Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-03-02
1996-08-06
Low, Christopher S. F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 241, 536 243, 536 2431, 536 2432, 536 2433, 536 252, 536 253, 435 911, 435 914, 435 9121, 435 915, C07H 2100, C07H 2102, C07H 2104
Patent
active
055435076
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: 5082934 (1992-01-01), Saba et al.
patent: 5223618 (1993-06-01), Cook et al.
patent: 5296350 (1994-03-01), Rokita et al.
patent: 5367066 (1994-11-01), Urdea et al.
patent: 5378825 (1995-01-01), Cook et al.
Webster's II New Riverside University Dictionary, 1984, Houghton Mifflin Co., Boston, MA, pp. 819 and 979.
Stryer, L., 1978, in: Biochemistry, W. H. Freeman and Company, San Francisco, CA pp. 528-529.
Grineva, N. I. and Karpova, G. G., "Complementarily Addressed Modification of rRNA with p-(Chloroethylamino) Benzylidene Hexanucleotides", FEBS., 32, (1973), 351-355.
Sumerton and Bartlett [see: Summerton, J. and Bartlett, P. A.], "Sequence-specific Crosslinking Agents for Nucleic Acids", J. Mol. Biol. 122, (1978), 145-162.
Summerton, J., "Sequence-specific Crosslinking Agents for Nucleic Acids: Design and Functional Group Testing", J. Theor. Biology, 78, (1979), 61-75.
Meyer et al., "Efficient, Specific Cross-Linking and Cleavage of DNA by Stable, Synthetic Complementary Oligodeoxynucleotides, J. Am. Chem. Soc., 111", (1989), 8517-8519.
Webb., T. R. and Matteucci, M. D., "Hybridization Triggered Cross-Linking of Deoxyoligonucleotides, Nucleic Acids", Res., 14, (1986), 7661-7674.
Matteucci et al., "Synthesis and Crosslinking Properties of a Deoxyoligonucleotide Containing N.sub.6, N.sub.6 -Ethano-Deoxyadenosine", Tetrahedron Ltrs., 28, (1987), 2469-2472.
Ferentz, A. E. and Verdine, G. L., "Disulfide Cross-Linked Oligonucleotides", J. Am. Chem. Soc., 113, (1991), 4000-4002.
Lee, B. L. et al., "Interaction of Psoralen-Derivatized Oligodeoxyribonucleoside Methylphosphonates with Single-Stranded DNA", Biochemistry, 27, (1988), 3197-3203.
Manoharan et al., "Coexistence of Conformations in a DNA Heteroduplex Revealed by Site Specific Labeling with .sub.13 C-Labeled Nucleotides", J. Am. Chem. Soc., 109, (1987), 7217-7219.
Manoharan, M. et al., "Mechanism of UV Endonuclease V Cleavage of Abasic Sites in DNA Determined by .sub.13 C Labeling", J. Am. Chem. Soc., 110, (1988), 2690-2691.
Vasseur, J.-J. et al., "Apurnic DNA: Modelisation and Reactivity Towards 9-Aminoellipticine and Related Amines", Nucleosides & Nucleotides, 8, (1989), 863-866.
Bertrand et al., "Synthesis, Thermal Stability and Reactivity Towards 9-Aminoellipticine of Double-Stranded Oligonucleotides Containing a True Abasic Site", Nucleic Acids Research, 17, (1989), 10307-10319.
P. Iyer et al., "Abasic Oligodeoxyribonucleoside Phosphorothioates Synthesis and Evaluation as Anti-HIV-1 Agents", Nucleic Acids Research, 18, (1990), 2855-2859.
Groebke, K. and Leumann, C., "A Method for Preparing Oligodeoxynucleotides Containing an Apurinic Site", Helvetica Chimica Acta, 73, (1990), 608-617.
Peoc'h, D. et al., "Efficient Chemical Synthesis of Oligodeoxynucleotides Containing a True Abasic Site", Tetrahedron Letters, 32, (1991), 207-210.
"Nucleic Acids In Chemistry And Biology", Edited by G. Michael Blackburn and Michael J. Gait, Oxford University Press, New York, (1991), 52-58.
Pfitzner, K. E. and Moffat, J. G., "Sulfoxide-Carbodiimide Reactions. I. A Facile Oxidation of Alcohols", J. Am. Chem. Soc., 87, (1965), 5661-5670.
Lemaitre et al., "Specific Antiviral Activity of a poly(L-lysine)-Conjugated Oligodeoxyribonucleotide Sequence Complementary to Vesicular Stromatitis Virus N Protein mRNA Initiation Site", Proc. Natl. Acad. Sci. USA, 84, (1987), 648-652.
Chang et al., "Periodate-Oxidized AMP as a Substrate, an Inhibitor and an Affinity Label of Human Placental Alkaline Phosphatase", Biochem. J., 199, (1981), 281-287.
Easterbrook-Smith et al., "Pyruvate Carboxylase: Affinity Labelling of the Magnesium Adenosine Tri-phosphate Binding Site", Eur. J. Biochem., 62, (1976), 125-130.
Akiyama et al., "The Selective Protection of Uridine with a p-Methoxybenzyl Chloride: A Synthesis of 2'-O-Methyluridine", Notes Bull. Chem. Soc. Jpn., 63, (1990), 3356-3357.
Sproat et al., "New Synthetic Routes to Protected Purine 2'-O-methylriboside-3'-O-phosphoramidites Using a Novel Alkylation Procedure", Nucleic Acid Res., 18, (1990), 41-49.
Sproat, B. S. et al., "New Synthetic Routes to Synthons Suitable for 2'-O-allyloligoribonucleotide Assembly", Nucleic Acids Research, 19, (1991), 733-738.
McArthur, C. R. et al., "Amino Group Blocking. Improved Method for N-Phthaloylation Using N-(Ethoxycarbonyl) Phthalimide", Synth. Commun. 13, (1983), 311-318.
Divakar, K. J. et al., "Approaches to the Synthesis of 2'-Thio Analogues of Pyrimidine Ribosides", J. Chem. Soc. Perkin Trans. 1, (1990), 969-974.
Butke, G. et al., "Facile Synthesis of 2'-Amino-2'-Deoxyadenosine, J. Carbohydrates", Nucleosides, Nucleotides, 7, (1988), 63-75.
Fiandor, J. and Tam, S. Y., "Synthesis of 3'-Deoxy-3'-(2-Propynyl)Thymidine and 3'-Cyanomethyl-3'-Deoxythymidine, Analogs of AZT", Tetrahedron Letters, 31, (1990), 597-600.
Hall, R. H. and Fleysher, M. H., "Synthetic Procedures in Nucleic Acid Chemistry", W. W. Zorbach and R. S. Tipson, Editors, vol. 1, John Wiley & Sons, (1968).
Hansske, F. et al., "2' and 3'-Ketonucleosides and Their Arabino and Xylo Reduction Products", Tetrahedron, 40, (1984) 125-135.
Francois, P. et al., "Flexible Aglycone Residues in Duplex DNA", Tetrahedron Letters, 31, (1990), 6347-6350.
Lindahl, T. et al., "DNA N-Glycosidases: Properties of Uracil-DNA Glycosidase From Escherichia Coli", J. Biol. Chem., 252, (1977), 3286-3294.
Horn, T. et al., "Controlled Chemical Cleavage of Synthetic DNA at Specific Sites", Nucleosides & Nucleotides, 10, (1991), 299-302.
Knorre et al., "Nucleotide and Oligonucleotide Derivates As Enzyme and Nucleic Acid Targeted Irreversible Inhibitors, Chemical Aspects", G. Weber (Ed.), Advance Press, Oxford, (1986), 277-299.
Ratner, "Can The Antisense Message Be Delivered", Biotechnology, 7, (1989), 207.
Stein, et al., "Antisense Oligonucleotides as Therapeutic Agents --Is the Bullet Really Magical?", Science, 261, (1993) 1004-1012.
Farahani, et al., "Hydroxyl Radical Induced Cross-Linking Between Phenylalanine and 2-Deoxyribose", Biochemistry, 27, No. 13 (1988) 4695-4698.
Cowart, et al., "A Novel Combined Chemical-Enzymatic Synthesis of Cross-Linked DNA Using a Nucleosside Triphosphate Analogue", Biochemistry, 30, No. 3, (1991), 788-796.
Manoharan, et al., "Introduction of a Lipophilic Thioether Tether in the Minor Groove of Nucleic Acids for Antisense Applications", Biorganic & Medicinal Chemistry Letters, 3, No. 12, (1993), 2765-2770.
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, (1990), 685-693.
Bartel, et al., "HIV-1 Rev Regulation Involves Recognition of Non-Watson-Crick Base Pairs in Viral RNA", Cell, 67, (1991), 529-536.
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, (1992), 505-512.
Dartmann, et al., "The Nucleotide Sequence and Genome Organization of Human Papilloma Virus Type 11", Virology, 151, (1986), 124-130.
Horne et al., 1990, J. Am. Chem. Soc. 112, 2435-2437.
Bruice Thomas
Cook Phillip D.
Manoharan Muthiah
ISIS Pharmaceuticals Inc.
Low Christopher S. F.
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-2191935