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BAPTA

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BAPTA
Skeletal formula of BAPTA
Ball-and-stick model of the BAPTA molecule
Names
Preferred IUPAC name 2,2′,2′′,2′′′-tetraacetic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.157.377 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C22H24N2O10/c25-19(26)11-23(12-20(27)28)15-5-1-3-7-17(15)33-9-10-34-18-8-4-2-6-16(18)24(13-21(29)30)14-22(31)32/h1-8H,9-14H2,(H,25,26)(H,27,28)(H,29,30)(H,31,32)Key: FTEDXVNDVHYDQW-UHFFFAOYSA-N
  • InChI=1/C22H24N2O10/c25-19(26)11-23(12-20(27)28)15-5-1-3-7-17(15)33-9-10-34-18-8-4-2-6-16(18)24(13-21(29)30)14-22(31)32/h1-8H,9-14H2,(H,25,26)(H,27,28)(H,29,30)(H,31,32)Key: FTEDXVNDVHYDQW-UHFFFAOYAD
SMILES
  • O=C(O)CN(c2ccccc2OCCOc1ccccc1N(CC(=O)O)CC(=O)O)CC(=O)O
Properties
Chemical formula C22H24N2O10
Molar mass 476.433
Density 1.494 g/cm
Melting point 177 to 179 °C (351 to 354 °F; 450 to 452 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

BAPTA (1,2-bis(o-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid) is a calcium-specific aminopolycarboxylic acid. The presence of four carboxylic acid functional groups makes possible the binding of two calcium ions. The extensive flexibility of the carboxylate ligands is critical to the coordination of calcium and other metal ions. Due to its properties, it is used in research to chelate Ca, similarly to EGTA and EDTA.

There is a range of reported values for the dissociation constant of BAPTA, though 0.2 μM appears consistently. The rate constant for calcium binding is 500 μM s.

BAPTA is a component of some fluorescent calcium ion indicators such as Calcium Green and Oregon Green 488 BAPTA-1 and -2 (OGB-1, OGB2). These indicators change their fluorescence intensity and fluorescence lifetime depending on the calcium ion concentration.

See also

References

  1. ^ Ricci AJ, Wu YC, Fettiplace R (15 October 1998). "The endogenous calcium buffer and the time course of transducer adaptation in auditory hair cells". The Journal of Neuroscience. 18 (20): 8261–77. doi:10.1523/JNEUROSCI.18-20-08261.1998. PMC 6792854. PMID 9763471.
  2. "Fluorescent Ca2+ Indicators Excited with Visible Light—Section 19.3". The Molecular Probes Handbook. Retrieved 2024-01-22.
Chelating agents / chelation therapy (V03AC, others)
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Iron
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