Backbone modified oligonucleotide analogues

Details Backbone modified oligonucleotide analogues Backbone modified oligonucleotide analogues

1996-12-11

1999-10-12

Marschel, Ardin H.

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

Organic compounds

Carbohydrates or derivatives

435 6, 436501, 514 44, 536 221, 536 245, 536 256, 536 253, 536 261, 935 77, 935 78, C07H 2100

Patent

active

059657219

ABSTRACT:
Therapeutic oligonucleotide analogues which have improved nuclease resistance and improved cellular uptake are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligomers with four atom linking groups forms unique di- and poly-nucleosides and nucleotides useful in regulating RNA expression and in therapeutics. Methods of synthesis and use are also disclosed.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 4469863 (1984-09-01), Ts'o et al.
patent: 4511713 (1985-04-01), Miller et al.
patent: 4591614 (1986-05-01), Miller et al.
patent: 5264562 (1993-11-01), Matteucci
patent: 5264564 (1993-11-01), Matteucci
patent: 5268464 (1993-12-01), Brill
patent: 5378825 (1995-01-01), Cook et al.
patent: 5658731 (1997-08-01), Sproat et al.
Abdel-Magid et al., "Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride", Tetrahedron Letts., 1990, 31, 5595-5598.
Bankston et al., "A Short Synthesis of 50'-O-Trityl-Protected threo-and erythro-3'-Cyano-3'-deoxythymidine Epimers Using Free-Radical Chemistry", J. Heterocylclic Chem. 1992, 29, 1405-1407.
Barton et al., "A `One-Pot ` Synthesis of Sulfenamides", J. Org. Chem., 1991, 56, 6702-6704.
Barton et al., "Stereoselectivity in Radical Reactions of 2'-Deoxynucleosides. A Synthesis of an Isostere of 3'-Azido-3'-Deoxythymidine-5'-Monophosphate", Tetra. Ltrs. 1989, 30, 4969-4972.
Baud et al., "Improved Procedure For The Regiospecific Synthesis of 2'-Deoxyribonucleosides", Tetra. Ltrs. 1990, 31, 4437-4440.
Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach", Tetra Ltrs., 1992, 48, 2223-2311.
Beaucage and Iyer, "The Synthesis of Modified Oligonucleotides by the Phosphoramidite Approach and Their Applications", Tetrahedron 1993, 49(28), 6123-6194.
Bergstrom, D.E., "An Improved Synthesis of 3-Keto-5-O-Tritylthymidine", Nucleosides and Nucleotides, 1989, 8(8), 1529-1535.
Bodenteich et al., "Synthesis of enantiomerically pure carbocyclic 3'-Azido 2', 3'-Dideoxythymidine, a potential anti-AIDS drug", Tetrahedron Letters 1987, 28, 5311-5312.
Brown et al., in Oligonucleotides and Analogues, Ed. by Eckstein, pp. 1-24, 1991.
Camarasa et al., "Aldol Reaction of Nucleoside 5'-Carboxaldehydes With Acetone Synthesis of 5'-C-Chain Extended Thymidine Derivatives", Nucleosides & Nucleotides 1990, 9, 533-546.
Cohen, J.S., Ed. Oligonucleotides: Antisense Inhibitors of Gene Expression, (CRC Press, Inc., Boca Raton FL, 1989.
Corimer and Ogilvie, "Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages", Nucleic Acids Research, 1988, 16, 4583-4594.
Cosstick et al., "Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymide", Nucleic Acids Research, 1990, 18, 829-835.
Coull et al., "Synthesis and Characterization of a Carbamate-linked Oligonucleoside", Tetra Ltrs., 1987, 28, 745-748.
Crooke, S.T. and Lebleu, C., Eds., Antisense Research and Applications, CRC Press, Inc., Boca Raton FL, 1993.
Curran, D.P., Radical Addition Reactions, in Comprehensive Organic Synthesis, Torst, B.M. and Fleming, I. Eds., vol. 4. p. 715-823 Pergamone Press, Oxford, 1991.
Debart et al. "Intermolecular Radical C-C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleosides", Tetrahedron Letts. 1992, 33(19), 2645-2648.
Egholm et al., "Recognition of Guanine and Adenine in DNA by Cytosine and Thymine Containing Peptide Nucleic Acids (PNA).sup.1,2 ", J. Am. Chem. Soc., 1992, 114, 9677-9678.
Egholm et al., "Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone," J. Am. Chem. Soc., 1992, 114, 1895-1897.
Etzold et al., "The Extension of the Sugar Chain of Thymidine: a New Route to 5'-Deoxyhexose Nucleosides", J.C.S. Chem. Comms. 1968, p. 422.
Finador, J. and Tam, "Synthesis of 3'-Deoxy-3'-(2-Propynyl Thymidine and 3'-Cyanomethyl-3'-Deoxythymidine, analogs of AZT.sup.1 ", Tetrahedron Letts., 1990, 33, 597-600.
Fikes et al., "Preassociating alpha-nucleophiles", J. Am. Chem. Soc., 1992, 114, 1493-1495.
Fleet et al., "Methyl 5-o-tert-buryldiphenylsislyl-2-deoxy .alpha..beta.-d-ThreoPentofuranoside as a Divergent Intermediate for the Synthesis of 3'-Substituted-2', 3'-Dideoxynucleosides: Synthesis of 3'-Azidio-3'-Deoxythymidine, 3'-Deoxy-3'-Flurothymidine and 3'-Cyano-3'-Deoxythymidine", Tetrahedron, 1988, 44, 625-636.
Gait, M.J., ed., Oligonucleotide Synthesis: A Practical Approach (IRL Press 1984).
Gait, et al., "Synthetic Analogues of Polynucleotides. Part XII. Synthesis of Thymidine Derivatives Containing an Oxyacetamido-or and Oxyformamido-Linkage Instead of a Phosphodiester Group", J.C.S. Perkins I, 1974, pp. 1684-1686.
Giannis et al., "Fragmentation and Wittg Olefination of Glucosamine Derivatives --A Sample Route to Open Chain Amino Sugars and Chiral Glycerols", Tetrahedron 1988, 44, 7177-7180.
Goodchild, J., "Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties", Bioconjugate Chemistry, 1990, 1, 165-187.
Goodchild, John, Inhibition of Gene Expression by Oligonucleotides: in Oligodeoxynucleotides, CRC Pres, Inc. (USA) pp. 53-78 1989.
Greene et al., Protective Groups in Organic Synthesis, John Wiley & Sons., Inc., 175-223, 1991.
Halford, M. & Jones, "Synthetic Analogues fo Polynucleotides", Nature, 1968, 217, 638-639.
Hanamoto et al., "Smi2-promoted Ketyl Radical Addition to O-Benzyl Formaldoxime. A New Aminoethylation", Tetrahedron Letters, 1991, 32, 3555-3556.
Hart et al., "Bis (trimethylstannyl)benzopinacolate-mediated Intermolecular Free-Radical Carbon-Carbon Bond-Forming Reactions: A New One-Carbon Homologation", J. Am. Chem. Soc., 1988, 110, 1631-1633.
Hata, T. et al., "One-step Synthesis of 5'-Azido-nucleosides", J. Chem. Soc. Perkin I, 1980, p. 306.
Hill, et al., "3, 4-dihydro-2h-1, 4-benzoxazines", J. Chem Soc., 1964, 716, 3709-3713.
Hillgartner, H. et al., "Bis(trimethylzinn)benzpinakolat, seine reversible radikalische Dissociation und Reaktionen", Liebigs Ann. Chem. 1975, 586-599.
Horwitz, J. et al., "Nucleosides. V. The monomesylates of 1-(2'-Deoxy-.beta.-D-Lyxofuranosyl) Thymine", J. Org. Chem. 1964, 29, 2076-2078.
Hronowski, J. et al., "Synthesis of new carbocyclic analogues Of 3'-Azido-and 3'-Aminno-2', 3'-dideoxynucleosides", J. Chem. Soc., Chem. Commun., 1990, 1547-1548.
Huang, Z. et al., "Building blocks for oligonucleotide analogues with dimethylhlene sulfide, sulfoxide, and sulfone groups replacing phosphodiester linkages", J. Am. Org. Chem., 1991, 56, 3869-3882.
Hyrup, B. et al., "Modification of the Binding Affinity of Peptide Nucleic Acids (PNA). PNA with Extended Backbones Consisting of 2-Aminoethyl-.beta.-alanine or 3-Aminopropylglycine Units", J. Chem. Soc. Chem. Commun., 1993, 518-519.
Inouye, M. et al., "Selective coloration of spiro pyridopyrans for guanosine derivatives", J. Am. Chem. Soc., 1992, 114, 778-780.
Jones, G.H. and J.G. Moffatt, "The Synthesis of 6'-Deoxyhomonucleoside-6'-phosphonic Acids", Journal of the American Chemical Society, 1968, 90, 5337-5338.
Jones, M. and Roberts, "Synthesis of Carbocyclic Nucleosides: Preparation of (-)-5'-Homoaristeromycin and Analogues", J. Chem. Soc. Perkin Tran., 1988, 2927-2932.
Kappler, F. and Hampton, "Homoadenosine (9-(5-Deoxy-.beta.-D-ribo-Hexofuranosyl)Adenine) Hydroboration of 5'6'-Anhydro-2'3'-O-Isopropylidenehomoadenosine Formed from 2'3'-O-Isopropylidenadenosine-5'-aldehyde by a Wittig Reaction", Nucleic Acid Chemistry, Part 4, Ed. L.B. Townsend and R.S. Tipson, Wiley-Interscience Publication, P. 240, 1991.
Kawai, J. et al., "Third Chemical Congress of North America, Organic Chemistry, 1988, Single-Stranded DNA & RNA Binding: Backbone-Modified Polynucleotide Analogues", Canada, 6/5/10/88, Abstract No. ORGN 318.
Kirshenbaum, M. et al., Novel Oligonucleotide Analogues with Sulfur-Based Linkage, The Fifth San Diego Conference on Nucleic Acids: New Frontiers, Poster Abstract 28, 11/16/19/90; Abstract CD210.
Kondo, K. et al., "Synthesis of 5'(3')-O-amino Nucleosides", Nuc. Acid Res. Symposium Series No. 16: 93-9

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