48
Views
8
CrossRef citations to date
0
Altmetric
Miscellaneous

DNA and RNA analogues – oligonucleotide phosphoramidates with bridging nitrogen

&
Pages 543-559 | Published online: 25 Feb 2005

Bibliography

  • HELENE C, TOULME J-J: Specific regulation of gene expression by antisense, sense and antigene nucleic acids. Biochim. Biophys. Acta (1990) 1049:99–125.
  • UHLMANN E, PEYMAN A: Antisense oligonucleotides: A new therapeutic principle. Chem. Rev (1990) 90:543–584.
  • CHRISTOFFERSEN RE, MARR JJ: Ribozymes as human therapeutic agents.j Med. Chem. (1995) 38:2023–2037.
  • SANTORO SW, JOYCE GF: A general purpose RNA-cleaving DNA enzyme. Proc. Natl. Acad. Li. USA (1997) 94:4262–4266.
  • UNRAU PJ, BARTEL DP: RNA-catalysed nucleotide synthesis. Nature (1998) 395:260–263.
  • PAGRATIS NC, BELL C, CHANG Y-F etal.: Potent 2'-amino- and 2'-fiuoro-2'-deoxyribonucleotide RNA inhibitors of keratinocyte growth factor. Nat. Biotech. (1997) 15:68–73.
  • GREEN GL, LETSINGER RL: Formationof internucleotide 3'-5' phosphoramidate links by direct coupling of phosphoryl and amino groups. Nucleic Acids Res. (1975) 2:1123–1127.
  • •Describes, for the first time, direct chemical synthesis of short 2'-deoxyoligonucleotide P3-N5 phosphoramidates.
  • AZHAYEV AV, KRAYEVSKY AA, SMRT J: Synthesis of phosphoramidates analogs of ribonucleoside phosphates. Collection Czechoslov. Chem. Commun. (1979) 44:792–798.
  • •First chemical synthesis of ritm-N3'-4P5' phosphoramidate dinucleotide, and description of its hydrolytic stability.
  • ZIELINSKI WS, ORGEL LE: Oligoaminonucleoside phosphoramidates. Oligomerization of dimers of 3'-amino-3'-deoxy-nucleosides (GC and CG) in aqueous solution. Nucleic Acids Res. (1987) 15:1699–1715.
  • •Synthesis of short self-complementary ribo-N3'-P5' phosphoramidates in aqueous solutions; relevant to origin of modem nucleic acids and other self-replicating systems.
  • LETSINGER RL, HEAVNER GA: Synthesis of phosphoromonoamidate diester nucleosides via the phosphite-azide coupling method. Tetrahedron Lett. (1975) 2:147–150.
  • GIBBS DE: The synthesis of phosphoramidates from silylphosphites and azides. Tetrahedron Lett. (1977) 8:679–682.
  • MAG M, ENGELS JW: Synthesis of dinucleotides containing a bridged non-chiral internucleoside 5'- or 3'-phosphoramidates linkage. Tetrahedron (1994) 50:10225–10234.
  • GRYAZNOV SM, LETSINGER RL: Synthesis and properties of oligonucleotides containing aminodeoxythymidine units. Nucleic Acids Res. (1992) 20:3403–3409.
  • GRYAZNOV S, CHEN J-K: Oligodeoxyribonucleotide phosphoramidates: synthesis and hybridization properties. I Am. Chem. Sac (1994) 116:3143–3144.
  • ••Application of oxidative phosphorylation synthetic methodology for preparation of uniformly modified 2'-deoxyoligo-nucleotide N3' -P5' phosphoramidates; first description of hybridisation properties of these compounds with RNA and DNA complements.
  • BARANIAK J, KORCZYNSKI D, KACZMAREK R, WASILEWSKA E: New approach to the solid-phase synthesis of phosphoramidate oligonucleotides. Nucleosides Nucleotides (1998) 17:1347–1354.
  • KERS I, STAWINSKI J, KRASZEWSKI A: A new synthetic method for the preparation of nucleoside phosphoramidate analogues with nitrogen atom in bridging positions of the phosphoramidate linkage. Tetrahedron Lett. (1998) 39:1219–1222.
  • BANNWARTH W: Helvetica. Chim. Acta (1988) 71:1517–1527.
  • •First description of the application of phosphoramidite transfer methodology for preparation of 2'-deoxyoligonudeotides containing P3'-N5 phosphoramidate linkages.
  • MCCURDY SN, NELSON JS, HIRSCHBEIN BL, FEARON KL: An improved method for the synthesis of phosphoramidate oligonucleotides. Tetrahedron Lett. (1997) 38:207–210.
  • •Application of phosphoramidite transfer methodology for synthesis of uniformly modified oligo-N3'-P5' phosphoramidates.
  • SCHULTZ RG, GRYAZNOV SM: Oligo-2'-fluoro-2'-deoxynucleotide phosphoramidates: synthesis and properties. Nucleic Acids Res. (1996) 24:2966–2973.
  • •Synthesis and acid stability of ribofluoro-N3'-P5' phosphoramidates.
  • GRYAZNOV SM, WINTER H: RNA mimetics: oligoribonucleotide phosphoramidates. Nucleic Acids Res. (1998) 26:4160–4167.
  • •Chemical synthesis and properties of uniformly modified ribo-N3'-P5' phosphoramidate oligonucleotides.
  • PONGRACZ K, GRYAZNOV S: Oligonucleotidethio- phosphoramidates: synthesis and properties. Tetrahedron Lett. (1999) 40:7661–7664.
  • NAWROT B, BOCZKOWSKA M, WOJCIK M, SOCHACKI M, KAZMIERSKI S, STEC WJ: Novel internucleotide 3'-NH-P (CH3) (0)-0-5' linkage. Oligo(deoxyribonucleoside methanephosphonamidates): synthesis, structure and hybridization properties. Nucleic Acid Res. (1998) 26:2650–2658.
  • BARANIAK J, KORCZYNSKI D, STEC WJ: Synthesis of 2',3'-dideoxynucleoside-3'-N-(2-oxo-1,3,2-oxathiaphospholanes) and their reactions with 5'-OH nucleosides and fluoride ion. J. Org. Chem. (1999) 64:4533–4536.
  • SHABAROVA ZA: Chemical development in the design of oligonucleotide probes for binding to DNA and RNA. Biochimie (1988) 70:1323–1334.
  • CHEN J-K, SCHULTZ RG, LLOYD DH, GRYAZNOV SM: Synthesis of oligodeoxyribonucleotide phosphoramidates. Nucleic Acids Res. (1995) 23:2661–2668.
  • GRYAZNOV SM: Syntheis and propertiesof the oligonucleotide phosphoramidates. Nucleosides Nucleotides (1997) 16:899–905.
  • LETSINGER RL, MUNGALL WS: Phosphoramidate analogs of oligonucleotides. j Org. Chem. (1970) 35:3800–3803.
  • LETSINGER RL, HAPKE B, PETERSEN GR, DUMAS LB: Enzymatic synthesis of duplex circular phiX174 DNA containing phosphoramidate bonds in the O strand, Nucleic Acids Res. (1976) 3:1053–1063.
  • •First description of enzymatic synthesis of oligonucleotides containing P3' -N5' phosphoramidate linkages using 5'-triphosphates of 5'-amino nucleosides and DNA polymerase.
  • SCHULTZ RG, GRYAZNOV SM: Arabino-fluorooligonucleotide phosphoramidates: synthesis and properties. Tetrahedron Lett. (2000) 41:1895–1899.
  • GRYAZNOV SM, LLOYD DH, CHEN J-K et al: Oligonucleotide phosphoramidates. Proc. Nati Acad. Sci. USA (1995) 92:5798–5802.
  • DING D, GRYAZNOV SM, LLOYD DH et al.: An oligodeoxyribonucleotide phosphoramidate duplex forms an A-type helix in solution. Nucleic Acids Res. (1996) 24:354–360.
  • DING D, GRYAZNOV SM, WILSON WD: NMR solution structure of the phosphoramidate duplex d(CGCGAATTCGCG) by iterative relaxation matrix approach. Biochemistry (1998) 37:12083–12093.
  • •RNA-like A-type conformation of 2'-deoxyoligonucleotide N3'-P5' phosphoramidate duplexes determined by
  • TERESHKO V, GRYAZNOV S, EGLI M: Consequences of replacing the DNA 3'-oxygen by an amino group: high-resolution crystal structure of a fully modified phosphoramidate DNA dodecamer duplex. j Am. Chem. Soc. (1998) 120:269–283.
  • •Conformation of N3'-,P5' phosphoramidate duplexes determined by x-ray crystallography; good general correlation with the NMR-based structure was found.
  • RIGL CT, LLOYD DH, TSOU DS, GRYAZNOV SM, WILSON WD: Structural RNA mimetics: phosphoramidate DNA analogs of HIV-1 RRE and TAR RNA form A-type helices that bind specifically to Rev and Tat -related peptides. Biochemistry (1997) 36:650–659.
  • GRYAZNOV S, PONGRACZ K, MATRAY T et al.: Telomerase inhibitors - oligonucleotide phosphoramidates as potential therapeutic agents. Nucleosides Nucleotides Nucleic Acids (2001) 20:401–410.
  • ESCUDE C, GIOVANNANGELI C, SUN J-S et al.: Stable triple helices formed by oligonucleotide phosphoramidates inhibit transcription elongation. Proc. Nati Acad. Li. USA (1996) 93:4365–4369.
  • ••Thermodynamic properties of N3'-P5'phosphoramidate triplexes with DNA.
  • ROBERTS RW, CROTHERS DM: Stability and properties of double and triple helices: dramatic effects of RNA or DNA backbone composition. Science (1992) 258:1463–1466.
  • SHIMIZU M, KONISHI A, SHIMADA Y,INOUE H, OHTSUKA E: Oligo(2'-0-methyflribonucleosides. Effective probes for duplex DNA. FEBS Lett. (1992) 302:155–158.
  • GUSCHLBAUER W, JANKOWSKI K: Nucleoside conformation is determined by the electronegativity of the sugar substituent. Nucleic Acids Res. (1980) 8:1421–1433.
  • TORIGOE H: Thermodynamic and kinetic effects of N3'-P5' phosphoramidate modification on pyrimidine motif triplex DNA formation. Biochemistry (2001) 40:1063–1069.
  • •Kinetic and thermodynamic parameters of N3-P5 phosphoramidate versus phosphodiester triplexes was determined.
  • TORIGOE H, HARI Y, SEKIGUCHI M, OBIKA S, IMANISHI T: 2'-0, 4'-C-Methylene bridged nucleic acid modification promotes pyrimidine motif triplex DNA formation at physiological pH. Biol. Chem. (2001) 276:2354–2360.
  • OBIKA S, ONODA M, MORITA K, AND OH J, KOIZUMI M, IMANISHI T: 3'-Amino-2',4'-BNA: novel bridged nucleic acids having anP5' phosphoramidate linkage. Chem. Comm. (2001) 1992–1993.
  • KVAERNO L, WIGHTMAN RH, WENGEL J: Synthesis of a novel bicyclic nucleoside restricted to an S-type conformation and initial evaluation of its hybridization properties when incorporated into oligonucleotides. I Org. Chem. (2001) 66:5106–5112.
  • WANG G, STOISAVLJEVIC V: Conformationally locked nucleosides. Synthesis of oligonucleotides containing 3'-amino-3'-deoxy-3'-N,5'(R)-C-ethylenethymidine. Nucleoside, Nucleotide, Nucl. Acids (2000) 19:1413–1425.
  • SEMERAD LJ, MAHER III: Exclusion of RNA strand from a purine motif triple helix. Nucleic Acids Res. (1994) 22:5321–5325.
  • GIOVANNANGELI C, PERROUAULT L, ESCUDE C, GRYAZNOV S, HELENE C: Efficient inhibition of transcription elongation in vitro by oligonucleotide phosphoramidates targeted to proviral HIV DNA. j Ma. Biol. (1996) 26:386–398.
  • ZHOU-SUN B-W, SUN J-S, GRYAZNOV SM et al.: A physicochemical study of triple helix formation by an oligothymidylate with N3'-P5' phosphoramidate linkages. Nucleic Acids Res. (1997) 25:1782–1787.
  • GRYAZNOV S, SKORSKI T, CUCCO C et al.: Oligonucleotide phosphoramidates as antisense agents. Nucleic Acids Res. (1996) 24:1508–1514.
  • •Antisense-based inhibition of cellular proliferation by oligonucleotide N3'-P5' phosphoramidates was demonstrated.
  • HEIDENREICH O, GRYAZNOV S, NERENBERG M: RNase H independent antisense activity of oligonucleotide phosphoramidates. Nucleic Adds Res. (1997) 25:776–780.
  • SKORSKI T, PERROTTI D, NIEBOROWSKA-SKORSKA M, GRYAZNOV S, CALABRETTA B: Antileukemia effect of c-myc phosphoramidate antisense oligonucleotides in vivo. Proc. Nati Acad. Sci. USA (1997) 94:3966–3971.
  • ••In vivo activity of N3'-P5'phosphoramidates versus phosphorothioate oligonucleotides.
  • FARIA M, SPILLER DG, DUBERTRET C et ai:Phosphoramidate oligonucleotides as potent antisense molecules in cells and in vivo. Nat. Biotech. (2001) 19:40–44.
  • •In vivo antisense-based inhibition of HIV replication by N3'-P5' phosphoramidates.
  • GIOVANNANGELI C, DIVIACCO S, LABROUSSE V, GRYAZNOV S, CHARNEAU P, HELENE C: Accessibility of nuclear DNA to triplex-forming oligonucleotides: the integrated HIV-1 provirus as a target. Proc. Nati Acad. Sci. USA (1997) 94:79–84.
  • FARIA M, WOOD CD, PERROUAULT L etal.: Targeted inhibition of transcription elongation in cells mediated by triplex-forming oligonucleotides. Proc. Natl. Acad. Sci. USA (2000) 97:3862–3867.
  • HANNA RL, GRYZANOV SM, DOUDNA JA: A phosphoramidate substrate analog is a competitive inhibitor of the Tetrahymena group I ribozyme. Chem. Biol. (2000) 7:845–854.
  • TESTA SM, GRYAZNOV SM, TURNER DH: In vitro suicide inhibition of self-splicing of group I intron from Prieumocystis carinii by an N3'-P5' phosphoramidate hexanucleotide. Proc. Natl. Acad. Sci. USA (1999) 96:2734–2739.
  • •Suicide inhibition of RNA Group I intron self-splicing by oligo-N3'-3P5' phosphoramidates.
  • DISNEY MD, MATRAY T, GRYAZNOV SM, TURNER DH: Binding enhancement by tertiary interactions and suicide inhibition of a Candida albicans group I intron by phosphoramidate and 2'-0-methyl hexanucleotides. Biochemistry (2001) 40:6520–6526.
  • DARFEUILLE F, CAZENAVE C, GRYAZNOV S, DUCONGE F, DIPRIMO C, JJ TOULME: RNA and N3'-P5' kissing aptamers targeted to the trans-activation responsive (TAR) RNA of the human immunodeficiency virus-1. Nucleosides Nucleotides Nud. Adds (2001) 20:441–449.
  • •Specific and efficient RNA-like aptamers from 2'-deoxyoligonucleotide N3'-P5' phosphoramidates.
  • FORD LE ZOU Y, PONGRACZ K, GRYAZNOV S, SHAY JW, WRIGHT WE: Telomerase can inhibit the recombination-based pathway of telomere maintenance in human cells. j. Biol. Chem. (2001) 276:198–203.
  • HERBERT B-S, PONGRACZ K, SHAY JW, GRYAZNOV SM: Oligonucleotide phosphoramidates as efficient telomerase inhibitors. Oncogene (2002) 21:638–642.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.