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N1,N11-Diethylnorspermine tetrahydrochloride (CAS 156886-85-0)

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Alternate Names:
N,N′-bis[3-(Ethylamino)propyl]-1,3-propanediamine tetrahydrochloride
Application:
N1,N11-Diethylnorspermine tetrahydrochloride is an inducer of spermidine/spermine N1-acetyltransferase
CAS Number:
156886-85-0
Molecular Weight:
390.27
Molecular Formula:
C13H32N44HCl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N1,N11-Diethylnorspermine tetrahydrochloride (DENSPM) stands as a highly potent inducer of spermidine/spermine N1-acetyltransferase (SSAT), a key enzyme within the polyamine catabolic pathway, demonstrating an ability to enhance SSAT activity by an impressive range of 200-1000 fold. This remarkable induction capability positions N1,N11-Diethylnorspermine tetrahydrochloride as a tool in research focusing on the modulation of polyamine metabolism, offering a unique window into understanding the intricate balance and regulatory mechanisms governing cellular polyamine levels. By driving the acetylation process through SSAT activation, N1,N11-Diethylnorspermine tetrahydrochloride facilitates the degradation and export of polyamines from cells, thereby influencing polyamine homeostasis and impacting cellular functions related to polyamine dynamics. This mechanism of action underscores the utility of N1,N11-Diethylnorspermine tetrahydrochloride in scientific studies aimed at elucidating the role of polyamines in cellular physiology and pathophysiology, beyond its immediate effects on SSAT activity. Its application in research applications provides valuable insights into the potential modulation of polyamine metabolism, making it an essential tool for investigators exploring the complexities of cellular growth, proliferation, and differentiation processes governed by polyamine concentrations.


N1,N11-Diethylnorspermine tetrahydrochloride (CAS 156886-85-0) References

  1. Treatment of cells with the polyamine analog N, N11-diethylnorspermine retards S phase progression within one cell cycle.  |  Alm, K., et al. 2000. Eur J Biochem. 267: 4157-64. PMID: 10866819
  2. Antitumor activity of the polyamine analog N(1), N(11)-diethylnorspermine against human prostate carcinoma cells.  |  Schipper, RG., et al. 2000. Prostate. 44: 313-21. PMID: 10951496
  3. Combination of 5-fluorouracil and N1,N11-diethylnorspermine markedly activates spermidine/spermine N1-acetyltransferase expression, depletes polyamines, and synergistically induces apoptosis in colon carcinoma cells.  |  Choi, W., et al. 2005. J Biol Chem. 280: 3295-304. PMID: 15546879
  4. Antitumor activity of N,N'-bis(ethyl)spermine homologues against human MALME-3 melanoma xenografts.  |  Bernacki, RJ., et al. 1992. Cancer Res. 52: 2424-30. PMID: 1568212
  5. Activation of polyamine catabolism by N1,N11-diethylnorspermine leads to cell death in glioblastoma.  |  Jiang, R., et al. 2007. Int J Oncol. 31: 431-40. PMID: 17611701
  6. Activation of polyamine catabolism by N1, N11-diethylnorspermine alters the cellular localization of mTOR and downregulates mTOR protein level in glioblastoma cells.  |  Jiang, R., et al. 2007. Cancer Biol Ther. 6: 1644-8. PMID: 17921698
  7. Different cell cycle kinetic effects of N1,N11-diethylnorspermine-induced polyamine depletion in four human breast cancer cell lines.  |  Myhre, L., et al. 2008. Anticancer Drugs. 19: 359-68. PMID: 18454046
  8. The alpha9beta1 integrin enhances cell migration by polyamine-mediated modulation of an inward-rectifier potassium channel.  |  deHart, GW., et al. 2008. Proc Natl Acad Sci U S A. 105: 7188-93. PMID: 18480266
  9. Molecular mechanisms underlying N1, N11-diethylnorspermine-induced apoptosis in a human breast cancer cell line.  |  Holst, CM., et al. 2008. Anticancer Drugs. 19: 871-83. PMID: 18766001
  10. Characterization of human spermidine/spermine N1-acetyltransferase purified from cultured melanoma cells.  |  Libby, PR., et al. 1991. Arch Biochem Biophys. 284: 238-44. PMID: 1989509
  11. Assay of N1-acetylpolyamine oxidase activity with N1,N11-didansylnorspermine as the substrate by ion-pair reversed phase high performance liquid chromatography.  |  Takao, K., et al. 2010. Biol Pharm Bull. 33: 1089-94. PMID: 20606294
  12. Apoptosis induced by the potential chemotherapeutic drug N1, N11-Diethylnorspermine in a neuroblastoma cell line.  |  Söderstjerna, E., et al. 2010. Anticancer Drugs. 21: 917-26. PMID: 20729713
  13. Spermidine/spermine N1-acetyltransferase-mediated polyamine catabolism regulates beige adipocyte biogenesis.  |  Yuan, F., et al. 2018. Metabolism. 85: 298-304. PMID: 29715464
  14. Antitumor activity of N1,N11-bis(ethyl)norspermine against human melanoma xenografts and possible biochemical correlates of drug action.  |  Porter, CW., et al. 1993. Cancer Res. 53: 581-6. PMID: 8425191
  15. Structural basis for differential induction of spermidine/spermine N1-acetyltransferase activity by novel spermine analogs.  |  Fogel-Petrovic, M., et al. 1997. Mol Pharmacol. 52: 69-74. PMID: 9224814
  16. Antitumor efficacy of N1,N11-diethylnorspermine on a human bladder tumor xenograft in nude athymic mice.  |  Sharma, A., et al. 1997. Clin Cancer Res. 3: 1239-44. PMID: 9815805

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N1,N11-Diethylnorspermine tetrahydrochloride, 1 mg

sc-204114
1 mg
$145.00

N1,N11-Diethylnorspermine tetrahydrochloride, 5 mg

sc-204114A
5 mg
$599.00

N1,N11-Diethylnorspermine tetrahydrochloride, 10 mg

sc-204114B
10 mg
$1195.00