Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1993-11-24
1997-12-23
Low, Christopher S. F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
514 44, 435 911, 435 915, 536 235, 536 241, 536 242, 536 2433, 536 251, 536 252, 536 253, 536 2531, 536 245, 536 2431, 536 2432, 935 5, 935 8, C07H 2102, C07H 2104
Patent
active
057009228
ABSTRACT:
Macromolecules are provided that have increased nuclease resistance, increasing binding affinity to a complementary strand, and that activate RNase H enzyme. The macromolecules have the structure PNA-DNA-PNA where the DNA portion is composed of subunits of 2'-deoxy-erythro-pentofuranosyl nucleotides and the PNA portions are composed of subunits of peptide nucleic acids. Such macromolecules are useful for diagnostics and other research purposes, for modulating protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to therapeutics.
REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4908307 (1990-03-01), Rodland et al.
patent: 5013830 (1991-05-01), Ohtsuka et al.
patent: 5134066 (1992-07-01), Rogers et al.
patent: 5149797 (1992-09-01), Pederson et al.
Jasenka Matulic-Adamic, et al., "Nucleosides. 150. Synthesis and Some Biological Properties of 5-Monofluoromethyl, 5-Difluoromethyl, and 5-Trifluoromethyl Derivatives of 2'-Deoxyuridine and 2'-Deoxy-2'-fluoro-.beta.-D-arabinofuranosyluracil", J. Med. Chem., 31, (1988), 1642-1647.
Wu-Pong, "Oligonucleotides: Opportunities for Drug Therapy and Research", Pharmaceutical Technology 1994, 102.
Agrawal et al., "Oligodeoxynucleoside Phosphoramidates and Phosphorothioates as Inhibitors of Human Immunodeficiency Virus", PNAS USA 85: 7079-7083 (1988).
Akashi, M. and Takemoto, K. "New Aspects of Polymer Drugs", Adv. Polym. Sci., 1990, 97, 108-146.
Beaton, et al., Chapter 5, Synthesis of oligonucleotide phosphorodithioates, p. 109, Oligonucleotides and Analogs, A Practical Approach, Eckstein, F., Ed.; The Practical Approach Series, IRL Press, New York, 1991.
Borer et al., "Stability of Ribonucleic Acid Double-Stranded Helices", J. Mol. Biol. 86: 843-853 (1974).
Brill et al., "Synthesis of Deoxydinucleotide Phosphorodithioates", 3972-3980, The Journal of the American Chemical Society 113: 3972-3980 (1991).
Buttrey, J.D., et. al. "Synthetic Analogues of Polynucleotides-XIII, The Resolution of DL-.beta.-(Thymin-1-YL)Alanine and Polymerisation of the .beta.-(Thymin-1-YL) Alanines", Tetrahedron, 1975, 31, 73-75.
Capon et al., "Complete Nucleotide Sequences of the T24 Human Bladder Carcinoma Oncogene and Its Normal Homologue", Nature 302: 33-37 (1983).
Cohen, "Oligodeoxynucleotides" Published 1989 by CRC Press, Inc., Boca Raton (FL) pp. 1-255 Note pp. 16, 35, 36, 38, 55, 62, 66, 67, 79-82, 85.
Concise Encyclopedia Of Polymer Science And Engineering, J.I. Kroschwitz, Ed. John Wiley & Sons, 1990 at pp. 858-859.
Dagle et al., "Targeted Degradation of mRNA in xenopus Oocytes and Embryos directed by modified oligonucleotides: Studies of An2 and Cyclin in Embryogenesis", Nucleic Acid Research 18: 4751-4757 (1990).
Dagle, et al., "Physical Properties of Oligonucleotides Containing Phosphoramidate-Modified Internucleoside Linkages", Nucleic Acids Research 19: 1805-1810 (1991).
Dagle et al, "Pathways of Degradation and Mechanism of Action of Antisense Oligonucleotidews in Xenopus Laevis Embryos", Antisense Research and Development, No. 1: 11-20 (1991).
De Koning, H., et. al. "Unconventional Nucleotide Analogues V. Derivatives of 6-(1-pyrimidinyl)-and 6-(9-purinyl)-2-aminocaproic acid.", Recueil, 1971, 90, 874-884.
Demidov et al., "Sequence Selective Double Strand DNA Cleavage by Peptide Nucleic Acid (PNA) Targeting Using Nuclease S1", Nucl. Acids Res 21 (19): 2103-2107 (1993).
Depto et al., "Regulated Expression of the Human Cytomegalovirus pp65 Gene: Octamer Sequence in the Promoter Is Required for Activation by Viral Gene Products," J. Virol., 1989, 63:1232-1238, 1989.
Doel, M.T., et. al. "The Synthesis of Peptides Containing Purine and Pyrimidine Derivatives of DL-Alanine", Tetrahedron 30: 2755-2759 (1974).
Doel, M.T., et. al. "An Approach to the Synthesis of Peptide Analogues of Oligonucleotides (Nucleopeptides)", Tetrahedron Letters 27: 2285-2288 (1969).
Dubochet et al., "A New Preparation Method for Dark-Field Electron Microscopy of Biomacromolecules," J. Ultrastruct. Res. 35: 147-167 (1971).
Egholm, "Peptide Nucleice Acids Containing Adenine or Guanine Recognize Thymine and Cytosine in Complementary DNA Sequences", J. Chem. Soc., Chem. Commun. 800-801 (1993).
Egholm et al., "Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide backbone," J. Am. Chem. Soc. 114: 1895-1897 (1992).
Englisch, U. and Gauss, D.H., "Chemically Modified Oligonucleotides as Probes and Inhibitors", Angewandte Chemie, International Edition 30: 613-629 (1991).
Froehlder et. al., "Oligodeoxynucleotides Containing C-5 Propyne Analogs of 2'-Deoxyuridine and 2'-Deoxycytidine," Tetrahedron Letters 33: 5307-5310 (1992).
Hahn et. al., "Molecular cloning and characterization of the HTLV-III virus associated with AIDS," Nature, 312:166-169, 1984.
Hall and Brown, "Human N-ras: cDNA Cloning and Genes Structure", Nucleic Acids Res. 13: 5255-5268 (1985).
Hanvey, J.C., et. al. "Antisense and Antigene Properties of Peptide Nucleic Acids", Science 258: 1481-1485 (1992).
Huang, S., et. al. "Acyclic Nucleic Acid Analogues: Synthesis and Oligomerization of .gamma.,4-Diamino-2-oxo-1 (2H)-pyrimidinepentanoic Acid of .sigma.4-Diamino-2-oxo-1 (2H)-pyrimidinehexanoic Acid", J. Org. Chem. 56: 6007-6018 (1991).
Inaki, Y. and Takemoto, K. "Functionality and Applicability of Synthetic Nucleic Acid Analogs", In Current Topics in Polymer Science; Ottenbrite, Utracki, Inoue, Eds. Munich; New York: Hanser Publishers; New York : Distributed in the U.S.A. by Macmillan Pub. Co., 1, 80-100 (1987).
Inaki, Y. "Synthetic Nucleic Analogs", Prog. Polym. Sci. 17: 515-570 (1992).
Inoue et al., "Synthesis and properties of novel nucleic acid probes", Nuc Acids Res Symposiou Series 16: 165 (1985).
Inoue et al., "Synthesis and Hybridization Studies on Two complementary NONa (2'-O-methyl) ribonucleotides" Nucleic Acids Res 15: 6131-6148 (1987).
Inoue et al., "Sequence-dependent hydrolysis of RNA using modified Oligonucleotide Splints and R Nase H.," FEBS Ltrs. 215: 327-330 (1987).
Kahn et al., "The c-K-ras Gene and Human Cancer" (Review) Anticancer Res 7: 639-652 (1987).
Kawasaki et al., "Uniformly modified 2'-Deoxy-2'-fluoro Phosphorothioate Oligonucleotides as nuclease-Resistant Antisense Compounds with High Affinity and Specificity for RNA Targets," J.Med. Chem. 36 831-841 (1993).
Kawasaki et al., "Synthesis and Biophysical Studies of 2'-dR1B0-2'-F Modifed Oligonucleotides", 1-9 disclosed (1991).
Lal et al., "Diphenylphosphoryl Azide A Novel Reagent for the Stereospecific Synthesis of Azides from Alcohols," Tetrahedron Letters 23 1977-1980 (1977).
Lima et al., "Implication of RNA Structure on Antisense Oligonucleotide Hybridization Kinetics", Biochemistry 31: 12055-12061 (1991).
Lu, C.X., et. al. "Synthesis of Polyesters Containing Nucleic Acid Base Derivatives as Pending Side Chains":, J. Polym. Sci.: Part A:Polymer Chemistry 24: 525-36 (1986).
McCurdy et al., "Deoxyoligonucleotides with Inverted Polarity: Synthesis and Use in Triple-Helix Formation," Nucleosides and Nucleotides 10: 287-290 (1991).
Miller and Ts'o, "A new approach to chemotherapy based on molecular biology and nucleic acid chemistry: Matagen (masking tape for gene expression)" Antic-Cancer Drug Design 2: 117-128 (1987).
Miller et al., "Annual Reports in Medicinal Chemistry 23, Chapter 30: Oligonucleotide Inhibitors of Gene Expression in Living Cells: New Opportunities in Drug Design", pp. 295-304 (1988).
Monia, et. al., "Evaluation of 2'-Modified Oligonucleotides Containing 2'-Deoxy Gaps as Antisense Inhibitors of Gene Expression", J. Bio. Chem. 268: 14514-14522 (1993).
Nagae, S., et. al. "Functional Monomers and Polymers. CLIV. Application of Nucleic Acid Base Containing Polymers to High Performance Liquid Chromatography":, J. Polym. Sci.: Part A:Polymer Chemistry 27: 2593-2609 (1989).
Nielsen et al., "Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted Polyamide," Science, 254:1497-1500, 1991.
Nollet, A.J.H., et. al. "Unconventional Nucleotide Analogues-III, 4-(N.sub.1 -Pyrimidyl)-2-Aminobutyric Acids", Tetrahedron 25: 5989-5994
ISIS Pharmaceuticals Inc.
Low Christopher S. F.
LandOfFree
PNA-DNA-PNA chimeric macromolecules does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with PNA-DNA-PNA chimeric macromolecules, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and PNA-DNA-PNA chimeric macromolecules will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1803623