N(1),N(11)-Diethylnorspermine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581386

CAS#: 121749-39-1

Description: N(1),N(11)-Diethylnorspermine tetrahydrochloride is a highly potent known inducer of the polyamine catabolic enzyme, spermidine/spermine N1-acetyltransferase (SSAT). A designed polyamines (PAs) analog which induces cell cycle arrest, inhibits proliferation and induces apoptosis in melanoma, breast, prostate, lung and colon cancer cells.


Price and Availability

Size
Price

5mg
USD 260
Size
Price

100mg
USD 750
Size
Price

500mg
USD 2000

N(1),N(11)-Diethylnorspermine , purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 581386
Name: N(1),N(11)-Diethylnorspermine
CAS#: 121749-39-1
Chemical Formula: C13H32N4
Exact Mass: 244.2627
Molecular Weight: 244.427
Elemental Analysis: C, 63.88; H, 13.20; N, 22.92


Synonym: N(1),N(11)-Diethylnorspermine; De 333; DE-333; BE 3-3-3; DENSPM;

IUPAC/Chemical Name: 1,11-Bis(ethylamino)-4,8-diazaundecan

InChi Key: UMJJGDUYVQCBMC-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H32N4/c1-3-14-8-5-10-16-12-7-13-17-11-6-9-15-4-2/h14-17H,3-13H2,1-2H3

SMILES Code: CCNCCCNCCCNCCCNCC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Gurkan AC, Arisan ED, Yerlikaya PO, Ilhan H, Unsal NP. Inhibition of autophagy
enhances DENSpm-induced apoptosis in human colon cancer cells in a p53
independent manner. Cell Oncol (Dordr). 2018 Jun;41(3):297-317. doi:
10.1007/s13402-017-0369-x. Epub 2018 Feb 28. PubMed PMID: 29492901.

2: Xie Y, Murray-Stewart T, Wang Y, Yu F, Li J, Marton LJ, Casero RA Jr, Oupický
D. Self-immolative nanoparticles for simultaneous delivery of microRNA and
targeting of polyamine metabolism in combination cancer therapy. J Control
Release. 2017 Jan 28;246:110-119. doi: 10.1016/j.jconrel.2016.12.017. Epub 2016
Dec 23. PubMed PMID: 28017891; PubMed Central PMCID: PMC5258827.

3: Akyol Z, Çoker-Gürkan A, Arisan ED, Obakan-Yerlikaya P, Palavan-Ünsal N.
DENSpm overcame Bcl-2 mediated resistance against Paclitaxel treatment in MCF-7
breast cancer cells via activating polyamine catabolic machinery. Biomed
Pharmacother. 2016 Dec;84:2029-2041. doi: 10.1016/j.biopha.2016.11.016. Epub 2016
Nov 20. PubMed PMID: 27881234.

4: Mounce BC, Cesaro T, Moratorio G, Hooikaas PJ, Yakovleva A, Werneke SW, Smith
EC, Poirier EZ, Simon-Loriere E, Prot M, Tamietti C, Vitry S, Volle R, Khou C,
Frenkiel MP, Sakuntabhai A, Delpeyroux F, Pardigon N, Flamand M, Barba-Spaeth G,
Lafon M, Denison MR, Albert ML, Vignuzzi M. Inhibition of Polyamine Biosynthesis
Is a Broad-Spectrum Strategy against RNA Viruses. J Virol. 2016 Oct
14;90(21):9683-9692. Print 2016 Nov 1. PubMed PMID: 27535047; PubMed Central
PMCID: PMC5068521.

5: Chanphai P, Tajmir-Riahi HA. Thermodynamic analysis of biogenic and synthetic
polyamines conjugation with PAMAM-G4 nanoparticles. J Photochem Photobiol B. 2016
Feb;155:13-9. doi: 10.1016/j.jphotobiol.2015.12.006. Epub 2015 Dec 17. PubMed
PMID: 26722998.

6: Çoker-Gürkan A, Arisan ED, Obakan P, Palavan-Unsal N. Lack of functional p53
renders DENSpm-induced autophagy and apoptosis in time dependent manner in colon
cancer cells. Amino Acids. 2015 Jan;47(1):87-100. doi: 10.1007/s00726-014-1851-7.
Epub 2014 Oct 14. PubMed PMID: 25311224.

7: Ray RM, Bhattacharya S, Bavaria MN, Viar MJ, Johnson LR. Spermidine, a sensor
for antizyme 1 expression regulates intracellular polyamine homeostasis. Amino
Acids. 2014 Aug;46(8):2005-13. doi: 10.1007/s00726-014-1757-4. Epub 2014 May 14.
PubMed PMID: 24824458; PubMed Central PMCID: PMC4104236.

8: Andersen SM, Taylor R, Holen E, Aksnes A, Espe M. Arginine supplementation and
exposure time affects polyamine and glucose metabolism in primary liver cells
isolated from Atlantic salmon. Amino Acids. 2014 May;46(5):1225-33. doi:
10.1007/s00726-014-1684-4. Epub 2014 Feb 6. PubMed PMID: 24500114.

9: Goyal L, Supko JG, Berlin J, Blaszkowsky LS, Carpenter A, Heuman DM,
Hilderbrand SL, Stuart KE, Cotler S, Senzer NN, Chan E, Berg CL, Clark JW, Hezel
AF, Ryan DP, Zhu AX. Phase 1 study of N(1),N(11) diethylnorspermine (DENSPM) in
patients with advanced hepatocellular carcinoma. Cancer Chemother Pharmacol. 2013
Dec;72(6):1305-14. PubMed PMID: 24121453.

10: Minarini A, Zini M, Milelli A, Tumiatti V, Marchetti C, Nicolini B, Falconi
M, Farruggia G, Cappadone C, Stefanelli C. Synthetic polyamines activating
autophagy: effects on cancer cell death. Eur J Med Chem. 2013 Sep;67:359-66. doi:
10.1016/j.ejmech.2013.06.044. Epub 2013 Jul 1. PubMed PMID: 23887056.

11: Perez-Leal O, Abou-Gharbia M, Gordon J, Childers WE, Merali S. A novel assay
platform for the detection of translation modulators of spermidine/spermine
acetyltransferase. Curr Pharm Des. 2014;20(2):245-52. PubMed PMID: 23701549;
PubMed Central PMCID: PMC3871977.

12: Tian Y, Wang S, Wang B, Zhang J, Jiang R, Zhang W. Overexpression of SSAT by
DENSPM treatment induces cell detachment and apoptosis in glioblastoma. Oncol
Rep. 2012 Apr;27(4):1227-32. doi: 10.3892/or.2011.1592. Epub 2011 Dec 14. PubMed
PMID: 22179681; PubMed Central PMCID: PMC3583519.

13: Uimari A, Merentie M, Sironen R, Pirnes-Karhu S, Peräniemi S, Alhonen L.
Overexpression of spermidine/spermine N1-acetyltransferase or treatment with
N1-N11-diethylnorspermine attenuates the severity of zinc-induced pancreatitis in
mouse. Amino Acids. 2012 Feb;42(2-3):461-71. doi: 10.1007/s00726-011-1025-9. Epub
2011 Aug 4. PubMed PMID: 21814793.

14: Fraser AV, Goodwin AC, Hacker-Prietz A, Sugar E, Woster PM, Casero RA Jr.
Knockdown of ornithine decarboxylase antizyme 1 causes loss of uptake regulation
leading to increased N1, N11-bis(ethyl)norspermine (BENSpm) accumulation and
toxicity in NCI H157 lung cancer cells. Amino Acids. 2012 Feb;42(2-3):529-38.
doi: 10.1007/s00726-011-1030-z. Epub 2011 Aug 4. PubMed PMID: 21814790; PubMed
Central PMCID: PMC3240712.

15: Johansson VM, Thuvesson I, Alm K, Oredsson SM. Novel anti-apoptotic effect of
the retinoblastoma protein: implications for polyamine analogue toxicity. Amino
Acids. 2012 Feb;42(2-3):929-37. doi: 10.1007/s00726-011-1007-y. Epub 2011 Aug 2.
PubMed PMID: 21809081.

16: Hyvönen MT, Uimari A, Vepsäläinen J, Khomutov AR, Keinänen TA, Alhonen L.
Tissue-specific alternative splicing of spermidine/spermine N1-acetyltransferase.
Amino Acids. 2012 Feb;42(2-3):485-93. doi: 10.1007/s00726-011-1027-7. Epub 2011
Aug 2. PubMed PMID: 21809078.

17: Kreutzer JN, Olsen BB, Lech K, Issinger OG, Guerra B. Role of polyamines in
determining the cellular response to chemotherapeutic agents: modulation of
protein kinase CK2 expression and activity. Mol Cell Biochem. 2011
Oct;356(1-2):149-58. doi: 10.1007/s11010-011-0949-4. Epub 2011 Jul 13. PubMed
PMID: 21750985.

18: Facchini A, Stanic I, Cetrullo S, Borzì RM, Filardo G, Flamigni F.
Sulforaphane protects human chondrocytes against cell death induced by various
stimuli. J Cell Physiol. 2011 Jul;226(7):1771-9. doi: 10.1002/jcp.22506. PubMed
PMID: 21506109.

19: Cervelli M, Bellavia G, Fratini E, Amendola R, Polticelli F, Barba M,
Federico R, Signore F, Gucciardo G, Grillo R, Woster PM, Casero RA Jr, Mariottini
P. Spermine oxidase (SMO) activity in breast tumor tissues and biochemical
analysis of the anticancer spermine analogues BENSpm and CPENSpm. BMC Cancer.
2010 Oct 14;10:555. doi: 10.1186/1471-2407-10-555. PubMed PMID: 20946629; PubMed
Central PMCID: PMC3027604.

20: Söderstjerna E, Holst CM, Alm K, Oredsson SM. Apoptosis induced by the
potential chemotherapeutic drug N1, N11-Diethylnorspermine in a neuroblastoma
cell line. Anticancer Drugs. 2010 Nov;21(10):917-26. doi:
10.1097/CAD.0b013e32833d1cae. PubMed PMID: 20729713.