Dimethylsilane polyamines: Cytostatic compounds with potentials as anticancer drugs

Anti-Cancer Drug Design

Volumn 12, Issue 8, 1997, Pages 621-633

  Douaud, Fabienne ^a   Le Roch, Nathalie ^b   Renault, Jacques ^a   Havouis, René ^a   Vaultier, Michel ^b   Moulinoux, Jacques Philippe ^a   Seiler, Nikolaus ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b Chimie et Photonique Moleculaires Rennes   (France)

Author keywords

Analogs; Growth inhibition; Polyamines

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOSTATIC AGENT; DOUBLE STRANDED DNA; ETHIDIUM BROMIDE; POLYAMINE DERIVATIVE; SPERMIDINE; SPERMINE; SPERMINE DERIVATIVE;

ANIMAL CELL; ARTICLE; BINDING SITE; CELL GROWTH; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DNA INTERACTION; DRUG MECHANISM; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, LEWIS LUNG; CHO CELLS; CRICETINAE; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; EFLORNITHINE; ENZYME INHIBITORS; LEUKEMIA L1210; MICE; POLYAMINES; PUTRESCINE; SILANES; SPERMIDINE;

ANIMALIA;

EID: 0031440246     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. 12-bis(ethyl)spermine. The Biochemical Journal, 291, 131.
2. BASU, H.S. & MARTON, L.J. (1987). The interaction of spermine and pentamines with DNA. The Biochemical Journal, 244, 243.
3. BASU, H.S., SCHWIETERT, H.C.A., FEUERSTEIN, B.G. & MARTON, L.J. (1990). Effects of variation in the structure of spermine on the association with DNA and the induction of DNA conformational changes. The Biochemical Journal, 269, 329.
4. 14-bis(ethyl)homospermine (BE-4-4-4) on the growth of U87 MG and SF-188 human brain tumor cells. International Journal of Cancer, 48, 873.
5. BASU, H.S , PELLARIN, M., FEUERSTEIN, B.G., SHIRAHATA, A., SAMEJIMA, K., DEEN, FE. & MARTON, L.J. (1993). Interaction of a polyamine analogue, 1,19-bis-(ethylamino)-(5,10,15-triazanonadecane (BE-4-4-4-4), with DNA and effect on growth, survival, and polyamine levels in seven brain tumor cell lines. Cancer Research, 53, 3948.
6. BASU, H.S., MARTON, L.J., PELLARIN, M., DEEN, D.F , MCMANIS, J.S., LIU, C Z., BERGERON, R.J. & FEUERSTEIN, B.G. (1994). Design and testing of novel cytotoxic polyamine analogues. Cancer Research, 54, 6210.
7. BERGERON, R.J., NEIMS, A.H., MCMANIS, J.S., HAWTHORNE, T.L. VINSON, J.R.T., BORTELL, R. & INGENO, M.J. (1988). Synthetic polyamine analogues as antineoplastics. Journal of Medicinal Chemistry, 31, 1183.
8. BERGERON, R.J., MCMANIS, J.S., LIU, C.Z., FENG, Y., WEIMAR, W.R., LUCHETTA, G.R., WU, Q., ORTIZ-OCASIO, O.J., VINSON, J.R.T., KRAMER, D & PORTER, C.W. (1994). Antiproliferative properties of polyamine analogues: a structure-activity study. Journal of Medicinal Chemistry, 37, 3464.
9. BERGERON, C.J., BASU, H.S , MARTON, L.J., DEEN, D.F., PELLARIN, M. & FEUERSTEIN, B.G. (1995). Two polyamine analogs (BE-4-4-4 and BE-4-4-4-4) directly affect growth, survival, and cell cycle progression in two human brain tumor cell lines. Cancer Chemotherapy and Pharmacology, 36, 411.
10. BLOOMFIELD, V.A. & WILSON, R.W. (1981). Interactions of polyamines with polynucleotides. In Polyamines in Biology and Medicine. Morris, D.R. & Marton, L.J. (eds), p. 183. Marcel Dekker: New York.
11. BOLKENIUS, F.N. & SEILER, N (1989). Polyamine oxidase inhibitors. In Design of Enzyme Inhibitors as Drugs. Sandier, M. & Smith, H.J. (eds), p. 245. Oxford University Press: Oxford.
12. BRUNTON, V.G., GRANT, M.H. & WALLACE, H.M. (1991). Mechanism of spermine toxicity in baby hamster kidney cells. The role of amine oxidases and oxidative stress. The Biochemical Journal, 280, 193.
13. CASERO, R A JR, MANX, A.R., SAAB, N.H., WU, R., DYER, W.J. & WOSTER, P.M. (1995). Growth and biochemical effects of unsymmetrically substituted polyamine analogues in human lung tumor cells. Cancer Chemotherapy and Pharmacology, 36, 69.
14. CHATTORAJ, D K., GOSULE, L C. & SCHELLMAN, J.A. (1978). DNA-condensation with polyamines II. Electron microscopic studies. Journal of Molecular Biology, 121, 327.
15. DELCROS, J.-G , VAULTIER, M., LE ROCH, N , HAVOUIS, R., MOULINOUX, J.-P. & SEILER, N. (1997). Bis(7-amino-4-azaheptyl)dimethylsilane: a new tetramine with polyamine-like features. Effects on cell growth. Anti-Cancer Drug Design, 12, 35.
16. EDWARDS, M.L., PRAKASH, N.J., STEMERICK, D.M., SUNKARA, PS., BITONTI, A.J., DAVIS, G.F., DUMONT, J.A. & BEY, P. (1990). Polyamine analogs with antitumor activity. Journal of Medicinal Chemistry, 33, 1369.
17. EDWARDS, M.L., SNYDER, R.D. & STEMERICK, D M. (1991). Synthesis and DNA-binding properties of polyamine analogues. Journal of Medicinal Chemistry, 34, 2414.
18. GOSULE, L.C. & SCHELLMAN, J.A (1976). Compact form of DNA induced by spermidine. Nature (London), 259, 333.
19. HALFMAN, C.J. (1981). Concentrations of binding protein and labelled analyte that are appropriate for measuring at any analyte concentration range in radioimmunoassays. Methods in Enzymology, 74, 481.
20. HE, Y., KASHIWAGI, K., FUKUCHI, J., TERAO, K., SHIRAHATA, A. & IGARASHI, K. (1993). Correlation between the inhibition of cell growth by accumulated polyamines and the decrease of magnesium and ATP. European Journal of Biochemistry, 217, 89.
21. LEATHERBARROW, R J. (1992). Erithacus Software Ltd. Imperial College of Science, Technology & Medicine, London.
22. LIBBY, R.P. & PORTER, C.W. (1987). Separation of isozymes of polyamine oxidase from murine L1210 leukemia cells. Biochemical and Biophysical Research Communications, 144, 528.
23. MORGAN, J.E. BLANKENSHIP, J.W. & MATTHEWS, H.R. (1986). Association constants for the interaction of double-stranded and single-stranded DNA with spermine, spermidine, putrescine, diaminopropane, N1- and N8-acetylspermidine and magnesium. Determination from analysis of broadening of thermal denaturation curves. Archives of Biochemistry and Biophysics, 246, 225.
24. MOSMANN, T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55.
25. PORSCHKE, D. (1994). Dynamics of DNA condensation. Biochemistry, 23, 4821.
26. PORTER, C.W. & SUFRIN, J. (1986). Interference with polyamine biosynthesis and/or function by analogs of polyamines or methionine as potential anticancer chemotherapeutic strategy. Anticancer Research, 6, 525.
27. PORTER, C.W., BERNACKI, R.J., MILLER, J. & BERGERON, R.J. (1993). Antitumor activity of N1,N11-bis(ethyl)norspermine against human melanoma xenografts and possible biochemical correlates of drug action. Cancer Research, 53, 581.
28. ROMANO, C. & WILLIAMS, K (1994). Modulation of NMDA receptors by polyamines. In The Neuropharmacology of Polyamines. Carter, C. (ed.), p. 81. Academic Press: London.
29. RUDKIN, B.B., MAMONT, P.S. & SEILER, N. (1984). Decreased protein-synthetic activity is an early consequence of spermidine depletion in rat hepatoma tissue-culture cells. The Biochemical Journal, 217, 731.
30. SEILER, N & HEBY, O. (1988). Regulation of cellular polyamines in mammals. Acta Biochimica et Biophysica Hungarica, 23, 1.
31. SEILER, N., SARHAN, S., MAMONT, P. CASARA, P. & DANZIN, C. (1991). Some biological consequences of S-adenosylmethionine decarboxylase inhibition by MDL 73811. Life Chemistry Reports, 9, 151.
32. SEILER, N., DELCROS, J.G., VAULTIER, M., LE ROCH, N , HAVOUIS, R., DOUAUD, F. & MOULINOUX, J.P. (1996). Bis(7-amino-4-azaheptyl)dimethylsilane and bis(7-ethylamino-4-azaheptyl)dimethylsilane: inhibition of tumor cell growth in vitro and in vivo. Cancer Research, 56, 5624.
33. SNYDER, R.D. (1989). Polyamine depletion is associated with altered chromatin structure in HeLa cells. The Biochemical Journal, 260, 697.
34. STEWART, K.D. (1988). The effect of structural changes in a polyamine backbone on its DNA-binding properties. Biochemical and Biophysical Research Communications, 152, 1441.
35. SUNKARA, P.S , BAYLIN, S.B. & LUK, G D. (1987). Inhibitors of polyamine biosynthesis: cellular and in vivo effects in tumor proliferation. In Inhibition of Polyamine Metabolism. McCann, P.P., Pegg, A.E. & Sjoerdsma, A. (eds), p. 121. Academic Press: Orlando, FL.
36. VAN DORSSELAER, V., SCHIRLIN, D., MARCHAL, P., WEBER, F. & DANZIN, C. (1996). Silicon-mediated inactivation of diamine oxidase. Bioorganic Chemistry, 24, 178.