메뉴 건너뛰기




Volumn 37, Issue 4, 2009, Pages 1353-1362

Synthesis and characterization of 2′-modified-4′-thioRNA: A comprehensive comparison of nuclease stability

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORORNA; 2' O METHYLRNA; APTAMER; COMPLEMENTARY RNA; DNA; OLIGONUCLEOTIDE; SINGLE STRANDED RNA; TRANSFER RNA; UNCLASSIFIED DRUG;

EID: 62549113972     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkn1088     Document Type: Article
Times cited : (55)

References (34)
  • 1
    • 33751430435 scopus 로고    scopus 로고
    • Building oligonucleotide therapeutics using non-natural chemistries
    • Wilson,C. and Keefe,A.D. (2006) Building oligonucleotide therapeutics using non-natural chemistries. Curr. Opin. Chem. Biol., 10, 607-614.
    • (2006) Curr. Opin. Chem. Biol , vol.10 , pp. 607-614
    • Wilson, C.1    Keefe, A.D.2
  • 2
    • 36849094017 scopus 로고    scopus 로고
    • Chemical modification: The key to clinical application of RNA interference?
    • Corey,D.R. (2007) Chemical modification: The key to clinical application of RNA interference? J. Clin. Invest., 117, 3615-3622.
    • (2007) J. Clin. Invest , vol.117 , pp. 3615-3622
    • Corey, D.R.1
  • 3
    • 0032750621 scopus 로고    scopus 로고
    • 2′-Carbohydrate modifications in antisense oligonucleotide therapy: Importance of conformation, configuration and conjugation
    • Manoharan,M. (1999) 2′-Carbohydrate modifications in antisense oligonucleotide therapy: Importance of conformation, configuration and conjugation. Biochim. Biophys. Acta, 1489, 117-130.
    • (1999) Biochim. Biophys. Acta , vol.1489 , pp. 117-130
    • Manoharan, M.1
  • 4
    • 0023651145 scopus 로고
    • Synthesis and hybridization studies on two complementary nona-(2′-O methyl)ribonucleotides
    • Inoue,H., Hayase,Y., Imura,A., Iwai,S., Miura,K. and Ohtsuka,E. (1987) Synthesis and hybridization studies on two complementary nona-(2′-O methyl)ribonucleotides. Nucleic Acids Res., 15, 6131-6148.
    • (1987) Nucleic Acids Res , vol.15 , pp. 6131-6148
    • Inoue, H.1    Hayase, Y.2    Imura, A.3    Iwai, S.4    Miura, K.5    Ohtsuka, E.6
  • 5
    • 0027479864 scopus 로고
    • Uniformly modified 2′-deoxy-2′-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets
    • Kawasaki,A.M., Casper,M.D., Freier,S.M., Lesnik,E.A., Zounes,M.C., Cummins,L.L., Gonzales,C. and Cook,P.D. (1993) Uniformly modified 2′-deoxy-2′-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets. J. Med. Chem., 36, 831-841.
    • (1993) J. Med. Chem , vol.36 , pp. 831-841
    • Kawasaki, A.M.1    Casper, M.D.2    Freier, S.M.3    Lesnik, E.A.4    Zounes, M.C.5    Cummins, L.L.6    Gonzales, C.7    Cook, P.D.8
  • 6
  • 8
    • 0034596301 scopus 로고    scopus 로고
    • The stereoselective synthesis of 4′-β-thioribonucleosides via the Pummerer reaction
    • Naka,T., Minakawa,N., Abe,H., Kaga,D. and Matsuda,A. (2000) The stereoselective synthesis of 4′-β-thioribonucleosides via the Pummerer reaction. J. Am. Chem. Soc., 122, 7233-7243.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 7233-7243
    • Naka, T.1    Minakawa, N.2    Abe, H.3    Kaga, D.4    Matsuda, A.5
  • 9
    • 26844449313 scopus 로고    scopus 로고
    • Practical synthesis of 2′-deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-thioDNA
    • Inoue,N., Kaga,D., Minakawa,N. and Matsuda,A. (2005) Practical synthesis of 2′-deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-thioDNA. J. Org. Chem., 70, 8597-8600.
    • (2005) J. Org. Chem , vol.70 , pp. 8597-8600
    • Inoue, N.1    Kaga, D.2    Minakawa, N.3    Matsuda, A.4
  • 10
    • 3142720243 scopus 로고    scopus 로고
    • Synthesis and physical and physiological properties of 4′-thioRNA: Application to post-modification of RNA aptamer toward NF-κB
    • Hoshika,S., Minakawa,N. and Matsuda,A. (2004) Synthesis and physical and physiological properties of 4′-thioRNA: Application to post-modification of RNA aptamer toward NF-κB. Nucleic Acids Res. 32, 3815-3825.
    • (2004) Nucleic Acids Res , vol.32 , pp. 3815-3825
    • Hoshika, S.1    Minakawa, N.2    Matsuda, A.3
  • 11
    • 33746857804 scopus 로고    scopus 로고
    • Synthesis and properties of 4′-thioDNA: Unexpected RNA-like behavior of 4′-thioDNA
    • Inoue,N., Minakawa,N. and Matsuda,A. (2006) Synthesis and properties of 4′-thioDNA: Unexpected RNA-like behavior of 4′-thioDNA. Nucleic Acids Res., 34, 3476-3483.
    • (2006) Nucleic Acids Res , vol.34 , pp. 3476-3483
    • Inoue, N.1    Minakawa, N.2    Matsuda, A.3
  • 12
    • 41849084875 scopus 로고    scopus 로고
    • Unexpected A-form formation of 4′-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease resistance
    • Matsugami,A., Ohyama,T., Inada,M., Inoue,N., Minakawa,N., Matsuda,A. and Katahira,M. (2008) Unexpected A-form formation of 4′-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease resistance. Nucleic Acids Res., 36, 1805-1812.
    • (2008) Nucleic Acids Res , vol.36 , pp. 1805-1812
    • Matsugami, A.1    Ohyama, T.2    Inada, M.3    Inoue, N.4    Minakawa, N.5    Matsuda, A.6    Katahira, M.7
  • 13
  • 14
    • 53749105287 scopus 로고    scopus 로고
    • Investigations toward the selection of fully-modified 4′-thioRNA aptamers: Optimization of in vitro transcription steps in the presence of 4′-thioNTPs
    • Minakawa,N., Sanji,M., Kato,Y. and Matsuda,A. (2008) Investigations toward the selection of fully-modified 4′-thioRNA aptamers: optimization of in vitro transcription steps in the presence of 4′-thioNTPs. Bioorg. Med. Chem., 16, 9450-9456.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 9450-9456
    • Minakawa, N.1    Sanji, M.2    Kato, Y.3    Matsuda, A.4
  • 15
    • 20444410838 scopus 로고    scopus 로고
    • RNA interference induced by siRNAs modified with 4′-thioribonucleosides in cultured mammalian cells
    • Hoshika,S., Minakawa,N., Kamiya,H., Harashima,H. and Matsuda,A. (2005) RNA interference induced by siRNAs modified with 4′-thioribonucleosides in cultured mammalian cells. FEBS Lett., 579, 3115-3118.
    • (2005) FEBS Lett , vol.579 , pp. 3115-3118
    • Hoshika, S.1    Minakawa, N.2    Kamiya, H.3    Harashima, H.4    Matsuda, A.5
  • 16
    • 36849060537 scopus 로고    scopus 로고
    • Study of modification pattern - RNA activity relationships by using siRNAs modified with 4′-thioribonucleosides
    • Hoshika,S., Minakawa,N., Shionoya,A., Imada,K., Ogawa,N. and Matsuda,A. (2007) Study of modification pattern - RNA activity relationships by using siRNAs modified with 4′-thioribonucleosides. Chem. Bio. Chem. 8, 2133-2138.
    • (2007) Chem. Bio. Chem , vol.8 , pp. 2133-2138
    • Hoshika, S.1    Minakawa, N.2    Shionoya, A.3    Imada, K.4    Ogawa, N.5    Matsuda, A.6
  • 17
    • 37848999066 scopus 로고    scopus 로고
    • Amplification of 4′-thioDNA in the presence of 4′-thio-dTTP and 4′-thio-dCTP, and 4′thioDNA-directed transcription in vitro and in mammalian cells
    • Inoue,N., Shionoya,A., Minakawa,N., Kawakami,A., Ogawa,N. and Matsuda,A. (2007) Amplification of 4′-thioDNA in the presence of 4′-thio-dTTP and 4′-thio-dCTP, and 4′thioDNA-directed transcription in vitro and in mammalian cells. J. Am. Chem. Soc., 129, 15424-15425.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 15424-15425
    • Inoue, N.1    Shionoya, A.2    Minakawa, N.3    Kawakami, A.4    Ogawa, N.5    Matsuda, A.6
  • 18
    • 41549138647 scopus 로고    scopus 로고
    • Synthesis and crystal structure of 2′-deoxy-2′- fluoro-4′-thioribonucleosides: Substrates for the synthesis of novel modified RNAs
    • Takahashi,M., Daidouji,S., Shiro,M., Minakawa,N. and Matsuda,A. (2008) Synthesis and crystal structure of 2′-deoxy-2′- fluoro-4′-thioribonucleosides: Substrates for the synthesis of novel modified RNAs. Tetrahedron, 64, 4313-4324.
    • (2008) Tetrahedron , vol.64 , pp. 4313-4324
    • Takahashi, M.1    Daidouji, S.2    Shiro, M.3    Minakawa, N.4    Matsuda, A.5
  • 20
    • 0034681342 scopus 로고    scopus 로고
    • Improved synthetic approaches toward 2′-O-methyl-adenosine and guanosine and their N-acyl derivatives
    • Beigelman,L., Haeberli,P., Sweedler,D. and Karpeisky,A. (2000) Improved synthetic approaches toward 2′-O-methyl-adenosine and guanosine and their N-acyl derivatives. Tetrahedron, 56, 1047-1056.
    • (2000) Tetrahedron , vol.56 , pp. 1047-1056
    • Beigelman, L.1    Haeberli, P.2    Sweedler, D.3    Karpeisky, A.4
  • 22
    • 0028500180 scopus 로고
    • Stabilizing effects of the RNA 2′-substituent: Crystal structure of an oligodeoxynucleotide duplex containing 2′-O-methylated adenosines
    • Lubini,P., Zürcher,W. and Egli,M. (1994) Stabilizing effects of the RNA 2′-substituent: Crystal structure of an oligodeoxynucleotide duplex containing 2′-O-methylated adenosines. Chem. Biol., 1, 39-45.
    • (1994) Chem. Biol , vol.1 , pp. 39-45
    • Lubini, P.1    Zürcher, W.2    Egli, M.3
  • 23
    • 0032510712 scopus 로고    scopus 로고
    • What affects the effect of 2′-alkoxy modification? 1. Stabilization effect of 2′-methoxy substitutions in uniformly modified DNA oligonucleotides
    • Lesnik,E.A. and Freier,S.M. (1998) What affects the effect of 2′-alkoxy modification? 1. Stabilization effect of 2′-methoxy substitutions in uniformly modified DNA oligonucleotides. Biochemistry, 37, 6991-6997.
    • (1998) Biochemistry , vol.37 , pp. 6991-6997
    • Lesnik, E.A.1    Freier, S.M.2
  • 24
    • 0035905574 scopus 로고    scopus 로고
    • Hydrophobic groups stabilize the hydration shell of 2′-O-methylated RNA duplexes
    • Auffinger,P. and Westhof,E. (2001) Hydrophobic groups stabilize the hydration shell of 2′-O-methylated RNA duplexes. Angew. Chem. Int. Ed., 40, 4648-4650.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 4648-4650
    • Auffinger, P.1    Westhof, E.2
  • 25
    • 22844448221 scopus 로고    scopus 로고
    • Synthesis of 4′-thioribonucleosides and thermodynamic stability and crystal structure of RNA oligomers with incorporated 4′-thiocytosine
    • Haeberli,P., Berger,L., Pallan,P.S. and Egli,M. (2005) Synthesis of 4′-thioribonucleosides and thermodynamic stability and crystal structure of RNA oligomers with incorporated 4′-thiocytosine. Nucleic Acids Res., 33, 3965-3975.
    • (2005) Nucleic Acids Res , vol.33 , pp. 3965-3975
    • Haeberli, P.1    Berger, L.2    Pallan, P.S.3    Egli, M.4
  • 26
    • 0030825878 scopus 로고    scopus 로고
    • 2′-Fluoro modified nucleic acids: Polymerase-directed synthesis, properties and stability to analysis by matrix-assisted laser desorption/ionization mass spectrometry
    • Ono,T., Scalf,M. and Smith,L.M. (1997) 2′-Fluoro modified nucleic acids: Polymerase-directed synthesis, properties and stability to analysis by matrix-assisted laser desorption/ionization mass spectrometry. Nucleic Acids Res., 25, 4581-4588.
    • (1997) Nucleic Acids Res , vol.25 , pp. 4581-4588
    • Ono, T.1    Scalf, M.2    Smith, L.M.3
  • 27
    • 0027263108 scopus 로고
    • 4′-Thio-oligo-β-D-ribonucleotides: Synthesis of β-4′-thio-oligouridylates nuclease resistance base pairing properties and interaction with HIV-1 reverse transcriptase
    • Bellon,L., Barascut,J.-L., Maury,G., Divita,G., Goody,R. and Imbach,J.-L. (1993) 4′-Thio-oligo-β-D-ribonucleotides: Synthesis of β-4′-thio-oligouridylates nuclease resistance base pairing properties and interaction with HIV-1 reverse transcriptase. Nucleic Acids Res. 21, 1587-1593.
    • (1993) Nucleic Acids Res , vol.21 , pp. 1587-1593
    • Bellon, L.1    Barascut, J.-L.2    Maury, G.3    Divita, G.4    Goody, R.5    Imbach, J.-L.6
  • 28
    • 0028820184 scopus 로고
    • 4′-Thio-RNA: Synthesis of mixed base 4′-thio-oligoribonucleotides, nuclease resistance, and base pairing properties with complementary single and double strand
    • Leydier,C., Bellon,L., Barascut,J.-L., Morvan,F., Rayner,B. and Imbach,J.-L. (1995) 4′-Thio-RNA: Synthesis of mixed base 4′-thio-oligoribonucleotides, nuclease resistance, and base pairing properties with complementary single and double strand. Antisense Res. Dev., 5, 167-174.
    • (1995) Antisense Res. Dev , vol.5 , pp. 167-174
    • Leydier, C.1    Bellon, L.2    Barascut, J.-L.3    Morvan, F.4    Rayner, B.5    Imbach, J.-L.6
  • 29
    • 0026175462 scopus 로고
    • Substrate specificity and kinetics of degradation of antisense oligonucleotides by a 3′ exonuclease in plasma
    • Eder,P.S., DeVine,R.J., Dagle,J.M. and Walder,J.A. (1991) Substrate specificity and kinetics of degradation of antisense oligonucleotides by a 3′ exonuclease in plasma. Antisense Res. Dev., 1, 141-151.
    • (1991) Antisense Res. Dev , vol.1 , pp. 141-151
    • Eder, P.S.1    DeVine, R.J.2    Dagle, J.M.3    Walder, J.A.4
  • 30
    • 0027227872 scopus 로고
    • Nuclease-resistant chimeric ribozymes containing deoxyribonucleotides and phosphorothioate linkages
    • Shimayama,T., Nishikawa,F., Nishikawa,S. and Taira,K. (1993) Nuclease-resistant chimeric ribozymes containing deoxyribonucleotides and phosphorothioate linkages. Nucleic Acids Res., 21, 2605-2611.
    • (1993) Nucleic Acids Res , vol.21 , pp. 2605-2611
    • Shimayama, T.1    Nishikawa, F.2    Nishikawa, S.3    Taira, K.4
  • 31
    • 0014238159 scopus 로고
    • The chain termini of polynucleotides formed by limited enzymic fragmentation of wheat embryo ribosomal RNA. Part 2. Studies of a snake venom rebonuclease and pancreas ribonuclease
    • McLennan,B.D. and Lane,B.G. (1968) The chain termini of polynucleotides formed by limited enzymic fragmentation of wheat embryo ribosomal RNA. Part 2. Studies of a snake venom rebonuclease and pancreas ribonuclease. Can. J. Biochem., 46, 93-107.
    • (1968) Can. J. Biochem , vol.46 , pp. 93-107
    • McLennan, B.D.1    Lane, B.G.2
  • 33
    • 0027258493 scopus 로고
    • Alcohol esterification reactions and mechanisms of snake venom 5′-nucleotide phosphodiesterase
    • Garcia-Diaz, M., Avalos,M. and Cameselle,J.C. (1993) Alcohol esterification reactions and mechanisms of snake venom 5′-nucleotide phosphodiesterase. Eur. J. Biochem., 213, 1139-1148.
    • (1993) Eur. J. Biochem , vol.213 , pp. 1139-1148
    • Garcia-Diaz, M.1    Avalos, M.2    Cameselle, J.C.3
  • 34
    • 0031224812 scopus 로고    scopus 로고
    • DNA recognition by structure-selective nucleases
    • Suck,D. (1997) DNA recognition by structure-selective nucleases. Biopolymers, 44, 405-421.
    • (1997) Biopolymers , vol.44 , pp. 405-421
    • Suck, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.