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Merck

P4413

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
NACRES:
NA.77
PubChem Substance ID:
24898538
UNSPSC Code:
12352116
MDL number:
MFCD00036918
Beilstein/REAXYS Number:
4211982

Product Name

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

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 string

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

InChI key

CVRXLMUYFMERMJ-UHFFFAOYSA-N

form

powder

Quality Level

100

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7899V
WXBF6572V
WXBF5583V
WXBF4441V
WXBF2356V

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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)
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
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)
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
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