Incorporation of 8-histaminyl-deoxyadenosine [8-(2-(4-imidazolyl)ethylamino)-2′-deoxyriboadenosine] into oligodeoxyribonucleotides by solid phase phosphoramidite coupling

Nucleosides, Nucleotides and Nucleic Acids

Volumn 21, Issue 10, 2002, Pages 651-664

  Lermer, Leonard ^a   Hobbs, John ^a   Perrin, David M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

8 [2 (4 IMIDAZOLYL)ETHYLAMINO] 2' DEOXYRIBOADENOSINE; ADENOSINE DERIVATIVE; OLIGODEOXYRIBONUCLEOTIDE; RIBONUCLEASE A; UNCLASSIFIED DRUG; DEOXYADENOSINE DERIVATIVE; DEOXYRIBOZYME; DRUG DERIVATIVE; HISTAMINE; IMIDAZOLE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID;

ARTICLE; CHEMICAL BINDING; CRYSTAL STRUCTURE; ENZYME ACTIVITY; NUCLEOTIDE SEQUENCE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; STEREOCHEMISTRY; SYNTHESIS; ANIMAL; BASE PAIRING; CHEMISTRY; CONFORMATION; MASS SPECTROMETRY; METHODOLOGY; POLYACRYLAMIDE GEL ELECTROPHORESIS;

ANIMALS; BASE PAIRING; BASE SEQUENCE; DEOXYADENOSINES; DNA, CATALYTIC; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HISTAMINE; IMIDAZOLES; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 1842845922     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120015723     Document Type: Article

References (46)

1. Raines, R.T. Ribonuclease A. Chem. Rev. 1998, 98, 1045-1065.
2. Sträter, N.; Lipscomb, W.N.; Klabunde, T.; Krebs, B. Two metal ion catalysis in enzymatic acyl and phosphoryl-transfer reactions. Angew. Chem. Int. Ed. Engl. 1996, 35, 2024-2055.
3. Solomon, E.I.; Yan, Z. The Electronic-Structures of Active Sites in Nonheme Iron Enzymes. Acc. Chem. Res. 1992, 25, 343-352.
4. Pabo, C.O.; Peisach, E.; Grant, R.A. Design and selection of novel cys(2)his(2) zinc finger proteins. Ann. Rev. Biochem. 2001, 70, 313-340.
5. Pichon, C.; Goncalves, C.; Midoux, P. Histidine-rich peptides and polymers for nucleic acids delivery. Adv. Drug Del. Rev. 2001, 53, 75-94.
6. Putnam, D.; Gentry, C.A.; Pack, D.W.; Langer, R. Polymer-based gene delivery with low cytotoxicity by a unique balance of side-chain termini. Proc. Natl. Acad. Sci. USA 2001, 98, 1200-1205.
7. Midoux, P.; Monsigny, M. Efficient gene transfer by histidylated polylysine DNA complexes. Bioconj. Chem. 1999, 10, 406-411.
8. Ushijima, K.; Shirakawa, M.; Kagoshima, K.; Park, W.S.; Miyano-Kurosaki, N.; Takaku, H. Anti-HIV-1 activity of an antisense phosphorothioate oligonucleotide bearing imidazole and primary amine groups. Bioorg. & Med. Chem. 2001, 9, 2165-2169.
9. Konevetz, D.A.; Beck, I.E.; Beloglazova, N.G.; Sulimenkov, I.V.; Sil'nikov, V.N.; Zenkova, M.A.; Shishkin, G.V.; Vlassov, V.V. Artificial ribonucleases: Synthesis and RNA cleaving properties of cationic conjugates bearing imidazole residues. Tetrahedron 1999, 55, 503-512.
10. Vlassov, V.; Abramova, T.; Godovikova, T.; Giege, R.; Sil'nikov, V. Sequence-specific cleavage of yeast tRNA(Phe) with oligonucleotides conjugated to a diimidazole construct. Antisense & Nucl. Acid Drug Dev. 1997, 7, 39-42.
11. Hovinen, J.; Guzaev, A.; Azhayeva, E.; Azhayev, A.; Lonnberg, H. Imidazole tethered oligonucleotides - Synthesis and RNA cleaving activity. J. Org. Chem. 1995, 60, 2205-2209.
12. Trawick, B.N.; Daniher, A.T.; Bashkin, J.K. Inorganic Mimics of Ribonucleases and Ribozymes: From Random Cleavage to Sequence-Specific Chemistry to Catalytic Antisense Drugs. Chem. Rev. 1998, 98, 939-960.
13. Oivanen, M.; Kuusela, S.; Lönnberg, H. Kinetics and mechanisms for the cleavage and isomerization of the phosphodiester bonds of RNA by bronsted acids and bases. Chem. Rev. 1998, 98, 961-990.
14. 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.; Arnold, L.J. Antisense oligonucleotides containing an internal, non-nucleotide-based linker promote site-specific cleavage of RNA. Nucl. Acids Res. 1996, 24, 760-765.
15. Verbeure, B.; Lacey, C.J.; Froeyen, M.; Rozenski, J.; Herdewijn, P. Synthesis and cleavage experiments of oligonucleotide conjugates with a diimidazole-derived catalytic center. Bioconj. Chem. 2002, 13, 333-350.
16. Sakthivel, K; Barbas, C.F. 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. 1998, 37, 2872-2875.
17. Matulic-Adamic, J.; Daniher, A.T.; Karpeisky, A.; Haeberli, P.; Sweedler, D.; Beigelman, L. Functionalized nucleoside 5′-triphosphates for in vitro selection of new catalytic ribonucleic acids. Bioorg. Med. Chem. Lett. 2000, 10, 1299-1302.
18. Matulic-Adamic, J.; Daniher, A.T.; Karpeisky, A.; Haeberli, P.; Sweedler, D.; Beigelman, L. Synthesis of modified nucleoside 5′-triphosphates for in vitro selection of catalytic nucleic acids. Nucleosides, Nucleotides & Nucleic Acids 2001, 20, 1113-1115.
19. Perrin, D.M.; Garestier, T.; Helene, C. Expanding the catalytic repertoire of nucleic acid catalysts: Simultaneous incorporation of two modified deoxyribonucleotide triphosphates bearing ammonium and imidazolyl functionalities. Nucleosides & Nucleotides 1999, 18, 377-391.
20. Gourlain, T.; Sidorov, A.; Mignet, N.; Thorpe, S.J.; Lee, S.E.; Grasby, J.A.; Williams, D.M. Enhancing the catalytic repertoire of nucleic acids II: Simulataneous incorporation of amino and imidazolyl functionalities by two modified triphosphates during PCR. Nucl. Acids. Res. 2001, 29, 1898-1905.
21. Perrin, D.M.; Garestier, T.; Helene, C. Expanding the catalytic repertoire of nucleic acid catalysts: Simultaneous incorporation of two modified deoxyribonucleotide triphosphates bearing ammonium and imidazolyl functionalities. Nucleosides & Nucleotides 1999, 18, 377-391.
22. Bashkin, J.K.; Gard, J.K.; Modak, A.S. Synthesis and characterization of oligonucleotide peptides. J. Org. Chem. 1990, 55, 5125-5132.
23. Beban, M.; Miller, P.S. Preparation of an imidazole-conjugated oligonucleotide. Bioconj. Chem. 2000, 11, 599-603.
24. Ramasamy, K.S.; Zounes, M.; Gonzalez, C.; Freier, S.M.; Lesnik, E.A.; Cummins, L.L.; Giffey, R.H.; Monia, B.P.; Cook, P.D. 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. 1994, 35, 215-218.
25. Singh, D.; Kumar, V.; Ganesh, K.N. 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. 1990, 18, 3339-3345.
26. Wlassoff, W.A.; Dobrikov, M.I.; Safronov, I.V.; Dudkor, Y.; Bogachev, V.S.; Kandaurova, V.V.; Shishkin, G.V.; Dymshits, G.M.; Lavrik, O.I. Synthesis and characterization of (d)NTP derivatives substituted with residues of different photoreagents. Binconj. Chem. 1995, 6, 352-360.
27. Lin, X.Y.; Robins, M.J. Nucleic acid related compounds: Mild and efficient functionalization at C6 of purine 2′-deoxynucleosides and ribonucleosides. Org. Lett. 2000, 2, 3497-3499.
28. Veliz, E.A.; Beal, P.A. 6-Bromopurine nucleosides as reagents for nucleoside analogue synthesis. J. Org. Chem. 2001, 55, 8592-8598.
29. Prakash, T.P.; Kumar, R.K.; Ganesh, K.N. Synthesis and conformational studies of D(TPA) and R(UPA) conjugated with histamine and ethylenediamine. Tetrahedron 1993, 49, 4035-4050.
30. Perrin, D.M.; Garestier, T.; Helene, C. Bridging the Gap Between Proteins and Nucleic Acids. J. Am. Chem. Soc. 2001, 123, 1556-1563.
31. Aviñó, A.; Morales, J.C.; Frieden, M.; de la Torre, B.G.; Garcia, R.G.; Cubero, E.; Luque, F.J.; Orozco, M.; Azorin, F.; Eritja, R. Parallel-stranded hairpins containing 8-aminopurines. Novel efficient probes for triple-helix formation. Bioorg. Med. Chem. Lett. 2001, 11, 1761-1763.
32. Cubero, E.; Aviñó, A.; de la Torre, B.G.; Frieden, M.; Eritja, R.; Luque, F.J.; González, C.; Orozco, M. Hoogsteen-based parallel-stranded duplexes of DNA. Effect of 8-amino-purine derivatives. J. Am. Chem. Soc. 2002, 124, 3133-3142.
33. Ikehara, M.; Kaneko, M. Purine cyclonucleosides-8 selective sulfonylation of 8-bromoadenosine derivatives and an alternate synthesis of 8,2′- and 8,3′-S-cyclonucleosides. Tetrahedron 1970, 26, 4251-4259.
34. Laayoun, A.; Decout, J.-L.; Defrancq, E.; Lhomme, J. Hydrolysis of oligonucleotides containing 8-substituted purine nucleosides. A new route for preparing abasic oligonucleotides. Tet. Lett. 1994, 35, 4991-4994.
35. Singh, D.; Kumar, V.; Ganesh, K.N. 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. 1990, 18, 3339-3345.
36. Luo, C.; Krishnasamy, R.; Basu, A.K.; Zou, Y. 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. 2002, 28, 3719-3724.
37. Huff, B.E.; LeTourneau, M.E.; Staszak, M.A.; Ward, J.A. Protection, Metallation, and Electrophilic Substitution of 5-methyl Tetrazole. Tet. Lett. 1996, 37, 3655-3658.
38. Dolensky, B.; Kirk, K.L. New building blocks for fluorinated imidazole derivatives: Preparation of β-fluoro- and β,β-difluorohistamine. J. Org. Chem. 2001, 66, 4687-4691.
39. Bashkin, J.K.; Gard, J.K.; Modak, A.S. Synthesis and characterization of oligonucleotide peptides. J. Org. Chem. 1990, 55, 5125-5132.
40. Santoro, S.W.; Joyce, G.F.; Sakthivel, K.; Gramatikova, S.; Barbas, C.F. RNA cleavage by a DNA enzyme with extended chemical functionality. J. Am. Chem. Soc. 2000, 122, 2433-2439.
41. Perrin, D.M.; Garestier, T.; Helene, C. Expanding the catalytic repertoire of nucleic acid catalysts: Simultaneous incorporation of two modified deoxyribonucleotide triphosphates bearing ammonium and imidazolyl functionalities. Nucleosides & Nucleotides 1999, 18, 377-391.
42. Perrin, D.M.; Garestier, T.; Helene, C. Bridging the gap between proteins and nucleic acids. J. Am. Chem. Soc. 2001, 123, 1556-1563.
43. Avino, A.; Morales, J.C.; Frieden, M.; de la Torre, B.G.; Garcia, R.G.; Cubero, E.; Luque, F.J.; Orozco, M.; Azorin, F.; Eritja, R. Parallel-stranded hairpins containing 8-aminopurines. Novel efficient probes for triple-helix formation. Bioorg. Med. Chem. Lett. 2001, 11, 1761-1763.
44. Cubero, E.; Aviñó, A.; de la Torre, B.G.; Frieden, M.; Eritja, R.; Luque, F.J.; González, C.; Orozco, M. Hoogsteen-based parallel-stranded duplexes of DNA. Effect of 8-amino-purine derivatives. J. Am. Chem. Soc. 2002, 124, 3133-3142.
45. Singh, D.; Kumar, V.; Ganesh, K.N. 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. 1990, 18, 3339-3345.
46. Ikehara, M.; Kaneko, M. Purine cyclonucleosides - 8 Selective sulfonylation of 8-bromoadenosine derivatives and an alternate synthesis of 8,2′- and 8,3′-S-cyclonucleosides. Tetrahedron 1970, 26, 4251-4259.