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Chemical Compound Review

BENSPM     N,N'-bis(3- ethylaminopropyl)propane- 1,3...

Synonyms: DENSPM, BENSM, Tocris-0468, CHEMBL44083, DE-333, ...
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Disease relevance of DENSPM


High impact information on DENSPM

  • Induction of SSAT by the polyamine analogue N(1),N(11)-diethylnorspermine reduced pancreatic polyamines levels only moderately and without signs of organ inflammation [6].
  • The latter was confirmed with the polyamine oxidase inhibitor MDL-75275 and the antioxidant N-acetyl-L-cysteine, which when used in combination with DENSPM, decreased MAPK activation and as previously shown, reduced apoptosis [7].
  • The MAP/extracellular signal-regulated kinase-1 inhibitor PD 98059 reduced activation of all three kinases but failed to alter apoptosis in DENSPM-treated SK-MEL-28 cells [7].
  • The generality of this effect was demonstrated in DENSPM-treated A375 and LOX human melanoma cells [7].
  • Taken together, the findings indicate that DENSPM-induced apoptosis is at least partially initiated via massive induction of SSAT and related oxidative events and subsequently mediated by the mitochondrial apoptotic signaling pathway as indicated by cytochrome c release and caspase activation [2].

Chemical compound and disease context of DENSPM


Biological context of DENSPM


Anatomical context of DENSPM

  • Treatment with the polyamine analogue N1,N11-diethylnorspermine (DENSPM) increased SSAT activity in the transgenic fibroblasts approximately 380-fold, whereas mRNA increased only approximately 3-fold, indicating post-mRNA regulation [13].
  • To demonstrate the utility of this approach, the impact of four polyamine analogues, N1,N11-diethylnorspermine (DENSPM), N1,N14-diethylhomospermine (DEHSPM), 1,6,12-triazadodecane [(4,5) triamine], and 1,7, 13-triazatridecane [(5,5) triamine], on hypusine levels in a human T-cell line (JURKAT) is evaluated [14].
  • Further, dominant negative IkappaB attenuated the CHX and DENSPM-induced SSAT expression and mitochondria damage [8].

Associations of DENSPM with other chemical compounds


Gene context of DENSPM


Analytical, diagnostic and therapeutic context of DENSPM


  1. Structures of wild-type and mutant human spermidine/spermine N1-acetyltransferase, a potential therapeutic drug target. Bewley, M.C., Graziano, V., Jiang, J., Matz, E., Studier, F.W., Pegg, A.E., Coleman, C.S., Flanagan, J.M. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  2. Apoptotic signaling in polyamine analogue-treated SK-MEL-28 human melanoma cells. Chen, Y., Kramer, D.L., Diegelman, P., Vujcic, S., Porter, C.W. Cancer Res. (2001) [Pubmed]
  3. Regulation of estrogenic and nuclear factor kappa B functions by polyamines and their role in polyamine analog-induced apoptosis of breast cancer cells. Shah, N., Thomas, T.J., Lewis, J.S., Klinge, C.M., Shirahata, A., Gelinas, C., Thomas, T. Oncogene (2001) [Pubmed]
  4. Effects of the polyamine analogues N1-ethyl-N11-((cyclopropyl)methyl)-4,8-diazaundecane and N1-ethylN-11-((cycloheptyl)methyl)-4,8-diazaundecane in human prostate cancer cells. McCloskey, D.E., Woster, P.M., Casero, R.A., Davidson, N.E. Clin. Cancer Res. (2000) [Pubmed]
  5. Phase I study of N(1),N(11)-diethylnorspermine in patients with non-small cell lung cancer. Hahm, H.A., Ettinger, D.S., Bowling, K., Hoker, B., Chen, T.L., Zabelina, Y., Casero, R.A. Clin. Cancer Res. (2002) [Pubmed]
  6. Activation of polyamine catabolism in transgenic rats induces acute pancreatitis. Alhonen, L., Parkkinen, J.J., Keinanen, T., Sinervirta, R., Herzig, K.H., Jänne, J. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  7. The role of mitogen-activated protein kinase activation in determining cellular outcomes in polyamine analogue-treated human melanoma cells. Chen, Y., Alm, K., Vujcic, S., Kramer, D.L., Kee, K., Diegelman, P., Porter, C.W. Cancer Res. (2003) [Pubmed]
  8. Inactivation of IkappaB contributes to transcriptional activation of spermidine/spermine N(1)-acetyltransferase. Choi, W., Proctor, L., Xia, Q., Feng, Y., Gerner, E.W., Chiao, P.J., Hamilton, S.R., Zhang, W. Mol. Carcinog. (2006) [Pubmed]
  9. Effects of polyamine analogues on prostatic adenocarcinoma cells in vitro and in vivo. Zagaja, G.P., Shrivastav, M., Fleig, M.J., Marton, L.J., Rinker-Schaeffer, C.W., Dolan, M.E. Cancer Chemother. Pharmacol. (1998) [Pubmed]
  10. Bis(ethyl)norspermine potentiates the apoptotic activity of the pure antiestrogen ICI 182780 in breast cancer cells. Balabhadrapathruni, S., Santhakumaran, L.M., Thomas, T.J., Shirahata, A., Gallo, M.A., Thomas, T. Oncol. Rep. (2005) [Pubmed]
  11. Polyamine analogue induction of the p53-p21WAF1/CIP1-Rb pathway and G1 arrest in human melanoma cells. Kramer, D.L., Vujcic, S., Diegelman, P., Alderfer, J., Miller, J.T., Black, J.D., Bergeron, R.J., Porter, C.W. Cancer Res. (1999) [Pubmed]
  12. Metabolism and pharmacokinetics of N1,N11-diethylnorspermine in a Cebus apella primate model. Bergeron, R.J., Merriman, R.L., Olson, S.G., Wiegand, J., Bender, J., Streiff, R.R., Weimar, W.R. Cancer Res. (2000) [Pubmed]
  13. Correlation of polyamine and growth responses to N1,N11-diethylnorspermine in primary fetal fibroblasts derived from transgenic mice overexpressing spermidine/spermine N1-acetyltransferase. Alhonen, L., Karppinen, A., Uusi-Oukari, M., Vujcic, S., Korhonen, V.P., Halmekytö, M., Kramer, D.L., Hines, R., Jänne, J., Porter, C.W. J. Biol. Chem. (1998) [Pubmed]
  14. Effect of polyamine analogues on hypusine content in JURKAT T-cells. Bergeron, R.J., Weimar, W.R., Müller, R., Zimmerman, C.O., McCosar, B.H., Yao, H., Smith, R.E. J. Med. Chem. (1998) [Pubmed]
  15. Effects of novel spermine analogues on cell cycle progression and apoptosis in MALME-3M human melanoma cells. Kramer, D.L., Fogel-Petrovic, M., Diegelman, P., Cooley, J.M., Bernacki, R.J., McManis, J.S., Bergeron, R.J., Porter, C.W. Cancer Res. (1997) [Pubmed]
  16. Properties of the spermidine/spermine N1-acetyltransferase mutant L156F that decreases cellular sensitivity to the polyamine analogue N1, N11-bis(ethyl)norspermine. McCloskey, D.E., Pegg, A.E. J. Biol. Chem. (2003) [Pubmed]
  17. Combination of 5-fluorouracil and N1,N11-diethylnorspermine markedly activates spermidine/spermine N1-acetyltransferase expression, depletes polyamines, and synergistically induces apoptosis in colon carcinoma cells. Choi, W., Gerner, E.W., Ramdas, L., Dupart, J., Carew, J., Proctor, L., Huang, P., Zhang, W., Hamilton, S.R. J. Biol. Chem. (2005) [Pubmed]
  18. Synthesis and evaluation of hydroxylated polyamine analogues as antiproliferatives. Bergeron, R.J., Müller, R., Huang, G., McManis, J.S., Algee, S.E., Yao, H., Weimar, W.R., Wiegand, J. J. Med. Chem. (2001) [Pubmed]
  19. Human prostatic carcinoma cell lines display altered regulation of polyamine transport in response to polyamine analogs and inhibitors. Mi, Z., Kramer, D.L., Miller, J.T., Bergeron, R.J., Bernacki, R., Porter, C.W. Prostate (1998) [Pubmed]
  20. Overexpression of spermidine/spermine N1-acetyltransferase under the control of mouse metallothionein I promoter in transgenic mice: evidence for a striking post-transcriptional regulation of transgene expression by a polyamine analogue. Suppola, S., Pietilä, M., Parkkinen, J.J., Korhonen, V.P., Alhonen, L., Halmekytö, M., Porter, C.W., Jänne, J. Biochem. J. (1999) [Pubmed]
  21. Induction of the PAOh1/SMO polyamine oxidase by polyamine analogues in human lung carcinoma cells. Devereux, W., Wang, Y., Stewart, T.M., Hacker, A., Smith, R., Frydman, B., Valasinas, A.L., Reddy, V.K., Marton, L.J., Ward, T.D., Woster, P.M., Casero, R.A. Cancer Chemother. Pharmacol. (2003) [Pubmed]
  22. Rapid induction of apoptosis by deregulated uptake of polyamine analogues. Hu, R.H., Pegg, A.E. Biochem. J. (1997) [Pubmed]
  23. The ability of polyamine analogues to induce Z-DNA structure in synthetic polynucleotides in vitro inversely correlates with their effects on cytotoxicity of cis-diaminedichloroplatinum (II) (CDDP) in human brain tumor cell lines. Basu, H.S., Pellarin, M., Feuerstein, B.G., Marton, L.J. Anticancer Res. (1996) [Pubmed]
  24. Antitumor activity of N1,N11-bis(ethyl)norspermine against human melanoma xenografts and possible biochemical correlates of drug action. Porter, C.W., Bernacki, R.J., Miller, J., Bergeron, R.J. Cancer Res. (1993) [Pubmed]
  25. The induction of spermidine/spermine N1-acetyltransferase (SSAT) is a common event in the response of human primary non-small cell lung carcinomas to exposure to the new antitumor polyamine analogue N1,N11-bis(ethyl)norspermine. Gabrielson, E.W., Pegg, A.E., Casero, R.A. Clin. Cancer Res. (1999) [Pubmed]
  26. Preclinical toxicologic evaluation of DENSPM (N1,N11-diethylnorspermine) in rats and dogs. Kanter, P.M., Bullard, G.A., King, J.M. Anticancer Drugs (1994) [Pubmed]
  27. Simultaneous determination of polyamines, N-acetylated polyamines and the polyamine analogues BE-3-3-3 and BE-4-4-4-4 by capillary gas chromatography with nitrogen-phosphorus detection. Dorhout, B., Kingma, A.W., de Hoog, E., Muskiet, F.A. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]
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