메뉴 건너뛰기




Volumn 31, Issue 18, 2003, Pages 5282-5290

Cationic phosphoramidate α-oligonucleotides efficiently target single-stranded DNA and RNA and inhibit hepatits C virus IRES-mediated translation

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; NUCLEOSIDE; PHOSPHORAMIDIC ACID DERIVATIVE; RIBONUCLEASE H; RNA; SINGLE STRANDED DNA;

EID: 0344875217     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkg733     Document Type: Article
Times cited : (40)

References (47)
  • 1
    • 0036636074 scopus 로고    scopus 로고
    • Nucleic-acid therapeutics: Basic principles and recent applications
    • Opalinska, J.B. and Gewirtz, A.M. (2002) Nucleic-acid therapeutics: basic principles and recent applications. Nature Rev. Drug Discov., 1, 503-513.
    • (2002) Nature Rev. Drug Discov. , vol.1 , pp. 503-513
    • Opalinska, J.B.1    Gewirtz, A.M.2
  • 5
    • 0002314680 scopus 로고    scopus 로고
    • Modified oligonucleotides as antisense therapeutics
    • Stein, C.A. and Krieg, A.M. (eds), Wiley-Liss Inc., New York, NY
    • Seeberger, P.H. and Caruthers, M.H. (1998) Modified oligonucleotides as antisense therapeutics. In Stein, C.A. and Krieg, A.M. (eds), Applied Antisense Oligonucleotide Technology. Wiley-Liss Inc., New York, NY, pp. 51-71.
    • (1998) Applied Antisense Oligonucleotide Technology , pp. 51-71
    • Seeberger, P.H.1    Caruthers, M.H.2
  • 6
    • 0005969961 scopus 로고    scopus 로고
    • Mechanisms of action of antisense oligonucleotides
    • Couvreur, P. and Malvy, C. (eds), Taylor & Francis, London, UK
    • Tidd, D.M. and Giles, R.V. (2000) Mechanisms of action of antisense oligonucleotides. In Couvreur, P. and Malvy, C. (eds), Pharmaceutical aspects of oligonucleotides. Taylor & Francis, London, UK, pp. 3-31.
    • (2000) Pharmaceutical Aspects of Oligonucleotides , pp. 3-31
    • Tidd, D.M.1    Giles, R.V.2
  • 8
    • 0035445947 scopus 로고    scopus 로고
    • Incorporation of a cationic aminopropyl chain in DNA hairpins: Thermodynamics and hydration
    • Soto, A.M., Kankia, B.I., Dande, P., Gold, B. and Marky, L.A. (2001) Incorporation of a cationic aminopropyl chain in DNA hairpins: thermodynamics and hydration. Nucleic Acids Res., 29, 3638-3645.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 3638-3645
    • Soto, A.M.1    Kankia, B.I.2    Dande, P.3    Gold, B.4    Marky, L.A.5
  • 9
    • 0033560690 scopus 로고    scopus 로고
    • 5-(1-propargylamino)-2′-deoxyuridine (UP): A novel thymidine analogue for generating DNA triplexes with increased stability
    • Bijapur, J., Keppler, M.d., Bergqvist, S., Brown, T. and Fox, K.R. (1999) 5-(1-propargylamino)-2′-deoxyuridine (UP): a novel thymidine analogue for generating DNA triplexes with increased stability. Nucleic Acids Res., 27, 1802-1809.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 1802-1809
    • Bijapur, J.1    Keppler, M.D.2    Bergqvist, S.3    Brown, T.4    Fox, K.R.5
  • 11
    • 0034686290 scopus 로고    scopus 로고
    • Zwitterionic oligonucleotides with 2′-O-[3-(N,N-dimethylamino)propyl]-RNA modification: Synthesis and properties
    • Prakash, T.P., Manoharan, M., Fraser, A.S., Kawasaki, A.M., Lesnik, E.A. and Owens, S.R. (2000) Zwitterionic oligonucleotides with 2′-O-[3-(N,N-dimethylamino)propyl]-RNA modification: synthesis and properties. Tetrahedron Lett., 41, 4855-4859.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4855-4859
    • Prakash, T.P.1    Manoharan, M.2    Fraser, A.S.3    Kawasaki, A.M.4    Lesnik, E.A.5    Owens, S.R.6
  • 12
    • 0037129802 scopus 로고    scopus 로고
    • Minimum number of 2′-O-(2-aminoethyl) residues required for gene knockout activity by triplex helix forming oligonucleotides
    • Puri, N., Majumdar, A., Cuenoud, B., Natt, F., Martin, P., Boyd, A., Miller, P.S. and Seidman, M.M. (2002) Minimum number of 2′-O-(2-aminoethyl) residues required for gene knockout activity by triplex helix forming oligonucleotides. Biochemistry, 41, 7716-7724.
    • (2002) Biochemistry , vol.41 , pp. 7716-7724
    • Puri, N.1    Majumdar, A.2    Cuenoud, B.3    Natt, F.4    Martin, P.5    Boyd, A.6    Miller, P.S.7    Seidman, M.M.8
  • 13
    • 0034701268 scopus 로고    scopus 로고
    • Highly nuclease-resistant phosphodiester-type oligodeoxynucleotides containing 4′α-C-aminoalkylthymidines form thermally stable duplexes with DNA and RNA. A candidate for potent antisense molecules
    • Kanazaki, M., Ueno, Y., Shuto, S. and Matsuda, A. (2000) Highly nuclease-resistant phosphodiester-type oligodeoxynucleotides containing 4′α-C-aminoalkylthymidines form thermally stable duplexes with DNA and RNA. A candidate for potent antisense molecules. J. Am. Chem. Soc., 122, 2422-2432.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2422-2432
    • Kanazaki, M.1    Ueno, Y.2    Shuto, S.3    Matsuda, A.4
  • 15
    • 0028307714 scopus 로고
    • Hybridization of alternating cationic/anionic oligonucleotides to RNA segments
    • Jung, P.M., Histand, G. and Letsinger, R.L. (1994) Hybridization of alternating cationic/anionic oligonucleotides to RNA segments. Nucl. Nucl., 13, 1597-1605.
    • (1994) Nucl. Nucl. , vol.13 , pp. 1597-1605
    • Jung, P.M.1    Histand, G.2    Letsinger, R.L.3
  • 16
    • 0030067307 scopus 로고    scopus 로고
    • Oligonucleotides with alternating anionic and cationic phosphoramidate linkages: Synthesis and hybridization of stereo-uniform isomers
    • Horn, T., Chaturvedi, S., Balasubramaniam, T.N. and Letsinger, R.L. (1996) Oligonucleotides with alternating anionic and cationic phosphoramidate linkages: synthesis and hybridization of stereo-uniform isomers. Tetrahedron Lett., 37, 743-746.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 743-746
    • Horn, T.1    Chaturvedi, S.2    Balasubramaniam, T.N.3    Letsinger, R.L.4
  • 17
    • 0029899722 scopus 로고    scopus 로고
    • Stabilization of triple-stranded oligonucleotide complexes: Use of probes containing alternating phosphodiester and stereo-uniform cationic phosphoramidate linkages
    • Chaturvedi, S., Horn, T. and Letsinger, R.L. (1996) Stabilization of triple-stranded oligonucleotide complexes: use of probes containing alternating phosphodiester and stereo-uniform cationic phosphoramidate linkages. Nucleic Acids Res., 24, 2318-2323.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 2318-2323
    • Chaturvedi, S.1    Horn, T.2    Letsinger, R.L.3
  • 18
    • 0029929050 scopus 로고    scopus 로고
    • Positively charged oligonucleotides overcome potassium-mediated inhibition of triplex DNA formation
    • Dagle, J.M. and Weeks, D.L. (1996) Positively charged oligonucleotides overcome potassium-mediated inhibition of triplex DNA formation. Nucleic Acids Res., 24, 2143-2149.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 2143-2149
    • Dagle, J.M.1    Weeks, D.L.2
  • 19
    • 0032213292 scopus 로고    scopus 로고
    • Cationic oligonucleotides can mediate specific inhibition of gene expression in Xenopus oocytes
    • Bailey, C.P., Dagle, J.M. and Weeks, D.L. (1998) Cationic oligonucleotides can mediate specific inhibition of gene expression in Xenopus oocytes. Nucleic Acids Res., 26, 4860-4867.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 4860-4867
    • Bailey, C.P.1    Dagle, J.M.2    Weeks, D.L.3
  • 20
    • 0345671508 scopus 로고    scopus 로고
    • Fluoresceine-labelled cationic oligonucleotide probes: Detection of hybrid formation in solution using fluorescence polarization spectroscopy
    • Kore, A. and Salunke, M. (1998) Fluoresceine-labelled cationic oligonucleotide probes: detection of hybrid formation in solution using fluorescence polarization spectroscopy. Indian J. Chem., Section A, 37B, 536-539.
    • (1998) Indian J. Chem., Section A , vol.37 B , pp. 536-539
    • Kore, A.1    Salunke, M.2
  • 21
    • 0033600703 scopus 로고    scopus 로고
    • Synthesis and triple helix-forming ability of oligonucleoties with N,N-dimethylaminoethyl phosphoramidate linkages
    • Robles, J., Ibanez, V., Grandas, A. and Pedroso, E. (1999) Synthesis and triple helix-forming ability of oligonucleoties with N,N-dimethylaminoethyl phosphoramidate linkages. Tetrahedron Lett., 40, 7131-7134.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7131-7134
    • Robles, J.1    Ibanez, V.2    Grandas, A.3    Pedroso, E.4
  • 22
    • 0034657596 scopus 로고    scopus 로고
    • Targeted elimination of zygotic messages in Xenopus laevis embryos by modified oligonucleotides possessing terminal cationic linkages
    • Dagle, J.M., Littig, J.L., Sutherland, L.B. and Weeks, D.L. (2000) Targeted elimination of zygotic messages in Xenopus laevis embryos by modified oligonucleotides possessing terminal cationic linkages. Nucleic Acids Res., 28, 2153-2157.
    • (2000) Nucleic Acids Res. , vol.28 , pp. 2153-2157
    • Dagle, J.M.1    Littig, J.L.2    Sutherland, L.B.3    Weeks, D.L.4
  • 23
    • 0035914386 scopus 로고    scopus 로고
    • Chromosome targeting at short polypurine sites by cationic triplex-forming oligonucletides
    • Vasquez, K.M., Dagle, J.M., Weeks, D.L. and Glazer, P.M. (2001) Chromosome targeting at short polypurine sites by cationic triplex-forming oligonucletides. J. Biol. Chem., 276, 38536-38541.
    • (2001) J. Biol. Chem. , vol.276 , pp. 38536-38541
    • Vasquez, K.M.1    Dagle, J.M.2    Weeks, D.L.3    Glazer, P.M.4
  • 24
    • 0002094968 scopus 로고    scopus 로고
    • The chirality problem in P-substituted oligonucleotides
    • Lebedev, A.V. and Wickstrom, E. (1996) The chirality problem in P-substituted oligonucleotides. Perspect. Drug Disc. Des., 4, 17-40.
    • (1996) Perspect. Drug Disc. Des. , vol.4 , pp. 17-40
    • Lebedev, A.V.1    Wickstrom, E.2
  • 25
    • 0033230088 scopus 로고    scopus 로고
    • Chiral and steric effects in the efficient binding of [alpha]-anomeric deoxyoligonucleoside N-alkylphosphoramidates to ssDNA and RNA
    • Laurent, A., Naval, M., Debart, F., Vasseur, J.-J. and Rayner, B. (1999) Chiral and steric effects in the efficient binding of [alpha]-anomeric deoxyoligonucleoside N-alkylphosphoramidates to ssDNA and RNA. Nucleic Acids Res., 27, 4151-4159.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 4151-4159
    • Laurent, A.1    Naval, M.2    Debart, F.3    Vasseur, J.-J.4    Rayner, B.5
  • 26
    • 0345239697 scopus 로고
    • α-Oligodeoxynucleotide Analogues
    • Cohen, J.S. (ed.), Oligodeoxynucleotides, Antisense Inhibitors of Gene Expression. MacMillan Press, London, UK
    • Rayner, B., Malvy, C., Paoletti, J., Lebleu, B., Paoletti, C. and Imbach, J.-L. (1989) α-Oligodeoxynucleotide Analogues. In Cohen, J.S. (ed.), Topics in Molecular and Structural Biology, Vol. 12: Oligodeoxynucleotides, Antisense Inhibitors of Gene Expression. MacMillan Press, London, UK, pp. 119-136.
    • (1989) Topics in Molecular and Structural Biology , vol.12 , pp. 119-136
    • Rayner, B.1    Malvy, C.2    Paoletti, J.3    Lebleu, B.4    Paoletti, C.5    Imbach, J.-L.6
  • 27
    • 0032531744 scopus 로고    scopus 로고
    • Anomeric inversion (from β to α) in methylphosphonate oligonucleosides enhances their affinity for DNA and RNA
    • Debart, F., Meyer, A., Vasseur, J.-J. and Rayner, B. (1998) Anomeric inversion (from β to α) in methylphosphonate oligonucleosides enhances their affinity for DNA and RNA. Nucleic Acids Res., 26, 4551-4556.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 4551-4556
    • Debart, F.1    Meyer, A.2    Vasseur, J.-J.3    Rayner, B.4
  • 31
    • 0026606239 scopus 로고
    • Advances in the synthesis of oligonucleotides by the phosphoramidite approach
    • Beaucage, S.L. and Iyer, R.P. (1992) Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron, 48, 2223-2311.
    • (1992) Tetrahedron , vol.48 , pp. 2223-2311
    • Beaucage, S.L.1    Iyer, R.P.2
  • 33
    • 0027711609 scopus 로고
    • Oligodeoxynucleotide synthesis. H-phosphonate approach
    • Agrawal, S. (ed.), Humana Press, Totowa, NJ
    • Froehler, B.C. (1993) Oligodeoxynucleotide synthesis. H-phosphonate approach. In Agrawal, S. (ed.), Methods in molecular biology. Protocols for oligonucleotides and analogs, Vol. 20. Humana Press, Totowa, NJ, pp. 63-80.
    • (1993) Methods in Molecular Biology Protocols for Oligonucleotides and Analogs , vol.20 , pp. 63-80
    • Froehler, B.C.1
  • 34
    • 0030592799 scopus 로고    scopus 로고
    • Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks
    • Ozola, V., Reese, C.B. and Song, Q. (1996) Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks. Tetrahedron Lett., 37, 8621-8624.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8621-8624
    • Ozola, V.1    Reese, C.B.2    Song, Q.3
  • 35
    • 0033970975 scopus 로고    scopus 로고
    • Cell cycle regulation of hepatitis C virus internal ribosomal entry site-directed translation
    • Honda, M., Kaneko, S., Matsushita, E., Kobayashi, K., Abell, G.A. and Lemon, S.M. (2000) Cell cycle regulation of hepatitis C virus internal ribosomal entry site-directed translation. Gastroenterology, 118, 152-162.
    • (2000) Gastroenterology , vol.118 , pp. 152-162
    • Honda, M.1    Kaneko, S.2    Matsushita, E.3    Kobayashi, K.4    Abell, G.A.5    Lemon, S.M.6
  • 36
    • 0033991577 scopus 로고    scopus 로고
    • Vesicular stomatitis virus as model system for studies of antisense oligonucleotide translation arrest
    • Robbins, I. and Lebleu, B. (2000) Vesicular stomatitis virus as model system for studies of antisense oligonucleotide translation arrest. Methods Enzymol., 313, 189-203.
    • (2000) Methods Enzymol. , vol.313 , pp. 189-203
    • Robbins, I.1    Lebleu, B.2
  • 37
    • 0037013420 scopus 로고    scopus 로고
    • 2-amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-oligodeoxynucleotides with RNA target
    • Naval, M., Michel, T., Vasseur, J.-J. and Debart, F. (2002) 2-amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-oligodeoxynucleotides with RNA target. Bioorg. Med. Chem. Lett., 12, 1435-1438.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1435-1438
    • Naval, M.1    Michel, T.2    Vasseur, J.-J.3    Debart, F.4
  • 38
    • 0035945251 scopus 로고    scopus 로고
    • Effects of polyamines on the thermal stability and formation kinetics of DNA duplexes with abnormal structure
    • Hou, M.-H., Lin, S.-B., Yuann, J.-M.P., Lin, W.-C., Wang, A.H.-J. and Kan, L.-S. (2001) Effects of polyamines on the thermal stability and formation kinetics of DNA duplexes with abnormal structure. Nucleic Acids Res., 29, 5121-5128.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 5121-5128
    • Hou, M.-H.1    Lin, S.-B.2    Yuann, J.-M.P.3    Lin, W.-C.4    Wang, A.H.-J.5    Kan, L.-S.6
  • 39
    • 0023573266 scopus 로고
    • Alpha-ADN VI: Comparative study of alpha- and beta-anomeric oligodeoxyribonucleotides in hybridization to mRNA and in cell free translation inhibition
    • Gagnor, C., Bertrand, J.-R., Thenet, S., Lemaître, M., Morvan, F., Rayner, B., Malvy, C., Lebleu, B., Imbach, J.-L. and Paoletti, C. (1987) Alpha-ADN VI: Comparative study of alpha- and beta-anomeric oligodeoxyribonucleotides in hybridization to mRNA and in cell free translation inhibition. Nucleic Acids Res., 15, 10419-10436.
    • (1987) Nucleic Acids Res. , vol.15 , pp. 10419-10436
    • Gagnor, C.1    Bertrand, J.-R.2    Thenet, S.3    Lemaître, M.4    Morvan, F.5    Rayner, B.6    Malvy, C.7    Lebleu, B.8    Imbach, J.-L.9    Paoletti, C.10
  • 40
    • 0032131491 scopus 로고    scopus 로고
    • Selective mRNA degradation by antisense oligonucleotide-2,5A chimeras: Involvement of RNase H and RNase L
    • Robbins, I., Mitta, G., Vichier-Guerre, S., Sobol, R., Ubysz, A., Rayner, B. and Lebleu, B. (1998) Selective mRNA degradation by antisense oligonucleotide-2,5A chimeras: involvement of RNase H and RNase L. Biochimie, 80, 1-10.
    • (1998) Biochimie , vol.80 , pp. 1-10
    • Robbins, I.1    Mitta, G.2    Vichier-Guerre, S.3    Sobol, R.4    Ubysz, A.5    Rayner, B.6    Lebleu, B.7
  • 42
    • 0032004967 scopus 로고    scopus 로고
    • A good antisense molecule is hard to find
    • Branch, A. (1998) A good antisense molecule is hard to find. Trends Biochem. Sci., 23, 45-50.
    • (1998) Trends Biochem. Sci. , vol.23 , pp. 45-50
    • Branch, A.1
  • 44
    • 0037440001 scopus 로고    scopus 로고
    • Antisense oligonucleotides targeted to the domain IIId of the hepatitis C virus IRES compete with 40S ribosomal subunit binding and prevent in vitro translation
    • Tallet-Lopez, B., Aldaz-Carroll, L., Chabas, S., Dausse, E., Staedel, C. and Toulme, J.J. (2003) Antisense oligonucleotides targeted to the domain IIId of the hepatitis C virus IRES compete with 40S ribosomal subunit binding and prevent in vitro translation. Nucleic Acids Res., 31, 734-742.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 734-742
    • Tallet-Lopez, B.1    Aldaz-Carroll, L.2    Chabas, S.3    Dausse, E.4    Staedel, C.5    Toulme, J.J.6
  • 45
    • 0033765890 scopus 로고    scopus 로고
    • Hepatitis C virus internal ribosome entry site (IRES) stem loop IIId contains a phylogenetically conserved GGG triplet essential for translation and IRES folding
    • Jubin, R., Vantuno, N.E., Kieft, J.S., Murray, M.G., Doudna, J.A., Lau, J.Y.N. and Baroudy, B.M. (2000) Hepatitis C virus internal ribosome entry site (IRES) stem loop IIId contains a phylogenetically conserved GGG triplet essential for translation and IRES folding. J. Virol., 74, 10430-10437.
    • (2000) J. Virol. , vol.74 , pp. 10430-10437
    • Jubin, R.1    Vantuno, N.E.2    Kieft, J.S.3    Murray, M.G.4    Doudna, J.A.5    Lau, J.Y.N.6    Baroudy, B.M.7
  • 47
    • 0345671507 scopus 로고    scopus 로고
    • Mechanisms of transmembrane transport of oligonucleotides
    • Couvreur, P. and Malvy, C. (eds), Taylor & Francis, London, UK
    • Juliano, R.L. (2000) Mechanisms of transmembrane transport of oligonucleotides. In Couvreur, P. and Malvy, C. (eds), Pharmaceutical Aspects of Oligonucleotides. Taylor & Francis, London, UK, pp.
    • (2000) Pharmaceutical Aspects of Oligonucleotides , pp. 213-225
    • Juliano, R.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.