Oligonucleotide mimics having nitrogen-containing linkages

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

530350, C07H 2104, C07K 100

Patent

active

057836825

ABSTRACT:
Novel compounds that mimic and/or modulate the activity of wild-type nucleic acids. In general, the compounds contain a selected sequence of nucleosidic bases or other reactive groups that are covalently bound through nitrogen-containing linear, hairpin, dumbbell, and circular shaped tethers.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 5142047 (1992-08-01), Summerton et al.
patent: 5264562 (1993-11-01), Matteucci
patent: 5489677 (1996-02-01), Sanghvi et al.
Augustyns, et al., "Influence of the incorporation of (S)-9-(3,4-dihydroxy-butyl)adenine on the enzymatic stability and base-pairing properties of oligodeoxynucleotides", Nucleic Acids Research, 19, No. 10, (1991), 2587-2593.
Hanvey, et al., "Antisense and Antigene Properties of Peptide Nucleic Acids", Science, 258, (1992), 1481-1485.
Hendra and Loader, "Synthetic Analogues of Polynucleotides", Nature, 217, (1968), 638-640.
Pitha, "Physiological Activities of Synthetic Analogs of Polynucleotides", Adv. in Polymer Science, 50, 1983, 2-16.
B. Hyrup et al., J. Am. Chem. Soc., vol. 116 ('94) 7964-7970.
D. Metzler, Biochemistry, Academic Press, Inc. (NY, NY, 1977) p. 820.
H. Kang et al., Biopolymers, 32(10) ('92) 1351-63 (Abstract).
R. McGraw et al., Biotechniques, 8(6) ('90) 674-78.
D. Hart et al., J. ACS, 110 ('88) 1631-33.
P. Weszermann et al. Biomed. Biochim. Acta, vol. 48 #1 ('89) pp. 85-93.
E. Uhlmann et al. Chemical Reviews, vol. 90 #4 (Jun. '90) pp. 543-584.
R. Morrison & R. Boyd, Organic Chemistry, 3rd Ed., Boston, Allyn and Bacon, Inc., 1973, pp. 738-740.
B. Erwin et al. Biochem J. ('86) 238: 581-587.
Wolfe, S. et al., "Five-Membered Rings. I. Inter and Intramolecular Reactions of Simple Amines with N-Substituted Phthalimides. Methylamine as a Reagent for Removal of a Phthaloyl Group from Nitrogen", Canadian Journal of Chemistry 1970, 48, 3572-3579.
Comprehensive Organic Synthesis, B.M. Trost & I. Fleming, Eds., 4, 758-776.
Cormier, et al., "Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages", Nucleic Acids Research, 16, No. 10, (1988), 4583-4594.
Debart, et al., "Intermolecular Radical C-C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleosides", Tetrahedron Letters, 33, No. 19, (1992), 2645-2648.
Egholm, et al., "Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone", J. Am. Chem. Soc., 114, (1992), 1895-1897.
Giannis, et al., "Fragmentation and Wittig Olefination of Glucosamine Derivatives--A Simple Route to Open Chain Amino Sugars and Chiral Glycerols", Tetrahedron Letters, 44, No. 23, (1988), 7177-7180.
Goodchild, "Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of their Synthesis and Properties", Bioconjugate Chemistry, 1, No. 3, (1990), 165-187.
"Protection for the Carbonyl Group", Protection Groups in Organic Synthesis, Greene and Wuts, Eds., John Wiley & Sons, Inc., (1991), 175-223.
Hart, et al., "Bis(trimethylstannyl)benzopinacolate-Mediated Intermolecular Fee-Radical Carbon-Carbon Bond-Forming Reactions: A New One-Carbon Homologation", J. Am. Chem. Soc., 110, (1988), 1631-1633.
Yamamoto, et al., "One-step Synthesis of 5'-Azido-nucleosides", J. Chem. Soc. Perkin I, (1980), 306-310.
Hillgartner, et al., "Bis(trimethylzinn)benzpinakolat, seine reversible radikalische Dissoziation und Reaktionen", Liebigs Ann. Chem., (1975), 586-599 in German--untranslated.
Hyrup, et al., "Modification of the Binding Affinity of Peptide Nucleic Acids (PNA). PNA with Extended Backbones consisting of 2-Aminoethyl-.beta.-alanine or 3-Aminopropylglycine Units", J. Chem. Soc., Chem. Commun., (1993), 518-519.
Inouye, et al., "Selective Coloration of Spiro Pyridopyrans for Guanosine Derivatives", J. Am. Chem. Soc., 114, No. 2, (1992), 778-780.
"Advanced Organic Chemistry, Reactions, Mechanisms and Structure", J. March, Ed., J. Wiley & Sons, New York, (1992), 352.
Prakash, et al., "Molecular Recognition by Circular Oligonucleotides. Strong Binding of Single-stranded DNA and RNA", J. Chem. Soc., Chem. Commun., (1991), 1161-1163.
Lin, et al., "Synthesis and Biological Activity of Several Amino Analogues of Thymidine", Journal of Medical Chemistry, 21, No. 1, (1978), 109-112.
Matteucci, "Deoxyoligonucleotide Analogs Based on Formacetal Linkages", Tetrahedron Letters, 31, No. 17, (1990), 2385-2388.
Loke, et al., "Delivery of c-myc Antisense Phosphorothioate Oligodeoxynucleotides to Hematopoietic Cells in Culture by Liposome Fusion: Specific Reduction in c-myc Protein Expression Correlates with Inhibition of Cell Growth and DNA Synthesis", Top. Microbiol. Immunol., 141, (1988), 282-289.
Ma, et al., "Design and synthesis of RNA miniduplexes via a synthetic linker approach. 2. Generation of covalently closed, double-stranded cyclic HIV-1 TAR RNA analogs with high Tat-binding affinity", Nucleic Acids Research, 21, No. 11, (1993), 2585-2589.
Marcus-Sekura, et al., "Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages", Nucleic Acids Research, 15, No. 14, (1987), 5749-5763.
Mazur, et al., "Isosteres of Natural Phosphates. 11. Synthesis of a Phosphonic Acid Analogue of an Oligonucleotide", Tetrahedron, 40, No. 20, (1984), 3949-3956.
Miller, et al., "Effects of a Trinucleotide Ethyl Phosphotriester, G.sup.m p(Et)G.sup.m p(Et)U, on Mammalian Cells in Culture", Biochemistry, 16, No. 9, (1977), 1988-1996.
Nair, et al., "Regiospecific 5'-Silylation of Nucleosides", Organic Preparations and Procedures Int. 22(1), (1990), 57-61.
Nielsen, et al., "Sequence-Selective Recognition of DNA by Strand Displacement with a Thymine-Substituted Polyamide", Science, 254, (1991), 1497-1500.
Pauling, "Molecular Architecture and Biological Reactions", Chemical and Engineering News, 24, No. 10, (1946), 1375-1377.
Perkins, et al., "Accelerated Displacement of Duplex DNA Strands by a Synthetic Circular Oligodeoxynucleotide", J. Chem. Soc., Chem. Commun., (1993), 215-216.
Rebek, "Molecular Recognition and Biophysical Organic Chemistry", Acc. of Chem. Res., 23, No. 12, (1990), 399-404.
Rentzeperis, et al., "Contribution of Loops and Nicks to the Formation of DNA Dumbbells: Melting Behavior and Ligand Binding", Biochemistry, 32, No. 10, (1993), 2564-2571.
Abdel-Magid, et al., "Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride", Tetrahedron Letters, 31, No. 39, (1990), 5595-5598.
Trapani, et al., "N-1-Alkenyl-N,S-Diacyl-2-Aminobenzenethiols (Enamides) by Ring-Opening of 2,3-Dihydro-1,3-benzothiazoles with Aliphatic Carboxylic Anhydrides", Synthesis, (1988), 84-87.
Tuladhar, et al., "A Synthetic Route to Poly-N,N'-Dimethylethylenediamines", Tetrahedron Letters, 33, No. 16, (1992), 2203-2206.
Wilson,"Cellular Transport Mechanisms", Ann. Rev. Biochem., 47, (1978), 933-965.
Zuckermann, et al., "Efficient Method for the Preparation of Peptoids Am. Chem. Soc., 114, (1992), 10646-10647.
Niitsu, et al., "Syntheses of a Series of Linear Pentaamines with Three and Four Methylene Chain Intervals", Chem. Pharm. Bull., 34, (1986), 1032-1038.
Cho, et al., "An Unnatural Biopolymer", Science, 261, (1993), 1303-1305.

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

Oligonucleotide mimics having nitrogen-containing linkages does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oligonucleotide mimics having nitrogen-containing linkages, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oligonucleotide mimics having nitrogen-containing linkages will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1647943

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