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

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid acetoxymethyl ester (BAPTA-AM) is a **cell-permeable chelator** used in research to **study intracellular calcium (Ca2+) signaling**.

Here's a breakdown:

* **1,2-bis(2-aminophenoxy)ethane:** This is the core structure of the molecule, a rigid linker with two amino groups attached to phenoxy rings.
* **N,N,N',N'-tetraacetic acid:** This part of the molecule is a chelating agent, meaning it can bind to metal ions. In this case, it specifically binds to Ca2+ ions.
* **Acetoxymethyl ester:** This is a protective group that allows the molecule to pass through cell membranes. Once inside the cell, it is cleaved off by intracellular esterases, releasing the active chelator.

**Importance in Research:**

* **Ca2+ Signaling:** Calcium is a crucial signaling molecule in cells, involved in a wide range of processes including muscle contraction, neurotransmitter release, and gene expression. BAPTA-AM is used to **study the role of Ca2+ in these processes** by temporarily reducing the intracellular calcium levels.
* **Cell Biology:** BAPTA-AM is a valuable tool for investigating **cellular mechanisms** related to calcium signaling, such as the function of calcium channels, the regulation of calcium pumps, and the effects of calcium on specific cellular pathways.
* **Drug Discovery:** BAPTA-AM is also used in **drug discovery** to identify compounds that modulate calcium signaling pathways and to study the effects of potential drugs on calcium homeostasis.

**Key Features of BAPTA-AM:**

* **High affinity for Ca2+:** BAPTA-AM binds Ca2+ with high affinity, making it effective at chelating calcium even at low concentrations.
* **Cell permeability:** The acetoxymethyl ester allows BAPTA-AM to cross cell membranes, enabling researchers to study intracellular calcium levels.
* **Reversibility:** BAPTA-AM is a reversible chelator, meaning that its effects can be reversed by removing it from the cell.

**In summary, 1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid acetoxymethyl ester (BAPTA-AM) is a valuable tool for researchers studying intracellular calcium signaling and its role in various cellular processes.**

Cross-References

ID SourceID
PubMed CID3034747
SCHEMBL ID1374716
MeSH IDM0191691

Synonyms (8)

Synonym
139890-68-9
1,2-bis(o-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester
2-[2-[2-[2-[[2-(acetyloxymethoxy)-2-oxoethyl]-(carboxymethyl)amino]phenoxy]ethoxy]-n-(carboxymethyl)anilino]acetic acid
n-(2-((acetyloxy)methoxy)-2-oxoethyl)-n-(2-(2-(2-(bis(carboxymethyl)amino)phenoxy)ethoxy)phenyl)glycine
glycine, n-(2-((acetyloxy)methoxy)-2-oxoethyl)-n-(2-(2-(2-(bis(carboxymethyl)amino)phenoxy)ethoxy)phenyl)-
SCHEMBL1374716
DTXSID70161192

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Contrary to their action in the toxic effect, both 100 microM amiloride and the intracellular loading of BAPTA failed to counteract the nontoxic effect of 1 microM ouabain."( Toxic and nontoxic effects of ouabain on the transmitter release from frog motor nerve terminals.
Enomoto, K; Hara, N; Ichinose, M; Maeno, T; Sawada, M, 1995
)
0.29
" Accordingly, intracellular hydrogen ion concentrations were measured in cultured hippocampal neurons with the fluorescent dye BCECF during and after toxic exposures."( Changes in intracellular pH associated with glutamate excitotoxicity.
Dubinsky, JM; Hartley, Z, 1993
)
0.29
" Furthermore, when cells reached confluence they were highly resistant to the toxic effects of peroxynitrite, hydrogen peroxide, and superoxide."( Role of intracellular calcium mobilization and cell-density-dependent signaling in oxidative-stress-induced cytotoxicity in HaCaT keratinocytes.
Bai, P; Bakondi, E; Csernoch, L; Gergely, P; Gönczi, M; Hunyadi, J; Kovács, L; Pacher, P; Szabó, C; Szabó, E; Virág, L, 2003
)
0.32
" Diverse cell-specific toxic effects were observed, with C2C12 being relatively resistant to tungsten-alloy mediated toxic impact."( In vitro profiling of epigenetic modifications underlying heavy metal toxicity of tungsten-alloy and its components.
Caretti, G; Galdzicki, Z; Jaiswal, MK; Mears, D; Olsen, C; Verma, R; Xu, X, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
"Harringtonine (HT), an anticancer drug with high chemotherapeutic efficiency to human chronic granulocytic/myelomonocytic leukemia, has been reported to rapidly induce apoptosis in HL-60 cells in a wide scope/range of dosage by investigators from our lab and others."( Intracellular calcium distribution in apoptosis of HL-60 cells induced by harringtonine: intranuclear accumulation and regionalization.
Fang, M; Li, N; Wang, L; Xue, S; Zhang, H, 1998
)
0.3
" The kinetics and colorimetric dose-response profile of DP-109 indicate that the compound inserts into the lipid bilayers rather than being localized at the bilayer surface."( Membrane interactions and metal ion effects on bilayer permeation of the lipophilic ion modulator DP-109.
Angel, I; Friedman, J; Jelinek, R; Kolusheva, S, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,136)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.09)18.7374
1990's312 (27.46)18.2507
2000's559 (49.21)29.6817
2010's243 (21.39)24.3611
2020's21 (1.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.09%)5.53%
Reviews3 (0.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other1,150 (99.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]