CAS Number16858-02-9
Synonymsn,n,n',n'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine; N,N,N',N'-Tetrakis(2-pyridinylmethyl)-1,2-ethanediamine; N,N,N',N'-Tetrakis(2-pyridylmethyl)ethylenediamine; MFCD00036918; N,N,N',N'-Tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine; N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine; N,N,N',N'-tetrakis-(2-Pyridylmethyl)ethylenediamine; N1,N1,N2,N2-Tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine; N,N,N′,N′-tetrakis(2-pyridylmethyl)ethane-1,2-diamine; TPEN
Molecular FormulaC26H28N6
Molecular Weight424.54
Purity98%
Density1.2±0.1 g/cm3
Boiling Point542.1±45.0 °C at 760 mmHg
Melting Point110-112 °C
Appearancepowder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 16858-02-9 |
| Catalog No. | 2A-9060722 |
| Chinese Name | N,N,N',N'-四(2-吡啶甲基)乙二胺 |
| Synonyms | n,n,n',n'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine; N,N,N',N'-Tetrakis(2-pyridinylmethyl)-1,2-ethanediamine; N,N,N',N'-Tetrakis(2-pyridylmethyl)ethylenediamine; MFCD00036918; N,N,N',N'-Tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine; N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine; N,N,N',N'-tetrakis-(2-Pyridylmethyl)ethylenediamine; N1,N1,N2,N2-Tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine; N,N,N′,N′-tetrakis(2-pyridylmethyl)ethane-1,2-diamine; TPEN |
| Molecular Formula | C26H28N6 |
| Molecular Weight | 424.54 |
| Purity | 98 |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 542.1±45.0 °C at 760 mmHg |
| Melting Point | 110-112 °C |
| Appearance | powder |
| Water Solubility | Soluble in: methanol |
| Storage Condition | Refrigerator |
| Application | TPEN is a specific cell-permeable heavy metal chelator. |
| HTC | 2933399090 |
| PubChem ID | 24898538 |
| MDL Number | MFCD00036918 |
| SMILES | 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 |
| Beilstein/REAXYS | 4211982 |
| NACRES Code | NA.77 |
| UNSPSC | 12352116 |
| MSDS | msds/60722_1_16858_02_9.pdf |
| Bioactivity | TPEN is a specific cell-permeable heavy metal chelator. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Cancer In Vitro Heavy metal chelator TPEN attenuates fura-2 fluorescence changes induced by cadmium, mercury and methylmercury. TPEN, a cell-permeable chelator for heavy metal cations with a low affinity for Ca2+. In cells stimulated with 10 or 30 μM cadmium chloride, the addition of TPEN at 3 hr after exposure significantly decreases the elevated fura-2 fluorescence ratio to the basal levels within 10 min (119.6±2.4% or 109±1.5% decrease in ΔRatio (F340/F380) induced by 10 or 30 μM cadmium chloride, respectively), suggesting that a cadmium chloride-induced increase in the fura-2 fluorescence ratio is dependent on an increase in intracellular heavy metal cations but not intracellular Ca2+[1]. TPEN is a metal chelator, which targets colon cancer cells through redox cycling of copper. TPEN reduces cell viability in a dose- and time-dependent manner. TPEN-induced cell death is also dependent on the redox cycling of copper since the copper chelator neocuproine inhibited DNA damage and reduced pChk1, γ-H2AX, and ATM protein expression. Cell death by low TPEN concentrations, involved ATM/ATR signaling in all 3 cell lines, since pre-incubation with specific inhibitors of ATM and DNA-PK led to the recovery of cells from TPEN-induced DNA damage[2]. Cell Assay Human neuroblastoma cell line SH-SY5Y, are grown in Dulbecco's Modified Eagle's Medium (DMEM) mixed 1:1 with Ham's F-12 nutrient mixture containing 10% fetal bovine serum, 100 unit/mL penicillin and 100 μg/mL streptomycin at 37°C in a humidified 5% CO2 atmosphere. Two days before experimentation, cells are seeded at a density of 7×104 cells/cm2 in a 96-well plate. Cells in a 96-well plate are serum-starved for 4 hr; calcium indicator fura-2 is then loaded into the cells by using Calcium kit II fura-2. In brief, SH-SY5Ycells are incubated with 5 μM fura-2/AM in the presence of 0.04% Pluronic F-127, a dispersing agent to improve the efficiency of loading with fura-2, and 1.25 mM probenecid, a blocker of organic anion transport to prevent leakage of fura-2 from cells. After 1 hr incubation at 37°C, fura-2 fluorescence is measured at 500 nm emission after excitation at 340 nm (F340) or 380 nm (F380) using an Infinite M200 plate reader at 37°C.The change in [Ca2+]i is reflected by the ratio of F340 and F380. To determine the changes in fura-2 fluorescence ratio induced by heavy metal compounds, cells are treated with manganese chloride, lead acetate, cadmium chloride , mercuric chloride and MeHg chloride dissolved in distilled water. We confirmed that the cells adhered to the bottom of the plate after 6 hr exposure to heavy metal compounds. The cells are also treated with three Ca2+ channel blockers, lanthanum chloride dissolved in distilled water, verapamil and 2-APB dissolved in DMSO, 30 min before heavy metal exposure. The heavy metal chelator TPEN is dissolved in DMSO and added 3 hr after the stimulation with heavy metals to determine the contribution of endogenous and exogenous heavy metals on fura-2 fluorescence changes. We measured the effect of TPEN (20 μM) on the fura-2 fluorescence ratio after a 10 min treatment with TPEN, since our preliminary experiments showed that the effect of TPEN on fura-2 fluorescence reached maximum and stabilized within 10 min of the treatment[1]. References [1]. Ohkubo M, et al. Heavy metal chelator TPEN attenuates fura-2 fluorescence changes induced by cadmium, mercury and methylmercury. J Vet Med Sci. 2016 Jun 1;78(5):761-7. [2]. Rahal ON, et al. Chk1 and DNA-PK mediate TPEN-induced DNA damage in a ROS dependent manner in human colon cancer cells. Cancer Biol Ther. 2016 Nov;17(11):1139-1148. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 542.1±45.0 °C at 760 mmHg Melting Point 110-112 °C Molecular Formula C26H28N6 Molecular Weight 424.541 Flash Point 281.7±28.7 °C Exact Mass 424.237549 PSA 58.04000 LogP 2.68 Vapour Pressure 0.0±1.4 mmHg at 25°C Index of Refraction 1.632 InChIKey CVRXLMUYFMERMJ-UHFFFAOYSA-N SMILES c1ccc(CN(CCN(Cc2ccccn2)Cc2ccccn2)Cc2ccccn2)nc1 Storage condition Refrigerator |
| Use of | TPEN is a specific cell-permeable heavy metal chelator. Properties Articles57 Name N,N,N′,N′-Tetrakis(2-pyridylmethyl)ethylenediamine Synonym More Synonyms TPEN Biological Activity Description TPEN is a specific cell-permeable heavy metal chelator. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Cancer References [1]. Ohkubo M, et al. Heavy metal chelator TPEN attenuates fura-2 fluorescence changes induced by cadmium, mercury and methylmercury. J Vet Med Sci. 2016 Jun 1;78(5):761-7. [2]. Rahal ON, et al. Chk1 and DNA-PK mediate TPEN-induced DNA damage in a ROS dependent manner in human colon cancer cells. Cancer Biol Ther. 2016 Nov;17(11):1139-1148. Chemical & Physical Properties Molecular Formula C26H28N6 Exact Mass 424.237549 PSA 58.04000 Index of Refraction 1.632 InChIKey CVRXLMUYFMERMJ-UHFFFAOYSA-N Storage condition Refrigerator |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 97.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine Modification number: 5 |
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