Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-08-30
1998-02-17
Elliott, George C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 243, 536 245, C07H 2100, C07H 2102, C07H 2104
Patent
active
057192715
ABSTRACT:
Covalent cross-linkages for two oligonucleotide strands or for first and second regions of a single oligonucleotide strand connect sugar moieties of nucleotides on the respective strands or the regions of the single strand. The cross-linkages are connected to at least one strand or region via a space-spanning group. The cross-linkage also can be connected to the other strand or other region via a space-spanning group or via an abasic site located on the other strand or other region.
REFERENCES:
patent: 4123610 (1978-10-01), Summerton et al.
patent: 4868103 (1989-09-01), Stavrianopoulos
patent: 5138045 (1992-08-01), Cook et al.
patent: 5223618 (1993-06-01), Cook et al.
patent: 5378825 (1995-01-01), Cook et al.
patent: 5399676 (1995-03-01), Froehler
patent: 5543507 (1996-08-01), Cook et al.
"Instructions to Authors for Bioconjugate Chemistry" Bioconjugate Chem. vol. 6, No. 1, p. 5A Jan. 1995.
Gura, "Antisense has Growing Pains" Science, vol. 270, pp. 575-577, Oct. 1995.
Zon et al. "Phosphorothioate Oligonucleotides in Oligonucleotides and Analogues", F. Eckstein, ed. IRL press, New York, pp. 87-108, 1991.
Matteucci et al, Tetrahedron Letters, vol. 28, pp. 2469-2472, 1987.
Meyer et al, J. Am. Chem. Soc, vol. 11, pp. 8517-8519, 1989.
Stein et al, Science, vol. 261, pp. 1009-1012, 1993.
Webb et al, Nuc. Acids Res, vol. 14, pp. 7661-7574, 1986.
Akiyama, et al., "The Selective Protection of Uridine with a p-Methoxybenzyl Chloride: A Synthesis of 2'-O-Methyluridine", Chem. Soc. Japan 63:3356-3357 (1990).
Bartel et al., "HIV-1 rev regulation involves recognition of non-Watson-Crick base pairs in viral RNA", Cell, 67:529-536, 1991.
Bertrand et al., "Synthesis, thermal stability And reactivity twoards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site", Nucleic Acids Research, 17, 10307-10319, 1989.
Butke et al., "Facile Synthesis of 2'-Amino-2-deoxynucleoside from the Corresponding Arabino Derivative", J. Carbohydrates.Nucleosides.Nucleotides 1980 7(1), 63.
Chang et al., "Periodate-oxidized AMP as a substrate, an inhibitor and an affinity label of human placental alkaline phosphate", Biochem. J. 199:281-287 (1981).
Cowart et al., A novel combined chemical-enzymatic synthesis of cross-linked dna using a nucleoside triphosphate analogue, Biochemistry, 30, 788-796, 1991.
Dartmann et al., "Short Communications: The Nucleotide Sequence and Genome Organization of Human Papilloma Virus Type 11", Virology 151:124-130 (1986).
Divakar et al., "Approaches to the Synthesis of 2'-Thio Analogues of Pyrimidine Ribosides", J.Chem.Soc.Perkin.Trans. 1:969-974 (1990).
Easterbrook-Smith et al., "Pyruvate Carboxylase: Affinity Labelling of the Magnesium Adenosine Triphosphate Binding Site", Eur. J. Biochem, 62:125-130 (1976).
Farahani et al., "Hydroxyl Radical Induced Cross-Linking Between Phenylalanine and 2-Deoxyribose", Biochemistry 27(13) :4695-4698 (1988).
Ferentz, A.E. and Verdine, G.L., "Disulfide Cross-Linked Oligonucleotides", J. Am. Chem. Soc. 113:4000-4003 (1991).
Fiandor, J. and Tam, S.Y., "Synthesis of 3'-Deoxy-3'-(Propynyl) Thymidine and 3'-Cyanomethyl-3'-Deoxythymidine, Analogs of AZT", Tetrahedron Letters 31:597-600 (1990).
Francois, et al., "Flexible Aglycone Residues in Duplex DNA", Tetrahedron Letters 31:6347-6350 (1990).
Grineva, N.I. and Karpova, G.G., "Complementarily Addressed Modification of rRNa With p-(Chloroethylmethylamino) Benzylidene Hexanucleotides", FEBS Letters 32:351-355 (1973).
Groebke and Leumann, "A method for preparing oigodeoxynucleotides containing an apurinic site", Helvetica Chimica Acta 73:608 (1990).
Meyer et al., "Efficient, Specific Cross-Linking and Cleavage of DNA by Stable, Synthetic Complementary Oligodeoxynucleotides", J.Am.Chem.Soc., 11:8517-8519 (1989).
Hall et al., Synthetic Procedures in Nucleic Acid Chemistry, Zorbach and Tipson, editors, vol. 1, John Wiley & Sons 1968.
Hansske et al., 2' And 3'-ketonucleosides and their Arabino and Xylo reduction products, Tetrahedron, 40, 125-135, 1984.
Heaphy et al., "HIV-1 Regulator of Virion Expression (rev) Protein Binds to an RNA Stem-loop Structure Located Within the Rev Response Element Region", Cell, 60:685-693, 1990.
Hegde et al., "Crystal Structure at 1..7 A of the bovine papillomavirus-1 E2 DNA-binding domain bound to its DNA target", Nature 359:505-512 (1992).
Horn, T. et al., "Controlled chemical cleavage of synthetic DNA at specific sites", Nucleosides & Nucleotides, 10:299 (1991).
Iyer et al., "Abasic oligodeoxyribonucleoside phosphorothioates synthesis and evaluation as anti-HIV-1 agents", Nucleic Acids Research, 18:2855-2859, 1990.
Knorre et al., Nucleotide and Oligonucleotide Derivatives as Enzyme and Nucleic Acid Targeted Irreversible Inhibitors, Chemical Aspects, G. Weber (Ed.), Advances Press, Oxford, pp. 277-320 (1986).
Lee et al., "Interaction of Psoralen-Derivatized Oligodeoxyribonucleoside Methylphosphonates with Single-Stranded DNA", Biochemistry 27:3197-3203 (1988).
Lemaitre et al., "Specific antiviral activity of a poly(L-lysine)-conjugated oligodeoxyribonucleotide sequence complementary to vesicular stomatitis virus N protein mRNA initiation site", Proc.Natl.Acad.Sci. USA 84:648-652 (1987).
Lindahl et al., "DNA N-Glycosidases: Properties of Uracil-DNA glycosidase from Escherichia coli", J.Biol.Chem. 252:3286-3294 (1977).
Manoharan et al., "Coexistence of Conformations in a DNA Heteroduplex Revealed by Site Specific Labeling with .sup.13 C-Labeled Nucleotides", J.Am.Chem.Soc. 109:7217-7219 (1987).
Manoharan et al., "Introduction of a Lipophilic Thioether Tether in the Minor Groove of Nucleic Acids for Antisense Applications", Biorganic & Medicinal Chemistry Letters 3:2765-2770 (1993).
Manoharan et al. "Mechanism of UV Endonuclease V Cleavage of Abasic Sites in DNA Determined by .sup.13 C Labeling", J.Am.Chem.Soc. 110:2690-2691 (1988).
Matteucci et al., "Synthesis and Crosslinking Properties of a Deoxyoligonucleotide Containing N.sup.6,N.sup.6 -Ethanodeoxyadenosine", Tetra.Ltrs. 28:2469-2472 (1987).
McArthur et al., "Amino Group Blocking. Improved Method for N-Phthaloylation Using N-(Ethoxycarbonyl)Phthalimide", Synthetic Communications 13: 311-318 (1983).
Nucleic Acids in Chemistry and Biology, Blackburn and Gait, eds., Oxford University Press, New York, 1991. (pp. 52-58 only).
Pfitzner and Moffatt, "Sulfoxide-carbodiimide reactions. I. A facile oxidation of alcohols", Journal of American Chemical Society 87(24) :5661-5670 (1965).
Ratner, "Can the antisense message be delivered", Biotechnology, 7, 207, 1989.
Peoch'h, D. et al., "Efficient chemical synthesis of oligodeoxynucleotides containing a true abasic site", Tetrahedron Letters 32:207 (1991).
Sproat et al., "New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure", Nucleic Acids Research 18:41-49 (1990).
Sproat et al., "New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly", Nucleic Acids Research, 19:733 (1991).
Stein et al., "Antisense oligonucleotides as therapeutic agents--is the bullet really magical?" Science 261:1009-1012 (1993).
Summerton et al., "Sequence-specific Crosslinking Agents for Nucleic Acids", J.Mol. Biol. 122:145-162 (1978).
Summerton, J., "Sequence-Specific Crosslinking Agents for Nucleic Acids: Design and Functional Group Testing", J. Theor.Biol. 78:61-75 (1979).
Vasseur, Jean-Jacques et al., "Apurinic DNA: Modelisation and Reactivity Towards 9-Aminoellipticine and Related Amines", Nucleosides & Nucleotides 8(5&6) :863-866 (1989).
Wagner et al., "Preparation and synthetic utility of some organotin derivatives of nucleosides", J. Org. Chem., 39:24 (1974).
"Webb and Matteucci., Hybridization triggered cross-linking of deoxyoligonucleotides", Nucleic Acids Research, 14, 7661-7674, 1986.
Bruice Thomas
Cook Phillip Dan
Manoharan Muthiah
Elliott George C.
ISIS Pharmaceuticals Inc.
Larson Thomas G.
LandOfFree
Covalently cross-linked oligonucleotides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Covalently cross-linked oligonucleotides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Covalently cross-linked oligonucleotides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1784937