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Volumn 32, Issue 3, 2013, Pages 109-123

Effective synthesis of 3'-deoxy-3'-azido nucleosides for antiviral and antisense ribonucleic guanidine (RNG) applications

Author keywords

Antisense; Nucleoside 3' azido; Ribonucleic guanidine; RNA; Solid phase synthesis

Indexed keywords

3' DEOXY 3' AZIDO NUCELOSIDE; ANTIVIRUS AGENT; GUANIDINE; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

EID: 84875942415     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2013.766752     Document Type: Article
Times cited : (6)

References (27)
  • 1
    • 0036636579 scopus 로고    scopus 로고
    • Nucleoside analogues and nucleobases in cancer treatment
    • Galmarini, C.M.; Mackey, J.R.; Dumontet, C. Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol. 2002, 3(7), 415-424.
    • (2002) Lancet Oncol. , vol.3 , Issue.7 , pp. 415-424
    • Galmarini, C.M.1    MacKey, J.R.2    Dumontet, C.3
  • 2
    • 77956647281 scopus 로고    scopus 로고
    • Antiretroviral drugs
    • De Clercq, E. Antiretroviral drugs. Curr. Opin. Pharmacol. 2010, 10(5), 507-515.
    • (2010) Curr. Opin. Pharmacol. , vol.10 , Issue.5 , pp. 507-515
    • De Clercq, E.1
  • 3
    • 11944267365 scopus 로고
    • Antisense oligonucleotides: A new therapeutic principle
    • Uhlmann, E.; Peyman, A. Antisense oligonucleotides: a new therapeutic principle. Chem. Rev. 1990, 90(4), 543-584.
    • (1990) Chem. Rev. , vol.90 , Issue.4 , pp. 543-584
    • Uhlmann, E.1    Peyman, A.2
  • 4
    • 0036636074 scopus 로고    scopus 로고
    • Nucleic-acid therapeutics: Basic principles and recent applications
    • Opalinska, J.B.; Gewirtz, A.M. Nucleic-acid therapeutics: basic principles and recent applications. Nat. Rev. Drug Discov. 2002, 1, 503-514.
    • (2002) Nat. Rev. Drug Discov. , vol.1 , pp. 503-514
    • Opalinska, J.B.1    Gewirtz, A.M.2
  • 5
    • 0026975584 scopus 로고
    • Selective anti-gene therapy for cancer: Principles and prospects
    • Cohen, J.S. Selective anti-gene therapy for cancer: principles and prospects. Tohoku J. Exp Med. 1992, 168(2), 351-359.
    • (1992) Tohoku J. Exp Med. , vol.168 , Issue.2 , pp. 351-359
    • Cohen, J.S.1
  • 6
    • 4644328087 scopus 로고    scopus 로고
    • The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics
    • Pellestor, F.; Paulasova, P. The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics. Eur. J. Hum. Genet. 2004, 12(9), 694-700.
    • (2004) Eur. J. Hum. Genet. , vol.12 , Issue.9 , pp. 694-700
    • Pellestor, F.1    Paulasova, P.2
  • 7
    • 0023921083 scopus 로고
    • Oligonucleotides as inhibitors of gene expression: A review
    • Stein, C.A.; Cohen, J.S. Oligonucleotides as inhibitors of gene expression: a review. Cancer Res. 1988, 48, 2659-2668.
    • (1988) Cancer Res. , vol.48 , pp. 2659-2668
    • Stein, C.A.1    Cohen, J.S.2
  • 8
    • 0027376439 scopus 로고
    • Antisense oligonucleotides as therapeutic agents - is the bullet really magical?
    • Stein, C.A.; Cheng, Y.C. Antisense oligonucleotides as therapeutic agents - is the bullet really magical? Science. 1993, 261(5124), 1004-1012.
    • (1993) Science. , vol.261 , Issue.5124 , pp. 1004-1012
    • Stein, C.A.1    Cheng, Y.C.2
  • 9
    • 0032530479 scopus 로고    scopus 로고
    • Synthesis, biophysical properties, and nuclease resistance properties of mixed backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: Deoxynucleic guanidine/DNA chimeras
    • Barawkar, D.A.; Bruice, T.C. Synthesis, biophysical properties, and nuclease resistance properties of mixed backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: deoxynucleic guanidine/DNA chimeras. Proc. Natl. Acad. Sci. USA. 1998, 95(19), 11047-11052.
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , Issue.19 , pp. 11047-11052
    • Barawkar, D.A.1    Bruice, T.C.2
  • 10
    • 0028059256 scopus 로고
    • Design and synthesis of deoxynucleic guanidine: A polycation analogue of DNA
    • Dempcy, R.O.; Almarsson, O.; Bruice, T.C. Design and synthesis of deoxynucleic guanidine: a polycation analogue of DNA. Proc. Natl. Acad. Sci. USA. 1994, 91(17), 7864-7868.
    • (1994) Proc. Natl. Acad. Sci. USA , vol.91 , Issue.17 , pp. 7864-7868
    • Dempcy, R.O.1    Almarsson, O.2    Bruice, T.C.3
  • 11
    • 0029001386 scopus 로고
    • Synthesis of the polycation thymidyl DNG, its fidelity in binding polyanionic DNA/RNA, and the stability and nature of the hybrid complexes
    • Dempcy, R.O.; Browne, K.A.; Bruice, T.C. Synthesis of the polycation thymidyl DNG, its fidelity in binding polyanionic DNA/RNA, and the stability and nature of the hybrid complexes. J. Am. Chem. Soc. 1995, 117(22), 6140-6141.
    • (1995) J. Am. Chem. Soc. , vol.117 , Issue.22 , pp. 6140-6141
    • Dempcy, R.O.1    Browne, K.A.2    Bruice, T.C.3
  • 12
    • 0035369053 scopus 로고    scopus 로고
    • Solid-phase synthesis of oligopurine deoxynucleic guanidine (DNG) and analysis of binding with DNA oligomers
    • Linkletter, B.A.; Szabo, I.E.; Bruice, T.C. Solid-phase synthesis of oligopurine deoxynucleic guanidine (DNG) and analysis of binding with DNA oligomers. Nucleic Acids Res. 2001, 29(11), 2370-2376.
    • (2001) Nucleic Acids Res. , vol.29 , Issue.11 , pp. 2370-2376
    • Linkletter, B.A.1    Szabo, I.E.2    Bruice, T.C.3
  • 13
    • 0029036905 scopus 로고
    • Synthesis of a thymidyl pentamer of deoxyribonucleic guanidine and binding studies with DNA homopolynucleotides
    • Dempcy, R.O.; Browne, K.A.; Bruice, T.C. Synthesis of a thymidyl pentamer of deoxyribonucleic guanidine and binding studies with DNA homopolynucleotides. Proc. Natl. Acad. Sci. USA. 1995, 92(13), 6097-6101.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , Issue.13 , pp. 6097-6101
    • Dempcy, R.O.1    Browne, K.A.2    Bruice, T.C.3
  • 14
    • 0029935167 scopus 로고    scopus 로고
    • Design and synthesis of ribonucleic guanidine: A polycationic analog of RNA
    • Dempcy, R.O.; Luo, J.; Bruice, T.C. Design and synthesis of ribonucleic guanidine: a polycationic analog of RNA. Proc. Natl. Acad. Sci. USA. 1996, 93(9), 4326-4330.
    • (1996) Proc. Natl. Acad. Sci. USA , vol.93 , Issue.9 , pp. 4326-4330
    • Dempcy, R.O.1    Luo, J.2    Bruice, T.C.3
  • 15
    • 0037185355 scopus 로고    scopus 로고
    • Synthesis of ribonucleic guanidine: Replacement of the negative phosphodiester linkages of RNA with positive guanidinium linkages
    • Kojima, N.; Szabo, I.E.; Bruice, T.C. Synthesis of ribonucleic guanidine: replacement of the negative phosphodiester linkages of RNA with positive guanidinium linkages. Tetrahedron. 2002, 58(2), 867-879.
    • (2002) Tetrahedron. , vol.58 , Issue.2 , pp. 867-879
    • Kojima, N.1    Szabo, I.E.2    Bruice, T.C.3
  • 16
    • 84862238812 scopus 로고    scopus 로고
    • A convenient synthesis of the cytidyl 3-terminal monomer for solid-phase synthesis of RNG oligonucleotides
    • Awad, A.M.; Collazo, M.J.; Carpio, K.; Flores, C.; Bruice, T.C. A convenient synthesis of the cytidyl 3-terminal monomer for solid-phase synthesis of RNG oligonucleotides. Tetrahedron Lett. 2012, 53, 3792-3794.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 3792-3794
    • Awad, A.M.1    Collazo, M.J.2    Carpio, K.3    Flores, C.4    Bruice, T.C.5
  • 17
    • 77949729607 scopus 로고    scopus 로고
    • Oligonucleotide N3→P5 phosphoramidates and thio-phoshoramidates as potential therapeutic agents
    • Gryaznov, S.M. Oligonucleotide N3→P5 phosphoramidates and thio-phoshoramidates as potential therapeutic agents. Chem. Biodivers. 2010, 7, 477-493.
    • (2010) Chem. Biodivers. , vol.7 , pp. 477-493
    • Gryaznov, S.M.1
  • 18
    • 0023732797 scopus 로고
    • Anchimeric assistance of a 5-O-carbonyl function for inversion of configuration at the 3-carbon atom of 2-deoxyadenosine. Synthesis of 3-azido-2,3-dideoxyadenosine and 3-azido-2,3- dideoxyinosine
    • Herdewijn, P. Anchimeric assistance of a 5-O-carbonyl function for inversion of configuration at the 3-carbon atom of 2-deoxyadenosine. Synthesis of 3-azido-2,3-dideoxyadenosine and 3-azido-2,3- dideoxyinosine. J. Org. Chem. 1988, 53, 5050-5053.
    • (1988) J. Org. Chem. , vol.53 , pp. 5050-5053
    • Herdewijn, P.1
  • 19
    • 3042800347 scopus 로고    scopus 로고
    • DNG cytidine: Synthesis and binding properties of octameric guanidiniumlinked deoxycytidine oligomer
    • Szabo, I.E.; Bruice, T.C. DNG cytidine: synthesis and binding properties of octameric guanidiniumlinked deoxycytidine oligomer. Bioorg. Med. Chem. 2004, 12(15), 4233-4244.
    • (2004) Bioorg. Med. Chem. , vol.12 , Issue.15 , pp. 4233-4244
    • Szabo, I.E.1    Bruice, T.C.2
  • 20
    • 0001756111 scopus 로고
    • The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII
    • Ogilvie, K.K.; Beaucage, S.L.; Schifman, A.L.; Theriault, N.Y.; Sadana, K.L. The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII. Can. J. Chem. 1978, 56(21), 2768-2780.
    • (1978) Can. J. Chem , vol.56 , Issue.21 , pp. 2768-2780
    • Ogilvie, K.K.1    Beaucage, S.L.2    Schifman, A.L.3    Theriault, N.Y.4    Sadana, K.L.5
  • 21
    • 3042673565 scopus 로고    scopus 로고
    • Selective monodeprotection of bis-silyl ethers
    • Crouch, R.D. Selective monodeprotection of bis-silyl ethers. Tetrahedron. 2004, 60, 5833-5871.
    • (2004) Tetrahedron. , vol.60 , pp. 5833-5871
    • Crouch . R, D.1
  • 23
    • 0038330762 scopus 로고    scopus 로고
    • An improved transient method for the synthesis of N-benzoylated nucleosides
    • Zhu, X.; Williams, H.J.; Scott, A.I. An improved transient method for the synthesis of N-benzoylated nucleosides. Synth. Commun. 2003, 33, 1233-1243.
    • (2003) Synth. Commun. , vol.33 , pp. 1233-1243
    • Zhu, X.1    Williams, H.J.2    Scott, A.I.3
  • 24
    • 0035207013 scopus 로고    scopus 로고
    • Dry column vacuum chromatography
    • Pedersen, D.S.; Rosenbohm, C. Dry column vacuum chromatography. Synthesis. 2001, 16, 2431-2434.
    • (2001) Synthesis. , vol.16 , pp. 2431-2434
    • Pedersen, D.S.1    Rosenbohm, C.2
  • 25
    • 33748942512 scopus 로고    scopus 로고
    • Synthesis of 2'-C-methylcytidine and 2'-C-methyluridine derivatives modified in the 3'-position as potential antiviral agents
    • Pierra, C.; Amador, A.; Badaroux, E.; Storer, R.; Gosselin, G. Synthesis of 2'-C-methylcytidine and 2'-C-methyluridine derivatives modified in the 3'-position as potential antiviral agents. Coll. Czech. C. C. 2006, 71, 991-1010.
    • (2006) Coll. Czech. C. C. , vol.71 , pp. 991-1010
    • Pierra, C.1    Amador, A.2    Badaroux, E.3    Storer, R.4    Gosselin, G.5
  • 26
    • 48449105138 scopus 로고    scopus 로고
    • Synthesis of 3'-deoxy-3'-C-methyl nucleoside derivatives
    • Aljarah, M.; Couturier, S.; Mathe, C.; Perigaud, C. Synthesis of 3'-deoxy-3'-C-methyl nucleoside derivatives. Bioorg. Med. Chem. 2008, 16, 7436-7442.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7436-7442
    • Aljarah, M.1    Couturier, S.2    Mathe, C.3    Perigaud, C.4
  • 27
    • 0030902963 scopus 로고    scopus 로고
    • Inhibitory activity of 3'-fluoro-2' deoxythymidine and related nucleoside analogues against adenoviruses in vitro
    • Mentel, R.; Kinder, M.; Wegner, U.; von Janta-Lipinski, M.; Matthes, E. Inhibitory activity of 3'-fluoro-2' deoxythymidine and related nucleoside analogues against adenoviruses in vitro. Antiviral Res. 1997, 34, 113-119.
    • (1997) Antiviral Res. , vol.34 , pp. 113-119
    • Mentel, R.1    Kinder, M.2    Wegner, U.3    Von Janta-Lipinski, M.4    Matthes, E.5


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