Pyranosyl nucleic acid conjugates

• US 6,608,186 B1
• Filed: 07/27/2000
• Issued: 08/19/2003
• Est. Priority Date: 09/22/1997
• Status: Expired due to Term

• Current Assignee: Sanofi-Aventis SA (Sanofi )
• Original Assignee: Nanogen Recognomics GmbH
• Inventors: Windhab, Norbert, Burdinski, Gerhard, Brandstetter, Tilmann, Miculka, Christian
• Primary Examiner(s): Wilson; James O.
• Assistant Examiner(s): CRANE, LAWRENCE E
• Application Number:
  US09/509,058
• Time in Patent Office: 1,118 Days
• Field of Search: 536/23.1,24.3,24.5 435/6
• US Class Current: 536/23.1
• CPC Class Codes: A61K 47/549 Sugars, nucleosides, nucleotides or nucleic acids
• CPC Class Codes: A61K 49/0013 Luminescence
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C07H 21/02 with ribosyl as saccharide radical
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: G01N 33/532 Production of labelled immunochemicals
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
• CPC Class Codes: Y10S 977/728 Nucleic acids, e.g. DNA or RNA
• CPC Class Codes: Y10S 977/80 Nucleic acid, e.g. DNA or RNA
• CPC Class Codes: Y10S 977/836 having biological reactive capability
• CPC Class Codes: Y10S 977/894 having step or means utilizing biological growth
• CPC Class Codes: Y10S 977/896 Chemical synthesis, e.g. chemical bonding or breaking
• CPC Class Codes: Y10S 977/904 for medical, immunological, body treatment, or diagnosis
• CPC Class Codes: Y10S 977/914 Protein engineering
• CPC Class Codes: Y10S 977/915 Therapeutic or pharmaceutical composition
• CPC Class Codes: Y10S 977/924 using nanostructure as support of dna analysis
• CPC Class Codes: Y10S 977/925 Bioelectrical

Abstract

The invention relates to a pentopyranosylnucleoside of the formula (I) or of the formula (II)

their preparation and use for the production of a therapeutic, diagnostic and/or electronic component.

Claims

1. A conjugate according to structures (I) or (II),

wherein A is selected from the group consisting of DNA, RNA, peptide, protein, antibody, and functional antibody fragment;

wherein 1 is an integer from 0-20, m is an integer from 0-20, and n is an integer from 1-20, with the proviso that 1 m is less than or equal to 20;

wherein B is selected from the group consisting of 9-adeninyl, 9-guaninyl, 1-thyminyl, 1-cytosinyl, 1-uracilyl, and 1-indolyl; and

wherein the structure (I) or (II) is hybridized to a complementary pyranosyl structure.

2. The conjugate according to claim 1, wherein the pyranosyl nucleotides of structures (I) or (II) are selected from the group consisting of ribo-, arabino-, lyxo-, and xylopyranosyl nucleotides.

3. The conjugate according to claim 1, wherein the pyranosyl nucleotides of structures (I) or (II) are in the D configuration.

4. The conjugate according to claim 1, wherein the pentopyranosyl nucleotides of structures (I) or (II) are in the L configuration.

5. The conjugate according to claim 1, wherein at least one of the pyranosyl nucleotides is a ribopyranosyl nucleotide.