Exploring the cellular activity of camptothecin-triple-helix-forming oligonucleotide conjugates

Molecular and Cellular Biology

Volumn 26, Issue 1, 2006, Pages 324-333

  Arimondo, Paola B ^a,d   Thomas, Craig J ^c   Oussedik, Kahina ^a   Baldeyrou, Brigitte ^b   Mahieu, Christine ^b   Halby, Ludovic ^a   Guianvarc'h, Dominique ^a,e   Lansiaux, Amélie ^b   Hecht, Sidney M ^c   Bailly, Christian ^b   Giovannangeli, Carine ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^b INSERM   (France)

^c UNIVERSITY OF VIRGINIA   (United States)

^d CNRS   (France)

^e SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN DERIVATIVE; CAMPTOTHECIN TRIPLE HELIX OLIGONUCLEOTIDE CONJUGATE; DNA TOPOISOMERASE; DOUBLE STRANDED DNA; LUCIFERASE; OLIGONUCLEOTIDE; RECEPTOR PROTEIN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; DNA;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CELL NUCLEUS; COVALENT BOND; DNA CLEAVAGE; DNA MODIFICATION; DNA PROTEIN COMPLEX; DNA SEQUENCE; DRUG ACTIVITY; DRUG PROTEIN BINDING; DRUG TARGETING; ENZYME MECHANISM; GENE EXPRESSION REGULATION; MUTATION; PRIORITY JOURNAL; REPORTER GENE; TRIPLE HELIX; CELL CULTURE; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; FIREFLY; GENE EXPRESSION; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE;

PHOTINUS PYRALIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BASE SEQUENCE; CAMPTOTHECIN; CELLS, CULTURED; DNA; DNA TOPOISOMERASES, TYPE I; FIREFLIES; GENE EXPRESSION; GENES, REPORTER; HUMANS; LUCIFERASES; MOLECULAR SEQUENCE DATA; OLIGONUCLEOTIDES; TUMOR CELLS, CULTURED;

EID: 33645220275     PISSN: 02707306     EISSN: None     Source Type: Journal    
DOI: 10.1128/MCB.26.1.324-333.2006     Document Type: Article

References (30)

1. Andersen, A. H., E. Gocke, B. J. Bonven, O. F. Nielsen, and O. Westergaard. 1985. Topoisomerase I has a strong binding preference for a conserved hexadecameric sequence in the promoter region of the rRNA gene from Tetrahymena pyriformis. Nucleic Acids Res. 13:1543-1557.
2. Arimondo, P. B., S. Angenault, L. Halby, A. Boutorine, F. Schmidt, C. Monneret, T. Garestier, J. S. Sun, C. Bailly, and C. Helene. 2003. Spatial organization of topoisomerase I-mediated DNA cleavage induced by camptothecin-oligonucleotide conjugates. Nucleic Acids Res. 31:4031-4040.
3. Arimondo, P. B., C. Bailly, A. Boutorine, P. Moreau, M. Prudhomme, J. S. Sun, T. Garestier, and C. Helene. 2001. Triple helix-forming oligonucleorides conjugated to indolocarbazole poisons direct topoisomerase I-mediated DNA cleavage to a specific site. Bioconjug. Chem. 12:501-509.
4. Arimondo, P. B., C. Bailly, A. Boutorine, M. Prudhomme, J.-S. Sun, T. Garestier, and C. Helene. 2000. Recognition and cleavage of DNA by rebeccamycin- or benzopyridoquinoxaline-triplex-forming oligonucleotide conjugates. Bioorg. Med. Chem. 8:1-8.
5. Arimondo, P. B., C. Bailly, A. Boutorine, V. Ryabinin, A. Syniakov, J. S. Sun, T. Garestier, and C. Helene. 2001. Directing topoisomerase I-mediated DNA cleavage to specific sites by camptothecin tethered to minor and major groove ligands. Angew. Chem. Int. Ed. Engl. 40:3045-3048.
6. Arimondo, P. B., C. Bailly, A. Boutorine, J. S. Sun, T. Garestier, and C. Helene. 1999. Targeting topoisomerase I cleavage to specific sequences of DNA by triple helix-forming oligonucleotide conjugates. A comparison between a rebeccamycin derivative and camptothecin. C. R. Acad. Sci. Ser. III Life Sci. 322:785-790.
7. Arimondo, P. B., A. Boutorine, B. Baldeyrou, C. Bailly, M. Kuwahara, S. M. Hecht, J. S. Sun, T. Garestier, and C. Helene. 2002. Design and optimization of camptothecin conjugates of triple helix-forming oligonucleotides for sequence-specific DNA cleavage by topoisomerase I. J. Biol. Chem. 277:3132-3140.
8. Bailly, C., C. OhUigin, C. Rivalle, E. Bisagni, J. P. Henichart, and M. J. Waring. 1990. Sequence-selective binding of an ellipticine derivative to DNA. Nucleic Acids Res. 18:6283-6291.
9. Bailly, C, J. F. Riou, C. Houssier, E. Rodrigues-Pereira, and M. Prudhomme. 1997. DNA cleavage by topoisomerase I on the presence of indolocarbazole derivatives of rebeccamycin. Biochemistry 36:3917-3929.
10. Besch, R., C. Giovannangeli, and K. Degitz. 2004. Triplex-forming oligonucleotides-sequence-specific DNA ligands as tools for gene inhibition and for modulation of DNA-associated functions. Curr. Drug Targets 5:691-703.
11. Cantor, C. R., M. M. Warshaw, and H. Shapiro. 1970. Oligonucleotide interactions. III. Circular dichroism studies of the conformation of deoxyoligonucleotides. Biopolymers 9:1059-1077.
12. Carbone, G. M., E. McGuffie, S. Napoli, C. E. Flanagan, C. Dembech, U. Negri, F. Arcamone, M. L. Capobianco, and C. V. Catapano. 2004. DNA binding and antigene activity of a daunomycin-conjugated triplex-forming oligonucleotide targeting the P2 promoter of the human c-myc gene. Nucleic Acids Res. 32:2396-2410.
13. Carbone, G. M., S. Napoli, A. Valentini, F. Cavalli, D. K. Watson, and C. V. Catapano. 2004. Triplex DNA-mediated downregulation of Ets2 expression results in growth inhibition and apoptosis in human prostate cancer cells. Nucleic Acids Res. 32:4358-4367.
14. Champoux, J. J. 2001. DNA topoisomerases: structure, function and mechanism. Annu. Rev. Biochem. 70:369-413.
15. Faria, M., C. D. Wood, L. Perrouault, J. S. Nelson, A. Winter, M. R. White, C. Helene, and C. Giovannangeli. 2000. Targeted inhibition of transcription elongation in cells mediated by triplex-forming oligonucleotides. Proc. Natl. Acad. Sci. USA 97:3862-3867.
16. Froehler, B. C., R. J. Jones, X. D. Cao, and T. J. Terhorst. 1993. Oligonucleotides derived from 5-(1-propynyl)-2′-O-allyl-uridine and 5-(1-propynyl)-2′-O-allyl-cytidine-synthesis and RNA duplex formation. Tetrahedron Lett. 34:1003-1006.
17. Kim, D. K., and N. Lee. 2002. Recent advances in topoisomerase I-targeting agents, camptothecin analogues. Mini Rev. Med. Chem. 2:611-619.
18. Lacroix, L., J. Lacoste, J. F. Reddoch, J. L. Mergny, D. D. Levy, M. M. Seidman, M. D. Matteucci, and P. M. Glazer. 1999. Triplex formation by oligonucleotides containing 5-(1-propynyl)-2′-deoxyuridine: decreased magnesium dependence and improved intracellular gene targeting. Biochemistry 38:1893-1901.
19. Matteucci, M., K.-Y. Lin, T. Huang, R. Wagner, D. D. Sternbach, M. Mehrotra, and J. M. Besterman. 1997. Sequence-specific targeting of duplex DNA using a camptothecin-triple helix forming oligonucleotide conjugate and topoisomerase I. J. Am. Chem. Soc. 119:6939-6940.
20. Pommier, Y., P. Pourquier, Y. Fan, and D. Strumberg. 1998. Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400:83-105.
21. Pommier, Y., P. Pourquier, Y. Urasaki, J. Wu, and G. S. Laco. 1999. Topoisomerase I inhibitors: selectivity and cellular resistance. Drug Resist. Updates 2:307-318.
22. Pommier, Y., C. Redon, V. A. Rao, J. A. Seiler, O. Sordet, H. Takemura, S. Antony, L. Meng, Z. Liao, G. Kohlhagen, H. Zhang, and K. W. Kohn. 2003. Repair of and checkpoint response to topoisomerase I-mediated DNA damage. Mutat. Res. 532:173-203.
23. Prudhomme, M. 2000. Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents. Curr. Med. Chem. 7:1189-1212.
24. Thomas, C. J., N. J. Rahier, and S. M. Hecht. 2004. Camptothecin: current perspectives. Bioorg. Med. Chem. 12:1585-1604.
25. Thomsen, B., S. Mollerup, B. J. Bonven, R. Frank, H. Blocker, O. F. Nielsen, and O. Westergaard. 1987. Sequence specificity of DNA topoisomerase I in the presence and absence of camptothecin. EMBO J. 6:1817-1823.
26. Wadkins, R. M., D. Bearss, G. Manikumar, M. C. Wani, M. E. Wall, and D. D. Von Hoff. 2004. Topoisomerase I-DNA complex stability induced by camptothecins and its role in drug activity. Curr. Med. Chem. Anti-cancer Agents 4:327-334.
27. Wang, C. C., and P. B. Dervan. 2001. Sequence-specific trapping of topoisomerase I by DNA binding polyamide-camptothecin conjugates. J. Am. Chem. Soc. 123:8657-8661.
28. Wang, J. C. 2002. Cellular roles of DNA topoisomerases: a molecular perspective. Nat. Rev. Mol. Cell Biol. 3:430-440.
29. Wang, J. C. 1996. DNA topoisomerases. Annu. Rev. Biochem. 65:635-692.
30. Woo, M. H., J. R. Vance, A. R. Marcos, C. Bailly, and M. A. Bjornsti. 2002. Active site mutations in DNA topoisomerase I distinguish the cytotoxic activities of camptothecin and the indolocarbazole, rebeccamycin. J. Biol. Chem. 277:3813-3822.