P4413

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

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

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

Properties

• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves