127
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

INCORPORATION OF 8-HISTAMINYL-DEOXYADENOSINE [8-(2-(4-IMIDAZOLYL)ETHYLAMINO)-2′-DEOXYRIBOADENOSINE] INTO OLIGODEOXYRIBONUCLEOTIDES BY SOLID PHASE PHOSPHORAMIDITE COUPLING

, &
Pages 651-664 | Received 15 Apr 2002, Accepted 05 Jul 2002, Published online: 17 Aug 2006

REFERENCES

  • Raines , R.T. 1998 . Ribonuclease A. Chem. Rev. , 98 : 1045 – 1065 .
  • Sträter , N. , Lipscomb , W.N. , Klabunde , T. and Krebs , B. 1996 . Two Metal Ion Catalysis in Enzymatic Acyl and Phosphoryl-Transfer Reactions . Angew. Chem. Int. Ed. Engl. , 35 : 2024 – 2055 .
  • Solomon , E.I. and Yan , Z. 1992 . The Electronic-Structures of Active Sites in Nonheme Iron Enzymes . Acc. Chem. Res. , 25 : 343 – 352 .
  • Pabo , C.O. , Peisach , E. and Grant , R.A. 2001 . Design and Selection of Novel Cys(2)His(2) Zinc Finger Proteins . Ann. Rev. Biochem. , 70 : 313 – 340 .
  • Pichon , C. , Goncalves , C. and Midoux , P. 2001 . Histidine-Rich Peptides and Polymers for Nucleic Acids Delivery . Adv. Drug Del. Rev. , 53 : 75 – 94 .
  • Putnam , D. , Gentry , C.A. , Pack , D.W. and Langer , R. 2001 . Polymer-Based Gene Delivery with Low Cytotoxicity by a Unique Balance of Side-Chain Termini . Proc. Natl. Acad. Sci. USA , 98 : 1200 – 1205 .
  • Midoux , P. and Monsigny , M. 1999 . Efficient Gene Transfer by Histidylated Polylysine DNA Complexes . Bioconj. Chem. , 10 : 406 – 411 .
  • Ushijima , K. , Shirakawa , M. , Kagoshima , K. , Park , W.S. , Miyano-Kurosaki , N. and Takaku , H. 2001 . Anti-HIV-1 Activity of an Antisense Phosphorothioate Oligonucleotide Bearing Imidazole and Primary Amine Groups . Bioorg. & Med. Chem. , 9 : 2165 – 2169 .
  • Konevetz , D.A. , Beck , I.E. , Beloglazova , N.G. , Sulimenkov , I.V. , Sil'nikov , V.N. , Zenkova , M.A. , Shishkin , G.V. and Vlassov , V.V. 1999 . Artificial Ribonucleases: Synthesis and RNA Cleaving Properties of Cationic Conjugates Bearing Imidazole Residues . Tetrahedron , 55 : 503 – 512 .
  • Vlassov , V. , Abramova , T. , Godovikova , T. , Giege , R. and Sil'nikov , V. 1997 . Sequence-Specific Cleavage of Yeast tRNA(Phe) with Oligonucleotides Conjugated to a Diimidazole Construct . Antisense & Nucl. Acid Drug Dev. , 7 : 39 – 42 .
  • Hovinen , J. , Guzaev , A. , Azhayeva , E. , Azhayev , A. and Lonnberg , H. 1995 . Imidazole Tethered Oligonucleotides – Synthesis and RNA Cleaving Activity . J. Org. Chem. , 60 : 2205 – 2209 .
  • Trawick , B.N. , Daniher , A.T. and Bashkin , J.K. 1998 . Inorganic Mimics of Ribonucleases and Ribozymes: From Random Cleavage to Sequence-Specific Chemistry to Catalytic Antisense Drugs . Chem. Rev. , 98 : 939 – 960 .
  • Oivanen , M. , Kuusela , S. and Lönnberg , H. 1998 . Kinetics and Mechanisms for the Cleavage and Isomerization of the Phosphodiester Bonds of RNA by Bronsted Acids and Bases . Chem. Rev. , 98 : 961 – 990 .
  • Reynolds , M.A. , Beck , T.A. , Say , P.B. , Schwartz , D.A. , Dwyer , B.P. , Daily , W.J. , Vaghefi , M.M. , Metzler , M.D. , Klem , R.E. and Arnold , L.J. 1996 . Antisense Oligonucleotides Containing an Internal, Non-Nucleotide-Based Linker Promote Site-Specific Cleavage of RNA . Nucl. Acids Res. , 24 : 760 – 765 .
  • Verbeure , B. , Lacey , C.J. , Froeyen , M. , Rozenski , J. and Herdewijn , P. 2002 . Synthesis and Cleavage Experiments of Oligonucleotide Conjugates with a Diimidazole-Derived Catalytic Center . Bioconj. Chem. , 13 : 333 – 350 .
  • Sakthivel , K. and Barbas , C.F. 1998 . Expanding the Potential of DNA for Binding and Catalysis: Highly Functionalized dUTP Derivatives that are Substrates for Thermostable DNA Polymerases . Angew. Chem. Int. Ed. Engl. , 37 : 2872 – 2875 .
  • Matulic-Adamic , J. , Daniher , A.T. , Karpeisky , A. , Haeberli , P. , Sweedler , D. and Beigelman , L. 2000 . Functionalized Nucleoside 5′-Triphosphates for In Vitro Selection of New Catalytic Ribonucleic Acids . Bioorg. Med. Chem. Lett. , 10 : 1299 – 1302 .
  • Matulic-Adamic , J. , Daniher , A.T. , Karpeisky , A. , Haeberli , P. , Sweedler , D. and Beigelman , L. 2001 . Synthesis of Modified Nucleoside 5′-Triphosphates for In Vitro Selection of Catalytic Nucleic Acids . Nucleosides, Nucleotides & Nucleic Acids , 20 : 1113 – 1115 .
  • Perrin , D.M. , Garestier , T. and Helene , C. 1999 . Expanding the Catalytic Repertoire of Nucleic Acid Catalysts: Simultaneous Incorporation of Two Modified Deoxyribonucleotide Triphosphates Bearing Ammonium and Imidazolyl Functionalities . Nucleosides & Nucleotides , 18 : 377 – 391 .
  • Gourlain , T. , Sidorov , A. , Mignet , N. , Thorpe , S.J. , Lee , S.E. , Grasby , J.A. and Williams , D.M. 2001 . Enhancing the Catalytic Repertoire of Nucleic Acids II: Simulataneous Incorporation of Amino and Imidazolyl Functionalities by Two Modified Triphosphates During PCR . Nucl. Acids. Res. , 29 : 1898 – 1905 .
  • Perrin , D.M. , Garestier , T. and Helene , C. 1999 . Expanding the Catalytic Repertoire of Nucleic Acid Catalysts: Simultaneous Incorporation of Two Modified Deoxyribonucleotide Triphosphates Bearing Ammonium and Imidazolyl Functionalities . Nucleosides & Nucleotides , 18 : 377 – 391 .
  • Bashkin , J.K. , Gard , J.K. and Modak , A.S. 1990 . Synthesis and Characterization of Oligonucleotide Peptides . J. Org. Chem. , 55 : 5125 – 5132 .
  • Beban , M. and Miller , P.S. 2000 . Preparation of an Imidazole-Conjugated Oligonucleotide . Bioconj. Chem. , 11 : 599 – 603 .
  • Ramasamy , K.S. , Zounes , M. , Gonzalez , C. , Freier , S.M. , Lesnik , E.A. , Cummins , L.L. , Giffey , R.H. , Monia , B.P. and Cook , P.D. 1994 . Remarkable Enhancement of Binding-Affinity of Heterocycle-Modified DNA to DNA and RNA – Synthesis, Characterization and Biophysical Evaluation of N-2-Imidazolylpropylguanine and N-2-Imidazolylpropyl-2-Aminoadenine Modified Oligonucleotides . Tet. Lett. , 35 : 215 – 218 .
  • Singh , D. , Kumar , V. and Ganesh , K.N. 1990 . Oligonucleotides, part 5+: Synthesis and Fluorescence Studies of DNA Oligomers d(AT)5 Containing Adenine Covalently Linked at C-8 with Dansyl Fluorophore . Nucl. Acids Res. , 18 : 3339 – 3345 .
  • Wlassoff , W.A. , Dobrikov , M.I. , Safronov , I.V. , Dudkor , Y. , Bogachev , V.S. , Kandaurova , V.V. , Shishkin , G.V. , Dymshits , G.M. and Lavrik , O.I. 1995 . Synthesis and Characterization of (d)NTP Derivatives Substituted with Residues of Different Photoreagents . Binconj. Chem. , 6 : 352 – 360 .
  • Lin , X.Y. and Robins , M.J. 2000 . Nucleic acid Related Compounds: Mild and Efficient Functionalization at C6 of purine 2′-Deoxynucleosides and Ribonucleosides . Org. Lett. , 2 : 3497 – 3499 .
  • Veliz , E.A. and Beal , P.A. 2001 . 6-Bromopurine Nucleosides as Reagents for Nucleoside Analogue Synthesis . J. Org. Chem. , 55 : 8592 – 8598 .
  • Prakash , T.P. , Kumar , R.K. and Ganesh , K.N. 1993 . Synthesis and Conformational Studies of D(TPA) and R(UPA) Conjugated with Histamine and Ethylenediamine . Tetrahedron , 49 : 4035 – 4050 .
  • Perrin , D.M. , Garestier , T. and Helene , C. 2001 . Bridging the Gap Between Proteins and Nucleic Acids . J. Am. Chem. Soc. , 123 : 1556 – 1563 .
  • Aviñó , A. , Morales , J.C. , Frieden , M. , de la Torre , B.G. , Garcia , R.G. , Cubero , E. , Luque , F.J. , Orozco , M. , Azorin , F. and Eritja , R. 2001 . Parallel-stranded Hairpins Containing 8-Aminopurines. Novel Efficient Probes for Triple-Helix Formation . Bioorg. Med. Chem. Lett. , 11 : 1761 – 1763 .
  • Cubero , E. , Aviñó , A. , de la Torre , B.G. , Frieden , M. , Eritja , R. , Luque , F.J. , González , C. and Orozco , M. 2002 . Hoogsteen-Based Parallel-Stranded Duplexes of DNA. Effect of 8-Amino-purine Derivatives . J. Am. Chem. Soc. , 124 : 3133 – 3142 .
  • Ikehara , M. and Kaneko , M. 1970 . Purine Cyclonucleosides – 8 Selective Sulfonylation of 8-Bromoadenosine Derivatives and an Alternate Synthesis of 8,2′- and 8,3′-S-Cyclonucleosides . Tetrahedron , 26 : 4251 – 4259 .
  • Laayoun , A. , Decout , J.-L. , Defrancq , E. and Lhomme , J. 1994 . Hydrolysis of Oligonucleotides Containing 8-Substituted Purine Nucleosides. A New Route for Preparing Abasic Oligonucleotides . Tet. Lett. , 35 : 4991 – 4994 .
  • Singh , D. , Kumar , V. and Ganesh , K.N. 1990 . Oligonucleotides, Part 5+: Synthesis and Fluorescence Studies of DNA Oligomers d(AT)5 Containing Adenine Covalently Linked at C-8 with Dansyl Fluorophore . Nucl. Acids Res. , 18 : 3339 – 3345 .
  • Luo , C. , Krishnasamy , R. , Basu , A.K. and Zou , Y. 2002 . Recognition and Incision of Site-Specifically Modified C8 Guanine Adducts Formed by 2-Aminofluorene, N-Acetyl-2-Aminofluorene and 1-Nitropyrene by UvrABC Nuclease . Nucl. Acids Res. , 28 : 3719 – 3724 .
  • Huff , B.E. , LeTourneau , M.E. , Staszak , M.A. and Ward , J.A. 1996 . Protection, Metallation, and Electrophilic Substitution of 5-methyl Tetrazole . Tet. Lett. , 37 : 3655 – 3658 .
  • Dolensky , B. and Kirk , K.L. 2001 . New Building Blocks for Fluorinated Imidazole Derivatives: Preparation of β-Fluoro- and β,β-Difluorohistamine . J. Org. Chem. , 66 : 4687 – 4691 .
  • Bashkin , J.K. , Gard , J.K. and Modak , A.S. 1990 . Synthesis and Characterization of Oligonucleotide Peptides . J. Org. Chem. , 55 : 5125 – 5132 .
  • Santoro , S.W. , Joyce , G.F. , Sakthivel , K. , Gramatikova , S. and Barbas , C.F. 2000 . RNA Cleavage by a DNA Enzyme with Extended Chemical Functionality . J. Am. Chem. Soc. , 122 : 2433 – 2439 .
  • Perrin , D.M. , Garestier , T. and Helene , C. 1999 . Expanding the Catalytic Repertoire of Nucleic Acid Catalysts: Simultaneous Incorporation of Two Modified Deoxyribonucleotide Triphosphates Bearing Ammonium and Imidazolyl Functionalities . Nucleosides & Nucleotides , 18 : 377 – 391 .
  • Perrin , D.M. , Garestier , T. and Helene , C. 2001 . Bridging the Gap Between Proteins and Nucleic Acids . J. Am. Chem. Soc. , 123 : 1556 – 1563 .
  • Avino , A. , Morales , J.C. , Frieden , M. , de la Torre , B.G. , Garcia , R.G. , Cubero , E. , Luque , F.J. , Orozco , M. , Azorin , F. and Eritja , R. 2001 . Parallel-stranded Hairpins Containing 8-Aminopurines. Novel Efficient Probes for Triple-Helix Formation . Bioorg. Med. Chem. Lett. , 11 : 1761 – 1763 .
  • Cubero , E. , Aviñó , A. , de la Torre , B.G. , Frieden , M. , Eritja , R. , Luque , F.J. , González , C. and Orozco , M. 2002 . Hoogsteen-Based Parallel-Stranded Duplexes of DNA. Effect of 8-Amino-purine Derivatives . J. Am. Chem. Soc. , 124 : 3133 – 3142 .
  • Singh , D. , Kumar , V. and Ganesh , K.N. 1990 . Oligonucleotides, Part 5+: Synthesis and Fluorescence Studies of DNA Oligomers d(AT)5 Containing Adenine Covalently Linked at C-8 with Dansyl Fluorophore . Nucl. Acids Res. , 18 : 3339 – 3345 .
  • Ikehara , M. and Kaneko , M. 1970 . Purine Cyclonucleosides – 8 Selective Sulfonylation of 8-Bromoadenosine Derivatives and an Alternate Synthesis of 8,2′- and 8,3′-S-Cyclonucleosides . Tetrahedron , 26 : 4251 – 4259 .

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.