOXYMETHYL ESTER;1,2-BIS(2-AMINOPHENOXY)ETHANE-N,N,N',N'-TETRAACETIC ACID TETRAKIS(ACETOXY-METHYL) ESTER;1,2-BIS(O-AMINOPHENOXY)ETHANE-N,N,N',N'-TETRAACETIC ACID TETRA(ACETOXYMETHYL) ESTER;O,O'-Bis(2-aminophenyl)ethyleneglycol-N,N,N',N'-tetraaceticacid,tetraacetoxymethylester;1,2-Bis(2-aminophenoxy)ethane-N,N,N'',N''-tetraacetic acidtetrakis(acetoxymethyl ester);N,N'-[1,2-Ethanediylbis(oxy-2,1-phenylene)]bis[N-[2-[(acetyloxy)Methoxy]-2-oxoethyl]glycine 1,1'-Bis[(acetyloxy)Methyl] Ester
Categories:
Organic Chemistry > Amides

Description

BAPTA-AM is an intracellular calcium chelator.

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.

BAPTA-AM Basic Attributes

Molecular Weight：

764.68

Exact Mass：

764.227600

EC Number：

2017-001-1

DSSTox ID：

DTXSID60274361

Characteristics

PSA：

235

XLogP3：

3.4

Appearance：

White powder

Density：

1.4±0.1 g/cm3

Melting Point：

86-90°C

Boiling Point：

796.1ºC at 760 mmHg

Flash Point：

435.3±32.9 °C

Refractive Index：

1.551

Water Solubility：

soluble in chloroform, dimethyl sulfoxide

Storage Conditions：

−20°C

Vapor Pressure：

2.42E-25mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Stability/Shelf Life：

Light Sensitive

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)

MeSH Entry Terms：

1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid acetoxymethyl ester

BAPTA-AM Use and Manufacturing

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).

Computed Properties

Molecular Weight:764.7
XLogP3:3.4
Hydrogen Bond Acceptor Count:20
Rotatable Bond Count:31
Exact Mass:764.22761243
Monoisotopic Mass:764.22761243
Topological Polar Surface Area:235
Heavy Atom Count:54
Complexity:1100
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes