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16858-02-9

16858-02-9 Structure

16858-02-9 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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 InformationBack 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
Spectrum DetailBack Directory
[Spectrum Detail]

TPEN(16858-02-9)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

16858-02-9(sigmaaldrich)
[TCI AMERICA]

N,N,N',N'-Tetrakis(2-pyridylmethyl)ethylenediamine,>97.0%(T)(16858-02-9)
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