Pentetic acid | CAS#67-43-6 | Metal chelating agent

MedKoo Cat#: 534960 | Name: Pentetic acid

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Description:

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

Pentetic acid is a cell-impermeable metal chelating agent. It chelates copper, iron, zinc, and manganese, as well as calcium, magnesium, and plutonium. Pentetic acid has been used as a metal chelating agent in the study of ferroptosis. It reduces the skeletal plutonium burden and incidence of bone tumors, as well as increases survival in a mouse model of intravenous plutonium exposure when administered at a dose of 500 mg/kg. Formulations containing Pentetic acid conjugated to radioactive compounds have been used as diagnostic agents for brain imaging, renal visualization, and lung imaging.

Chemical Structure

Pentetic acid

CAS#67-43-6

Theoretical Analysis

MedKoo Cat#: 534960

Name: Pentetic acid

CAS#: 67-43-6

Chemical Formula: C14H23N3O10

Exact Mass: 393.1383

Molecular Weight: 393.35

Elemental Analysis: C, 42.75; H, 5.89; N, 10.68; O, 40.67

Price and Availability

Size	Price	Availability
25g	USD 210.00	2 Weeks
50g	USD 340.00	2 Weeks
100g	USD 540.00	2 Weeks
250g	USD 810.00	2 Weeks

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Related CAS #

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Synonym

Pentetic acid; DTPA; Diethylenetriaminepentaacetic Acid; NSC 7340; NSC7340; NSC-7340;

IUPAC/Chemical Name

1,1,4,7,7-Diethylenetriaminepentaacetic acid

InChi Key

QPCDCPDFJACHGM-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H23N3O10/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27)

SMILES Code

O=C(O)CN(CC(O)=O)CCN(CC(O)=O)CCN(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

2934.99.9001

More Info

1: Benes DM, Burnett CL. Final report on the safety assessment of pentasodium pentetate and pentetic acid as used in cosmetics. Int J Toxicol. 2008;27 Suppl 2:71-92. doi: 10.1080/10915810802244546. PMID: 18830865. 2: Arts J, Bade S, Badrinas M, Ball N, Hindle S. Should DTPA, an Aminocarboxylic acid (ethylenediamine-based) chelating agent, be considered a developmental toxicant? Regul Toxicol Pharmacol. 2018 Aug;97:197-208. doi: 10.1016/j.yrtph.2018.06.019. Epub 2018 Jun 28. PMID: 29964121. 3: Guilmette RA, Parks JE, Lindenbaum A. Synthesis and therapeutic testing of mono- and dialkyl esters of pentetic (diethylenetriaminepentaacetic) acid for decorporation of polymeric plutonium. J Pharm Sci. 1979 Feb;68(2):194-6. doi: 10.1002/jps.2600680219. PMID: 423090. 4: Akizawa H, Saito M, Tsukamoto I, Ohkura T, Shimizu T, Kitamura Y, Mifune M, Saito Y, Arano Y, Saji H. Effect of carboxyl-group of D-glutamic acid or gamma- carboxy-D-glutamic acid as N-terminal amino acid of (111)in- diethylenetriaminepentaacetic acid-octreotide on accumulation of radioactivity in kidney. Biol Pharm Bull. 2007 Nov;30(11):2226-8. doi: 10.1248/bpb.30.2226. PMID: 17978507. 5: Kilcar AY, Biber Muftuler FZ, Unak P, Avci CB, Gunduz C. Diethylenetriamine pentaacetic acid derivative of toremifene and in vitro evaluation in human breast cancer cell line MCF-7. Cancer Biother Radiopharm. 2011 Feb;26(1):105-11. doi: 10.1089/cbr.2010.0860. PMID: 21355781. 6: Grémy O, Miccoli L, Lelan F, Bohand S, Cherel M, Mougin-Degraef M. Delivery of DTPA through Liposomes as a Good Strategy for Enhancing Plutonium Decorporation Regardless of Treatment Regimen. Radiat Res. 2018 May;189(5):477-489. doi: 10.1667/RR14968.1. Epub 2018 Mar 12. PMID: 29528770. 7: Yu L, Meng F, Guo M, Yang Y, He J, Dong J, Guo J, Peng S. Developing a robust LC-MS/MS method to quantify Zn-DTPA, a zinc chelate in human plasma and urine. Biomed Chromatogr. 2018 Oct;32(10):e4298. doi: 10.1002/bmc.4298. Epub 2018 Jun 21. PMID: 29799632. 8: Kazzi ZN, Heyl A, Ruprecht J. Calcium and zinc DTPA administration for internal contamination with plutonium-238 and americium-241. Curr Pharm Biotechnol. 2012 Aug;13(10):1957-63. doi: 10.2174/138920112802273308. PMID: 22352730. 9: Wilson JP, Cobb RR, Dungan NW, Matthews LL, Eppler B, Aiello KV, Curtis S, Boger T, Guilmette RA, Weber W, Doyle-Eisele M, Talton JD. Decorporation of systemically distributed americium by a novel orally administered diethylenetriaminepentaacetic acid (DTPA) formulation in beagle dogs. Health Phys. 2015 Mar;108(3):308-18. doi: 10.1097/HP.0000000000000199. PMID: 25627942. 10: Oshima N, Akizawa H, Kawashima H, Zhao S, Zhao Y, Nishijima KI, Kitamura Y, Arano Y, Kuge Y, Ohkura K. Redesign of negatively charged 111In-DTPA- octreotide derivative to reduce renal radioactivity. Nucl Med Biol. 2017 May;48:16-25. doi: 10.1016/j.nucmedbio.2017.01.006. Epub 2017 Jan 17. PMID: 28160666. 11: Huckle JE, Sadgrove MP, Mumper RJ, Jay M. Species-dependent chelation of (241)Am by DTPA Di-ethyl ester. Health Phys. 2015 Apr;108(4):443-50. doi: 10.1097/HP.0000000000000230. PMID: 25706138; PMCID: PMC4339263. 12: Sillanpää M. Environmental fate of EDTA and DTPA. Rev Environ Contam Toxicol. 1997;152:85-111. doi: 10.1007/978-1-4612-1964-4_3. PMID: 9297986. 13: Lee RT, Lee YC. A derivative of diethylenetriaminepentaacetic acid for europium labeling of proteins. Bioconjug Chem. 2001 Nov-Dec;12(6):845-9. doi: 10.1021/bc000112f. PMID: 11716672. 14: Pulido D, Albericio F, Royo M. Controlling multivalency and multimodality: up to pentamodal dendritic platforms based on diethylenetriaminepentaacetic acid cores. Org Lett. 2014 Mar 7;16(5):1318-21. doi: 10.1021/ol500022n. Epub 2014 Feb 14. PMID: 24527761. 15: Tofts PS. Modeling tracer kinetics in dynamic Gd-DTPA MR imaging. J Magn Reson Imaging. 1997 Jan-Feb;7(1):91-101. doi: 10.1002/jmri.1880070113. PMID: 9039598. 16: Nwe K, Xu H, Regino CA, Bernardo M, Ileva L, Riffle L, Wong KJ, Brechbiel MW. A new approach in the preparation of dendrimer-based bifunctional diethylenetriaminepentaacetic acid MR contrast agent derivatives. Bioconjug Chem. 2009 Jul;20(7):1412-8. doi: 10.1021/bc900057z. PMID: 19555072; PMCID: PMC2737254. 17: Grémy O, Coudert S, Renault D, Miccoli L. Decorporation Approach after Rat Lung Contamination with Plutonium: Evaluation of the Key Parameters Influencing the Efficacy of a Protracted Chelation Treatment. Radiat Res. 2017 Nov;188(5):552-561. doi: 10.1667/RR14782.1. Epub 2017 Sep 25. PMID: 28945525. 18: Akizawa H, Takimoto H, Saito M, Iwado A, Mifune M, Saito Y, Uehara T, Arano Y, Mukai T, Hanaoka H, Saji H. Effect of carboxylation of N-terminal phenylalanine of (111)in-DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney. Biol Pharm Bull. 2004 Feb;27(2):271-2. doi: 10.1248/bpb.27.271. PMID: 14758051. 19: Staatz G, Wenzl T, Alzen G, Adam G. MRT bei tuberkulöser Gonarthritis im Kindesalter [MRT in tuberculous gonarthritis in childhood]. Rofo. 1997 Aug;167(2):210-2. German. doi: 10.1055/s-2007-1015520. PMID: 9333367. 20: Rigauts H, Casselman J, Pattyn G, Ampe J. MR findings in müllerian duct cysts. Rofo. 1995 Mar;162(3):263-5. doi: 10.1055/s-2007-1015880. PMID: 7718788.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 393.35 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.

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

1: Mortezazadeh T, Gholibegloo E, Alam NR, Dehghani S, Haghgoo S, Ghanaati H, Khoobi M. Gadolinium (III) oxide nanoparticles coated with folic acid- functionalized poly(β-cyclodextrin-co-pentetic acid) as a biocompatible targeted nano-contrast agent for cancer diagnostic: in vitro and in vivo studies. MAGMA. 2019 Aug;32(4):487-500. doi: 10.1007/s10334-019-00738-2. Epub 2019 Feb 7. PMID: 30730021. 2: Gi M, Jeong J, Lee K, Lee KM, Toyofuku M, Yong DE, Yoon SS, Choi JY. A drug- repositioning screening identifies pentetic acid as a potential therapeutic agent for suppressing the elastase-mediated virulence of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2014 Dec;58(12):7205-14. doi: 10.1128/AAC.03063-14. Epub 2014 Sep 22. PMID: 25246397; PMCID: PMC4249511. 3: Benes DM, Burnett CL. Final report on the safety assessment of pentasodium pentetate and pentetic acid as used in cosmetics. Int J Toxicol. 2008;27 Suppl 2:71-92. doi: 10.1080/10915810802244546. PMID: 18830865. 4: Coleman RE, MacIntyre N, Snyder G, Pattishall E, Zaccardelli D. Aerosol characteristics of 99mTc-pentetic acid (DTPA) and synthetic surfactant (Exosurf). Chest. 1994 Jun;105(6):1765-9. doi: 10.1378/chest.105.6.1765. PMID: 8205874. 5: Capra R, Marcianò N, Vignolo LA, Chiesa A, Gasparotti R. Gadolinium-pentetic acid magnetic resonance imaging in patients with relapsing remitting multiple sclerosis. Arch Neurol. 1992 Jul;49(7):687-9. doi: 10.1001/archneur.1992.00530310029008. PMID: 1497493.

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