A transition metal chelator
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Product Categories

Product Type

Biochemicals
Metal Chelators

Research Area

Cell Biology
Cell Death
Apoptosis

TPEN

Item No. 13340

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N,N',N'-tetrakis(2-pyridinylmethyl)-1,2-ethanediamine
CAS Number
16858-02-9
Synonyms
  • TPEDA
Molecular Formula
C26H28N6
Formula Weight
424.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 0.15 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:10): 0.1 mg/ml
λmax
262 nm
SMILES
c1ccc(nc1)CN(CCN(Cc1ccccn1)Cc1ccccn1)Cc1ccccn1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $19

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    25 mg

    $41

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    50 mg

    $74

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    100 mg

    $130

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    Product Description

    As a cofactor of more than 300 enzymes, zinc is integral for a wide variety of cellular processes that affect most biological functions.1 Most notably, its bioavailability is important to the regulation of apoptosis, cell proliferation, and differentiation. TPEN is a cell permeant metal ion chelator that is used in zinc treatment studies to limit intra- and extracellular concentrations of the mineral.2 At a concentration as low as 6 µM, TPEN-induced zinc depletion decreases X-linked inhibitor of apoptosis (XIAP) levels in human PC-3 prostate cancer cells and promotes caspase-3 and -9 activation.3 At 25 µM, TPEN attenuates hypoxic pulmonary vasoconstriction in rodent isolated perfused lung.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beyersmann, D., and Haase, H. Functions of zinc in signaling, proliferation and differentiation of mammalian cells. BioMetals 14(3-4), 331-341 (2001).

    2. Cho, Y.E., Lomeda, R.A.R., Ryu, S.H., et al. Cellular Zn depletion by metal ion chelators (TPEN, DTPA and chelex resin) and its application to osteoblastic MC3T3-E1 cells. Nutr. Res. Pract. 1(1), 29-35 (2007).

    3. Makhov, P., Golovine, K., Uzoo, R.G., et al. Zinc chelation induces rapid depletion of the X-linked inhibitor of apoptosis (XIAP) and sensitizes prostate cancer cells to TRAIL-mediated apoptosis. Cell Death Differ. 15(11), 1745-1751 (2008).

    4. Bernal, P.J., Leelavanichkul, K., Bauer, E., et al. Nitric oxide mediated zinc release contributes to hypoxic regulation of pulmonary vascular tone. Circ. Res. 102(12), 1575-1583 (2008).

    Product Citations

    Du, W., Gu, M., Hu, M., et al. Lysosomal Zn2+ release triggers rapid, mitochondria-mediated, non-apoptotic cell death in metastatic melanoma. Cell Rep. 37(3), 109848 (2021).