N(1),N(11)-Diethylnorspermine tetrahydrochloride

Names

[ Name ]:
N(1),N(11)-Diethylnorspermine tetrahydrochloride

[Synonym ]:
Bisethyl norspermine
denspm
de333
be3-3-3
3,7,11,15-Tetraazaheptadecane
N1,N11-Diethylnorspermine4HCl
N1,N11-Diethylnorspermine tetrahydrochloride

Biological Activity

[Description]:

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

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Apoptosis >> Caspase

[Target]

Caspase 3

[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].

[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.

[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.

[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.

Chemical & Physical Properties

[ Density]:
0.877 g/cm3

[ Boiling Point ]:
357.1ºC at 760 mmHg

[ Molecular Formula ]:
C₁₃H₃₂N₄

[ Molecular Weight ]:
244.42

[ Flash Point ]:
171.9ºC

[ Exact Mass ]:
388.16900

[ PSA ]:
48.12000

[ LogP ]:
5.32650

[ Vapour Pressure ]:
2.79E-05mmHg at 25°C

[ Index of Refraction ]:
1.462

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TX7032250

CHEMICAL NAME :: 1,3-Propanediamine, N,N'-bis(3-(ethylamino)propyl)-

CAS REGISTRY NUMBER :: 121749-39-1

LAST UPDATED :: 199510

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H32-N4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: ANTDEV Anti-Cancer Drugs. (Rapid Communications of Oxford Ltd., The Old Malthous, Paradise St., Oxford OX1 1LD, UK) V.1- 1990- Volume(issue)/page/year: 5,448,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 325 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 37,3464,1994