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Diethylnorspermine HCl

    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. ).


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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 sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

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


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


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, not in water

Shelf Life:
>5 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:
2934990300


Additional Information

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
  
 
 


References

1: 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.

2: 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.

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, Borzì 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, Jönsson 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, Jönsson 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, Borzì 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.