메뉴 건너뛰기




Volumn 33, Issue 13, 2005, Pages 4223-4234

Intercalator conjugates of pyrimidine locked nucleic acid-modified triplex-forming oligonucleotides: Improving DNA binding properties and reaching cellular activities

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PYRIMIDINE LOCKED NUCLEIC ACID TRIPLEX FORMING OLIGONUCLEOTIDE; UNCLASSIFIED DRUG; ANTISENSE OLIGONUCLEOTIDE; DNA; DNA BINDING PROTEIN; INTERCALATING AGENT; LOCKED NUCLEIC ACID; PYRIMIDINE DERIVATIVE; TRIPLEX DNA;

EID: 22844432244     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gki726     Document Type: Article
Times cited : (31)

References (37)
  • 1
    • 0035404317 scopus 로고    scopus 로고
    • Triplex-forming molecules: From concepts to applications
    • Faria,M. and Giovannangeli,C. (2001) Triplex-forming molecules: From concepts to applications. J. Gene. Med., 3, 299-310.
    • (2001) J. Gene. Med. , vol.3 , pp. 299-310
    • Faria, M.1    Giovannangeli, C.2
  • 2
    • 10044225983 scopus 로고    scopus 로고
    • Triplex-forming oligonucleotides - Sequence-specific DNA ligands as tools for gene inhibition and for modulation of DNA-associated functions
    • Besch,R., Giovannangeli,C. and Degitz,K. (2004) Triplex-forming oligonucleotides - sequence-specific DNA ligands as tools for gene inhibition and for modulation of DNA-associated functions. Current Drug Targets, 5, 691-703.
    • (2004) Current Drug Targets , vol.5 , pp. 691-703
    • Besch, R.1    Giovannangeli, C.2    Degitz, K.3
  • 3
    • 1542609295 scopus 로고    scopus 로고
    • Targeted gene modification using triplex-forming oligonucleotides
    • Kuan,J.Y. and Glazer,P.M. (2004) Targeted gene modification using triplex-forming oligonucleotides. Methods Mol. Biol., 262, 173-194.
    • (2004) Methods Mol. Biol. , vol.262 , pp. 173-194
    • Kuan, J.Y.1    Glazer, P.M.2
  • 4
    • 0032508095 scopus 로고    scopus 로고
    • Novel convenient syntheses of LNA [2.2.1] bicyclo nucleosides
    • Koshkin,A., Rajwanshi,V.K. and Wengel,J. (1998) Novel convenient syntheses of LNA [2.2.1] bicyclo nucleosides. Tetrahedron Lett., 39, 4381-4384.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4381-4384
    • Koshkin, A.1    Rajwanshi, V.K.2    Wengel, J.3
  • 5
    • 0032560835 scopus 로고    scopus 로고
    • Stability and structural features of the duplexes containing nucleoside analogues with a fixed N-type conformation, 2′-O,4′-C-methyleneribonucleosides
    • Obika,S., Nanbu,D., Hari,Y., Andoh,J., Morio,K., Doi,T. and Imanishi,T. (1998) Stability and structural features of the duplexes containing nucleoside analogues with a fixed N-type conformation, 2′-O,4′-C-methyleneribonucleosides. Tetrahedron Lett., 39, 5401-5404.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5401-5404
    • Obika, S.1    Nanbu, D.2    Hari, Y.3    Andoh, J.4    Morio, K.5    Doi, T.6    Imanishi, T.7
  • 6
    • 0034744290 scopus 로고    scopus 로고
    • 2′-O,4′-C-Methylene bridged nucleic acid (2′,4′-BNA): Synthesis and triplex-forming properties
    • Obika,S., Uneda,T., Sugimoto,T., Nanbu,D., Minami,T., Doi,T. and Imanishi,T. (2001) 2′-O,4′-C-Methylene bridged nucleic acid (2′,4′-BNA): Synthesis and triplex-forming properties. Bioorg. Med. Chem., 9, 1001-1011.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 1001-1011
    • Obika, S.1    Uneda, T.2    Sugimoto, T.3    Nanbu, D.4    Minami, T.5    Doi, T.6    Imanishi, T.7
  • 7
    • 0037901806 scopus 로고    scopus 로고
    • Triplex formation with 2′-O,4′-C-ethylene-bridged nucleic acids (ENA) having C3′-endo conformation at physiological pH
    • Koizumi,M., Morita,K., Daigo,M., Tsutsumi,S., Abe,K., Obika,S. and Imanishi,T. (2003) Triplex formation with 2′-O,4′-C-ethylene-bridged nucleic acids (ENA) having C3′-endo conformation at physiological pH. Nucleic Acids Res., 31, 3267-3273.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 3267-3273
    • Koizumi, M.1    Morita, K.2    Daigo, M.3    Tsutsumi, S.4    Abe, K.5    Obika, S.6    Imanishi, T.7
  • 8
    • 0035951767 scopus 로고    scopus 로고
    • 2′-O,4′-C-methylene bridged nucleic acid modification promotes pyrimidine motif triplex DNA formation at physiological pH: Thermodynamic and kinetic studies
    • Torigoe,H., Hari,Y., Sekiguchi,M., Obika,S. and Imanishi,T. (2001) 2′-O,4′-C-methylene bridged nucleic acid modification promotes pyrimidine motif triplex DNA formation at physiological pH: thermodynamic and kinetic studies. J. Biol. Chem., 276, 2354-2360.
    • (2001) J. Biol. Chem. , vol.276 , pp. 2354-2360
    • Torigoe, H.1    Hari, Y.2    Sekiguchi, M.3    Obika, S.4    Imanishi, T.5
  • 9
    • 0344874534 scopus 로고    scopus 로고
    • Use of locked nucleic acid oligonucleotides to add functionality to plasmid DNA
    • Hertoghs,K.M., Ellis,J.H. and Catchpole,I.R. (2003) Use of locked nucleic acid oligonucleotides to add functionality to plasmid DNA. Nucleic Acids Res., 31, 5817-5830.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 5817-5830
    • Hertoghs, K.M.1    Ellis, J.H.2    Catchpole, I.R.3
  • 12
    • 0000333462 scopus 로고    scopus 로고
    • Nucleic acids: Supramolecular structures and rational design of sequence-specific ligands
    • Murakami,Y. (ed.), Pergamon
    • Giovannangeli,C., Sun,J.-S. and Helene,C. (1996) Nucleic acids: supramolecular structures and rational design of sequence-specific ligands. In Murakami,Y. (ed.), Comprehensive supramolecular chemistry. Pergamon, Vol. 4, pp. 177-192.
    • (1996) Comprehensive Supramolecular Chemistry , vol.4 , pp. 177-192
    • Giovannangeli, C.1    Sun, J.-S.2    Helene, C.3
  • 13
    • 0024341224 scopus 로고
    • Sequence-specific intercalating agents: Intercalation at specific sequences on duplex DNA via major groove recognition by oligonucleotide-intercalator conjugates
    • Sun,J.S., Francois,J.C., Montenay-Garestier,T., Saison-Behmoaras,T., Roig,V., Thuong,N.T. and Helene,C. (1989) Sequence-specific intercalating agents: Intercalation at specific sequences on duplex DNA via major groove recognition by oligonucleotide-intercalator conjugates. Proc. Natl Acad. Sci. USA, 86, 9198-9202.
    • (1989) Proc. Natl. Acad. Sci. USA , vol.86 , pp. 9198-9202
    • Sun, J.S.1    Francois, J.C.2    Montenay-Garestier, T.3    Saison-Behmoaras, T.4    Roig, V.5    Thuong, N.T.6    Helene, C.7
  • 14
    • 1842378588 scopus 로고    scopus 로고
    • Triple helix formation with purine-rich phosphorothioate-containing oligonucleotides covalently linked to an acridine derivative
    • Lacoste,J., Francois,J.C. and Helene,C. (1997) Triple helix formation with purine-rich phosphorothioate-containing oligonucleotides covalently linked to an acridine derivative. Nucleic Acids Res., 25, 1991-1998.
    • (1997) Nucleic Acids Res. , vol.25 , pp. 1991-1998
    • Lacoste, J.1    Francois, J.C.2    Helene, C.3
  • 16
    • 0026677170 scopus 로고
    • A computational and experimental study of the bending induced at a double-triple helix junction
    • Chomilier,J., Sun,J.S., Collier,D.A., Garestier,T., Helene,C. and Lavery,R. (1992) A computational and experimental study of the bending induced at a double-triple helix junction. Biophys. Chem., 45, 143-152.
    • (1992) Biophys. Chem. , vol.45 , pp. 143-152
    • Chomilier, J.1    Sun, J.S.2    Collier, D.A.3    Garestier, T.4    Helene, C.5    Lavery, R.6
  • 18
    • 0035914386 scopus 로고    scopus 로고
    • Chromosome targeting at short polypurine sites by cationic triplex-forming oligonucleotides
    • Vasquez,K.M., Dagle,J.M., Weeks,D.L. and Glazer,P.M. (2001) Chromosome targeting at short polypurine sites by cationic triplex-forming oligonucleotides. 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
  • 20
    • 0003448581 scopus 로고    scopus 로고
    • Incorporation of halogenoalkyl, 2-pyridyldithioalkyl, or isothiocyanate linkers into ligands
    • Beaucage,S.L., Bergstrom,D.E., Glick,G.D. and Jones,R.A. (eds), John Wiley and Sons, Chap. 4.8
    • Asseline,U. and Thuong,N.T. (2001) Incorporation of halogenoalkyl, 2-pyridyldithioalkyl, or isothiocyanate linkers into ligands. In Beaucage,S.L., Bergstrom,D.E., Glick,G.D. and Jones,R.A. (eds), Current Protocols in Nucleic Acid Chemistry. John Wiley and Sons, Vol. 1, Chap. 4.8, pp. 1-13.
    • (2001) Current Protocols in Nucleic Acid Chemistry , vol.1 , pp. 1-13
    • Asseline, U.1    Thuong, N.T.2
  • 21
    • 0025923396 scopus 로고
    • Synthesis and physicochemical properties of oligonucleotides built with either alpha-L or beta-L nucleotides units and covalently linked to an acridine derivative
    • Asseline,U., Hau,J.F., Czernecki,S., Le Diguarher,T., Perlat,M.C., Valery,J.M. and Thuong,N.T. (1991) Synthesis and physicochemical properties of oligonucleotides built with either alpha-L or beta-L nucleotides units and covalently linked to an acridine derivative. Nucleic Acids Res., 19, 4067-4074.
    • (1991) Nucleic Acids Res. , vol.19 , pp. 4067-4074
    • Asseline, U.1    Hau, J.F.2    Czernecki, S.3    Le Diguarher, T.4    Perlat, M.C.5    Valery, J.M.6    Thuong, N.T.7
  • 22
    • 0029797724 scopus 로고    scopus 로고
    • Specific inhibition of in vitro transcription elongation by triplex-forming oligonucleotide-intercalator conjugates targeted to HIV proviral DNA
    • Giovannangeli,C., Perrouault,L., Escude,C., Nguyen,T. and Helene,C. (1996) Specific inhibition of in vitro transcription elongation by triplex-forming oligonucleotide-intercalator conjugates targeted to HIV proviral DNA. Biochemistry, 35, 10539-10548.
    • (1996) Biochemistry , vol.35 , pp. 10539-10548
    • Giovannangeli, C.1    Perrouault, L.2    Escude, C.3    Nguyen, T.4    Helene, C.5
  • 23
    • 0035830485 scopus 로고    scopus 로고
    • Transcription inhibition induced by modified triple helix-forming oligonucleotides: A quantitative assay for evaluation in cells
    • Faria,M., Wood,C.D., White,M.R., Helene,C. and Giovannangeli,C. (2001) Transcription inhibition induced by modified triple helix-forming oligonucleotides: A quantitative assay for evaluation in cells. J. Mol. Biol., 306, 15-24.
    • (2001) J. Mol. Biol. , vol.306 , pp. 15-24
    • Faria, M.1    Wood, C.D.2    White, M.R.3    Helene, C.4    Giovannangeli, C.5
  • 25
    • 21244489606 scopus 로고    scopus 로고
    • Exploring cellular activity of Locked Nucleic Acid-modified triplex-forming oligonucleotides and defining its molecular basis
    • Brunet,E., Alberti,P., Perrouault,L., Babu,R., Wengel,J. and Giovannangeli,C. (2005) Exploring cellular activity of Locked Nucleic Acid-modified triplex-forming oligonucleotides and defining its molecular basis. J. Biol. Chem., 80, 20076-20085.
    • (2005) J. Biol. Chem. , vol.80 , pp. 20076-20085
    • Brunet, E.1    Alberti, P.2    Perrouault, L.3    Babu, R.4    Wengel, J.5    Giovannangeli, C.6
  • 26
    • 0027965903 scopus 로고
    • HIV-1 reverse transcription. A termination step at the center of the genome
    • Charneau,P., Mirambeau,G., Roux,P., Paulous,S., Buc,H. and Clavel,F. (1994) HIV-1 reverse transcription. A termination step at the center of the genome. J. Mol. Biol., 241, 651-662.
    • (1994) J. Mol. Biol. , vol.241 , pp. 651-662
    • Charneau, P.1    Mirambeau, G.2    Roux, P.3    Paulous, S.4    Buc, H.5    Clavel, F.6
  • 27
  • 28
    • 0032488878 scopus 로고    scopus 로고
    • The contribution of cytosine protonation to the stability of parallel DNA triple helices
    • Asensio,J.L., Lane,A.N., Dhesi,J., Bergqvist,S. and Brown,T. (1998) The contribution of cytosine protonation to the stability of parallel DNA triple helices. J. Mol. Biol., 275, 811-822.
    • (1998) J. Mol. Biol. , vol.275 , pp. 811-822
    • Asensio, J.L.1    Lane, A.N.2    Dhesi, J.3    Bergqvist, S.4    Brown, T.5
  • 29
    • 0036567147 scopus 로고    scopus 로고
    • Design of antisense oligonucleotides stabilized by locked nucleic acids
    • Kurreck,J., Wyszko,E., Gillen,C. and Erdmann,V.A. (2002) Design of antisense oligonucleotides stabilized by locked nucleic acids. Nucleic Acids Res., 30, 1911-1918.
    • (2002) Nucleic Acids Res. , vol.30 , pp. 1911-1918
    • Kurreck, J.1    Wyszko, E.2    Gillen, C.3    Erdmann, V.A.4
  • 30
    • 0026739476 scopus 로고
    • Triple-helix formation by oligonucleotides containing the three bases thymine, cytosine, and guanine
    • Giovannangeli,C., Rougee,M., Garestier,T., Thuong,N.T. and Helene,C. (1992) Triple-helix formation by oligonucleotides containing the three bases thymine, cytosine, and guanine. Proc. Natl Acad. Sci. USA, 89, 8631-8635.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 8631-8635
    • Giovannangeli, C.1    Rougee, M.2    Garestier, T.3    Thuong, N.T.4    Helene, C.5
  • 31
    • 4544379668 scopus 로고    scopus 로고
    • Down-regulation of MDM2 and activation of p53 in human cancer cells by antisense 9-aminoacridine-PNA (peptide nucleic acid) conjugates
    • Shiraishi,T. and Nielsen,P.E. (2004) Down-regulation of MDM2 and activation of p53 in human cancer cells by antisense 9-aminoacridine-PNA (peptide nucleic acid) conjugates. Nucleic Acids Res., 32, 4893-4902.
    • (2004) Nucleic Acids Res. , vol.32 , pp. 4893-4902
    • Shiraishi, T.1    Nielsen, P.E.2
  • 32
    • 0026640729 scopus 로고
    • A triple helix-forming oligonucleotide-intercalator conjugate acts as a transcriptional repressor via inhibition of NF kappa B binding to interleukin-2 receptor alpha-regulatory sequence
    • Grigoriev,M., Praseuth,D., Robin,P., Hemar,A., Saison-Behmoaras,T., Dautry-Varsat,A., Thuong,N.T., Helene,C. and Harel-Bellan,A. (1992) A triple helix-forming oligonucleotide-intercalator conjugate acts as a transcriptional repressor via inhibition of NF kappa B binding to interleukin-2 receptor alpha-regulatory sequence. J. Biol. Chem., 267, 3389-3395.
    • (1992) J. Biol. Chem. , vol.267 , pp. 3389-3395
    • Grigoriev, M.1    Praseuth, D.2    Robin, P.3    Hemar, A.4    Saison-Behmoaras, T.5    Dautry-Varsat, A.6    Thuong, N.T.7    Helene, C.8    Harel-Bellan, A.9
  • 33
    • 16844375686 scopus 로고    scopus 로고
    • Chemical approaches to the discovery and development of cancer therapies
    • Neidle,S. and Thurston,D.E. (2005) Chemical approaches to the discovery and development of cancer therapies. Nat. Rev. Cancer, 5, 285-296.
    • (2005) Nat. Rev. Cancer , vol.5 , pp. 285-296
    • Neidle, S.1    Thurston, D.E.2
  • 34
    • 25644434052 scopus 로고    scopus 로고
    • DNA and RNA cleavage mediated by phenanthroline-cuprous oligonucleotides: From properties to applications
    • Zenkova,M. A. (ed.), Springer-Verlag, Germany
    • François,J.-C., Faria,M., Perrin,D. and Giovannangeli,C. (2004) DNA and RNA cleavage mediated by phenanthroline-cuprous oligonucleotides: from properties to applications. In Zenkova,M. A. (ed.), Nucleic Acids and Molecular Biology - Artificial Nucleases. Springer-Verlag, Germany, Vol. 13, pp. 223-242.
    • (2004) Nucleic Acids and Molecular Biology - Artificial Nucleases , vol.13 , pp. 223-242
    • François, J.-C.1    Faria, M.2    Perrin, D.3    Giovannangeli, C.4
  • 35
    • 0036479132 scopus 로고    scopus 로고
    • Design and optimization of camptothecin conjugates of triple helix-forming oligonucleotides for sequence-specific DNA cleavage by topoisomerase I
    • Arimondo,P.B., Boutorine,A., Baldeyrou,B., Bailly,C., Kuwahara,M., Hecht,S.M., Sun,J.S., Garestier,T. and Helene,C. (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.
    • (2002) J. Biol. Chem. , vol.277 , pp. 3132-3140
    • Arimondo, P.B.1    Boutorine, A.2    Baldeyrou, B.3    Bailly, C.4    Kuwahara, M.5    Hecht, S.M.6    Sun, J.S.7    Garestier, T.8    Helene, C.9
  • 36
    • 0032542023 scopus 로고    scopus 로고
    • Triple-helix formation at different positions on nucleosomal DNA
    • Brown,P.M., Madden,C.A. and Fox,K.R. (1998) Triple-helix formation at different positions on nucleosomal DNA. Biochemistry, 37, 16139-16151.
    • (1998) Biochemistry , vol.37 , pp. 16139-16151
    • Brown, P.M.1    Madden, C.A.2    Fox, K.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.