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Compositions and methods for conjugating oligonucleotides

A kind of technology of oligonucleotide and compound, applied in the field of composition of oligonucleotide derivatives

Inactive Publication Date: 2015-01-28
AGILENT TECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These new chemical entities may be problematic if oligonucleotide conjugates are used in humans as they may produce toxicity unrelated to the oligonucleotide product

Method used

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  • Compositions and methods for conjugating oligonucleotides
  • Compositions and methods for conjugating oligonucleotides
  • Compositions and methods for conjugating oligonucleotides

Examples

Experimental program
Comparison scheme
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Embodiment

[0075] Synthesis of oligonucleotide-squarate monoconjugates

[0076] Oligonucleotides are synthesized with linked amino linkers by any method known in the art (see discussion above). figure 2 The example shown in uses a TFA-protected amine C6 linker phosphoramidite (i.e., CF 3 -CO-NH-(CH 2 ) 6 -O-P((O-CH(CH 3 ) 2 ) 2 (O-CH 2 -CH 2 -CN), which adopts suitable synthesis conditions to couple with the 5'-OH end of the oligonucleotide on the solid support. This coupling can be performed under similar conditions as for nucleomonomer coupling and can be accomplished while the oligonucleotide is also attached to the solid support. After following the usual synthesis and deprotection (standard ammonia and TEA 3HF for RNA), the mixture can be ultrafiltered against NaCl to remove all ammonia and ammonium salts. Finally, the retentate was washed with water to remove any excess salt. The oligonucleotide solution can then be concentrated. Concentrates can be lyophilized or use...

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Abstract

An oligonucleotide derivative having the structure of formula (A) and methods for preparing the oligonucleotide derivative are disclosed. wherein R3 is a first oligonucleotide; R1 is selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, a polyethylene glycol, a peptide, a protein, a polysaccharide, and a second oligonucleotide; R2 is a linker or a direct bond; Z1 is NR4, S, or O, and Z2 is NR4 or S, wherein R4 is selected from H, alkyl, aryl, heterocyclyl, or heteroaryl. A method includes: synthesizing an oligonucleotide derivative comprising an amino or thiol group; and reacting a 3,4-dialkoxycyclobutene-l,2-dione with the oligonucleotide derivative to produce an oligonucleotide-squarate mono-conjugate.

Description

[0001] Priority claims and related patent applications [0002] This application claims the benefit of priority from US Provisional Application Serial No. 61 / 649,766, filed May 21, 2012, the entire contents of which are incorporated herein by reference in their entirety. field of invention [0003] This application generally relates to the field of reagents, synthesis and purification of oligonucleotides. More specifically, the present invention relates to compositions of oligonucleotide derivatives and methods of conjugating oligonucleotides. Background of the invention [0004] Many methods are available for conjugating oligonucleotides to other molecules. These methods typically involve attaching a reactive moiety to the targeting entity for coupling to the oligonucleotide. Targeting entities and reactive moieties are usually prepared separately, usually by organic synthesis, and purified prior to use. [0005] The oligonucleotides are in each case modified with suitab...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/00C07H19/052C07H19/167C07H21/00C12N15/113
CPCC07H21/00C07H1/00C07H21/02C07K19/00
Inventor K·W·希尔V·R·默克勒
Owner AGILENT TECH INC