TPEN CAS: 16858-02-9
MF: C26H28N6
MW: 424.54
An apoptosis inducer and heavy metal chelator.

TPEN (CAS 16858-02-9)

TPEN | CAS 16858-02-9 is rated 5.0 out of 5 by 3.
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Alternate Names: N,N,N',N'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine
Application: TPEN is an apoptosis inducer and heavy metal chelator
CAS Number: 16858-02-9
Purity: ≥97%
Molecular Weight: 424.54
Molecular Formula: C26H28N6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
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TPEN is a cell permeable, high-affinity heavy metal (Zn2+>Fe2+>Mn2+) chelator that exhibits low affinity for Mg2+ and Ca2+. The compound is lipid-soluble and has been shown to permeate artificial and natural membranes. Research shows that TPEN induces apoptosis in human and rat thymocytes through DNA fragmentation and Caspace-3 activation. TPEN also induces mitochondrial cytochrome C translocation to the cytosol in human PBL. A recent study has proved this chelator to work in conjunction with the fluorescent probe Fura-2 (sc-202163) in biophysical studies of Ca2+.


References

1. Treves, S., et al. 1994. Exp. Cell Res. 211: 339-343. PMID: 8143781

2. Aizenman, E., et al. 2000. J Neurochem. 75: 1878-88. PMID:11032877

3. Kolenko, V.M., et al. 2001. Apoptosis. 6: 419-429. PMID: 11595831

4. Chimienti, F., et al. 2001. Biochem. Pharmacol. 6: 51-62. PMID: 11377396

5. Matias, C.M., et al. 2010. J Fluoresc. 20: 377-380. PMID: 19821015

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in ethanol (~20 mg/ml), DMF (~1 mg/ml), DMSO (~0.15 mg/ml), methanol, chloroform, PBS, and 1:10 solution of ethanol:PBS (pH 7.2) (~0.1 mg/ml). Insoluble in water.
Storage :
Store at 4° C
Melting Point :
110-114° C
Boiling Point :
~542.1° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.63
pK Values :
pKb: 5.19
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
MDL Number :
MFCD00036918
Beilstein Registry :
4211982
SMILES :
C1=CC=NC(=C1)CN(CCN(CC2=CC=CC=N2)CC3=CC=CC=N3)CC4=CC=CC=N4

Download SDS (MSDS)

Certificate of Analysis

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TPEN (CAS 16858-02-9)  Product Citations

See how others have used TPEN (CAS 16858-02-9). Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

PMID: # 33490979  Horton, TM.|Kraemer, BR.|Annes, JP.| et al. 2021. STAR Protoc. 2: 100263.

PMID: # 31869222  Feng, Y.|Zhang, J.|Miao, Y.|Guo, W.|Feng, G.|Yang, Y.|Guo, T.|Wu, H.|Zeng, M.| et al. 2020. J Agric Food Chem. 68: 652-659.

PMID: # 29370118  Uchiyama, H.|Tsujimoto, M.|Shimada, N.|Tsutsui, K.|Nitta, A.|Yoshida, T.|Furukubo, T.|Izumi, S.|Yamakawa, T.|Tachiki, H.|Minegaki, T.|Nishiguchi, K.| et al. 2018. Toxins (Basel). 10:

PMID: # 27057544  Li, D.|Wang, G.|Han, D.|Bi, J.|Li, C.|Wang, H.|Liu, Z.|Gao, W.|Gao, K.|Yao, T.|Wan, Z.|Li, H.|Mei, X.| et al. 2016. Biomed Res Int. 2016: 6090316.

PMID: # 26784148  Barresi, V.|Spampinato, G.|Musso, N.|Trovato Salinaro, A.|Rizzarelli, E.|Condorelli, DF.| et al. 2016. J Inorg Biochem. 156: 145-52.

PMID: # 26712852  Qian, C. et al. 2016. The Journal of general physiology. 147: 95-102.

PMID: # 25032698  Kashyap, DR. et al. 2014. PLoS pathogens. 10: e1004280.

Citations 1 to 7 of 7 total

What is the affinity TPEN has for zinc?

Asked by: Elam21
Thank you for your question. Unfortunately this is not information we have, but according to the below paper, TPEN has a high affinity for Zn2+ (KD = 0.26 fM). Aizenman, E., et al. 2002. J Neurochem. 2000 Nov;75: 1878-88. PMID:11032877 https://onlinelibrary.wiley.com/doi/full/10.1046/j.1471-4159.2000.0751878.x
Answered by: Tech Service
Date published: 2019-06-03

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. TPEN, sc-200131, is in pale yellow to grayish yellow red crystalline/powder form.
Answered by: Chemical Support 4
Date published: 2018-09-14
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Rated 5 out of 5 by from Matias et al Matias et al. (PubMed ID 19821015) confirmed the use of TPEN as a chelator for the biophysical study of calcium in the presence of zinc using Fura-2. -SCBT Publication Review
Date published: 2015-06-02
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