Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-06-02
1998-12-22
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 5, 536 221, 536 2431, 536 253, 536 2532, 536 276, 536 278, 536 2781, 536 281, 536 284, 536 285, 536 2853, 536 2854, 536 553, 530395, C07H 2100
Patent
active
058521828
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 (1972-08-01), Merigan et al.
patent: 4511713 (1985-04-01), Miller et al.
patent: 4689320 (1987-08-01), Kaji
patent: 4760017 (1988-07-01), McCormick
patent: 4876335 (1989-10-01), Yamane et al.
patent: 4958013 (1990-09-01), Letsinger
patent: 4965350 (1990-10-01), Inoue et al.
Agarwal, K.L. and Riftina, "Synthesis and Enzymatic Properties of Deoxyribooligonucleotides Containing Methyl and Phenylphosphonate Linkages", Nucleic Acids Research 1979, 6, 3009-3024.
Agris, C.H. et al., "Inhibition of Vesicular Stomatitis Virus Protein Synthesis and Infection by Sequence-Specific Oligodeoxyribonucleoside Methylphosphonates", Biochemistry 1986, 25, 6268-6275.
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. USA 1984 81, 3297-3301.
Asseline, U. et al., "Solid-Phase Preparation of 5',3'-Heterobifunctional Oligodeoxyribonucleotides Using Modified Solid Supports" Tetrahedron 1992 48 1233-1254.
Atherton et al., "The Fluorenylmethoxycarbonyl Amino Protecting Group", Chapter 1 in The Peptides, Gross and Meienhofer, Eds., Academic Press, New York, 1983, 9, 1-38.
Baker, B., "Decapitation of a 5-capped oligoribonucleotide by o-phenanthroline:Cu(II)", J. Am. Chem. Soc. 1993, 115, 3378-3379.
Beaucage, S. and Iyer, R., "Advances in the synthesis of oligonucleotides by the phosphoramidite approach", Tetrahedron Letters 1992, 48, 2223-2311.
Betebenner, D. 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-111 chelate", Bioconjugate Chem 1991, 2, 117-123.
Biggadike, K. et al., "Short convergent route to homochiral carbocylic 2'-deoxynucleosides and carbocyclic robonucleosides", J. Chem. Soc., Chem. Commun. 1987, 1083-1084.
Bischoff, R. et al., "Introduction of 5'-Terminal functional groups into synthetic oligonuleotides for selective immobilization", Analytical Biochemistry 1987, 164, 336-344.
Brill, W. et al., "Synthesis of oligodeoxynucleoside phosphorodithioates via thioamidites", Journal of the American Chemical Society 1989, 111, 2321-2322.
Butke, G. et al., in "Nucleic Acid Chemistry," Part 3, pp. 149-152, Townsend, L.B. and Tipson, eds., J. Wiley and Sons, New York, 1986. Derivatives", Journal of Organic Chemistry 1958, 23, 1534-1538.
Cazenave et al., "Enzymatic Amplification of Translation Inhibition of Rabbit .beta.-globin mRNA Mediated by Anti-Messenger Oligodeoxynucleotides Covalently Linked to Intercalating Agents", Nucleic Acid Research 1987, 15, 4717-4736.
Chiang 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 & Nucleotides 1990 9(7), 957-966.
Cohen, "Oligonucleotides: Antisense Inhibitors of Gene Expression", CRC Press, Inc., Boca Raton, FL 1989.
Constant, J.F. et al. "Heterodimeric Molecules Including Nucleic Acid Bases and 9-Aminoacridine Spectroscopic Studies, Conformations, and Interactions with DNA" Biochemistry 1988, 27, 3997-4003.
Corey et al., "Sequence-Selective Hydrolysis of Duplex DNA by an Oligonucleotide-Directed Nuclease", J. Am. Chem. Soc. 1989, 111, 8523-8525.
Corey et al., "Generation of a Hybrid Sequence-Specific Single-Stranded Deoxyribonuclease", Science 1987, 238 1401-1403.
Damha et al., "An improved procedure for derivatization of controlled-pore glass beads for solid-phase oligonucleotide synthesis", Nucleic Acids Res. 1990, 18, 3813-3821.
Dingwall et al., "Protein Import Into The Cell Nucleus", Ann. Rev. Cell Biol. 1986, 2, 367-390.
DiZio et al., "Progestin-Rhenium Complexes: Metal-Labeled Steroids with High Receptor Binding Affinity, Potential Receptor-Directed Agents for Diagnostic Imaging or Therapy" Bioconjugate Chem. 1991, 2, 353-366.
Dreyer, G. and Dervan, "Sequence-specific cleavage of single-stranded DNA: Oligodeoxynucleotide-EDTA-Fe(II)", PNAS USA 1985, 82, 968-972.
Eckstein, F. et al., "Polynucleotides Containing 2'-Chloro-2'-Deoxyribose", Biochemistry 1972, 11, 4336-4344.
Ferentz, A.E. and Verdine, G.L., "Disulfide cross-linked oligonucleotides", J. Am. Chem. Soc. 1991, 113, 4000-4002.
Fidanza, J.A. and McLaughlin L.W., "Use of a Thiol Tether for the Site-Specific Attachment of Reporter Groups to DNA", J. Org. Chem. 1992, 57, 2340-2346.
Fidanza et al., "Site-Specific Labeling of DNA Sequences Containing Phosphorothioate Diesters", J. Am. Chem. Soc. 1992, 114, 5509-5517.
Froehler, et al., "Synthesis of DNA Via Deoxynucleoside H-Phosphonate Intermediates", Nucleic Acids Res. 1986, 14, 5399-5407.
Gait, ed., "Oligonucleotide Synthesis", IRL Press, 1985.
Gaur, et al., "A Simple Method for the Introduction of Thiol Group 5'-Termini of Oligdeoxynucleotides", Nucleic Acids Res. 1989, 17(11), 4404.
Greene and Wuts, "Protective Groups in Organic Synthesis", 2nd Edition, John Wiley & Sons, New York, 1991.
Greenfield, L. et al., "Thiol-containing cross-linking agent with enhanced steric hindrance", Bioconjugate Chem. 1990, 1, 400-410.
Guerra, F., "Synthetic 6-glucosyl Phospholipid as a Drug Transport System", Tetrahedron Letters 1987, 28(31), 3581-3584.
Guschlbauer, W. and Jankowski, "Nucleoside conformation is Determined by the Electronegativity of the Sugar Substituent", Nucleic Acids Research 1980, 8, 1421-1433.
Haralambidis, J. et al., "The solid phase synthesis of Oligonucleotides containing a 3'-peptide moiety", Tetrahedron Letters 1987, 28, 5199-5202.
Haralambidis et al., "Preparation of base-modified nucleosides suitable for non-radioactive label attachment and their incorporation into synthetic ologodeoxyribonucleotides", Nucleic Acids Research 1987, 15, 4857-4876.
Harris, C.M. 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.
Ikehara, M. et al., "A Linear Relationship Between Electronegativitiy of 2'-Substituents and Conformation of Adenine Nucleosides", Tetrahedron Letters 1979, 42, 4073-4076.
Ikehara, M. et al., "Recognition by Restriction Endonuclease EcoRI of Deoxyoctanucleotides Containing Modified Sugar Moieties", European Journal of Biochemistry 1984, 139, 447-450.
Ikehara, M. et al., "Polynucleotides. LVI. Synthesis and Properties of Poly(2'-deoxy-2'-fluoroinosinic Acid", Nucleic Acids Research 1978, 5, 3315-3324.
Ikehara, M. et al., "Polynucleotides. LII.synthesis and properties of poly (2'-deox-2'-fluoroadenylic acid)", Nucleic Acids Research 1978, 5, 1877-1887.
Inoue, H. et al., "Synthesis and hybridization studies on two complementary nona(2'-O-methyl) ribonucleotides", Nucleic Acids Research 1987, 15, 6131-6148.
Iyer, R., Beaucage, Serge L. et al., "3H-1,2-benzodithiole-3-one 1,1-dioxide as an improved sulfurizing reagent in the solid-phase synthesis of oligodeoxyribonucleosides phosphorothiioates", 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 Acids Research 1986, 14(15), 6115-6128.
Jager, A. et al., "Oligonucleotide N-Alkylphosphoramidates: Synthesis and Binding to Polynucleotides", Biochemistry 1988, 27, 7237-7246.
Jayaraman, K. et al., "Selective inhibition of escherichia coli protein synthesis and growth by nonionic oligonucleotides complementary to the 3' end of 16S rRNA", PNAS USA 1981, 78, 1537-1541.
Jones, G. et al., "4'-substituted nucleosides. 5. hydroxymethy
Cook Phillip Dan
Manoharan Muthiah
Isis Pharmaceuticals , Inc.
Wilson James O.
LandOfFree
Thiol-derivatized 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 Thiol-derivatized oligonucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Thiol-derivatized oligonucleosides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2049344