Synthesis and properties of fluorescent NF-κB-recognizing hairpin oligodeoxyribonucleotide decoys

Bioconjugate Chemistry

Volumn 15, Issue 6, 2004, Pages 1481-1487

  Metelev, Valeri ^b   Weissleder, Ralph ^c   Bogdanov Jr , Alexei ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; FLUORESCENCE QUENCHING;

AMINOPROPYL; BINDING-SITES; CYANINE DYES; FLUORESCENCE QUENCHING; MONOFUNCTIONAL; N-HYDROXYSUCCINIMIDE; PROPERTY; QUENCHING OF FLUORESCENCE; REVERSE PHASE HPLC; SYNTHESISED;

OLIGONUCLEOTIDES;

ANTISENSE OLIGODEOXYNUCLEOTIDE; CYANINE DYE; FLUORESCENT DYE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; OLIGODEOXYNUCLEOTIDE DERIVATIVE;

ABSORPTION SPECTROSCOPY; CONFERENCE PAPER; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; PROTEIN DNA INTERACTION; PROTEIN PURIFICATION; SYNTHESIS; TRANSCRIPTION REGULATION;

EID: 9244242611     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc049916b     Document Type: Conference Paper

References (31)

1. Xu, J., Wu, Y., He, L., Yang, Y., Moore, S. A., and Hsu, C. Y. (1997) Regulation of cytokine-induced iNOS expression by a hairpin oligonucleotide in murine cerebral endothelial cells. Biochem. Biophys. Res. Commun. 235, 394-397.
2. Nakamura, T., Morishita, R., Asai, T., Tsuboniwa, N., Aoki, M., Sakonjo, H., Yamasaki, K., Hashiya, N., Kaneda, Y., and Ogihara, T. (2002) Molecular strategy using cis-element 'decoy' of E2F binding site inhibits neointimal formation in porcine balloon-injured coronary artery model. Gene Ther. 9, 488-494.
3. Kume, M., Komori, K., Matsumoto, T., Onohara, T., Takeuchi, K., Yonemitsu, Y., and Sugimachi, K. (2002) Administration of a decoy against the activator protein-1 binding site suppresses neointimal thickening in rabbit balloon-injured arteries. Circulation 105, 1226-1232.
4. Buchwald, A. B., Wagner, A. H., Webel, C., and Hecker, M. (2002) Decoy oligodeoxynucleotide against activator protein-1 reduces neointimal proliferation after coronary angioplasty in hypercholesterolemic minipigs. J. Am. Coll. Cardiol. 39, 732-738.
5. Novina, C. D., Murray, M. F., Dykxhoorn, D. M., Beresford, P. J., Riess, J., Lee, S. K., Collman, R. G., Lieberman, J., Shankar, P., and Sharp, P. A. (2002) siRNA-directed inhibition of HIV-1 infection. Nat Med. 8, 681-686.
6. Cullen, B. R. (2002) RNA interference: antiviral defense and genetic tool. Nat. Immunol. 3, 597-599.
7. Cho-Chung, Y. S., Park, Y. G., and Lee, Y. N. (1999) Oligonucleotides as transcription factor decoys. Curr. Opin. Mol. Ther. 1, 386-392.
8. Xia, H., Mao, Q., Paulson, H. L., and Davidson, B. L. (2002) siRNA-mediated gene silencing in vitro and in vivo. Nat Biotechnol. 20, 1006-1010.
9. Lewis, D. L., Hagstrom, J. E., Loomis, A. G., Wolff, J. A., and Herweijer, H. (2002) Efficient delivery of siRNA for inhibition of gene expression in postnatal mice. Nat. Genet. 32, 107-108.
10. Rapaport, E., Levina, A., Metelev, V., and Zamecnik, P. C. (1996) Antimycobacterial activities of antisense oligodeoxynucleotide phosphorothioates in drug-resistant strains. Proc. Natl. Acad. Sci. U.S.A. 93, 709-713.
11. Barker, R. H., Jr., Metelev, V., Rapaport, E., and Zamecnik, P. (1996) Inhibition of Plasmodium falciparum malaria using antisense oligodeoxynucleotides. Proc. Natl. Acad. Sci. U.S.A. 93, 514-518.
12. Alama, A., Barbieri, F., Cagnoli, M., and Schettini, G. (1997) Antisense oligonucleotides as therapeutic agents. Pharmacol. Res. 36, 171-178.
13. Agrawal, S., and Iyer, R. P. (1997) Perspectives in antisense therapeutics. Pharmacol. Ther. 76, 151-160.
14. Nielsen, P. E. (1999) Peptide nucleic acids as therapeutic agents. Curr. Opin. Struct. Biol. 9, 353-357.
15. Kurreck, J. (2003) Antisense technologies. Improvement through novel chemical modifications. Eur. J. Biochem. 270, 1628-1644.
16. Bridge, A. J., Pebernard, S., Ducraux, A., Nicoulaz, A. L., and Iggo, R. (2003) Induction of an Interferon response by RNAi vectors in mammalian cells. Nat. Genet. 34, 263-264.
17. Sledz, C. A., Holko, M., de Veer, M. J., Silverman, R. H., and Williams, B. R. (2003) Activation of the Interferon system by short-interfering RNAs. Nat. Cell Biol. 5, 834-839.
18. Lesage, D., Metelev, V., Borisova, O., Dolinnaya, N., Oretskaya, T., Baran-Marszak, F., Taillandier, E., Raphael, M., and Fagard, R. (2003) Specific covalent binding of a NF-kappaB decoy hairpin oligonucleotide targeted to the p50 subunit and induction of apoptosis. FEBS Lett. 547, 115-118.
19. Metelev, V. G., Kubareva, E. A., Vorob'eva, O. V., Romanenkov, A. S., and Oretskaya, T. S. (2003) Specific conjugation of DNA binding proteins to DNA templates through thiol-disulfide exchange. FEBS Lett. 538, 48-52.
20. Metelev, V. G., Borisova, O. A., Volkov, E. M., Oretskaya, T. S., and Dolinnaya, N. G. (2001) New chemically reactive dsDNAs containing single internucleotide monophosphoryldithio links: reactivity of 5′-mercapto- oligodeoxyribonucleotides. Nucl. Acids. Res. 29, 4062-4069.
21. Thierry, A. R., Vives, E., Richard, J. P., Prevot, P., Martinand-Mari, C., Robbins, I., and Lebleu, B. (2003) Cellular uptake and intracellular fate of antisense oligonucleotides. Curr. Opin. Mol. Ther. 5, 133-138.
22. Hu, Q., Bally, M. B., and Madden, T. D. (2002) Subcellular trafficking of antisense oligonucleotides and down-regulation of bcl-2 gene expression in human melanoma cells using a fusogenic liposome delivery system. Nucl. Acids. Res. 30, 3632-3641.
23. Islam, A., Handley, S. L., Thompson, K. S., and Akhtar, S. (2000) Studies on uptake, sub-cellular trafficking and efflux of antisense oligodeoxynucleotides in glioma cells using self-assembling cationic lipoplexes as delivery systems. J. Drug Target. 7, 373-382.
24. Marcusson, E. G., Bhat, B., Manoharan, M., Bennett, C. F., and Dean, N. M. (1998) Phosphorothioate oligodeoxyribonucleotides dissociate from cationic lipids before entering the nucleus. Nucl. Acids. Res. 26, 2016-2023.
25. Hnatowich, D. J. (1996) Pharmacokinetics of 99mTc-labeled oligonucleotides. Quart. J. Nucl. Med. 40, 202-208.
26. Tavitian, B. (2000) In vivo antisense imaging. Quart. J. Nucl. Med. 44, 236-255.
27. Broude, N. E. (2002) Stem-loop oligonucleotides: a robust tool for molecular biology and biotechnology. Trends Biotechnol. 20, 249-256.
28. Johansson, M. K., and Cook, R. M. (2003) Intramolecular dimers: a new design strategy for fluorescence-quenched probes. Chemistry Eur. J. 9, 3466-3471.
29. Weissleder, R., Tung, C. H., Mahmood, U., and Bogdanov, A., Jr. (1999) In vivo imaging of tumors with protease-activated near-infrared fluorescent probes. Nat. Biotechnol 17, 375-378.
30. Neri, D., Carnemolla, B., Nissim, A., Leprini, A., Querze, G., Balza, E., Pini, A., Tarli, L., Halin, C., Neri, P., Zardi, L., and Winter, G. (1997) Targeting by affinity-matured recombinant antibody fragments of an angiogenesis associated fibronectin isoform. Nat. Biotechnol. 15, 1271-1275.
31. Mujumdar, S., Mujumdar, R., Grant, C., and Waggoner, A. (1995) Cyanine-labeling reagents: sulfobenzindocyanine succinimidyl esters. Bioconjugate Chem. 7, 356-362.