BAPTA

BAPTA
Names
	Preferred IUPAC name 2,2′,2′′,2′′′-[Ethane-1,2-diylbis(oxy-2,1-phenylenenitrilo)]tetraacetic acid
Identifiers
CAS Number	85233-19-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:60888 ;
ChemSpider	94562 ;
ECHA InfoCard	100.157.377
PubChem CID	104751;
UNII	K22DDW77C0 ;
CompTox Dashboard (EPA)	DTXSID30234432 ;
	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/cm3
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

BAPTA (1,2-bis(o-amino phenoxy)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 Ca²⁺, similarly to EGTA and EDTA.

There is a range of reported values for the dissociation constant of BAPTA, though 0.2 μM appears consistently.^[1] The rate constant for calcium binding is 500 μM⁻¹ s⁻¹.^[1]

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.^[2]

References

^ ^a ^b 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.
^ "Fluorescent Ca2+ Indicators Excited with Visible Light—Section 19.3". The Molecular Probes Handbook. Retrieved 2024-01-22.

[pmid9763471-1] 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.

[1]

[2]

v t e Chelating agents / chelation therapy (V03AC, others)
Copper	Penicillamine^#
Iron	Deferasirox Deferiprone Deferoxamine^#
Lead	BAL^# EDTA^# Dexrazoxane
Thallium	Prussian blue^#
Other	ALA BAPTA DMPS DMSA^# DTPA EGTA
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

See also

References