Derivatized oligonucleotides having improved uptake and...

Details Derivatized oligonucleotides having improved uptake and... Derivatized oligonucleotides having improved uptake and...

2005-07-19

2005-07-19

Riley, Jezia (Department: 1637)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S022100, C536S025300, C536S025320, C536S026600, C514S04400A

Reexamination Certificate

active

06919439

ABSTRACT:
Linked nucleosides having at least one functionalized nucleosid that bears a substituent such as a steroid molecule, a reporter molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, lipid soluble vitamin, an RNA cleaving complex, a metal chelator, a porphyrin, an alkylator, a pyrene, a hybrid photonuclease/intercalator, or an aryl azide photo-crosslinking agent exhibit increased cellular uptake and other properties. The substituent can be attached at the 2′-position of the functionalized nucleoside via a linking group. If at least a portion of the remaining linked nucleosides are 2′-deoxy-2′-fluoro, 2′-O-methoxy, 2′-O-ethoxy, 2′-O-propoxy, 2′-O-aminoalkoxy or 2′-O-allyloxy nucleosides, the substituent can be attached via a linking group at any of the 3′ or the 5′ positions of the nucleoside or on the heterocyclic base of the nucleoside or on the inter-nucleotide linkage linking the nucleoside to an adjacent nucleoside.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4381344 (1983-04-01), Rideout et al.
patent: 4511713 (1985-04-01), Miller et al.
patent: 4689320 (1987-08-01), Kaji
patent: 4760017 (1988-07-01), McCormick
patent: 4876335 (1989-10-01), Yamane et al.
patent: 4910300 (1990-03-01), Urdea et al.
patent: 4958013 (1990-09-01), Letsinger
patent: 4965350 (1990-10-01), Inoue et al.
patent: 5015733 (1991-05-01), Smith et al.
patent: 5108921 (1992-04-01), Low et al.
patent: 5296350 (1994-03-01), Rokita et al.
patent: 5466786 (1995-11-01), Buhr et al.
patent: 5470967 (1995-11-01), Huie et al.
patent: 5578718 (1996-11-01), Cook et al.
patent: 6153737 (2000-11-01), Manoharan et al.
patent: 6395492 (2002-05-01), Manoharan et al.
patent: 251283 (1988-07-01), None
patent: WO 86/02929 (1922-05-01), None
patent: WO 89/02931 (1989-04-01), None
patent: WO 90/10448 (1990-09-01), None
patent: WO 91/00243 (1991-10-01), None
patent: WO 91/15500 (1991-10-01), None
patent: WO 91/14696 (1991-11-01), None
patent: WO 92/05186 (1993-04-01), None
patent: WO 93/07883 (1993-04-01), None
Agrawal, S. et al., “Oligodeoxynucleoside phosphoramidates and phosphorothioates as inhibitors of human immunodeficiency virus,”Proc. Natl. Acad Sci.,1988, 85, 7079-7083.
Agris, C. H. et al., “Inhibition of Vesicular Stomatitis Virus Protein Synthesis and Infection by Sequence-Specivid Oligodeoxyribonucleoside Methylphosphonates,”Biochem.,1986, 25, 6268-6275.
Biggadike, K. et al., “Short Convergent Route to Homochiral Carbocyclic 2′-Deoxynucleosides and Carbocyclic Ribonucleosides,”J. Chem. Soc. Chem. Commun.,1987, 1083-1084.
Brill, W. K. et al., “Synthesis of of oligodeoxynucleoside phosphorodithioates via thioamidites,”J. Am. Chem. Soc.,1989, 111, 2321-2322.
Carbohydr. Res. 44, 1975, 112.
Castle, R. N. et al., “Imidazo[4,5-d] pyridazines. I. Synthesis of 4,7-Disubstituted Derivatives,”J. Org. Chem.,1958, 23, 1534-1538.
Cazenave, C. et al., “Enzymatic amplication of translation inhibition of rabbit β-globin mRNA mediated by antimessenger oligodeoxynucleotides covalently linked to intercalating agents,”Nucl. Acids Res.,1987, 15, 4717-4736.
Constant, J.F. et al., “Heterodimeric Molecules Including Nucleic Acid Bases and 9-Aminoacridine. Spectroscopic Studies, Conformations, and Interactions with DNA,”Biochem.,1988, 27, 3997-4003.
Deazaguanine Nucleosides and Nucleotides,J. Med. Chem.,1984, 27, 1389-1396.
Eckstein, F., et al.,Biochemistry,1972, 11, 4336.
Gait, M. J. ed., “An Introduction to Modern Methods of DNA Synthesis,”Oligonucleotide Synthesis, A Practical Approach,IRL Press, Oxford, 1985, IRL Press, Oxford, Ch. 1, 1-22.
Guschlbauer, W. et al., “Nucleoside conformation is determined by the electronegativity of the sugar subtituent,”Nucl. Acids Res.,1980, 8(6), 1421-1433.
Heterocyclic Compounds,Weissberger, A. (ed.), Interscience Publishers,Inc., New York, 1953, Part 1, 3-447.
Ikehara, M., et al.,European J. Biochem.,1984, 139, 447-450.
Ikehara, M., et al.,Tett. Lett.,1979, 42, 4073.
Ikehara, M., et al.,Nucleic Acids Res.,1978, 5, 1877.
Ikehara, M. et al., “Polynucleotides. LVI. Synthesis and properties of poly(2′-deoxy-2′-fluroadenylic acid),”Nucl. Acids Res.,1978, 5, 3315-3325.
Ikehara, M. et al., “Polynucleotides. L. Synthesis and properties of poly(2′-chloro-2′-deoxyadenylic acid) and poly(2′-bromo-2′-deoxyadenylic acid),”Nucl. Acids Res.,1977, 4(12), 4249-4260.
Inone, et al.,Nucleic Acids Res.,1987, 15, 6131-6148.
Jager, A. et al., “Oligonucleotide N-Alkylphosphoramidates: Synthesis and Binding to Polynucleotides,”Biochem.,1988, 27, 7237-7246.
Jayaraman, K. et al., “Selective Inhibition ofEscherichia coliprotein synthesis and growth by nonionic olignucleotides complementary to the 3′ end of 16S rRNA,”Proc. Natl. Acad. Sci.,1981, 78, 1537-1541.
Jones, R.A., inOligonucleotide Synthesis—A Practical Approach,M. Gait, (Ed.), IRL Press, Washington, D.C. 1985.
Jones, G.H. et al., “4′-Substituted Nucleosides. 5. Hydroxymethylation of Nucleoside 5′-Aldehydes,”J. Org. Chem.,1979, 44, 1309-1317.
Knorre, D. G. et al., “Complementary-Addressed (Sequence-Specific) Modification of Nucleic Acids,” 1985, 32, 291-321.
Le Doan, T. et al., “Sequence-targeted chemical modification of nucleic acids by complementary oligonucleotides covalently linked to porphyrins,”Nucl. Acids Res.,1987, 15, 8643-8659.
Letsinger, R. L. et al., “Effects of pendant groups at phosphorus on binding properties of d-ApA analogues,”Nuc. Acids. Res.,1986, 14, 3487-3498.
Marcus-Sekura, C.J.,Anal. Biochemistry,1988, 172, 289-295.
Marcus-Sekura, C.J. et al., “Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages,”Nucl. Acids Res.,1987, 15(14), 5749-5763.
Matsukura, M. et al., “Phosphorothioate analogs of oligodeoxynucleotides: Inhibitors of replication and cytopathic effects of human immunodeficiency virus,”Proc. Natl. Acad. Sci.,1987, 84, 7706-7710.
Miller, P. S. et al., “Nonionic Nucleic Acid Analogues. Synthesis and Characterization of Dideoxyribonucleoside Methylphosphonates,”Biochem.,1979, 18, 5134-5143.
Miller, P. S. et al., “Biochemical and Biological Effects of Nonionic Nucleic Acid Methylphosphonates,”Biochem.,1981, 20, 1874-1880.
Miller, P. S. et al., “Synthesis and Properties of Adenine and Thymine Nucleoside Alkyl Phosphotriesters, the Neutral Analogs of Dinucleoside Monophosphates,”J. Am. Chem. Soc.,1971, 93, 6657-6664.
Nucleic Acids Res.,1979, 6, 3009-3024.
Nucleic Acid Chemistry, Improved and New Synthetic Procedures, Methods, and Techniques, Part 3, 1986, 229.
Outten, R. A. et al., “Synthetic 1-Methoxybenzol[d]naphtho[1,2-b]pyran-6-one C-Glycosides,”J. Org. Chem.,1987, 52, 5064-5066.
Rec. Trav. Chim., 89, 1979, 2.6g, 1189.
Robins, M. J. et al., “Nucleic Acid Related Compounds. 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversion of Ribonucleosides to 2′-Deoxynucleosides,”J. Am. Chem. Soc.,1983, 105, 4059-4065.
Roelen, H.C.P.F. et al., “Synthesis of nucleic acid methylphosphonthioates,”Nucl. Acids Res.,1988, 16(15), 7633-7645.
Ruby, S. W. et al., “An Early Hierarchic Role of U1 Small Nuclear Ribonucleoprotein in Spliceosome Assembly,”Science,1988, 242, 1028-1035.
Shibahara, S. et al., “Inhibition of human immunodeficiency virus (HIV-1) replication by synthetic oligo-RNA derivatives,” 1989, 17(1), 239-252.
Sigman, D. S. et al., “Nuclease Activity of 1,10-Phenanthroline-Copper Ion,”Acc. Chem. Res.,1986, 19, 180-186.
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