Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2005-05-31
2005-05-31
Fredman, Jeffrey (Department: 1637)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S023100, C536S024300, C435S006120
Reexamination Certificate
active
06900297
ABSTRACT:
Nucleotides and oligonucleosides functionalized to include alkylamino functionality, and derivatives thereof. In certain embodiments, the compounds of the invention further include steroids, reporter molecules, reporter enzymes, lipophilic molecules, peptides or proteins attached to the nucleotides through the alkylamino group.
REFERENCES:
patent: 4743535 (1988-05-01), Carrico
patent: 4910300 (1990-03-01), Urdea et al.
patent: 5138045 (1992-08-01), Cook et al.
patent: 5378825 (1995-01-01), Cook et al.
patent: 5466786 (1995-11-01), Buhr et al.
patent: WO 89/12060 (1989-12-01), None
Morrison and Boyd (Organic Chemistry (1983) Allyn and Bacon, Publishers), p. 1161.*
Hart et al (Organic Chemistry (1995) Houghton Mifflin Company) p. 458.*
Lancelot et al, Biochemistry (1988) 27:1265-1273.*
Guesnet et al, Biochemistgry (1990) 29:4982-4991.*
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.
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 Sythesis of Oligonucleotides by the Phosphoramidite Approach,”Tetrahedron1992, 48, 2223-2311.
Bennett, C.F. et al., “Cationic Lipids Enhace 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-lll 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. 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 Labeling 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 Stearic Hindrance”,Bioconjugate 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 Suitabe 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 Oligodeoxyribonucleotides by Lymphoid Cells Is Heterogeneous and Inducible”,Antisense Research 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, 1, 149-153.
Letsinger, R.L., et al., “Cholesteryl-Conjugated Oligonucleotides: Synthesis, Properties, and Activity as Inhibitors of Replication of Human Immunodeficiency Virus in Cell Culture”,Proc. Natl. Acad. Sci. USA1989, 86, 6553-6556.
MacMillan, A. et al, “Synthesis of Functionally Tethered Oligodeoxynucleotides by the Convertible Nucleoside Approach”,J. Org. Chem. 1990, 55, 5931-5933.
Manoharan, M. et al., “Novel Functionalization of the Sugar Moiety of Nucleic Acids For Multiple Labeling in the Minor Groove”, Tetra.Ltrs. 32:7171-7174 (1991).
Meyer, R. et al., “Efficient, Specific Cross-Linking and Cleavage of DNA by Stable, Synthetic Complementary Oligodeoxynucleotides”,J. Am. Chem. Soc. 1989, 111, 8517-8519.
Miller, P.S. et al., “A New Approach to Chemotherapy Based on Molecular Biology and Nucleic Acid Chemistry: Matagen: Masking Tape for Gene Expression”,Anti-Cancer Drug Design1987, 2, 117-128.
Mirabelli, C.K. et al., “In vitro and In vivo pharmacologic activities of antisense oligonucleotides”,Anti-Cancer Drug Design1991, 6, 647-661.
Mori, K. et al., “Synthesis and Properties of Novel 5'-Linked Oligos”,Nucleosides&Nucleotides1989, 8, 649-657.
Nelson, P. et al., “Bifinctional
Cook Phillip Dan
Guinosso Charles J.
Manoharan Muthiah
Fredman Jeffrey
Isis Patent Department
ISIS Pharmaceuticals Inc.
Woodcock & Washburn LLP
LandOfFree
Amine-derivatized nucleosides and oligonucleosides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Amine-derivatized nucleosides and oligonucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amine-derivatized nucleosides and oligonucleosides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3426081