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P4413

Sigma-Aldrich

N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine

≥98% (TLC), powder, membrane-permeable zinc chelator

Synonyme(s) :

TPEN

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About This Item

Formule empirique (notation de Hill):
C26H28N6
Numéro CAS:
16858-02-9
Poids moléculaire :
424.54
Numéro Beilstein :
4211982
Numéro MDL:
MFCD00036918
Code UNSPSC :
12352116
ID de substance PubChem :
24898538
Nomenclature NACRES :
NA.77

product name

N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine,

Forme

powder

Chaîne SMILES 

C(CN(Cc1ccccn1)Cc2ccccn2)N(Cc3ccccn3)Cc4ccccn4

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

Clé InChI

CVRXLMUYFMERMJ-UHFFFAOYSA-N

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Application

N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine has been used:
  • in the treatment of human embryonic kidney (HEK293T) cells for assessing its effect on the Jembrana disease virus (JDV) viral infectivity factor (Vif) functionality
  • in P19 embryonic carcinoma cells for chelation of zinc ions released during apoptosis
  • to evaluate its effect on lentiviral Vpx infection on human monocytic THP-1 cells

Actions biochimiques/physiologiques

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.
TPEN is a membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis (i.e., cell shrinkage and formation of apoptotic bodies with DNA fragmentation and formation of a typical DNA ladder pattern).

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Elodie Mattio et al.
Talanta, 183, 201-208 (2018-03-24)
In recent years, the development of 3D printing in flow analysis has allowed the creation of new systems with various applications. Up to now, 3D printing was mainly used for the manufacture of small units such as flow detection cells
Influence of extracellular zinc on M1 microglial activation
Higashi Y, et al.
Scientific Reports, 7(5), 43778-43778 (2017)
Synthesis of a highly Zn 2+-selective cyanine-based probe and its use for tracing endogenous zinc ions in cells and organisms
Guo Z, et al.
Nature Protocols, 9(6), 1245-1245 (2014)
Zinc depletion by TPEN induces apoptosis in human acute promyelocytic NB4 cells
Zhu B, et al.
Cellular Physiology and Biochemistry, 42(5), 1822-1836 (2017)
Nicholas Dietrich et al.
Nucleic acids research, 45(20), 11658-11672 (2017-10-05)
The essential element zinc plays critical roles in biology. High zinc homeostasis mechanisms are beginning to be defined in animals, but low zinc homeostasis is poorly characterized. We investigated low zinc homeostasis in Caenorhabditis elegans because the genome encodes 14
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