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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').
→top: | Altered template type. Add: isbn, pmid, pages, volume, date, title, chapter, doi, chapter-url, authors 1-1. Removed or converted URL. Changed bare reference to CS1/2. | Use this tool. Report bugs. | #UCB_Gadget
 
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{{chembox
{{chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 414445833
| verifiedrevid = 443717205
| ImageFile = EGTA.svg
| ImageFile = EGTA.svg
| ImageSize = 200px
| ImageSize = 260px
| ImageAlt = Skeletal formula of EGTA
| IUPACName = ethylene glycol-bis(2-aminoethylether)-''N'',''N'',''N′'',''N′''-tetraacetic acid
| ImageFile1 = EGTA 3D ball.png
| OtherNames =
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick model of the EGTA molecule
| Name = EGTA
| PIN = 3,12-Bis(carboxymethyl)-6,9-dioxa-3,12-diazatetradecane-1,14-dioic acid
| OtherNames = Triethylene glycol diamine tetraacetic acid
| SystematicName =
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5972
| ChemSpiderID = 5972
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
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| StdInChIKey = DEFVIWRASFVYLL-UHFFFAOYSA-N
| StdInChIKey = DEFVIWRASFVYLL-UHFFFAOYSA-N
| CASNo = 67-42-5
| CASNo = 67-42-5
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (free acid)
⚫
| PubChem = 6207
| CASNo2_Ref = {{cascite|unknown|CAS}}
⚫
| ChEBI = 30740
| CASNo2 = 13368-13-3
| CASNo2_Comment = (tetrasodium salt)
⚫
| PubChem = 6207
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| ChEBI = 30740
| SMILES = O=C(O)CN(CC(=O)O)CCOCCOCCN(CC(=O)O)CC(=O)O
| SMILES = O=C(O)CN(CC(=O)O)CCOCCOCCN(CC(=O)O)CC(=O)O
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=14 | H=24 | N=2 | O=10
| Formula = C<sub>14</sub>H<sub>24</sub>N<sub>2</sub>O<sub>10</sub>
| Appearance =
| MolarMass = 380.35 g/mol
| Appearance =
| Density =
| Density =
| MeltingPtC = 241
| MeltingPtC = 241
| BoilingPt =
| BoilingPt =
| Solubility =
| pKa = 2.0, 2.68, 8.85, 9.43<ref>{{cite book | chapter-url=https://onlinelibrary.wiley.com/doi/abs/10.1002/9780470110195.ch10 | doi=10.1002/9780470110195.ch10 | chapter=Applications of Metal Buffers and Metal Indicators in Biochemistry | title=Methods of Biochemical Analysis | date=1956 | last1=Raaflaub | first1=Jürg | volume=3 | pages=301–325 | pmid=13369167 | isbn=978-0-470-30492-1 }}</ref>
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition =
| AutoignitionPt =
}}
}}
| Section4 =
| Section5 =
| Section6 =
}}
}}


'''EGTA''' ('''ethylene glycol tetraacetic acid''') is a [[polyamino carboxylic acid]], a [[chelating agent]] that is related to the better known [[EDTA]], but with a much higher affinity for [[calcium]] than for [[magnesium]] [[ion]]s. It is useful for making [[buffer solution]]s that resemble the environment inside living [[cell (biology)|cell]]s<ref>{{cite book
'''EGTA''' ('''ethylene glycol-bis(β-aminoethyl ether)-''N'',''N'',''N''′,''N''′-tetraacetic acid'''), also known as '''egtazic acid''' ([[International Nonproprietary Name|INN]], [[United States Adopted Name|USAN]]),<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/egta#section=Top|title=EGTA {{!}} C14H24N2O10 - PubChem|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2017-04-24}}</ref> is an [[aminopolycarboxylic acid]], a [[chelating agent]]. It is a white solid that is related to the better known [[EDTA]]. Compared to EDTA, it has a lower affinity for [[magnesium]], making it more selective for [[calcium]] [[ion]]s. It is useful in [[buffer solution]]s that resemble the environment in living [[cell (biology)|cell]]s<ref>{{cite book
| first1 = Glenna C. L.
| first1 = Glenna C. L.
| last1 = Bett
| last1 = Bett
Line 55: Line 69:
| editor2-last = Rosenbaum
| editor2-last = Rosenbaum
| title = Quantitative Cardiac Electrophysiology
| title = Quantitative Cardiac Electrophysiology
| url = https://archive.org/details/quantitativecard00rose
| url-access = limited
| chapter = 1. Computer Models of Ion Channels
| chapter = 1. Computer Models of Ion Channels
| page = 48
| page = [https://archive.org/details/quantitativecard00rose/page/n61 48]
| publisher = [[Marcel Dekker]]
| publisher = [[Marcel Dekker]]
| year = 2002
| year = 2002
| isbn = 0-8247-0774-5}}</ref> where calcium ions are usually at least a thousandfold less concentrated than magnesium.
| isbn = 0-8247-0774-5}}</ref> where calcium ions are usually at least a thousandfold less concentrated than magnesium.


The [[Acid dissociation constant|pKa]] for binding of calcium ions by tetrabasic EGTA is 11.00, but the [[Protonation|protonated forms]] do not significantly contribute to binding, so at pH 7, the apparent pKa becomes 6.91. See Qin ''et al.'' for an example of a [[Protein pKa calculations|pKa calculation]].<ref>{{cite journal | title = Ca<sup>2+</sup>-induced inhibition of the cardiac Ca<sup>2+</sup> channel depends on calmodulin | journal = [[PNAS]] | volume = 96 | issue = 5 | pages = 2435–2438 | month = March | year = 1999 | url = http://www.pnas.org/cgi/content/full/96/5/2435 | accessdate = 2007-10-22 | author = Ning Qin, Riccardo Olcese, Michael Bransby, Tony Lin, and Lutz Birnbaumer | pmid = 10051660 | doi = 10.1073/pnas.96.5.2435 | pmc = 26802}}</ref>
The [[Acid dissociation constant|p''K''<sub>a</sub>]] for binding of calcium ions by tetrabasic EGTA is 11.00, but the [[Protonation|protonated forms]] do not significantly contribute to binding, so at pH 7, the apparent p''K''<sub>a</sub> becomes 6.91. See Qin ''et al.'' for an example of a [[Protein pKa calculations|p''K''<sub>a</sub> calculation]].<ref>{{cite journal | title = Ca<sup>2+</sup>-induced inhibition of the cardiac Ca<sup>2+</sup> channel depends on calmodulin | journal = [[PNAS]] | volume = 96 | issue = 5 | pages = 2435–2438 |date=March 1999 |author1=Ning Qin |author2=Riccardo Olcese |author3=Michael Bransby |author4=Tony Lin |author5=Lutz Birnbaumer | pmid = 10051660 | doi = 10.1073/pnas.96.5.2435 | pmc = 26802| bibcode = 1999PNAS...96.2435Q| doi-access = free }}</ref>


EGTA has also been used experimentally for the treatment of animals with [[cerium]] poisoning and for the [[Separation process|separation]] of [[thorium]] from the mineral [[monazite]]. EGTA is used as a compound in [[elution volume|elution]] buffer in the protein purification technique known as [[Tandem Affinity Purification| Tandem Affinity Purification (TAP)]], in which [[recombinant fusion protein]]s are bound to [[calmodulin]] beads and eluted out by adding EGTA.
EGTA has also been used experimentally for the treatment of animals with [[cerium]] poisoning and for the [[Separation process|separation]] of [[thorium]] from the mineral [[monazite]]. EGTA is used as a compound in [[elution volume|elution]] buffer in the protein purification technique known as [[tandem affinity purification]], in which [[recombinant fusion protein]]s are bound to [[calmodulin]] beads and eluted out by adding EGTA.


EGTA is often employed in [[dentistry]] and [[endodontics]] for the removal of smear layer.
EGTA is often employed in [[dentistry]] and [[endodontics]] for the removal of the [[smear layer]].


== See also ==
== See also ==
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==References==
==References==
{{Refimprove|article|October 2007|date=October 2007}}
<references />
<references />


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[[Category:Chelating agents]]
[[Category:Chelating agents]]
[[Category:Acetic acids]]
[[Category:Acetic acids]]
[[Category:ethers]]
[[Category:Ethers]]

[[ja:グリコールエーテルジアミン四酢酸]]
[[pl:EGTA]]
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