Diethylnorspermine HCl
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MedKoo CAT#: 581386

CAS#: 156886-85-0 (4HCl)

Description: Diethylnorspermine, also known as DENSPM, BE-333, DE-333 and N(1),N(11)-Diethylnorspermine, 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.

Chemical Structure

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Diethylnorspermine HCl
CAS# 156886-85-0 (4HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 581386
Name: Diethylnorspermine HCl
CAS#: 156886-85-0 (4HCl)
Chemical Formula: C13H36Cl4N4
Exact Mass: 244.26
Molecular Weight: 390.259
Elemental Analysis: C, 40.01; H, 9.30; Cl, 36.33; N, 14.36

Price and Availability

Size Price Availability Quantity
10mg USD 550 2 Weeks
50mg USD 1650 2 Weeks
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Related CAS #: 121749-39-1 (free base)   156886-85-0 (HCl)   1384898-58-1 (HBr)    

Synonym: BE-333 HCl; BE-333 tetrahydrochloride; N(1),N(11)-Diethylnorspermine; DE 333; DE-333; DE333; BE 3-3-3; BE 333; BE333; BE-333; BENSPM; DENSPM; Diethyl-norspermine; N1,N11-Bis(ethyl)norspermine; N1,N11-Diethylnorspermine;

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

InChi Key: LAWBSOKBIROCQP-UHFFFAOYSA-N

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

SMILES Code: CCNCCCNCCCNCCCNCC.[H]Cl.[H]Cl.[H]Cl.[H]Cl

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).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 390.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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
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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
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Nov 20. PubMed PMID: 27881234.


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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
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5: Chanphai P, Tajmir-Riahi HA. Thermodynamic analysis of biogenic and synthetic
polyamines conjugation with PAMAM-G4 nanoparticles. J Photochem Photobiol B. 2016
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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
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7: Ray RM, Bhattacharya S, Bavaria MN, Viar MJ, Johnson LR. Spermidine, a sensor
for antizyme 1 expression regulates intracellular polyamine homeostasis. Amino
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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
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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
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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
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platform for the detection of translation modulators of spermidine/spermine
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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
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Central PMCID: PMC3240712.


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PubMed PMID: 21809081.


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Tissue-specific alternative splicing of spermidine/spermine N1-acetyltransferase.
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Aug 2. PubMed PMID: 21809078.


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PMID: 21750985.


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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,
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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.