MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 581386 | Name: Diethylnorspermine HCl
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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

Theoretical Analysis

MedKoo Cat#: 581386

Name: Diethylnorspermine HCl

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

Chemical Formula: C13H36Cl4N4

Exact Mass: 244.2627

Molecular Weight: 390.26

Elemental Analysis: C, 40.01; H, 9.30; Cl, 36.33; N, 14.36

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
121749-39-1 (free base) 156886-85-0 (4HCl) 1384898-58-1 (4HBr)
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
Certificate of Analysis
View CoA: current batch, Lot#T21O03R19
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
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.