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P4413

Sigma-Aldrich

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

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

Synonym(s):

TPEN

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About This Item

Empirical Formula (Hill Notation):
C26H28N6
CAS Number:
16858-02-9
Molecular Weight:
424.54
Beilstein:
4211982
MDL number:
MFCD00036918
UNSPSC Code:
12352116
PubChem Substance ID:
24898538
NACRES:
NA.77

Product Name

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

form

powder

Quality Level

100

SMILES string

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

InChI key

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

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.
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).

Features and Benefits

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4441V
WXBF2356V
WXBD9832V
WXBD9384V
SLCN8758

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Jembrana disease virus Vif antagonizes the inhibition of bovine APOBEC3 proteins through ubiquitin-mediate protein degradation
Su X, et al.
Virology, 519(11), 53-63 (2018)
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
Inhibition of Vpx-mediated SAMHD1 and Vpr-mediated HLTF degradation by selective disruption of viral CRL4 (DCAF1) E3 ubiquitin ligase assembly
Wang H, et al.
Journal of Virology, JVI-00225 (2017)
Xin Li et al.
Frontiers in molecular neuroscience, 10, 414-414 (2018-01-10)
Transient receptor potential melastatin-related 2 (TRPM2) channel, a molecular sensor for reactive oxygen species (ROS), plays an important role in cognitive dysfunction associated with post-ischemia brain damage thought to result from ROS-induced TRPM2-dependent neuronal death during reperfusion. Emerging evidence further
Influence of extracellular zinc on M1 microglial activation
Higashi Y, et al.
Scientific Reports, 7(5), 43778-43778 (2017)
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