WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200900
CAS#: 156886-85-0 (HCl)
Description: Diethylnorspermine, also known as DENSPM, is a potent inducer of spermidine/spermine N1-acetyltransferase, is able to increase enzyme activity 200-1000 fold. The cell death induced by DENSPM treatment was apoptotic, as evidenced by cleavage of procaspase 3 and induction of caspase-3 activity. The DENSPM-induced polyamine depletion was also caused by the inhibition of ornithine decarboxylase. LA-N-1 cells contained a higher level of the prosurvival protein survivin, which was further increased after DENSPM treatment. (Source: Anticancer Drugs . 2010 Nov;21(10):917-26. ).
MedKoo Cat#: 200900
Name: Diethylnorspermine HCl
CAS#: 156886-85-0 (HCl)
Chemical Formula: C13H32N4
Exact Mass: 244.2627
Molecular Weight: 244.43
Elemental Analysis: C, 63.88; H, 13.20; N, 22.92
Diethylnorspermine HCl is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to email@example.com to inquire quote.
Related CAS #: 121749-39-1 (free base) 156886-85-0 (HCl)
Synonym: Diethylnorspermine; BE-333; BENSPM; CI-1006; DE-333; DENSPM; BE333; CI1006; DE333.
IUPAC/Chemical Name: N1,N1'-(propane-1,3-diyl)bis(N3-ethylpropane-1,3-diamine) 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
The following data is based on the product molecular weight 244.43 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.
|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: Uimari A, Merentie M, Sironen R, Pirnes-Karhu S, PerÃ¤niemi 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.
2: SÃ¶derstjerna 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.
3: Tummala R, Diegelman P, Hector S, Kramer DL, Clark K, Zagst P, Fetterly G, Porter CW, Pendyala L. Combination effects of platinum drugs and N1, N11 diethylnorspermine on spermidine/spermine N1-acetyltransferase, polyamines and growth inhibition in A2780 human ovarian carcinoma cells and their oxaliplatin and cisplatin-resistant variants. Cancer Chemother Pharmacol. 2011 Feb;67(2):401-14. doi: 10.1007/s00280-010-1334-9. Epub 2010 May 5. PubMed PMID: 20443003; PubMed Central PMCID: PMC3028085.
4: Myhre L, Alm K, Johansson M, Oredsson SM. Normal-like breast cells, but not breast cancer cells, recovered from treatment with N',N''-diethylnorspermine. Anticancer Drugs. 2009 Apr;20(4):230-7. PubMed PMID: 19288605.
5: Stanic' I, Facchini A, BorzÃ¬ RM, Stefanelli C, Flamigni F. The polyamine analogue N1,N11-diethylnorspermine can induce chondrocyte apoptosis independently of its ability to alter metabolism and levels of natural polyamines. J Cell Physiol. 2009 Apr;219(1):109-16. doi: 10.1002/jcp.21655. PubMed PMID: 19097065.
6: Holst CM, Staaf J, JÃ¶nsson G, Hegardt C, Oredsson SM. Molecular mechanisms underlying N1, N11-diethylnorspermine-induced apoptosis in a human breast cancer cell line. Anticancer Drugs. 2008 Oct;19(9):871-83. doi: 10.1097/CAD.0b013e32830f902b. PubMed PMID: 18766001.
7: Myhre L, Alm K, Hegardt C, Staaf J, JÃ¶nsson G, Larsson S, Oredsson SM. Different cell cycle kinetic effects of N1,N11-diethylnorspermine-induced polyamine depletion in four human breast cancer cell lines. Anticancer Drugs. 2008 Apr;19(4):359-68. doi: 10.1097/CAD.0b013e3282f7f518. PubMed PMID: 18454046.
8: Stanic I, Cetrullo S, Facchini A, Stefanelli C, BorzÃ¬ RM, Tantini B, Guarnieri C, Caldarera CM, Flamigni F. Effect of the polyamine analogue N1,N11-diethylnorspermine on cell survival and susceptibility to apoptosis of human chondrocytes. J Cell Physiol. 2008 Jul;216(1):153-61. doi: 10.1002/jcp.21387. PubMed PMID: 18231987.
9: Hector S, Tummala R, Kisiel ND, Diegelman P, Vujcic S, Clark K, Fakih M, Kramer DL, Porter CW, Pendyala L. Polyamine catabolism in colorectal cancer cells following treatment with oxaliplatin, 5-fluorouracil and N1, N11 diethylnorspermine. Cancer Chemother Pharmacol. 2008 Aug;62(3):517-27. Epub 2007 Nov 7. PubMed PMID: 17987291.
Polyamine analogue treatment results in growth inhibition and sometimes in cell death. Therefore, polyamine analogues are considered in the treatment of cancer. see Anti-Cancer Drugs: 2008,19(19):871-883