16858-02-9

Basic information

• Product Name: TPEN
• 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)
• CAS NO: 16858-02-9
• Molecular Formula: C₂₆H₂₈N₆
• Molecular Weight: 424.54
• Product Categories: Apoptosis;Aromatics;Chelating Agents & Ligands;Heterocycles;Inhibitors;Apoptosis Inducers
• Mol File: 16858-02-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 110-112 °C
• Boiling Point: 530.56°C (rough estimate)
• Flash Point: 281.7 °C
• Appearance: Colourless Crystals
• Density: 1.3893 (rough estimate)
• Refractive Index: 1.4570 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Soluble in DMSO (up to 10 mg/ml).
• PKA: 5.19±0.12(Predicted)
• 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.
• BRN: 4211982
• CAS DataBase Reference: TPEN(CAS DataBase Reference)
• NIST Chemistry Reference: TPEN(16858-02-9)
• EPA Substance Registry System: TPEN(16858-02-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 16858-02-9(Hazardous Substances Data)

Usage

Description

TPEN, also known as N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine, is a membrane-permeable metal chelator with the chemical formula (C11H10N2)4. It is a colorless crystalline compound that is frequently used to study the effects of zinc depletion on cellular processes. TPEN is an N-substituted diamine where the four amino hydrogens are replaced by 2-pyridylmethyl groups, making it a versatile tool in various applications.

Uses

1. Used in Cellular Research:
TPEN is used as a membrane-permeable zinc chelator for studying the effects of zinc depletion on cellular processes. It helps researchers understand the role of zinc in cellular functions and its impact on cell viability.
2. Used in Apoptosis Induction:
TPEN is used as an apoptosis inducer by decreasing the intracellular level of zinc. This application is particularly relevant in cancer research, where the induction of apoptosis can be a potential therapeutic strategy.
3. Used in Anticancer Applications:
TPEN can be employed in anticancer research as a zinc chelator that may potentially disrupt zinc-dependent signaling pathways in cancer cells, leading to cell death and reduced tumor growth.
4. Used in Drug Delivery Systems:
TPEN can be utilized in the development of novel drug delivery systems to enhance the efficacy of chemotherapeutic agents. By chelating zinc, TPEN may improve the delivery, bioavailability, and therapeutic outcomes of certain drugs, particularly in cancer treatment.
5. Used in Analytical Chemistry:
TPEN can be used as a reagent in analytical chemistry for the determination of metal ions, particularly zinc, due to its high affinity for this metal.
6. Used in Environmental Applications:
TPEN can be employed in environmental applications to remove excess zinc from contaminated water sources or soil, helping to mitigate the negative effects of zinc pollution on ecosystems.

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.

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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Prevention of cell death by the zinc ion chelating agent TPEN (cas 16858-02-9) in cultured PC12 cells exposed to Oxygen–Glucose Deprivation (OGD)07/26/2019

To elucidate the role of Zn2+-associated glutamate signaling pathway and voltage-dependent outward potassium ion currents in neuronal death induced by hypoxia–ischemia, PC12 cells were exposed to Oxygen–Glucose Deprivation (OGD) solution mimicking the hypoxic–ischemic condition in neuron, and...detailed

Synthesis of TPEN (cas 16858-02-9) variants to improve cancer cells selective killing capacity07/23/2019

TPEN is an amino chelator of transition metals that is effective at the cellular and whole organism levels. Although TPEN of often used as a selective zinc chelators, it has affinity for copper and iron and has been shown to chelate both biologically. We have previously shown that TPEN selective...detailed