Page last updated: 2024-12-07

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

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

Description

1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid, also known as **BAPTA**, is a chemical compound that is a **calcium chelator**. This means it can bind to calcium ions (Ca2+) and remove them from solution.

**Why is BAPTA important for research?**

BAPTA is a powerful tool for researchers studying cellular processes because calcium plays a crucial role in many cellular functions, including:

* **Muscle contraction:** Calcium triggers the release of muscle fibers for contraction.
* **Neurotransmitter release:** Calcium influx at nerve terminals triggers the release of neurotransmitters.
* **Cell signaling:** Calcium acts as a second messenger in various signaling pathways.
* **Gene expression:** Calcium can regulate the expression of certain genes.
* **Cell growth and differentiation:** Calcium plays a role in cell growth and differentiation.

By using BAPTA, researchers can:

* **Investigate the role of calcium in various cellular processes:** By chelating calcium, researchers can observe the effects of calcium depletion on different cellular functions.
* **Study the dynamics of calcium signaling:** BAPTA can be used to manipulate calcium levels and study the kinetics of calcium signaling pathways.
* **Develop new drugs:** BAPTA and its analogs are potential drug targets for diseases related to calcium dysregulation, such as epilepsy, heart disease, and cancer.
* **Develop new tools for imaging:** BAPTA-based fluorescent probes can be used to visualize calcium concentrations in living cells.

**In summary, BAPTA is a valuable research tool due to its ability to chelate calcium and manipulate its levels in cells. This allows researchers to investigate the importance of calcium in various cellular processes and develop new treatments for diseases related to calcium dysregulation.**

1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID104751
CHEMBL ID1590868
CHEBI ID60888
SCHEMBL ID232103
MeSH IDM0085132

Synonyms (48)

Synonym
2,2',2'',2'''-[ethane-1,2-diylbis(oxy-2,1-phenylenenitrilo)]tetraacetic acid
CHEBI:60888 ,
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid
NCGC00166094-01
glycine, n,n'-(1,2-ethanediylbis(oxy-2,1-phenylene)bis(n-(carboxymethyl)-
glycine, n,n'-(1,2-ethanediylbis(oxy-2,1-phenylene))bis(n-(carboxymethyl)-,tetrapotassium salt
1,2-bis(o-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid
bapta ,
ca(ii)-bapta
bapeta
85233-19-8
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid, 98%
AKOS005146505
2-[2-[2-[2-[bis(carboxymethyl)amino]phenoxy]ethoxy]-n-(carboxymethyl)anilino]acetic acid
B3895
unii-k22ddw77c0
k22ddw77c0 ,
FT-0606288
bapta tetrasodium salt hydrate
1,2-bis-(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid
bapta [mi]
SCHEMBL232103
1,2-bis-(2-aminophenoxy) ethane-n,n,n,-tetra acetic acid
DTXSID30234432
CHEMBL1590868
SY017396
mfcd00036255
1,2-bis(2-aminophenoxy)ethane-n,n,n inverted exclamation mark ,n inverted exclamation mark -tetraacetic acid
J-100044
2,2',2'',2'''-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanetriyl))tetraacetic acid
1,2-bis-(o-aminophenoxy)-ethane-n,n,n',n'-tetraacetic acid
1,2-bis(2-aminophenoxy)ethane-n,n,na(2),na(2)-tetraacetic acid
CS-6069
HY-100168
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid, >=96.0% (hplc)
AS-73034
2-{[2-(2-{2-[bis(carboxymethyl)amino]phenoxy}ethoxy)phenyl](carboxymethyl)amino}acetic acid
FTEDXVNDVHYDQW-UHFFFAOYSA-N
BCP06682
bapeta;1,2-bis(o-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid
Q4834614
1,2-bis(2-aminophenoxy)ethane-n,n,n'n'-tetraacetic acid
2,2',2'',2'''-(2,2'-(ethane-1,2-diylbis(oxy))bis(2,1-phenylene))bis(azanetriyl)tetraacetic acid
glycine,n,n'-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[n-(carboxymethyl)-
bapta, free acid
AB89757
1,2-bis-(2-amino-phenoxy)ethane n,n,n',n'-tetraacetic
bapta free acid

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
"D-myo-Inositol hexakisphosphate (InsP6, phytate), a normal cellular constituent, was found to be toxic to neuronal perikarya when injected into the rat hippocampus."( Neuronal cytotoxicity of inositol hexakisphosphate (phytate) in the rat hippocampus.
Lees, GJ; Leong, W, 1996
)
0.29
" While this process could occur at the expense of NO production, NO alone does play a toxic role, with its production leading to the formation of the toxicant peroxynitrite."( Nitric oxide-mediated toxicity in paraquat-exposed SH-SY5Y cells: a protective role of 7-nitroindazole.
Bravo-San Pedro, JM; Fuentes, JM; González-Polo, RA; Morán, JM; Niso-Santano, M; Ortiz-Ortiz, MA; Soler, G, 2009
)
0.35

Bioavailability

ExcerptReferenceRelevance
"The peptide hormone calcitonin is a potent inhibitor of osteoclastic resorption, but it is unstable and poorly absorbed following oral administration."( Regulation of osteoclasts by calcitonin and amphiphilic calcitonin conjugates: role of cytosolic calcium.
Dixon, SJ; Komarova, SV; Paige, LA; Shum, JB; Sims, SM, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves demonstrated that H-7 is the most effective among the inhibitors, and the transepithelial resistance was 70% of control up to 1 h after calcium removal."( Protein kinase inhibitors prevent junction dissociation induced by low extracellular calcium in MDCK epithelial cells.
Citi, S, 1992
)
0.28
" The priming effect of MCAF was maximal within 5 minutes of preincubation, and the dose-response curves for priming were identical to those for triggering of an increase in [Ca2+]i."( Activation and priming of human monocytes by monocyte chemotactic activating factor: cooperation with other inflammatory cytokines and close association between an increase in cytoplasmic free Ca2+ and intracellular acidification.
Azuma, EK; Kasahara, T; Kitagawa, S; Matsushima, T; Mizoguchi, H; Saito, M; Takaku, F; Yuo, A, 1996
)
0.29
" Dose-response curves were constructed for the chorion cell cultures with CRH or 8-bromo-cAMP."( Regulation of 15-hydroxy prostaglandin dehydrogenase by corticotrophin-releasing hormone through a calcium-dependent pathway in human chorion trophoblast cells.
Challis, JR; McKeown, KJ, 2003
)
0.32
" 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
" ACh and Ca2+ dose-response studies demonstrated that NO3- solution does not shift their dose-response curves, and ATP depletion studies by dinitrophenol or anoxia demonstrated that exposure of NO3- solution prior to ATP depletion induced an enhanced initial phase followed by a sustained phase, whereas exposure of NO3- solution after ATP depletion induced only a sustained phase."( [Cl-]i modulation of Ca2+-regulated exocytosis in ACh-stimulated antral mucous cells of guinea pig.
Fujiwara, S; Kato, M; Katsu, K; Kubota, T; Nakahari, T; Shimamoto, C; Umegaki, E, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
chelatorA ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
polyamino carboxylic acidAn amino acid containing one or more nitrogen atoms connected through carbon atoms to one or more carboxy groups.
tetracarboxylic acidAn oxoacid containing four carboxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency1.99530.004023.8416100.0000AID485290
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency3.97160.140911.194039.8107AID2451
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1669222Inhibition of human recombinant-Sialin expressed in HEK293 cells assessed as reduction in [3H]Neu5Ac uptake at 30 to 300 uM incubated for 15 mins by liquid scintillation counting method2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,764)

TimeframeStudies, This Drug (%)All Drugs %
pre-199065 (3.68)18.7374
1990's780 (44.22)18.2507
2000's684 (38.78)29.6817
2010's216 (12.24)24.3611
2020's19 (1.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.10

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.10 (24.57)
Research Supply Index7.49 (2.92)
Research Growth Index5.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews8 (0.44%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other1,790 (99.56%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]