Modified oligonucleotides, their preparation and their use

Details Modified oligonucleotides, their preparation and their use Modified oligonucleotides, their preparation and their use

2006-01-17

2006-01-17

Riley, Jezia (Department: 1637)

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

Organic compounds

Carbohydrates or derivatives

C536S024300, C536S024500, C536S025300, C536S027200, C435S006120, C435S091100

Reexamination Certificate

active

06987177

ABSTRACT:
Modified oligonucleotides which possess at least one substituted 7-deazapurine base form more stable hybridization complexes with nucleic acids than unsubstituted analogs. They are useful as inhibitors of gene expression, as probes for detecting nucleic acids, as aids in molecular biology and as pharmaceuticals or diagnostic agents. Processes for preparing them are provided.

REFERENCES:
patent: 5241060 (1993-08-01), Engelhardt et al.
patent: 5470967 (1995-11-01), Huie et al.
patent: 5489677 (1996-02-01), Sanghui et al.
patent: 5594121 (1997-01-01), Froehler
patent: 6150510 (2000-11-01), Seela et al.
patent: 3 529 478 (1987-02-01), None
patent: 44 15 370 (1994-05-01), None
patent: 0 251 786 (1987-07-01), None
patent: 0 252 683 (1987-07-01), None
patent: 0 286 028 (1988-10-01), None
patent: 0 063 879 (1992-11-01), None
patent: 0 552 766 (1993-07-01), None
patent: 0 672 677 (1995-03-01), None
patent: 0 672 700 (1995-03-01), None
patent: 0 212 536 (1997-03-01), None
patent: 6-3241356 (1988-11-01), None
patent: 92/02258 (1992-02-01), None
patent: 92/06219 (1992-04-01), None
patent: 93/09127 (1992-10-01), None
patent: 93/10820 (1992-11-01), None
patent: 93/12130 (1992-12-01), None
patent: 94/24144 (1994-04-01), None
patent: 94/22892 (1994-10-01), None
patent: 95/04747 (1995-02-01), None
Uhlman et al., “Antisense Oligonucleotides: A New Therapeutic Principle”, Chemical Reviews, vol. 90, No. 4, pp. 544-584, (1990).
Beaucage et al., “Advances in the Synthesis of Oligonucleotides By the Phosphoramidite Approach” Tetrahedron Report No. 309, vol. 48, No. 12, pp. 2223-2311, (1992).
Ludwig, “A New Route to Nucleosides 5′-Triphosphates”, Acta Biochim. et Biophys. Acad. Sci. Hung. Tetrahedron Report No. 309, vol. 48, No. 12, pp. 2223-2311, (1992).
Koga et al., “Altern. a,B-Oligothymidylates w/Altern. (3′-3′) & (5′-5′)-Internucleotidic Phosphod. Linkages ad Models for Antisense Oligodeoxribonuc.”, J. Organ. Chem. 56(12), pp. 3757-3759, (1991).
McBridge et al., “N6 (N-Methyl-2-Pyrrolidine Amidine) Deoxyadenosine-A New Deoxynucleoside Protecting Group”, Tetrahedron Letters, vol. 24, No. 29, pp. 2953-2956, (1983).
Ti et al., “Transient Protection: Efficient One-Flask Syntheses of Protected Deoxynucleosides”, J. Am. Chem. Soc., No. 104, pp. 1316-1319, (1982).
Schaller et al., “Synthesis Of Deoxyribonucleosides-3′ Phosphates”, pp. 3821-3825, (1963).
Reese, “The Chemical Synthesis of Oligo-and Poly-Nucleotides By The Phosphotriester Approach”, Tetrahedron Report No. 56, vol. 34, pp. 3143-3179, (1978).
Flockerzi et al., Synth. & Properties of 2′0- & 3′-0-(tert-Butyldimethylsily)-5′-0-(4-methoxytrity . . . Nucleoside, XXXVII, Liebigs Ann. Chem., pp. 1568-1585, (1981).
Froehler et al., “Synthesis of DNA via Deoxynucleoside H-Phosphonate Intermediates”, Nucleic Acids Research, vol. 14, No. 13, pp. 5309-5407, (1986).
Sinha, Polymer Support Oligonucleotide Synthesis XVIB: Use of B-Cyanocthyl-N, N-Dialkylamino . . . Nucleic Acids Research, vol. 12, No. 11, pp. 4538-4557, (1984).
Sonveaux, “The Organic Chemistry Underlying DNA Synthesis”, Bioorganic Chemistry vol. 14, pp. 274-325, (1986).
Milligan et al., “Current Concepts in Antisense Drug Design”, Journal of Medicinal Chemistry, vol. 36, No. 14, pp. 1923-1937, (1993).
Chollet et al., “DNA Containing The Base Analogue 2-Aminoadenine: Preparation, Use As Hybirdization Probes and Cleavage By Restriction Endonucleases”, Nucleic Acids Res. vol. 16, No. 1, pp. 305-317, (1988).
Watanabe et al., Thiocyanation of Tubercidin of Tubercidin and Its Derivatization to 6-Proply . . . Nucleosides & Nucleotides, vol. 1, No. 2, pp. 191-203, (1982).
Nair et al., “Novel, Stable Congeners of the Antiretroviral Compound 2′,3′-Dideoxyadenosine”, J. Am. Chem. Soc., vol. 111, pp. 8502-8504, (1989).
Grein et al., “3-Deaza and 7-Deazapurines: Duplex Stability of Oligonucleotides Containing Modified Adenine and Guanine Bases,” Bioorg. Med. Chem. Lett., Bd. 4(2): 971-76 (1994).
Cottam et al., “Synthesis and Biological Activity of Certain 6-Substituted and 2,6-Disubstituted 2′-Deoxytubercidins,” J. Med. Chem., 28: 1461-67 (1985).
Seela et al., “Assignment of Anomeric Configuration of D-Ribo-, Arabino-, 2′ Deoxyribo-, and 2′,3′-t Dideoxyribonucleosides by NOE Difference Spectroscopy,” Nucleosides, Nucleotides, bd. 8: 587-97 (1989).
Eger et al., “Synthesis of Pyrrolo 2,3-dlpyrimidine Ribosides and their Potential in Chemotherapeutics,” J. Heterocyclic Chem., 27: 2069-75 (1990).
Prober et al., “A System for Rapid DNA Sequencing with Fluorescent Chain-Terminating Dideoxynucleotides,” Science 238: 336-41 (1987).
Winkeler et al., “Synthesis and Furanosie/Pyranosid-Isomerisierung von 7-Desaza-2′desoxy-7methylguanosin,” Lieb. Ann. Chem. 708-21 (1984) (English abstract provided).
Nakagawa et al., “Poly(8-bromodeoxyadenylic acid): Properties of the Polymer and Contrast with the Ribo of nucleotide Analogue” Biochemistry 23:4219-25 (1984).
Seela et al., “Oligonucleotides with Unnatural bases or an altered sugar-phosphate bacbone” Nucleid Acid Symp. Set. 31:1511-52 (1994).
Livak et al., “Detection of single base differences using biotinylated nucleotides with very long linker arms”, Nucleic Acids Res. 20(18): 4831-37 (1992).
Hughes et al., “2′, 5′-Oligoadenylates and Related 2′, 5′-Oligonucleotides Analogs,” Biochemistry 22(9) 2116-26 (1983) Abstract.
Seela et al, “Duplex Stabilization of DNA,” Helv. Chim. ACTA 78(1): 94-108 (1995) Abstract.
Nakagawa et al., “Poly(2-amino-t-methyldeoxyadenylis acids): Contrasting Effects in Deoxy- and Ribopolynucleotides of 2-Amino and 8-Methyl Substituents,” Biochemistry 26: 7159-65 (1987).
Seela et al., “Synthesis of Certain 5-Substituted 2′-Deoxytubercidin Derivatives,” helv. Chim. ACTA 77:897-903,(1994).
Turro et al., “Photochemical Analogue of the Bergman Cycloaromatization Reaction,” Tetrahedron 35(44), pp. 8089-92 (1994).
Beaucage et al., “The Functionalization of Oligonucleotides Via Phosphoramidite Derivatives,” Tetrahedron 49(10): 1925-63 (1993).
Seela et al., “Poly(adenylic acids) containing the antibiotic tubercidin—base pairing and hydrolysis by nuclease S1,” Nucleic Acids. Res. 10(4): 1389-97 (1982).
Auflage et al., “Preformulation,” Remington's Pharmaceutical Science 76: 1415-21 (1985).

Affiliated with

Also associated with

Rating

Modified oligonucleotides, their preparation and their use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Modified oligonucleotides, their preparation and their use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Modified oligonucleotides, their preparation and their use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3580762