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TPEN

Product NameTPEN
CAS16858-02-9
MFC26H28N6
MW424.54
EINECS
MOL File16858-02-9.mol

Chemical Properties

Melting point	110-112 °C
Boiling point	530.56°C (rough estimate)
Density	1.3893 (rough estimate)
refractive index	1.4570 (estimate)
storage temp.	Sealed in dry,2-8°C
solubility	Soluble in DMSO (up to 10 mg/ml).
pka	5.19±0.12(Predicted)
form	Tan solid
color	Off-white or tan
BRN	4211982
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI	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
InChIKey	CVRXLMUYFMERMJ-UHFFFAOYSA-N
SMILES	C(N(CC1=NC=CC=C1)CC1=NC=CC=C1)CN(CC1=NC=CC=C1)CC1=NC=CC=C1
CAS DataBase Reference	16858-02-9(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
F	8-10-23
HS Code	29333990

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

TPEN (16858-02-9) is a cell permeable metal chelator. Frequently used to study effects of zinc depletion on cellular processes.1,2

Chemical Properties

Colourless Crystals

Uses

Membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis.

Definition

ChEBI: An N-substituted diamine that is ethylenediamine in which the four amino hydrogens are replaced by 2-pyridylmethyl groups.

reaction suitability

reagent type: chelator

Biochem/physiol Actions

N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine (TPEN) elicits pro-apoptotic effect in human acute promyelocytic NB4 cells by inhibiting nitric oxide signalling and Zn2+ signaling. In microglia pretreated with zinc, TPEN inhibits the interleukin 6 secretion and nitric oxide synthase (iNOS) mRNA expression. It induces damage on DNA structure by activating ATM (ataxia telangiectasia mutated) and ATR (ATM-Rad3-related) signaling in human colon cancer cells.

storage

Store at +4°C

References

[1] FABRICE CHIMIENTI . Role of cellular zinc in programmed cell death: temporal relationship between zinc depletion, activation of caspases, and cleavage of Sp family transcription factors1[J]. Biochemical pharmacology, 2001, 62 1: Pages 51-62. DOI:10.1016/s0006-2952(01)00624-4
[2] CATHERINE MÉPLAN Pierre H Marie Jeanne Richard. Metalloregulation of the tumor suppressor protein p53: zinc mediates the renaturation of p53 after exposure to metal chelators in vitro and in intact cells[J]. Oncogene, 2000, 19 46: 5227-5236. DOI:10.1038/sj.onc.1203907

TPEN

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