| Identification | More | [Name]
TPEN | [CAS]
16858-02-9 | [Synonyms]
N,N,N',N'-TETRAKIS(2-PYRIDYLMETHYL)ETHYLENEDIAMINE
TETRAKIS-(2-PYRIDYLMETHYL)ETHYLENEDIAMINE
TPEN
N,N,N',N',-TETRAKIS(2-PYRIDYLMETHYL)*ETH YLENEDIAMIN
TPEN/CH63857
N,N,NNTetrakis(2-pyridylmethyl)-1,2-ethylenediamine
N,N,NNTetrakis-pyridin-2-ylmethyl-ethane-1,2-diamine
N,N,N'',N''-TETRAKIS(2-PYRIDYLMETHYL)ETHYLENEDIAMINE (TPEN)
N,N,N'',N''-Tetrakis-(2-pyridylmethyl)-ethylenediame
N,N,N',N'-Tetra(2-pyridyl)-1,2-ethanediamine
N,N'-Ethylenebis[bis(2-pyridyl)amine] | [Molecular Formula]
C26H28N6 | [MDL Number]
MFCD00036918 | [Molecular Weight]
424.54 | [MOL File]
16858-02-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless Crystals | [Melting point ]
110-112 °C | [Boiling point ]
530.56°C (rough estimate) | [density ]
1.3893 (rough estimate) | [refractive index ]
1.4570 (estimate) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Soluble in DMSO (up to 10 mg/ml). | [form ]
Tan solid | [pka]
5.19±0.12(Predicted) | [color ]
Off-white or tan | [Usage]
Membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis | [BRN ]
4211982 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChI]
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 | [InChIKey]
CVRXLMUYFMERMJ-UHFFFAOYSA-N | [SMILES]
C(N(CC1=NC=CC=C1)CC1=NC=CC=C1)CN(CC1=NC=CC=C1)CC1=NC=CC=C1 | [CAS DataBase Reference]
16858-02-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
8-10-23 | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Description]
TPEN (16858-02-9) is a cell permeable metal chelator. Frequently used to study effects of zinc depletion on cellular processes.1,2 | [Chemical Properties]
Colourless Crystals | [Uses]
Membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis | [Uses]
Membrane-permeable zinc chelator; decreased the intracellular level of zinc and induced apoptosis. | [Definition]
ChEBI: An N-substituted diamine that is ethylenediamine in which the four amino hydrogens are replaced by 2-pyridylmethyl groups. | [reaction suitability]
reagent type: chelator | [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. | [storage]
Store at -20°C | [References]
1) Chimienti et al. (2001) Role of cellular zinc in programmed cell death: temporal relationship between zinc depletion, activation of caspases and cleavage of Sp family transcription factors; Biochem. Pharmacol. 62 51
2) Meplan et al. (2000) Metalloregulation of the tumor suppressor protein p53: zinc mediates the renaturation of p53 after exposure to metal chelators in vitro and in intact cells; Oncogene 19 5227 |
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