Thiol-derivatized nucleosides

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

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 276, 536 278, 536 2781, 536 281, 536 284, 536 285, 536 2853, 536 2854, 536 553, C07H 1906, C07H 1916, C07H 2100

Patent

active

055787185

ABSTRACT:
Nucleosides and linked nucleosides functionalized to include alkylthiol chemical functionality at ribofuranosyl positions, nucleosidic base positions, or on internucleoside linkages. In certain embodiments, the compounds of the invention further include steroids, reporter molecules, reporter enzymes, lipophilic molecules, peptides or proteins attached to the nucleosides through the alkylthio group.

REFERENCES:
patent: 3687808 (1969-08-01), Merigan, Jr. et al.
patent: 4958013 (1990-09-01), Letsinger
patent: 5466786 (1995-11-01), Buhr et al.
Mirabelli et al., Anti-Cancer Drug Design, vol. 6, pp. 647-661, (1991).
Uhlmann et al., Chemical Reviews, vol. 90, No. 4, pp. 544-584, (1990).
Englisch, et al., "Chemically Modified Oligonucleotides as Probes and Inhibitors" Angew. Chem. Int. Ed. Eng. 1991, 30, 613.
Manoharan, et al., "Novel Functionalizationof the Sugar Moiety of Nucleic Acids for Multiple Labeling in the Minor Grove" Tetrahedron Letters 1991, 32, 7171.
Goodchild, "Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties" Bioconjugate Chemistry 1990, 1, 165.
Monoharan, et al., "Chemical Modifications to Improve Uptake and Bioavailability of Antisense Oligonucleotides" Database Embase Elsevier Science Publishers 1992, 660, 306 (abstract).
Asseline et al., "Nucleic acid-binding molecules with high affinity and base sequence specificity: Intercalating agents covalently linked to oligodeoxynucleotides," Proc. Natl. Acad. Sci. USA 81:3297-3301, 1984.
Asseline et al., "Solid-Phase Preparation of 5'-3'-Heterobifunctional Oligodeoxyribonucleotides Using Modified Solid Supports," Tetrahedron, 48:1233-1254, 1992.
Baker, B. F., "Decapitation of a 5'-Capped Oligoribonucleotide by o-Phenanthroline: CU(II)," J. Am. Chem. Soc., 115:3378-3379, 1993.
Beaucage et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach," Tetrahedron 48:2223-2311, 1992.
Bischoff et al., "Introduction of 5'-Terminal Functional Groups into Synthetic Oligonucleotides for Selective Immobilization," Analy. Biochem., 164:336-344, 1987.
Chollet, A. "Selective Attachment of Oligonucleotides to Interleukin-1 beta and Targeted Delivery to Cells," Nucleosides & Nucleotides, 9:957-966, 1990.
Cohen in Oligonucleotides: Antisense Inhibitors of Gene Expression, CRC Press, Inc., Boca Raton, Florida, 1989.
Corey et al., "Generation of a Hybrid Sequence-Specific Single-Stranded Deoxyribonuclease," Science, 238:1401-1403, 1987.
Corey et al., "Sequence-Selective Hydrolysis of Duplex DNA by an Oligonucleotide-Directed Nuclease," J. Am. Chem. Soc., 111:8523-8525, 1989.
Damha et. al., "An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis," Nucl. Acids Res. 18:3813-3821, 1990.
DiZio et al., "Progestin-Rhenium Complexes: Metal-Labeled Steroids with High Receptor Binding Affinity, Potential Receptor-Directed Agents for Diagnostic or Therapy," Bioconjugate Chem., 2:353-366, 1991.
Dreyer et al., "Sequence-specific cleavage of single-stranded DNA: Oligodoexynucleotide-EDTA.Fe(II)", Proc. Natl. Acad. Sci. USA, 82:968-972, 1985.
Ferentz et al., "Disulfide Cross-Linked Oligonucleotides," J. Am. Chem. Soc., 113:4000-4002, 1991.
Todd et al., J. Chem. Soc., 239, 1966.
Fidanza et al., "Site-Specific Labeling of DNA Sequences Containing Phosphorothioate Diesters," J. Am. Chem. Soc., 114:5509-5517, 1992.
Fidanza et al., "Use of a Thiol Tether for the Site-Specific Attachment of Reporter Groups of DNA," J. Org. Chem., 57:2340-2346, 1992.
Gaur et al., Nucl. Acids. Res., 17:4404, 1989.
Greene et al., Protective Groups in Organic Synthesis, 2d edition, New York: John Wiley & Sons, 1991.
Greenfield et al., "Thiol-Containing Cross-Linking Agent with Enhanced Steric Hindrance," Bioconjugate Chem., 1:400-410, 1990.
Guerra et al., "Synthetic 6-Glucosyl Phospholipid as a Drug Transport System," Tetrahedron Letters, 28:3581-3584, 1987.
Haralambidis et al., "The Solid Phase Synthesis of Oligonucleotides Containing a 3'-Peptide Moiety," Tetrahedron Letters, 28:5199-5202, 1987.
Haralambidis et al., "Preparation of base-modified nucleosides suitable for non-radioactive label attachment and their incorporation into synthetic oligodeoxyribonucleotides," Nucleic Acid Research, 15: 4857-4877, 1987.
Harris et al., "New Strategy for the Synthesis of Oligodeoxynucleotides Bearing Adducts at Exocyclic Amino Sites of Purine Nucleosides," J. Am. Chem. Soc., 113:4328-4329, 1991.
Iyer 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., 112:1253-1254, 1990.
Juby et al., "Facile Preparation of 3'Oligonucleotide-Peptide Conjugates," Tetrahedron Letters, 32:879-882, 1991.
Froehler et al., Nucleic Acids Research, 14:160, 1986.
Krieg et al., Antisense Research and Development, 1:161, 1991.
Lemaitre et al., "Specific antiviral activity of a poly(L-lysine)-conjugated oligodeoxyribonucleotide sequence complementary to vesicular stomatitis virus N protein mRNA initiation site," Proc. Natl. Acad. Sci. USA, 84:648-652, 1987.
Leonetti et al., "Biological Activity of Oligonucleotide-Poly(L-lysine) Conjugates: Mechanism of Cell Uptake," Bioconjugate Chem., 1:149-153, 1990.
Letsinger et al., "Cholesteryl-conjugated oligonucleotides: Synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture," Proc. Natl. Acad. Sci. USA, 86:6553-6556, 1989.
MacMillan et al., "Synthesis of Functionally Tethered Oligodeoxynucleotides by the Convertible Nucleoside Approach," J. Org. Chem., 55:5931-5933, 1990.
Meyer et al., "Efficient, Specific Cross-Linking and Cleavage of DNA by Stable, Synthetic Complementary Oligodeoxynucleotides," J. Am. Chem. Soc., 111:8517-8519, 1989.
Miller et al., "A new approach to chemotherapy based on molecular biology and nucleic acid chemistry: Matagen: masking tape for gene expression," Anti-Cancer Drug Design, 2:117-128, 1987.
Mori et al., "Synthesis and Properties of Novel 5'-Linked Oligos," Nucleosides & Nucleotides, 8:649-657, 1989.
Nelson et al., "Bifunctional oligonucleotide probes synthesized using a novel CPG support are able to detect single base pair mutants," Nuc. Acids Res., 17:7187-7194, 1989.
Ramirez et al., "Nucleotidophospholipids: Oligonucleotide Derivatives with mebrane-Recognition Groups," J. Am. Chem. Soc., 104:5483-5486, 1982.
Shea et al., "Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugates," Nuc. Acids Res., 18:3777-3783, 1990.
Sigman, D. S., "Chemical Nucleases," Biochemistry, 29:9097-9105, 1990.
Sinha et al., "The preparation and application of functionalised synthetic oligonucleotides: III. Use of H-phosphonate derivatives of protected amino-hexanol and mercapto-propanol or -hexanol," Nucleic Acids Research, 16:2659-2669, 1988.
Smith-Jones et. al., "Antibody Labeling with Cooper-67 Using the Bifunctional Marcrocycle 4-[(1,4,8,11-Tetraazacyclotetradec-1-yl)methyl]benzoic Acid," Bioconjugate Chem., 2:415-421, 1991.
Sproat et al., "The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides," Nucleic Acids Research, 15:4837-4848, 1987.
Studer et al., "One-Step Synthesis of Mono-N-substituted Azamacrocycles with a Carboxylic Group in the Side-Chain and their Complexes with Cu.sup.2+ and Ni.sup.2+," Helvetica Chimica Acta, 69:2081-2086, 1986.
Telser et al., "Synthesis and Characterization of DNA Oligomers and Duplexes Containing Covalently Attached Molecular Labels: Comparison of Biotin, Fluorescein, and Pyrene Labels by Thermodynamic and Optical Spectroscopic Measurements," J. Am. Chem. Soc., 111:6966-6976, 1989.
Veber et al., "Isonicotinyloxycarbonyl, a Novel Amino Protecting Group for Peptide Synthesis," J. Org. Chem. 42:3286-3288, 1977.
Vasseur et al., "Oligonucleosides: Synthesis of a Novel Methylhydroxylamine-Linked Nucleoside Dimer and Its Incorporation into Antisense Sequences," J. Am. Chem. Soc., 114:4006-4007, 199

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

Thiol-derivatized nucleosides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Thiol-derivatized nucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Thiol-derivatized nucleosides will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1974078

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