Stock solutions of TPEN in DMSO can be prepared at 50 mM. This is inferred from a study where the authors used TPEN on rat liver nuclei at 1 mM, with DMSO at 2%. The study titled "1,10-Phenanthroline stimulates internucleosomal DNA fragmentation in isolated rat-liver nuclei by promoting the redox activity of endogenous copper ions" was published in the Biochemical Journal in 1996 by Burkitt, M.J., et al.
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:
Molecular Weight:
424.54
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352116
MDL number:
Beilstein/REAXYS Number:
4211982
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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
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This Item | D0260 | D6571 | C8988 |
|---|---|---|---|
| form powder | form powder | form powder | form powder |
| Quality Level 100 | Quality Level 200 | Quality Level 100 | Quality Level 100 |
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[1]
- in P19 embryonic carcinoma cells for chelation of zinc ions released during apoptosis[2]
- to evaluate its effect on lentiviral Vpx infection on human monocytic THP-1 cells[3]
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.[4] In microglia pretreated with zinc, TPEN inhibits the interleukin 6 secretion and nitric oxide synthase (iNOS) mRNA expression.[5] It induces damage on DNA structure by activating ATM (ataxia telangiectasia mutated) and ATR (ATM-Rad3-related) signaling in human colon cancer cells.[6]
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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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
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)
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)
Articles
Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.
Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.
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