Peptide nucleic acids having amino acid side chains

Details Peptide nucleic acids having amino acid side chains Peptide nucleic acids having amino acid side chains

1997-05-01

1998-07-28

Marschel, Ardin H.

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

Organic compounds

Carbohydrates or derivatives

435 6, 436501, 530300, 530332, 536 221, 935 77, 935 78, C07H 2100, C07K 500, C12Q 168

Patent

active

057864616

ABSTRACT:
A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than the corresponding DNA or RNA strands, and exhibit increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain alkylamine side chains.

REFERENCES:
patent: 5034506 (1991-07-01), Summerton et al.
patent: 5166315 (1992-11-01), Summerton et al.
patent: 5340716 (1994-08-01), Uhlman et al.
Akashi et al., "New Aspects of Polymer Drugs", Adv. Polym. Sci., 1990, 97, 108-146.
Buttrey et al., "The Resolution of DL-.beta.-(Thymin-1-YL) Alanine and Polymerisation of the .beta.-(Thymin-1-YL) Alanines", Tetrahedron, 1975, 31, 73-75.
De Koning et al., "Unconventional Nucleotide Analogues V. Derivatives of 6-(1-pyrimidinyl)-and 6-(9-purinyl)-2-aminocaproic acid", Recueil, 1971, 90, 874-884.
Doel et al., "An Approach tothe Synthesis of Peptide Analogues of Oligonucleotides (Nucleopeptides)", Tetrahedron Lett., 1969, 27, 2285-2288.
Doel et al., "The Synthesis of Peptides Containing Purine and Pyrimidine Derivatives of DL-Alanine", Tetrahedron, 1974, 30, 2755-2759.
Hanvey et al., "Antisense and Antigene Properties of Peptide Nucleic Acids", Science, 1992, 258, 1481-1485.
Huang et al., "Acyclic Nucleic Acid Analogues: Synthesis and Oligomerization of .gamma., .alpha.-Diamino-2-oxo-1(2H)-pyrimidinepentanoic Acid and .sigma. 4-Diamino-2-oxo-1(2H)-pyrimidinehexanoic Acid", J. Org. Chem., 1991, 56, 6007-6018.
Inaki et al., "Functionality and Applicability of Synthetic Nucleic Acid Analogs", In Current Topics in Polymer Science, Ottenbrite, Utracki Inoue, Eds., New York: Macmillan Pub. Co., 1987, 1, 80-100.
Inaki, Y., "Synthetic Nucleic Analogs", Prog. Polym. Sci., 1992, 17, 515-570.
Lu et al., "Synthesis of Polyesters Containing Nucleic Acid Base Derivatives as Pending Side Chains", J. Polym. Sci.: Part A: Polymer Chemistry, 1986, 24, 525-536.
Matthews et al., Analytical Bioch., 1988, 169, 1-25.
Nagae 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, 1989, 27, 2593-2609.
Nollet et al., "Unconventional Nucleotide Analogues-III, 4-(N.sub.1 -Pyrimidyl)-2-Aminobutyric Acids", Tetrahedron, 1968, 25, 5989-5994.
Nollet et al., "Unconventional Nucleotide Analogues-I, N.sub.9 -Purinyl .alpha.-Amino Acids", Tetrahedron, 1969, 25, 5971-5981.
Nollet et al., "Unconventional Nucleotide Analogues-II, Synthesis of the Adenyl Analogue of Willardiine", 1969, 25, 5983-5987.
Nollet et al., "Michael Addition of 4-O-Ethyluracil. A Method for Specific N.sub.1 -Alkylation of Hydroxpyrimidines", Tetrahedron Letters, 1969, 53, 4605-4606.
Pitha et al., "Inhibition of Murine Leukemia Virus Replication by Poly(vinyluracil) and Poly(vinyladenine)", Proc. Natl Acad. Sci. USA, 1973, 70, 1204-1208.
Pitha, J., "Physiological Activities of Synthetic Analogs of Polynucleotides", Adv. Polym. Sci., 1983, 50, 1-16.
Simon et al., "Peptoids: A modular approach to drug discovery", Proc. Natl. Acad. Sci. USA, 1992, 89, 9367-9371.
Takemoto et al., "Synthetic Nucleic Acid Analogs. Preparation and Interactions", Adv. Polym. Sci., 1981, 3-51.
Uhlmann et al., "Antisense Oligonucleotides: A New Therapeutic Principle", Chem. Reviews, 1990, 90, 544-584.
Weller et al., "Molecular Modeling of Acyclic Polyamide Oligonucleotide Analogues", J. Org. Chem., 1991, 6000-6006.
Brady et al., "Large-Scale Synthesis of a Cyclic Hexapeptide Analogue of Somatostatin", J. Org. Chem., 1987, 52, 764-769.
Almarsson, O. et al., "Molecular Mechanics Calculations of the Structures of Polyamide Nucleic Acid DNA Duplexes and Triple Helical Hybrids", Proc. Natl. Acad. Sci. USA, 1993, 90, 7518-7522.
Almarsson O. et al., Peptide Nucleic Acid (PNA) Conformation and Polymorphism in PNA-DNA and PNA-RNA Hybrids, Proc. Natl. Acad. Sci. USA, 1993, 90, 9542-9546.
Brown, S.C. et al., "NMR Solution Structure of a Peptide Nucleic Acid Complexed with RNA", Science, 1994, 265, 777-780.
Chen, S. et al., "Molecular Dynamics and NMR Studies of Single-Stranded PNAs", Tetrahedron Letters, 1994, 35(29), 5105-5108.
Demidov, V. et al., "Stability of Peptide Nucleic Acids in Human Serum and Cellular Extracts", Biochem. Pharmacol., 1994, 48(6), 1310-1313.
Demidov, V. et al., "Sequence Selective Double Strand DNA Cleavage by PNA Targeting Using Nuclease S1", Nucleic Acids Res., 1993, 21(9), 2103-2107.
Dueholm, K.L. et al., "An Efficient Synthetic Approach to Bocaminoacetaldehyde and its Application in the Synthesis of 2-Boc-Aminoethylglycine Methyl Ester", Org. Prep. Proc. Int., 1993, 25, 457-461.
Dueholm, K.L. et al., "Peptide Nucleic Acid (PNA) with a Chiral Backbone Based on Alanine", Bioorg. Med. Chem. Lett., 1994, 4(8), 1077-1080.
Dueholm, K.L. et al., "Synthesis of Peptide Nucleic Acids Monomers Containing the Four Natural Nucleobases: Tyymine, Cytosine, Adenine and Guanine, and Their Oligomerization", J. Org. Chem., 1994, 59(19), 5767-5773.
Egholm, M. et al., "Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone", J. Am. Chem. Soc., 1992, 114, 1895-1897.
Egholm, M. et al., "Recognition of Guanine and Adenine in DNA by Cytosine and Thymine Containing Peptide Nucleic Acids (PNA)", J. Am. Chem. Soc., 1992, 114, 9677-9678.
Egholm, M. et al., "Peptide Nucleic Acids Containing Adenine or Guanine Recognize Thymine and Cytosine in Complentary DNA Sequences", J. Chem. Soc. Chem. Comm., 1993, 800-801.
Flam, F., "Can DNA Mimics Improve on the Real Thing?", Science, 1993, 262, 1647-1649.
Frank-Kamenetskii, M., "A Change of Backbone", Nature, 1991, 354, 505.
Griffith, M.C. et al., "Single and Bis Peptide Nucleic Acids as Triplexing Agents: Binding and Stoichiometry", J. Am. Chem. Soc., 1995, 117(2), 831-832.
Hyrup, B. et al., "Modification of the Binding Affinity of Peptide Nucleic Acids (PNA). PNA with Extended Backbones Consisting of 2-Aminoethyl-B-Alanine or 3-Aminopropylglycine Units", J. Chem. Soc. Chem. Comm., 1993, 6, 518-519.
Hyrup, B. et al., "Structure-Activity Studies of the Binding of Modified Peptide Nucleic acids (PNA) to DNA", J. Am. Chem. Soc., 1994, 35(29), 5173-5176.
Kosynkina, L. et al., "A convenient Synthesis of Chiral Peptide Nucleic Acid (PNA) Monomers", Tetrahedron Letters, 1994, 35(29), 5173-5176.
Lagriffoul, P.H. et al., "The Synthesis, Co-Oligomerization and Hybridization of a Thymine-Thymine Heterodimer Containing PNA", Bioorg. Med. Chem. Lett., 1994, 4(8), 1081-1085.
Leijon, M. et al., "Structural Characterization of PNA-DNA Duplexes by NMR Evidence for DNA in B-Like Conformation", Biochem., 1994, 33(33), 9820-9825.
Mollegaard, N.E. et al., "Peptide Nucleic Acid-DNA Strand Displacement Loops as Artificial Transcription Promoters", Proc. Natl. Acad. Sci, USA, 1994, 91, 3892-3895.
Nielsen, P.E. et al., "Peptide Nucleic Acids (PNAs): Protein Antisense and Anti-Gene Agents", Anti-Cancer Drug Design, 1993, 8, 53-63.
Nielsen, P.E., "Peptide Nucleic Acids (PNA): Potential Antiviral Agents", Int'l Antiviral News, 1993, 1, 37-39.
Nielsen, P.E. et al., "Peptide Nucleic Acids (PNA): Oligonucleotide Analogs with a Polyamide Backbone", Antisense Research and Applications, 1993, Crooke and B. Lebleu (Eds.), CRC Press, Boca Raton, FL, 363-373.
Nielsen, P.E., "Peptide Nucleic Acid (PNA): A Model Structure for the Primordial Genetic Material?", Orig. Life Evol. Biosphere, 1993, 23, 323-327.
Nielsen, P.E., "Peptide Nucleic Acid (PNA): A DNA Mimic with a Peptide Backbone", Bioconjugate Chem., 1994, 5, 3-7.
Nielsen, P.E., "Sequence-Specific Transcription Arrest by peptide Nucleic Acid Bound to the NDA Template Strand", Gene, 1994, 149, 139-145.
Orum, H. et al., "Single Base Pair Mutation Analysis by PNA Directed PCR Clamping", Nucleic Acids Research, 1993, 21(23), 5332-5336.
Parkanyi, C. et al., "Synthesis of Polymethylene Chain-Bridged 6-Substituted 8-Azapurines and Related Compounds", Collect. Czech. Chem. Commun., 1991, 56, 238

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