P4413
N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine
≥98% (TLC), powder, membrane-permeable zinc chelator
Sinónimos:
TPEN
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Fórmula empírica (notación de Hill):
C26H28N6
Número CAS:
Peso molecular:
424.54
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352116
MDL number:
Beilstein/REAXYS Number:
4211982
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Permítanos ayudarleNombre del producto
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
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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.
Clase de almacenamiento
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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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)
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
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
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)
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