Derivatized oligonucleotides having improved uptake and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S025300, C536S026600, C514S001000, C514S04400A, C435S006120

Reexamination Certificate

active

07125975

ABSTRACT:
Linked nucleosides having at least one functionalized nucleoside 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, a 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 liked 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: 4910300 (1990-03-01), Urdea et al.
patent: 4958013 (1990-09-01), Letsinger
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: 5416203 (1995-05-01), Letsinger
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: 251283 (1988-07-01), None
patent: WO 86/02929 (1986-05-01), None
patent: WO 89/02931 (1989-04-01), None
patent: WO 90/10448 (1990-09-01), None
patent: WO 91/00243 (1991-01-01), None
patent: WO 91/14696 (1991-03-01), None
patent: WO 91/15500 (1991-10-01), None
patent: WO 92/05186 (1993-04-01), None
Asseline, U. et al., “Solid-Phase Preparation of 5′-3′-Heterobifunctional Oligodeoxyribonucleotides Using Modified Solid Supports,”Tetrahedron1992, 48, 1233-1254.
Asseline, U. et al., “Nucleic acid-binding molecules with high affinity and base sequence specificity: Intercalating agents covalently linked to oligodeoxynucleotides,”Proc. Natl. Acad. Sci. USA1984, 81, 3297-3301.
Atherton,E. et al.,The Peptides, Gross and Meienhofer, Eds, Academic Press; New York, vol. 9:1-38, 1983.
Baker, B.F., “Decapitation of a 5′-Capped Oligoribonucleotide by o-Phenanthroline: CU(II),”J. Am. Chem. Soc.1993, 115, 3378-3379.
Beaucage, S. et al., “Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach,”Tetrahedron1992, 48, 2223-2311.
Bennett, C.F. et al., “Cationic Lipids Enhance Cellular Uptake and Activity of Phosphorothioate Antisense Oligonucleotides”,Molecular Pharmacology1991, 41, 1023-1033.
Betebenner, D.A., et al., “Hepatobiliary Delivery of Polyaminopolycarboxylate Chelates: Synthesis and Characterization of a Cholic Acid Conjugate of EDTA and Biodistribution and Imaging Studies with Its Indium-111 Chelate”,Bioconjugate Chem.1991, 2, 117-123.
Bischoff, R. et al., “Introduction of 5′-Terminal Functional Groups into Synthetic Oligonucleotides for Selective Immobilization,”Analy. Biochem.1987, 164, 336-344.
Blackburn, G. et al., “Studies in Phosphorylation. Part XXIX. The Synthesis of Dialkyl Phosphates from Monoalkyl Phosphonates: Direct Oxidative Esterification”,J. Chem. Soc.1966, 239-245.
Chiang, M.-Y. et al., “Antisense Oligonucleotides Inhibit Intercellular Adhesion Molecule 1 Expression by Two Distinct Mechanisms”,J. of Biol. Chem.1991, 266, 18162-18171.
Chollet, A., “Selective Attachment of Oligonucleotides to Interleukin-1 beta and Targeted Delivery to Cells”,Nucleosides&Nucleotides1990, 9, 957-966.
Cohen, J. inOligonucleotides: Antisense Inhibitors of Gene Expression, CRC Press, Inc., Boca Raton, FL, pp. 1-255, 1989.
Corey, D. et al., “Sequence-Selective Hydrolysis of Duplex DNA by an Oligonucleotide-Directed Nuclease”,J. Am. Chem. Soc.1989, 111, 8523-8525.
Corey, D. et al., “Generation of a Hybrid Sequence-Specific Single-Stranded Deoxyribonuclease”,Science1987, 238, 1401-1403.
Damha, M. et al., “An Improved Procedure for Derivatization of Controlled-Pore Glass Beads for Solid- Phase Oligonucleotide Synthesis”,Nuc. Acids Res.1990, 18, 3813-3821.
Delgado, C. et al., “The Uses and Properties of PEG-Linked Proteins”,Critical Reviews in Therapeutic Drug Carrier Systems1992, 9, 249-304.
Dingwall, C., et al., “Protein Import Into the Cell Nucleus”,Ann. Rev. Cell Biol.1986, 2, 367-90.
DiZio, J. et al., “Progestin-Thenium Complexes: Metal-Labeled Steroids with High Receptor Binding Affinity, Potential Receptor-Directed Agents for Diagnostic of Therapy”,Bioconjugate Chem.1991, 2, 353-366.
Dreyer, G. et al., “Sequence-Specific Cleavage of Single-Stranded DNA: Oligodeoxynucleotide-EDTA.Fe(II)”,PNAS USA1985, 82, 968-972.
Egholm, M. et al., “Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone”,J. Am. Chem. Soc.1992, 114, 1895-1897.
Ferentz, A.E. and Verdine, G.L., “Disulfide Cross-Linked Oligonucleotides”,J. Am. Chem. Soc.1991, 113, 4000-4003.
Fidanza, J. et al., “Site-Specific Labelingl of DNA Sequences Containing Phosphorothioate Diesters”,J. Am. Chem. Soc.1992, 114, 5509-5517.
Fidanza, J. et al., “Use of a Thiol Tether for the Site-Specific Attachment of Reporter Groups of DNA”,J. Org. Chem.1992, 57, 2340-2346.
Froehler, B. et al., “Synthesis of DNA via Deoxynucleoside H-Phosphonate Intermediates”,Nucleic Acids Research1986, 14, 5399-5407.
Gaur, R. et al., “A Simple Method for the Introduction of Thiol Group at 5′-Termini of Oligodeoxynucleotides”,Nuc. Acids Res.1989, 17, 4404.
Greene et al.,Protective Groups in Organic Synthesis, 2d edition, New York, John Wiley & Sons, pp. 178-223, 1991.
Greenfield, L. et al., “Thiol-Containing Cross-Linking Agent with Enhanced Steric Hindrance”,Biodonjugate Chem.1990, 1, 400-410.
Guerra, F.I. et al., “Synthetic 7-Glucosyl Phospholipid as a Drug Transport System”,Tetrahedron Letters1987, 28, 3581-3584.
Haralambidis J., et al., “Preparation of Base-modified Nucleosides Suitable for Non-Radioactive Label Attachment and Their Incorporation Into Synthetic Oligodeoxyribonucleotides”,Nucleic Acids Research1987, 15, 4857-4876.
Haralambidis, J. et al., “The Solid Phase Synthesis of Oligonucleotides containing a 3′-Peptide Moiety”,Tetrahedron Letters1987, 28, 5199-5202.
Harris, C. et al., “New Strategy for the Synthesis of Oligodeoxynucleotides Bearing Adducts at Exocyclic Amino Sites of Purine Nucleosides”,J. Am. Chem. Soc.1991, 113, 4328-4329.
Iyer, R. et al., “3H-1, 2-Benzodithiole-3-one, 1,1,-Dioxide as an Improved Sulfurizing Reagent in the Solid-Phase Synthesis of Oligodeoxyribonucleoside Phosphorothioates”,J. Am. Chem. Soc.1990, 112, 1253-1254.
Jablonski, E. et al., “Preparation of Oligodeoxynucleotide-Alkaline Phosphatase Conjugates and Their Use as Hybridization Probes”,Nucleic Acid Research1986, 14, 6115-28.
Juby, C.D., et al., “Facile Preparation of 3′Oligonucleotide-Peptide Conjugates”,Tetrahedron Letters1991, 32, 879-882.
Krieg, A.M., et al., “Uptake of Oligodeoxyribonucleo-tides by Lymphoid Cells Is Heterogeneous and Inducible”,Antisense Resea and Development1991 1, 161-171.
Lemaitre, M. et al., “Specific Antiviral Activity of a Poly(L-lysine)-Conjugated Oligodeoxyribonucleotide Sequence Complementary to Vesicular Stomatitis Virus N Protein mRNA Initiation Site”,PNAS USA1987, 84, 648-652.
Leonetti, J.P. et al, “Biological Activity of Oligonucleotide-Poly(L-lysine) Conjugates: Mechanism of Cell Uptake”,Bioconjugate Chem.1990, I, 149-153.
Letsinger,

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Derivatized oligonucleotides having improved uptake and... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Derivatized oligonucleotides having improved uptake and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Derivatized oligonucleotides having improved uptake and... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3714197

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.