Pyrrolo[2,3-α]carbazole derivatives as topoisomerase I inhibitors that affect viability of glioma and endothelial cells in vitro and angiogenesis in vivo

Biomedicine and Pharmacotherapy

Volumn 65, Issue 3, 2011, Pages 142-150

  Lampropoulou, Evgenia ^a   Manioudaki, Maria ^a   Fousteris, Manolis ^a   Koutsourea, Anna ^a   Nikolaropoulos, Sotirios ^a   Papadimitriou, Evangelia ^a  

^a UNIVERSITY OF PATRAS   (Greece)

Author keywords

Angiogenesis; Cancer; Endothelial cells; Glioma; Indolocarbazoles; Pyrrolo 2,3 carbazoles; Topoisomerase I

Indexed keywords

DNA TOPOISOMERASE INHIBITOR; PYRROLO[2,3 ALPHA]CARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL GROWTH; CELL VIABILITY; CHICK EMBRYO; CHORIOALLANTOIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG POTENCY; EMBRYO; ENDOTHELIUM CELL; GLIOMA CELL; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL;

ANGIOGENESIS INHIBITORS; ANIMALS; CARBAZOLES; CELL LINE, TUMOR; CELL PROLIFERATION; CHICK EMBRYO; CHORIOALLANTOIC MEMBRANE; DNA TOPOISOMERASES, TYPE I; ENDOTHELIAL CELLS; GLIOMA; HUMANS; NEOVASCULARIZATION, PATHOLOGIC; NEOVASCULARIZATION, PHYSIOLOGIC; PYRROLES; RATS; TOPOISOMERASE I INHIBITORS;

EID: 79959635539     PISSN: 07533322     EISSN: 19506007     Source Type: Journal    
DOI: 10.1016/j.biopha.2011.02.006     Document Type: Article

References (34)

1. Husain I., Mohler J.L., Seigler H.F., Besterman J.M. Elevation of topoisomerase I messenger RNA, protein, and catalytic activity in human tumors: demonstration of tumor-type specificity and implications for cancer chemotherapy. Cancer Res 1994, 54:539-546.
2. Pfister T.D., Reinhold R.C., Agama K., Gupta S., Khin S.A., Kinders R.J., et al. Topoisomerase I levels in the NCI-60 cancer cell line panel determined by validated ELISA and microarray analysis and correlation with indenoisoquinoline sensitivity. Mol Cancer Ther 2009, 8:1878-1884.
3. Reinhold W.C., Mergny J.L., Liu H., Ryan M., Pfister T.D., Kinders R., et al. Exon array analyses across the NCI-60 reveal potential regulation of TOP1 by transcription pausing at guanosine quartets in the first intron. Cancer Res 2010, 70:2191-2203.
4. Zhao C., Yasui K., Lee C.J., Kurioka H., Hosokawa Y., Oka T., et al. Elevated expression levels of NCOA3, TOP1, and TFAP2C in breast tumors as predictors of poor prognosis. Cancer 2003, 98:18-23.
5. Pommier Y. Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer 2006, 6:789-802.
6. Feun L., Savaraj N. Topoisomerase I inhibitors for the treatment of brain tumors. Expert Rev Anticancer Ther 2008, 8:707-716.
7. Vredenburgh J.J., Desjardins A., Reardon D.A., Friedman H.S. Experience with irinotecan for the treatment of malignant glioma. Neuro-Oncology 2009, 11:80-91.
8. Giles G.I., Sharma R. Topoisomerase enzymes as therapeutic targets for cancer chemotherapy. Med Chem 2005, 1:383-394.
9. Asche C., Demeunynck M. Antitumor carbazoles. Anticancer Agents Med Chem 2007, 7:247-267.
10. Sánchez C., Méndez C., Salas J.A. Indolocarbazole natural products: occurrence, biosynthesis, and biological activity. Nat Prod Rep 2006, 23:1007-1045.
11. Lazareno S., Popham A., Birdsall N.J.M. Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-3H] scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site. Mol Pharmacol 2000, 58:194-207.
12. Ho F.M., Kang H.C., Lee S.T., Chao Y., Chen Y.C., Huang L.J., et al. The anti-inflammatory actions of LCY-2-CHO, a carbazole analogue, in vascular smooth muscle cells. Biochem Pharmacol 2007, 74:298-308.
13. Fousteris M.A., Papakyriakou A., Koutsourea A., Manioudaki M., Lampropoulou E., Papadimitriou E., et al. Pyrrolo[2,3-a]carbazoles as potential cyclin dependent kinase 1 (CDK1) inhibitors. Synthesis, biological evaluation, and binding mode through docking simulations. J Med Chem 2008, 51:1048-1052.
14. Ferro A.M., Higgins N.P., Olivera B.M. Poly (ADP-ribosylation) of a DNA topoisomerase. J Biol Chem 1983, 258:6000-6003.
15. Papadimitriou E., Heroult M., Courty J., Polykratis A., Stergiou C., Katsoris P. Endothelial cell proliferation induced by HARP: implication of N or C terminal peptides. Biochem Biophys Res Commun 2000, 274:242-248.
16. Papadimitriou E., Polykratis A., Courty J., Koolwijk P., Heroult M., Katsoris P. HARP induces angiogenesis in vivo and in vitro: implication of N or C terminal peptides. Biochem Biophys Res Commun 2001, 282:306-313.
17. Staker B.L., Feese M.D., Cushman M., Pommier Y., Zembower D., Stewart L., et al. Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex. J Med Chem 2005, 48:2336-2345.
18. Chen T.C., Su S., Fry D., Liebes L. Combination therapy with irinotecan and protein kinase C inhibitors in malignant glioma. Cancer 2003, 97(Suppl. 9):2363-2373.
19. Janss A.J., Maity A., Tang C.B., Muschel R.J., McKenna W.G., Sutton L., et al. Decreased cyclin B1 expression contributes to G2 delay in human brain tumor cells after treatment with camptothecin. Neuro-Oncology 2001, 3:11-21.
20. Nakamizo A., Inamura T., Inoha S., Amano T., Ochi H., Ikezaki K., et al. Suppression of Cdc2 dephosphorylation at the tyrosine 15 residue during nitrosourea-induced G2M phase arrest in glioblastoma cell lines. J Neurooncol 2002, 59:7-13.
21. Harmalkar M.N., Shirsat N.V. Staurosporine-induced growth inhibition of glioma cells is accompanied by altered expression of cyclins, CDKs and CDK inhibitors. Neurochem Res 2006, 31:685-692.
22. Nomura N., Nomura M., Newcomb E.W., Zagzag D. Geldanamycin induces G2 arrest in U87MG glioblastoma cells through downregulation of Cdc2 and cyclin B1. Biochem Pharmacol 2007, 73:1528-1536.
23. Chen H., Huang Q., Dong J., Zhai D.Z., Wang A.D., Lan Q. Overexpression of CDC2/CyclinB1 in gliomas, and CDC2 depletion inhibits proliferation of human glioma cells in vitro and in vivo. BMC Cancer 2008, 8:29.
24. Kim Y.Y., Park C.K., Kim S.K., Phi J.H., Kim J.H., Kim C.Y., et al. CKD-602, a camptothecin derivative, inhibits proliferation and induces apoptosis in glioma cell lines. Oncol Rep 2009, 21:1413-1419.
25. Baeriswyl V., Christofori G. The angiogenic switch in carcinogenesis. Semin Cancer Biol 2009, 19:329-337.
26. Tuettenberg J., Friedel C., Vajkoczy P. Angiogenesis in malignant glioma-a target for antitumor therapy?. Crit Rev Oncol Hematol 2006, 59:181-193.
27. Yang X.C., Tu C.X., Luo P.H., Zhu H., Zhu D.F., Wu H.H., et al. Antimetastatic activity of MONCPT in preclinical melanoma mice model. Invest New Drugs 2010, 28:800-811.
28. Merritt W.M., Danes C.G., Shahzad M.M., Lin Y.G., Kamat A.A., Han L.Y., et al. Anti-angiogenic properties of metronomic topotecan in ovarian carcinoma. Cancer Biol Ther 2009, 8:1596-1603.
29. Puppo M., Battaglia F., Ottaviano C., Delfino S., Ribatti D., Varesio L., et al. Topotecan inhibits vascular endothelial growth factor production and angiogenic activity induced by hypoxia in human neuroblastoma by targeting hypoxia-inducible factor-1alpha and -2alpha. Mol Cancer Ther 2008, 7:1974-1984.
30. Yang X., Luo P., Yang B., He Q. Antiangiogenesis response of endothelial cells to the antitumour drug 10-methoxy-9-nitrocamptothecin. Pharmacol Res 2006, 54:334-340.
31. Yang X., Zhang C., Ying M., Yang B., He Q. Antiproliferation in human EA.hy926 endothelial cells and inhibition of VEGF expression in PC-3 cells by topotecan. Pharmazie 2007, 62:534-538.
32. Xiao D., Tan W., Li M., Ding J. Antiangiogenic potential of 10-hydroxycamptothecin. Life Sci 2001, 69:1619-1628.
33. Qiao M., Shapiro P., Fosbrink M., Rus H., Kumar R., Passaniti A. Cell cycle-dependent phosphorylation of the RUNX2 transcription factor by cdc2 regulates endothelial cell proliferation. J Biol Chem 2006, 281:7118-7128.
34. Ferrari G., Cook B.D., Terushkin V., Pintucci G., Mignatti P. Transforming growth factor-beta 1 (TGF-beta1) induces angiogenesis through vascular endothelial growth factor (VEGF)-mediated apoptosis. J Cell Physiol 2009, 219:449-458.