Backbone modified oligonucleotide analogs and preparation thereo

Details Backbone modified oligonucleotide analogs and preparation thereo Backbone modified oligonucleotide analogs and preparation thereo

1993-03-31

1995-01-31

Rollins, John W.

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

Organic compounds

Carbohydrates or derivatives

536 2533, 536 2534, 536 256, 536 231, C07H 100

Patent

active

053860233

ABSTRACT:
Methods for preparing oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. In preferred embodiments, the methods involve reductive coupling of 3'- and 4'-substituted or 4'- and 3'-substituted nucleosidic synthons.

REFERENCES:
patent: 3687808 (1980-05-01), Merigan et al.
patent: 4707440 (1987-11-01), Stavrianopoulos
Can. Gen Therapy, vol. I, No. 1, 1994, pp. 65-71, Author: Tseng, B. Y and Brown, K. D.
Anti-Cancer Drug Design, vol. 6, pp. 647-661, Dec. 1991, Author: C. K. Mirabelli.
Chemical Reviews, vol. 90, No. 4, Jun. 1990, pp. 563-584, Author: Uhlmann et al.
Barton et al., Stereoselectivity in Radical Reactions of 2'-Deoxynucleosides. A Synthesis of an Isostere of 3'-Azido-3'-Deoxythymidine-5'-Monophosphate (AZT-5' Monophosphate) Tetrahedron Letters, 1989, 30:4969.
Barton et al., A "One-Pot" Synthesis of Sulfenamides, J. Org. Chem., 1991, 56:6702.
Bodenteich et al., Synthesis if Enantiomerically Pure Carbocyclic 3'-Azido-2',3'-Dideoxythymidine, A Potential Anti-Aids Drug, Tetrahedron Letters, 1987, 28:5311.
Camarasa et al., Aldol Reaction of Nucleoside 5'-Carboxaldehydes with Acetone-Synthesis of 5'-C-Chain Extended Thymidine Derivatives, Nucleosides and Nucleotides, 1990, 9:533.
Cohen, ed. Oligodeoxynucleotides: Antisense Inhibitors of Gene Expression, (CRC Press, Inc., Boca Raton, Fla., 1989).
Cormier et al., Synthesis of Hexanucleotide Analogues Containing Diisopropysilyl Internucleotide Linkages, Nucleic Acids Research, 1988, 16:4583.
Cosstick et al., Synthesis and Properties of Dithymidine Phosphate Analogues Containing 3'-Thiothymidine, Nucleic Acids Res., 1990, 18:829.
Etzold et al., The Extension of the Sugar Chain of Thymidine: a New Route to 5'-Deoxyhexose Nucleosides, Chemical Communications, 1968, 422.
Fikes et al., Preassociating .alpha.-Nucleophiles, J. Am. Chem. Soc., 1992, 14:1493.
Fleet et al., Methyl 5-0-Tert-Butyldiphenylsilyl-2-Deoxy-.alpha..beta.-D-Threo-Pentofuranoside as a Divergent Intermediate for the Synthesis of 3'-Substituted-2',3'-Dideoxynucleosides: Synthesis of 3'-Azido-3'-Deoxythymidine, 3'-Deoxy-3'-Flurothymidine and 3'-Cyano-3'-Deoxythymidine, Tetrahedron, 1988, 44:625.
Gait M. J., ed., Oligonucleotide Synthesis, A Practical Approach (IRL Press 1984).
Goodchild, Bioconjugate Chemistry, 1990, 1:165, (Missing Page).
Hanamoto et al., Sml.sub.2 -Promoted Ketyl Addition to O-Benzyl Formaldoxime. A New Aminomethylation, Tet. Letts., 1991, 32:3555.
Horwitz et al., Nucleosides. V. The Monomesylates of 1-(2'-Deoxy-.beta.-D-Lyxofuranosyl) Thymine, J. Org. Chem., 1964, 29:2076.
Jones et al., Synthesis of Carbocyclic Nucleosides: Preparation of (-)-5'-Homoaristeromycin and Analogues, J. Chem. Soc. Perkin Trans., 1988, 1:2927.
Loke et al., Delivery of c-myc Antisense Phosphorothioate Oligodeoxynucleotides to Hematopoietic Cells in Culture by Liposome Fusion: Specific Reduction in c-myc Protein Expression Correlates with Inhibition of Cell Growth and DNA Synthesis, Top. Microbiol. Immunol., 1988, 141:282.
Magid et al., Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride, Tetrahyderon Letters., 1990, 31:5595.
Marcus-Sekura et al., Comparative Inhibition of Chloramphenicol Acetyltransferase Gene Expression by Antisense Oligonucleotide Analogues having Alkyl Phosphotriester, Methylphosphonate and Phosphorothioate Linkages, Nuc. Acids Res., 1987, 15:5749.
Matsuda et al., Synthesis and Biological Activities of 3'-Deoxy-3'-Isocyano, -Isothiocyano, and -Isoselenocyano- Thymidines, 1990, 9:587.
Matteucci, Deoxyoligonucleotide Analogs Based on Formacetal Linkages, Tetrahedron Letters, 1990, 31:2385.
Mazur et al., Isosteres of Natural Phosphates. 11. Synthesis of a Phosphonic Acid Analogue of an Oligonucleotide, Tetrahedron, 1984, 40:3949.
Miller et al., Effects of a Trinucleotide Ethyl Phosphotriester, G.sup.m p(Et)G.sup.m p(Et)U, on Mammalian Cells in Culture, Biochemistry, 1977, 16:1988.
Rawson et al., The Synthesis of 5'-Homo-2'-Deoxycytidine, Nucleosides & Nucleotides, 1990, 9:89.
Verheyden et al., Halo Sugar Nucleosides. I. Iodination of the Primary Hydroxyl Groups of Nucleosides with Methyltriphenoxyphosphonium Iodide, J. Org. Chem., 1970, 35:2119.
Wilson, Cellular Transport Mechanisms, Ann. Rev. Biochem., 1978, 47:933.
Abdel-Magid et al., Reductive Amination of Aldehydes and Ketones By Using Sodium Triacetoxyborohydride, Tetrahydron Ltrs., (1990), vol. 31, No. 39, pp. 5595-5598.
Bankston et al., A Short Synthesis of 5'-O-Trityl-Protected threo- and erythro-3'-Cyano-3'-deoxythymidine Epimers, J. Het. Chem., (1992), vol. 29, pp. 1405-1407.
Baud et al., Improved Procedure For The Regiospecific Synthesis of 2'-Deoxyribonucleosides, Tetrahedron Letters, (1990), vol. 31, pp. 4437-4440.
Beaucage et al., Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach, Tetrahedron, (1992), vol. 48, No. 12, pp. 2223-2311.
Comprehensive Organic Synthesis: Ed. by B. M. Trost & J. Fleming, vol. 4, p. 760.
Curran, Radical Addition Reactions, In Comprehensive Organic Synthesis: Trost, B. M. and Fleming, I., Eds., vol. 4, pp. 715-832, Pergamon Press, Oxford (1991).
Debart et al., Intermolecular Radical C--C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleosides, Tetrahedron Ltrs., (1992), vol. 33, No. 19, pp. 2645-2648.
Fiandor et al., Tetrahedron Letts., 1990, 33:597.
Hata et al., J. Chem. Soc. Perkin I, 1980, 306.
Hillgartner et al., Bis(trimethylzinn)benzpinakolat, siene reversible radikalische Dissoziation und Reaktionen, Liebigs Ann. Chem., (1975), 586-599.
Hronowski et al., Synthesis of New Carbocyclic Analogues of 3'-Azido- and 3'-Amino-2',3'-dideoxynucleosides, J. Chem. Soc., Chem. Commun., (1990), pp. 1547-1548.
Vasseur et al., Oligonucleosides: Synthesis of a Novel, J. Am. Chem. Soc., (1992), vol. 114, pp. 4006-4007.
Jenkins et al., Synthetic Procedures in Nucleic Acid Chemistry, Zorbach and Tipson, Ed., vol. 1, John Wiley & Sons, p. 149.
Kappler F. and Hampton, A., Nucleic Acid Chemistry, Part 4, Ed. L. B. Townsend and R. S. Tipson, Wiley-Interscience Publication, 1991, p. 240.
Koster et al., Dialkyl Aluminum Chloride, Tetrahedron Ltrs., (1982), vol. 23, No. 26, pp. 2641-2644.
Lim et al., Book of Abstracts, 203 ACS National Meeting, San Francisco, Calif., Apr. 5-10, 1992, of the procedure of Hill, et al., J. Chem. Soc., 1964, 3709.
Moffatt et al., The Sythesis of 6'-Deoxyhomonucleoside-6'-phosphonic Acids, J. Am. Chem. Soc., (1968), vol. 90, pp. 5337-5338.
Motawia et al., A New Route to 2'-3'-Dideoxycytidine, Liebigs Ann. Chem., (1990), pp. 599-602.
Nair et al., Org. Prep. Procedures Int., 1990, 22:57.
Nicolaou et al., Carbocyclic Thromboxane A.sub.2.sup.1, J. Am. Chem. Soc., 102:4, (1980), pp. 1404-1409.
Shaw et al., Modified deoxyoligonucleotides stable to exonuclease degradation in serum, Nucleic Acids Res., vol. 19, No. 4, (1991), pp. 747-750.
Nucleosides and Nucleotides, 1990, 9:533.
Nucleosides & Nucleotides, 1990, 9:89.
Poopeiko, et al., Syn. Lett., 1991, 342.
Secrist et al., Abstract 21, Synthesis and Biological Activity of 4'-Thionucleosides, Program & Abstracts, Tenth International Roundtable, Nucleosides, Nucleotides and their Biological Applications, Park City, Utah, Sep. 16-20, 1992.
Sproat et al., 2'-O-Methyloligoribonucleotides: Synthesis and Applications, Oligonucleotides and Analogs, F. Eckstein Ed., IRL Press, 1991, p. 55.
Stirchak et al., Unchanged Stereoregular Nucleic Acid Analogues, J. Org. Chem., (1987), 52, 4202-4206.
Wu et al., New Synthesis of 2'-3'-Dideoxy-3'-C-Cyano-2'-Substituted Thymidines by Michael Additiona React-tions, Tet. Lts., (1989), vol. 45, No. 3, pp. 855-862.
Tetrahedron, 1900, 44:625.
Parkes et al., A Short Sythesis of 3'-Cyano-3'-Deoxythymidine, Tetrahedron Lts., (1988), vol. 29, No. 24, pp. 2995-2996.
Verheyden et al., Halo Sugar Nucleosides. II., J. Org. Chem., (1970), vol. 35, No. 9, pp. 2868-2877.
Yang et al., Construction of Glycosidic N--O Linkages in Oligosaccharides, J. Am. Chem. Soc., (1991), vol. 113, pp. 4715-4716.
Zon et al., Phosphorothioate oligonucleotides, Oligo

Affiliated with

Also associated with

Rating

Backbone modified oligonucleotide analogs and preparation thereo does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Backbone modified oligonucleotide analogs and preparation thereo, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Backbone modified oligonucleotide analogs and preparation thereo will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1103357