ChemicalBook CAS DataBase List 121749-39-1

121749-39-1

Name	N',N''-DIETHYLNORSPERMINE TETRAHYDROCHLORIDE
CAS	121749-39-1
Molecular Formula	C13H32N4
MDL Number	MFCD00209844
Molecular Weight	244.42
MOL File	121749-39-1.mol

Synonyms

de333 BENSPM denspm be3-3-3 DiethylnorsperMine N1,N11-Diethylnorspe Bisethyl norspermine 3,7,11,15-Tetraazaheptadecane n(1),n(11)-diethylnorspermine N1,N11-Diethylnorspermine4HCl n(sup1),n(sup11)-diethylnorspermine n(sup1),n(sup11)-bis(ethyl)norspermine N1,N11-Diethylnorspermine tetrahydrochloride N',N''-DIETHYLNORSPERMINE TETRAHYDROCHLORIDE N',N''-DIETHYLNORSPERMINE TETRAHYDROCHLORIDE n,n’-bis(3-(ethylamino)propyl)-3-propanediamine N,N''-Trimethylenebis(N'-ethylpropane-1,3-diamine) 1,3-Propanediamine,N1,N3-bis[3-(ethylamino)propyl]- N,N'-(Trimethylenebisiminobistrimethylene)bis(ethanamine) N,N'-BIS[3-(ETHYLAMINO)PROPYL]-1,3-PROPANEDIAMINE TETRAHYDROCHLORIDE

Chemical Properties

Boiling point	357.1±10.0 °C(Predicted)
density	0.877±0.06 g/cm3(Predicted)
storage temp.	Store at RT
pka	10.95±0.19(Predicted)

Hazard Information

Uses

N1,N11-Diethylnorspermine (DENSPM tetrahydrochloride) is a potent anticancer agent. N1,N11-Diethylnorspermine activates polyamine catabolism and downregulates mTOR protein. N1,N11-Diethylnorspermine induces the release of cytochrome c from mitochondria, resulting in activation of caspase 3. N1,N11-Diethylnorspermine tetrahydrochloride kills glioblastoma multiforme (GBM) through induction of SSAT (spermidine/spermine N1-acetyltransferase) coupled with H2O2 production[1][2][3][4][5][6].

Biological Activity

Highly potent inducer of spermidine/spermine N 1 -acetyltransferase, able to increase enzyme activity 200-1000 fold.

in vivo

N1,N11-Diethylnorspermine (40 mg/kg, three times per day for two cycles of 6 days) clearly prevents tumor growth in mice bearing xenografts of the DU-145 cell line^[1].
N1,N11-Diethylnorspermine (120-360 mg/kg, s.c., 4 days) results in prolonged inhibition of tumor growth and long-term tumor regressions in nude athymic mice with MALME-3M melanoma xenografts^[5].
N1,N11-Diethylnorspermine (12.5-50 mg/kg, i.v., 5 days) is well tolerated and induces no physical signs in CD rats^[6].

IC 50

Caspase 3

References

[1] Schipper RG, et al. Antitumor activity of the polyamine analog N(1), N(11)-diethylnorspermine against human prostate carcinoma cells. Prostate. 2000 Sep 1;44(4):313-21. DOI:10.1002/1097-0045(20000901)44:43.0.co;2-d
[2] Holst CM, et al. 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
[3] Jiang R, et al. Activation of polyamine catabolism by N1,N11-diethylnorspermine leads to cell death in glioblastoma. Int J Oncol. 2007 Aug;31(2):431-40. PMID:17611701
[4] Jiang R, et al. Activation of polyamine catabolism by N1, N11-diethylnorspermine alters the cellular localization of mTOR and downregulates mTOR protein level in glioblastoma cells. Cancer Biol Ther. 2007 Oct;6(10):1644-8. DOI:10.4161/cbt.6.10.4800
[5] Bernacki RJ, et al. Preclinical antitumor efficacy of the polyamine analogue N1, N11-diethylnorspermine administered by multiple injection or continuous infusion. Clin Cancer Res. 1995 Aug;1(8):847-57. PMID:9816054
[6] Kanter PM, et al. Preclinical toxicologic evaluation of DENSPM (N1,N11-diethylnorspermine) in rats and dogs. Anticancer Drugs. 1994 Aug;5(4):448-56. DOI:10.1097/00001813-199408000-00010

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