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MedKoo Cat#: 558564 | Name: Nitrilotriacetic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nitrilotriacetic acid is a chelating agent. It is also used as a complexing agent, metal masking agent.

Chemical Structure

Nitrilotriacetic acid
CAS#139-13-9

Theoretical Analysis

MedKoo Cat#: 558564

Name: Nitrilotriacetic acid

CAS#: 139-13-9

Chemical Formula: C6H9NO6

Exact Mass: 191.0430

Molecular Weight: 191.14

Elemental Analysis: C, 37.70; H, 4.75; N, 7.33; O, 50.22

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Synonym
Nitrilotriacetic acid; Nitriloacetate; Nitrilotriacetate;
IUPAC/Chemical Name
Glycine, N,N-bis(carboxymethyl)-
InChi Key
MGFYIUFZLHCRTH-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)
SMILES Code
O=C(O)CN(CC(O)=O)CC(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nitrilotriacetic acid is a chelating agent.
In vitro activity:
This work focused on the effects of nitrilotriacetic acid (NTA) on rhizosphere characteristics to investigate the mechanisms of lead (Pb) accumulation in Athyrium wardii (Hook.) Makino with exposure to 800 mg kg-1 Pb. Soil respiration decreased by 8.9%, and microbial biomass carbon decreased by 8.9% in the rhizosphere soils, indicating that NTA addition might recruit some microorganisms to maintain rhizosphere functions in Pb-contaminated soils while inhibiting others with low tolerance to Pb. Results suggest that lower pH, more DOC exudation, and higher soil enzyme activities after NTA application contributed to the increase of Pb accumulation in A. wardii. Reference: Environ Sci Pollut Res Int. 2022 Jan;29(4):6184-6193. https://pubmed.ncbi.nlm.nih.gov/34436720/
In vivo activity:
This study compared three lipids: a mono-NTA (nitrilotriacetic acid) lipid (ca. 10 microM affinity) and two tris-NTA lipid derivatives (ca. 3 nM and 0.2 nM affinity) in their ability to retain two different his(6)-containing proteins on NTA-liposomes in the presence of serum or plasma and after intravenous injection in mice. There was no difference in circulation time of the protein when it was intravenously administered by itself or attached to any of the NTA-modified liposomes because in vivo the protein was rapidly released from the NTA liposomes. Upon recovery from blood, liposomes containing tris-NTA accumulated a different plasma protein profile than control liposomes, suggesting that Ni-NTA specifically interacts with some plasma proteins. Reference: Bioconjug Chem. 2010 May 19;21(5):892-902. https://pubmed.ncbi.nlm.nih.gov/20384362/

Preparing Stock Solutions

The following data is based on the product molecular weight 191.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhang Y, Huang H, Yu H, Zhan J, Ye D, Zheng Z, Zhang X, Wang Y, Li T. The changes of rhizosphere characteristics contributed to enhanced Pb accumulation in Athyrium wardii (Hook.) Makino after nitrilotriacetic acid application. Environ Sci Pollut Res Int. 2022 Jan;29(4):6184-6193. doi: 10.1007/s11356-021-15476-z. Epub 2021 Aug 26. PMID: 34436720. 2. Zhang LS, Yin YL, Wang L, Xia Y, Ryu S, Xi Z, Li LY, Zhang ZS. Self-assembling nitrilotriacetic acid nanofibers for tracking and enriching His-tagged proteins in living cells. J Mater Chem B. 2021 Jan 7;9(1):80-84. doi: 10.1039/d0tb02302g. Epub 2020 Dec 14. PMID: 33313613. 3. Platt V, Huang Z, Cao L, Tiffany M, Riviere K, Szoka FC Jr. Influence of multivalent nitrilotriacetic acid lipid-ligand affinity on the circulation half-life in mice of a liposome-attached His6-protein. Bioconjug Chem. 2010 May 19;21(5):892-902. doi: 10.1021/bc900448f. PMID: 20384362; PMCID: PMC2874083. 4. Sultana S, Prasad L, Jahangir T. Luteolin ameliorates ferric nitrilotriacetic acid induced renal toxicity and tumor promotional response in rat. Indian J Exp Biol. 2009 May;47(5):355-60. PMID: 19579801.
In vitro protocol:
1. Zhang Y, Huang H, Yu H, Zhan J, Ye D, Zheng Z, Zhang X, Wang Y, Li T. The changes of rhizosphere characteristics contributed to enhanced Pb accumulation in Athyrium wardii (Hook.) Makino after nitrilotriacetic acid application. Environ Sci Pollut Res Int. 2022 Jan;29(4):6184-6193. doi: 10.1007/s11356-021-15476-z. Epub 2021 Aug 26. PMID: 34436720. 2. Zhang LS, Yin YL, Wang L, Xia Y, Ryu S, Xi Z, Li LY, Zhang ZS. Self-assembling nitrilotriacetic acid nanofibers for tracking and enriching His-tagged proteins in living cells. J Mater Chem B. 2021 Jan 7;9(1):80-84. doi: 10.1039/d0tb02302g. Epub 2020 Dec 14. PMID: 33313613.
In vivo protocol:
1. Platt V, Huang Z, Cao L, Tiffany M, Riviere K, Szoka FC Jr. Influence of multivalent nitrilotriacetic acid lipid-ligand affinity on the circulation half-life in mice of a liposome-attached His6-protein. Bioconjug Chem. 2010 May 19;21(5):892-902. doi: 10.1021/bc900448f. PMID: 20384362; PMCID: PMC2874083. 2. Sultana S, Prasad L, Jahangir T. Luteolin ameliorates ferric nitrilotriacetic acid induced renal toxicity and tumor promotional response in rat. Indian J Exp Biol. 2009 May;47(5):355-60. PMID: 19579801.
1: Njagi JI, Goia DV. Nitrilotriacetic acid: a novel reducing agent for synthesizing colloidal gold. J Colloid Interface Sci. 2014 May 1;421:27-32. doi: 10.1016/j.jcis.2014.01.025. Epub 2014 Jan 25. PubMed PMID: 24594028. 2: Wieneke R, Labòria N, Rajan M, Kollmannsperger A, Natale F, Cardoso MC, Tampé R. Live-cell targeting of his-tagged proteins by multivalent N-nitrilotriacetic acid carrier complexes. J Am Chem Soc. 2014 Oct 8;136(40):13975-8. doi: 10.1021/ja5063357. Epub 2014 Sep 30. PubMed PMID: 25238106. 3: Zhang C, He Z, Wu J, Fu D. Chemometric study on the electrochemical incineration of nitrilotriacetic acid using platinum and boron-doped diamond anode. Chemosphere. 2015 Jul;130:1-7. doi: 10.1016/j.chemosphere.2015.02.018. Epub 2015 Mar 3. PubMed PMID: 25747300. 4: National Toxicology Program. Nitrilotriacetic acid. Rep Carcinog. 2011;12:284-5. PubMed PMID: 21860491. 5: Loh CT, Graham B, Abdelkader EH, Tuck KL, Otting G. Generation of pseudocontact shifts in proteins with lanthanides using small "clickable" nitrilotriacetic acid and iminodiacetic acid tags. Chemistry. 2015 Mar 23;21(13):5084-92. doi: 10.1002/chem.201406274. Epub 2015 Feb 12. PubMed PMID: 25676727. 6: Conzuelo F, Gamella M, Campuzano S, Martínez-Ruiz P, Esteban-Torres M, de las Rivas B, Reviejo AJ, Muñoz R, Pingarrón JM. Integrated amperometric affinity biosensors using Co2+-tetradentate nitrilotriacetic acid modified disposable carbon electrodes: application to the determination of β-lactam antibiotics. Anal Chem. 2013 Mar 19;85(6):3246-54. doi: 10.1021/ac303604b. Epub 2013 Mar 4. PubMed PMID: 23421824. 7: Zhang Y, Klamerth N, Chelme-Ayala P, Gamal El-Din M. Comparison of Nitrilotriacetic Acid and [S,S]-Ethylenediamine-N,N'-disuccinic Acid in UV-Fenton for the Treatment of Oil Sands Process-Affected Water at Natural pH. Environ Sci Technol. 2016 Oct 4;50(19):10535-10544. Epub 2016 Sep 19. PubMed PMID: 27588553. 8: Wang M, Lei C, Nie Z, Guo M, Huang Y, Yao S. Label-free fluorescent detection of thrombin activity based on a recombinant enhanced green fluorescence protein and nickel ions immobilized nitrilotriacetic acid-coated magnetic nanoparticles. Talanta. 2013 Nov 15;116:468-73. doi: 10.1016/j.talanta.2013.07.017. Epub 2013 Jul 15. PubMed PMID: 24148431. 9: Bahnemann R, Leibold E, Kittel B, Mellert W, Jäckh R. Different patterns of kidney toxicity after subacute administration of Na-nitrilotriacetic acid and Fe-nitrilotriacetic acid to Wistar rats. Toxicol Sci. 1998 Nov;46(1):166-75. PubMed PMID: 9928680. 10: Platt V, Huang Z, Cao L, Tiffany M, Riviere K, Szoka FC Jr. Influence of multivalent nitrilotriacetic acid lipid-ligand affinity on the circulation half-life in mice of a liposome-attached His6-protein. Bioconjug Chem. 2010 May 19;21(5):892-902. doi: 10.1021/bc900448f. PubMed PMID: 20384362; PubMed Central PMCID: PMC2874083. 11: Watson DS, Platt VM, Cao L, Venditto VJ, Szoka FC Jr. Antibody response to polyhistidine-tagged peptide and protein antigens attached to liposomes via lipid-linked nitrilotriacetic acid in mice. Clin Vaccine Immunol. 2011 Feb;18(2):289-97. doi: 10.1128/CVI.00425-10. Epub 2010 Dec 15. PubMed PMID: 21159923; PubMed Central PMCID: PMC3067350. 12: Mero A, Ishino T, Chaiken I, Veronese FM, Pasut G. Multivalent and flexible PEG-nitrilotriacetic acid derivatives for non-covalent protein pegylation. Pharm Res. 2011 Oct;28(10):2412-21. doi: 10.1007/s11095-011-0468-8. Epub 2011 May 25. PubMed PMID: 21611874. 13: Sy JC, Phelps EA, García AJ, Murthy N, Davis ME. Surface functionalization of polyketal microparticles with nitrilotriacetic acid-nickel complexes for efficient protein capture and delivery. Biomaterials. 2010 Jun;31(18):4987-94. doi: 10.1016/j.biomaterials.2010.02.063. Epub 2010 Mar 25. PubMed PMID: 20346498; PubMed Central PMCID: PMC2866531. 14: Schmidt J, Guillaume P, Irving M, Baumgaertner P, Speiser D, Luescher IF. Reversible major histocompatibility complex I-peptide multimers containing Ni(2+)-nitrilotriacetic acid peptides and histidine tags improve analysis and sorting of CD8(+) T cells. J Biol Chem. 2011 Dec 2;286(48):41723-35. doi: 10.1074/jbc.M111.283127. Epub 2011 Oct 11. PubMed PMID: 21990358; PubMed Central PMCID: PMC3308881. 15: White VE, Knowles CJ. Effect of metal complexation on the bioavailability of nitrilotriacetic acid to Chelatobacter heintzii ATCC 29600. Arch Microbiol. 2000 May-Jun;173(5-6):373-82. PubMed PMID: 10896217. 16: Soleimani M, Hajabbasi MA, Afyuni M, Akbar S, Jensen JK, Holm PE, Borggaard OK. Comparison of natural humic substances and synthetic ethylenediaminetetraacetic acid and nitrilotriacetic acid as washing agents of a heavy metal-polluted soil. J Environ Qual. 2010 Apr 13;39(3):855-62. doi: 10.2134/jeq2009.0292. Print 2010 May-Jun. PubMed PMID: 20400581. 17: Padala AN, Bhaskarapillai A, Velmurugan S, Narasimhan SV. Sorption behaviour of Co(II) and Cu(II) on chitosan in presence of nitrilotriacetic acid. J Hazard Mater. 2011 Jul 15;191(1-3):110-7. doi: 10.1016/j.jhazmat.2011.04.046. Epub 2011 Apr 16. PubMed PMID: 21592656. 18: Ansar S, Iqbal M. Ascorbic acid inhibits ferric nitrilotriacetate induction of ornithine decarboxylase, DNA synthesis, oxidative stress, and hepatotoxicity in rats. Toxicol Ind Health. 2015 Nov;31(11):1008-14. doi: 10.1177/0748233713493824. Epub 2013 Jul 17. PubMed PMID: 23863956. 19: Ansar S, Iqbal M. Role of ascorbic acid in counteracting ferric nitrilotriacetate-induced nephrotoxicity in rats. Pharm Biol. 2013 Dec;51(12):1559-63. doi: 10.3109/13880209.2013.802811. Epub 2013 Sep 12. PubMed PMID: 24024952. 20: Sultana S, Prasad L, Jahangir T. Luteolin ameliorates ferric nitrilotriacetic acid induced renal toxicity and tumor promotional response in rat. Indian J Exp Biol. 2009 May;47(5):355-60. PubMed PMID: 19579801.