TPEN | TPEDA | CAS#16858-02-9 | metal ion chelator

MedKoo Cat#: 530391 | Name: TPEN

Description:

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

TPEN, also known as TPEDA, is a cell permeant metal ion chelator that is used in zinc treatment studies to limit intra- and extracellular concentrations of the mineral. TPEN Attenuates Neuronal Death/apoptosis Caused by Hypoxia/ischemia Via Mediating the Pathophysiological Cascade Including Excitotoxicity, Oxidative Stress, and Inflammation. TPEN prevents rapid pacing-induced calcium overload and nitration stress in HL-1 myocytes.

Chemical Structure

TPEN

CAS#16858-02-9

Theoretical Analysis

MedKoo Cat#: 530391

Name: TPEN

CAS#: 16858-02-9

Chemical Formula: C26H28N6

Exact Mass: 0.0000

Molecular Weight: 424.55

Elemental Analysis: C, 73.56; H, 6.65; N, 19.80

Price and Availability

Size	Price	Availability
500mg	USD 550.00	2 Weeks
1g	USD 950.00	2 Weeks
2g	USD 1,750.00	2 Weeks
5g	USD 3,650.00	2 Weeks

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Related CAS #

No Data

Synonym

TPEN; TPEDA.

IUPAC/Chemical Name

N,N,N',N'-tetrakis(2-pyridinylmethyl)-1,2-ethanediamine

InChi Key

CVRXLMUYFMERMJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H28N6/c1-5-13-27-23(9-1)19-31(20-24-10-2-6-14-28-24)17-18-32(21-25-11-3-7-15-29-25)22-26-12-4-8-16-30-26/h1-16H,17-22H2

SMILES Code

N(CC1=NC=CC=C1)(CC2=NC=CC=C2)CCN(CC3=NC=CC=C3)CC4=NC=CC=C4

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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 424.55 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: Lee K, Davis A, Zhang L, Ryu J, Spate LD, Park KW, Samuel MS, Walters EM, Murphy CN, Machaty Z, Prather RS. Pig oocyte activation using a Zn²⁺ chelator, TPEN. Theriogenology. 2015 Oct 1;84(6):1024-32. doi: 10.1016/j.theriogenology.2015.05.036. PubMed PMID: 26143360; PubMed Central PMCID: PMC4553067. 2: Kim HL, Ra H, Kim KR, Lee JM, Im H, Kim YH. Poly(ADP-ribosyl)ation of p53 contributes to TPEN-induced neuronal apoptosis. Mol Cells. 2015 Apr;38(4):312-7. doi: 10.14348/molcells.2015.2142. PubMed PMID: 25813624; PubMed Central PMCID: PMC4400305. 3: Meeusen JW, Nowakowski A, Petering DH. Reaction of metal-binding ligands with the zinc proteome: zinc sensors and N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine. Inorg Chem. 2012 Mar 19;51(6):3625-32. doi: 10.1021/ic2025236. PubMed PMID: 22380934; PubMed Central PMCID: PMC3564517. 4: Carraway RE, Dobner PR. Zinc pyrithione induces ERK- and PKC-dependent necrosis distinct from TPEN-induced apoptosis in prostate cancer cells. Biochim Biophys Acta. 2012 Feb;1823(2):544-57. doi: 10.1016/j.bbamcr.2011.09.013. PubMed PMID: 22027089. 5: Liu Z, Huang YY, Wang YX, Wang HG, Deng F, Heng B, Xie LH, Liu YQ. Prevention of cell death by the zinc ion chelating agent TPEN in cultured PC12 cells exposed to Oxygen-Glucose Deprivation (OGD). J Trace Elem Med Biol. 2015;31:45-52. doi: 10.1016/j.jtemb.2015.03.003. PubMed PMID: 26004891. 6: Stuart CH, Singh R, Smith TL, D'Agostino R Jr, Caudell D, Balaji KC, Gmeiner WH. Prostate-specific membrane antigen-targeted liposomes specifically deliver the Zn(2+) chelator TPEN inducing oxidative stress in prostate cancer cells. Nanomedicine (Lond). 2016 May;11(10):1207-22. doi: 10.2217/nnm-2015-0017. PubMed PMID: 27077564; PubMed Central PMCID: PMC4910947. 7: Wang WM, Liu Z, Liu AJ, Wang YX, Wang HG, An D, Heng B, Xie LH, Duan JL, Liu YQ. The Zinc Ion Chelating Agent TPEN Attenuates Neuronal Death/apoptosis Caused by Hypoxia/ischemia Via Mediating the Pathophysiological Cascade Including Excitotoxicity, Oxidative Stress, and Inflammation. CNS Neurosci Ther. 2015 Sep;21(9):708-17. doi: 10.1111/cns.12428. PubMed PMID: 26190227. 8: Matias CM, Matos NC, Arif M, Dionisio JC, Quinta-Ferreira ME. Effect of the zinc chelator N,N,N',N'-tetrakis (2-pyridylmethyl)ethylenediamine (TPEN) on hippocampal mossy fiber calcium signals and on synaptic transmission. Biol Res. 2006;39(3):521-30. PubMed PMID: 17106583. 9: López JJ, Redondo PC, Salido GM, Pariente JA, Rosado JA. N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine induces apoptosis through the activation of caspases-3 and -8 in human platelets. A role for endoplasmic reticulum stress. J Thromb Haemost. 2009 Jun;7(6):992-9. doi: 10.1111/j.1538-7836.2009.03431.x. PubMed PMID: 19548908. 10: Zhang F, Ma XL, Wang YX, He CC, Tian K, Wang HG, An D, Heng B, Xie LH, Liu YQ. TPEN, a Specific Zn(2+) Chelator, Inhibits Sodium Dithionite and Glucose Deprivation (SDGD)-Induced Neuronal Death by Modulating Apoptosis, Glutamate Signaling, and Voltage-Gated K(+) and Na(+) Channels. Cell Mol Neurobiol. 2016 Mar 16. [Epub ahead of print] PubMed PMID: 26983717. 11: Strand OA, Aziz G, Ali SF, Paulsen RE, Hansen TV, Rongved P. Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1. Bioorg Med Chem. 2013 Sep 1;21(17):5175-81. doi: 10.1016/j.bmc.2013.06.037. PubMed PMID: 23859779. 12: Sztretye M, Almássy J, Deli T, Szentesi P, Jung C, Dienes B, Simut CA, Niggli E, Jona I, Csernoch L. Altered sarcoplasmic reticulum calcium transport in the presence of the heavy metal chelator TPEN. Cell Calcium. 2009 Nov-Dec;46(5-6):347-55. doi: 10.1016/j.ceca.2009.10.002. PubMed PMID: 19900703. 13: Rahal ON, Fatfat M, Hankache C, Osman B, Khalife H, Machaca K, Muhtasib HG. Chk1 and DNA-PK mediate TPEN-induced DNA damage in a ROS dependent manner in human colon cancer cells. Cancer Biol Ther. 2016 Nov;17(11):1139-1148. PubMed PMID: 27690730; PubMed Central PMCID: PMC5137490. 14: Ra H, Kim HL, Lee HW, Kim YH. Essential role of p53 in TPEN-induced neuronal apoptosis. FEBS Lett. 2009 May 6;583(9):1516-20. doi: 10.1016/j.febslet.2009.04.008. PubMed PMID: 19364507. 15: Yang S, Xu W, Dong Z, Zhou M, Lin C, Jin H, Su Y, Li Q, Wang X, Chang H, Han W. TPEN prevents rapid pacing-induced calcium overload and nitration stress in HL-1 myocytes. Cardiovasc Ther. 2015 Aug;33(4):200-8. doi: 10.1111/1755-5922.12134. PubMed PMID: 25973665. 16: Morgan AJ, Parrington J, Galione A. The luminal Ca(2+) chelator, TPEN, inhibits NAADP-induced Ca(2+) release. Cell Calcium. 2012 Dec;52(6):481-7. doi: 10.1016/j.ceca.2012.09.001. PubMed PMID: 23099186; PubMed Central PMCID: PMC3526783. 17: Shmist YA, Kamburg R, Ophir G, Kozak A, Shneyvays V, Appelbaum YJ, Shainberg A. N,N,N',N'-tetrakis(2-pyridylmethyl)-ethylenediamine improves myocardial protection against ischemia by modulation of intracellular Ca2+ homeostasis. J Pharmacol Exp Ther. 2005 Jun;313(3):1046-57. PubMed PMID: 15681657. 18: Lee JM, Kim YJ, Ra H, Kang SJ, Han S, Koh JY, Kim YH. The involvement of caspase-11 in TPEN-induced apoptosis. FEBS Lett. 2008 Jun 11;582(13):1871-6. doi: 10.1016/j.febslet.2008.04.056. PubMed PMID: 18474237. 19: Mendivil-Perez M, Velez-Pardo C, Jimenez-Del-Rio M. TPEN induces apoptosis independently of zinc chelator activity in a model of acute lymphoblastic leukemia and ex vivo acute leukemia cells through oxidative stress and mitochondria caspase-3- and AIF-dependent pathways. Oxid Med Cell Longev. 2012;2012:313275. doi: 10.1155/2012/313275. PubMed PMID: 23320127; PubMed Central PMCID: PMC3540963. 20: Fukuyama S, Matsunaga Y, Zhanghui W, Noda N, Asai Y, Moriwaki A, Matsumoto T, Nakano T, Matsumoto K, Nakanishi Y, Inoue H. A zinc chelator TPEN attenuates airway hyperresponsiveness and airway inflammation in mice in vivo. Allergol Int. 2011 Sep;60(3):259-66. doi: 10.2332/allergolint.09-OA-0167. PubMed PMID: 21364313.