Bisnaphthalimidopropyl spermidine induces apoptosis within colon carcinoma cells

Chemico-Biological Interactions

Volumn 177, Issue 1, 2009, Pages 1-6

  Ralton, Lynda D ^a,b   Bestwick, Charles S ^b   Milne, Lesley ^b   Duthie, Susan ^b   Kong Thoo Lin, Paul ^a  

^a ROBERT GORDON UNIVERSITY   (United Kingdom)

^b ROWETT RESEARCH INSTITUTE   (United Kingdom)

Author keywords

Apoptosis; Bisnaphthalimidopropylpolyamines; Colon cancer; DNA damage; Polyamines

Indexed keywords

BISNAPHTHALIMIDOPROPYLSPERMIDINE; CASPASE 3; SPERMIDINE DERIVATIVE; SPERMINE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CHROMATIN CONDENSATION; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DNA FRAGMENTATION; DNA STRAND BREAKAGE; DRUG STRUCTURE; HUMAN; HUMAN CELL; PROTEIN EXPRESSION;

ACRIDINE ORANGE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CACO-2 CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLONIC NEOPLASMS; DNA DAMAGE; DRUG SCREENING ASSAYS, ANTITUMOR; ETHIDIUM; HT29 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; INTRACELLULAR SPACE; POLYAMINES; QUINOLONES; SPERMIDINE;

EID: 57349144337     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.09.033     Document Type: Article

References (42)

1. Bailly C., Brana M.F., and Waring M.J. Sequence-selective intercalation of antitumour bis-naphthalimides into DNA. Evidence for an approach via the major groove. Eur. J. Biochem. 240 (1996) 195-208
2. Brana M.F., Castellano J.M., Moran M., de Vega M.P., Qian X.D., Romerdahl C., and Keilhauer G. Bis-naphthalimides. 2. Synthesis and biological activity of 5,6-acenaphthalimidoalkyl-1,8-naphthalimidoalkyl amines. Eur. J. Med. Chem. 30 (1995) 235-239
3. Brana M.F., Castellano J.M., Moran M., Perez de Vega M.J., Romerdahl C.R., Qian X.D., Bousquet P.F., Emling F., Schlick E., and Keilhauer G. Bis-naphthalimides: a new class of antitumor agents. Anticancer Drug Des. 8 (1993) 257-268
4. Ralton L., Bestwick C.S., and Kong Thoo Lin P. Polyamine analogues and derivatives as potential anticancer agents. Curr. Bioactive Compds. 3 (2007) 179-191
5. Brana M.F., Castellano J.M., Perron D., Maher C., Conlon D., Bousquet P.F., George J., Qian X.D., and Robinson S.P. Chromophore-modified bis-naphthalimides: synthesis and antitumor activity of bis-dibenz[de,h]isoquinoline-1,3-diones. J. Med. Chem. 40 (1997) 449-454
6. Brana M.F., Cacho M., Ramos A., Dominguez M.T., Pozuelo J.M., Abradelo C., Rey-Stolle M.F., Yuste M., Carrasco C., and Bailly C. Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides. Org. Biomol. Chem. 1 (2003) 648-654
7. Villalona-Calero M.A., Eder J.P., Toppmeyer D.L., et al. Phase I and pharmacokinetic study of LU79553, a DNA intercalating bisnaphthalimide, in patients with solid malignancies. J. Clin. Oncol. 19 (2001) 857-869
8. Kong Thoo Lin P., and Pavlov V.A. The synthesis and in vitro cytotoxic studies of novel bis-naphthalimidopropyl polyamine derivatives. Bioorg. Med. Chem. Lett. 10 (2000) 1609-1612
9. Pavlov V.A., Kong Thoo Lin P., and Rodilla V. Cytotoxicity, DNA binding and localisation of novel bis-naphthalimidopropyl polyamine derivatives. Chem. Biol. Interact. 137 (2001) 15-24
10. Dance A.M., Ralton L., Fuller Z., Milne L., Duthie S.J., Bestwick C.S., and Kong Thoo Lin P. Synthesis and biological activities of bisnaphthalimido polyamines derivatives: cytotoxicity, DNA binding, DNA damage and drug localization in breast cancer MCF 7 cells. Biochem. Pharmacol. 69 (2005) 19-27
11. Kong Thoo Lin P., Dance A.M., Bestwick C.S., and Milne L. The biological activities of new polyamine derivatives as potential therapeutic agents. Biochem. Soc. Trans. 31 (2003) 407-410
12. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
13. Singh N., McCoy M., Tice R., and Schneider E. A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175 (1988) 184-191
14. Collins A., Ma A., and Duthie S.J. The kinetics of repair of oxidative DNA damage (strand breaks and oxidised pyrimidines) in human cells. Mutat. Res. 336 (1995) 69-77
15. Duthie S.J., Ma A., Ross M., and Collins A. Antioxidant supplementation decreases oxidative DNA damage in human lymphocytes. Cancer Res. 56 (1996) 1291-1295
16. Ferlini C., Kunkl A., Scambia G., and Fattorossi A. The use of apostain in identifying early apoptosis. J. Immunol. Methods 205 (1997) 95-101
17. Zamzami N., and Kroemer G. Condensed matter in cell death. Nature 401 (1999) 127-128
18. Bestwick C.S., and Milne L. Influence of galangin on HL-60 cell proliferation and survival. Cancer Lett. 243 (2006) 80-89
19. McGahon A., Martin S., Bissonnette R., Mahboubi A., Shi Y., Mogil R., Nishioka W., and Green D. The end of the (cell) line: methods for the study of apoptosis in vitro. Methods Cell Biol. 46 (1995) 153-185
20. Kabra P., Lee H., Lubich W., and Marton L.J. Solid-phase extraction and determination of dansyl derivatives of unconjugated and acetylated polyamines by reversed-phase liquid chromatography: improved separation systems for polyamines in cerebrospinal fluid, urine and tissue. J. Chromatogr. 380 (1986) 19-32
21. Seiler N., and Knodgen B. Determination of polyamines and related compounds by reversed-phase high-performance liquid chromatography: improved separation systems. J. Chromatogr.: Biomed. Sci. Appl. 339 (1985) 45-57
22. Frisch S., and Ruoslahti E. Integrins and anoikis. Curr. Opin. Cell Biol. 9 (1997) 701-706
23. Goldberg G.S., Jin Z., Ichikawa H., Naito A., Ohki M., El-Deiry W.S., and Tsuda H. Global effects of anchorage on gene expression during mammary carcinoma cell growth reveal role of tumor necrosis factor-related apoptosis-inducing ligand in anoikis. Cancer Res. 61 (2001) 1334-1337
24. Valentijn A., Zouq N., and Gilmore A. Anoikis. Biochem. Soc. Trans. 32 (2004) 421-425
25. Brana M.F., Cacho M., Gradillas A., de Pascual-Teresa B., and Ramos A. Intercalators as anticancer drugs. Curr. Pharm. Des. 7 (2001) 1745-1780
26. Brana M.F., and Ramos A. Naphthalimides as anti-cancer agents: synthesis and biological activity. Curr. Med. Chem. Anti-Cancer Agents 1 (2001) 237-255
27. Fraser A.V., Woster P.M., and Wallace H.M. Induction of apoptosis in human leukaemic cells by IPENSpm, a novel polyamine analogue and anti-metabolite. Biochem. J. 367 (2002) 307-312
28. McCloskey D.E., Woster P.M., Casero Jr. R.A., and Davidson N.E. 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. Clin. Cancer Res. 6 (2000) 17-23
29. Schipper R.G., Penning L.C., and Verhofstad A.A. Involvement of polyamines in apoptosis. Facts and controversies: effectors or protectors?. Semin. Cancer Biol. 10 (2000) 55-68
30. Tabor C.W., and Tabor H. Polyamines. Annu. Rev. Biochem. 53 (1984) 749-790
31. Ha H., Sirisoma N., Kuppusamy P., Zweier J., Woster P., and Casero Jr. R. The natural polyamine spermine functions directly as a free radical scavenger. PNAS 95 (1998) 11140-11145
32. Stefanelli C., Pignatti C., Tantini B., Fattori M., Stanic I., Mackintosh C., Flamigni F., Guarnieri C., Caldarera C., and Pegg A. Effect of polyamine depletion on caspase activation: a study with spermine synthase-deficient cells. Biochem. J. 355 (2001) 199-206 199
33. Yuan Q., Ray R., and Johnson L. Polyamine depletion prevents camptothecin-induced apoptosis by inhibiting the release of cytochrome c. Am. J. Physiol. Cell Physiol. 282 (2002) C1290-C1297
34. Zou T., Rao J., Guo X., Liu L., Zhang H., Strauch E., Bass B., and Wang J. NF-{kappa}B-mediated IAP expression induces resistance of intestinal epithelial cells to apoptosis after polyamine depletion. Am. J. Physiol. Cell Physiol. 286 (2004) C1009-C1018
35. Snyder R. Effects of metal treatment on DNA repair in polyamine-depleted HeLa cells with special reference to nickel. Environ. Health Perspect. 102 Suppl. 3 (1994) 51-55
36. Milovic V., and Turchanowa L. Polyamines and colon cancer. Biochem. Soc. Trans. 31 (2003) 381-383
37. Hegardt C., Andersson G., and Oredsson S. Different roles of spermine in glucocorticoid- and fas-induced apoptosis. Exp. Cell Res. 266 (2001) 333-341
38. Seiler N., Delcros J.G., and Moulinoux J.P. Polyamine transport in mammalian cells. An update. Int. J. Biochem. Cell Biol. 28 (1996) 843-861
39. Mitchell J., Diveley R., Bareyal-Leyser A., and Mitchell J. Abnormal accumulation and toxicity of polyamines in a difluoromethylornithine-resistant HTC cell variant. Biochim. Biophys. Acta 1136 (1992) 136-142
40. Bergeron R.J., McManis J.S., Liu C.Z., Feng Y., Weimar W.R., Luchetta G.R., Wu Q., Ortiz-Ocasio J., Vinson J.R., and Kramer D. Antiproliferative properties of polyamine analogues: a structure-activity study. J. Med. Chem. 37 (1994) 3464-3476
41. Bergeron R.J., Feng Y., Weimar W.R., McManis J.S., Dimova H., Porter C.W., Raisler B., and Phanstiel IV O. A comparison of structure-activity relationships between spermidine and spermine analogue antineoplastics. J. Med. Chem. 40 (1997) 1475-1494
42. Ikeguchi Y., Mackintosh C.A., McCloskey D.E., and Pegg A.E. Effect of spermine synthase on the sensitivity of cells to anti-tumour agents. Biochem. J. 373 (2003) 885-892