Basic information
- CAS
126150-97-8- Standard SMILES
CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)c1ccccc1OCCOc1ccccc1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O- InChIKey
YJIYWYAMZFVECX-UHFFFAOYSA-N- Molecular formula
- C34H40N2O18
- Average molar mass
- 764.7 g/mol
- Monoisotopic mass
- 764.22761243
Overview
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.
Names & identifiers
- Preferred name
- Bapta-AM
- IUPAC
- acetyloxymethyl 2-[N-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]anilino]acetate
- English name
- BAPTA-AM
- Molecular formula
- C34H40N2O18
- Molecular weight
- 764.68
Names & synonyms
BAPTA-AMDTXSID60274361RefChem:1077465DTXCID30225840126150-97-8BAPTA/AMBAPTA AMacetyloxymethyl 2-[N-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]anilino]acetateMFCD00036696Tetrakis(acetoxymethyl) 2,2',2'',2'''-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanetriyl))tetraacetate(acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy}ethoxy)phenyl]amino)acetateGlycine, N,N'-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, 1,1'-bis[(acetyloxy)methyl] ester
Show more names
CS-968DAPTA-AMBAPTA AM, >=98%BAPTA/AM(BAPTA-AM)BAPTA-AM, Ca2+ chelatorBAPTA-AM, 10 mM in DMSOBAPTA, AM *CAS 126150-97-8*BAPTAAMBAPTA, AM *UltraPure Grade* *CAS 126150-97-8*
Tetrakis(acetoxymethyl) 1,2-Bis(2-aminophenoxy)ethane-N,N,N,N-tetraacetateTetrakis(acetoxymethyl) 1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetateBio1_000382Glycine, N,N'-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, 1,1'-bis[(acetyloxy)methyl] ester; Glycine, N,N'-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]-, bis[(acetyloxy)methyl] ester (9CI); BAPTA-AMC34H40N2O181,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetrakis(acetoxymethyl ester)BAPTA,AMFT-0606289
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 235 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 20
- Rotatable bonds
- 31
- Heavy atoms
- 54
- Formal charge
- 0
- Complexity
- 1,100
Physicochemical properties
- Melting point
- 86 · 86-90°C
- Boiling point
- 796.1 · 796.1±60.0 °C(Predicted)
- Density
- 1.35 · 1.350±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in chloroform, dimethyl sulfoxide
- form
- powder
- pka
- 1.69 · 1.69±0.50(Predicted)
- color
- White
- Appearance
- white to beige solid
- λmax
- 287 nm · 287 nm
- BRN
- 7458534 · 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
- SMILES
- C(OC1=CC=CC=C1N(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O)COC1=CC=CC=C1N(CC(OCOC(C)=O)=O)CC(OCOC(C)=O)=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8-10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 2921490090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P271-P261-P280
Chemistry & industry
Applications
DescriptionBAPTA-AM is a selective, membrane-permeable calcium chelator.
DescriptionBAPTA-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
UsesA membrane-permeable form of BAPTA;Selective chelator of intracellular Ca2+ stores.
UsesBAPTA 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).
UsesBAPTA-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
UsesA cell permeable derivative of BAPTA which is widely used as an intracellular calcium sponge. Fluorescence: max. Abs. 287nm; e x 10-3: 5.9
General DescriptionBAPTA-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.
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Related reactions
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Compound notes
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