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TPEN

Name: TPEN
Brand: MM

Synonym(s):

TPEN, N,N,Nʹ,Nʹ- tetrakis-(2-Pyridylmethyl)ethylenediamine

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₂₈N₆

CAS Number:

16858-02-9

Molecular Weight:

424.54

UNSPSC Code:

12352116

NACRES:

NA.25

MDL number:

MFCD00036918

Assay:

≥97% (titration)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze

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Properties

assay

≥97% (titration)

Quality Level

100

form

solid

reaction suitability

reagent type: chelator

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

color

tan

solubility

ethanol: 10 mg/mL, 0.1 M phosphate pH 7.0: 25 μM, DMSO: soluble

shipped in

ambient

storage temp.

15-25°C

SMILES string

N(CCN(Cc4ncccc4)Cc3ncccc3)(Cc2ncccc2)Cc1ncccc1

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

InChI key

CVRXLMUYFMERMJ-UHFFFAOYSA-N

Description

General description

Lipid-soluble heavy metal chelator that crosses artificial and natural membranes. Auxiliary reagent in certain techniques used for measuring free Ca²⁺ levels in cells. Also useful in extracting Aβ amyloid deposits from Alzheimer’s disease brain tissue. Has extremely high affinity for heavy metals but low affinity for Ca²⁺ and Mg²⁺. Induces DNA fragmentation when chelated with Zn²⁺ and induces apoptosis in thymocytes. Strips heavy metals from liposome-trapped QUIN 2 (Cat. No. 551826).

Application

Poly(ADP-ribosyl)ation of p53 contributes to TPEN-induced neuronal apoptosis.: This study investigates the role of poly(ADP-ribosyl)ation of the tumor suppressor protein p53 in neuronal apoptosis induced by TPEN, highlighting mechanisms of cell death in neurodegenerative diseases (Kim HL et al., 2015).

Essential role of p53 in TPEN-induced neuronal apoptosis.: This article explores the critical involvement of the p53 protein in apoptosis initiated by TPEN in neuronal cells, offering insights into potential therapeutic targets for neuroprotection (Ra H et al., 2009).

Clioquinol induces autophagy in cultured astrocytes and neurons by acting as a zinc ionophore.: Demonstrates how Clioquinol, similar to TPEN, functions as a zinc ionophore to induce autophagy, particularly in neurological contexts, which may be relevant for understanding TPEN′s mechanisms (Park MH et al., 2011).

Preparation Note

Following reconstitution, aliquot and freeze (-20°C) under an inert gas. Alternately, acidify (pH ≤3) with HCl for long term storage. Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Fonte, J., et al. 2001. J. Alzheimer’s Dis. 3, 209.
Cherny, R.A., et al. 1999. J. Biol. Chem. 274, 23223.
Aballay, A., et al. 1995. Biochem. J.312, 919.
Jiang, S., et al. 1995. Lab. Invest.73, 111.
Sheridan, R.E. and Deshpande, S.S. 1995. Toxicon33, 539.
McCabe, M.J., et al. 1993. Lab. Invest. 69, 101.
Hinkle, P.M., et al. 1992. J. Biol. Chem.267, 25553.
Baba, A., et al. 1991. Brain Res. 557, 103.
Forbes, I.J., et al. 1991. Exp. Cell Res. 195, 224.
Csermely, P. and Somogyi, J. 1989. J. Cellular Physiol.138, 593.
Raspe, E., et al. 1989. Eur. J. Pharmacol.163, 345.
Arslan, L.P., et al. 1985. J. Biol. Chem.260, 2719.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c