Oligonucleotide 5' End Modification for AGO2 Affinity

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Solution Overview

Problem

Current oligonucleotides lack a specific method to improve affinity for Argonaute 2 (AGO2) and enhance knockdown activity, which is essential for effective RNA interference.

Innovation Solution

An oligonucleotide with a nucleotide residue or nucleoside residue represented by a specific formula at the 5' end, featuring modifications such as 8-Br-dA, which binds to adjacent residues through an oxygen atom, improving affinity for AGO2 and enhancing knockdown activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If natural nucleotides are used in oligonucleotides, then the structure is simple and easy to manufacture, but the affinity for AGO2 and knockdown activity are insufficient

Engineering Contradiction:
Improveaffinity for AGO2VSAvoidstructural complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of nucleotides at specific positions (5' end and adjacent position) of the oligonucleotide. This involves changing physical and chemical parameters such as adding bromine atoms, modifying sugar moieties, or altering base structures to enhance affinity for AGO2 while maintaining manufacturability through systematic structural modifications

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite materials by creating oligonucleotides with hybrid structures that combine natural nucleotide components with modified unnatural nucleotide components. This composite approach allows the oligonucleotide to maintain recognizability by biological systems while incorporating enhanced binding properties through the modified nucleotides at critical positions

Inventive Principle:
Principle #40Composite materials

2Productivity

If natural nucleotides are used in oligonucleotides, then the synthesis process is simple, but the knockdown activity against target mRNA is insufficient

Engineering Contradiction:
Improveknockdown activityVSAvoidoligonucleotide structure
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing modified nucleotides specifically at local critical positions (5' end and adjacent position) rather than throughout the entire oligonucleotide structure. This localized modification strategy enhances knockdown activity at the binding interface with AGO2 while keeping the rest of the structure simple and easy to synthesize

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent changes chemical parameters of nucleotides at specific positions to enhance knockdown activity. This includes modifying properties such as electronegativity, steric bulk, or hydrogen bonding capacity of nucleotides at the 5' end and adjacent position to improve interaction with AGO2 and thereby enhance overall knockdown efficacy

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The modified oligonucleotide demonstrates increased affinity for AGO2 and enhanced knockdown activity, as shown by increased inhibition of target mRNA expression compared to natural nucleotides.

Implementation Method 1

a nucleotide residue or a nucleoside residue represented by formula (I) at the 5' end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3... the oligonucleotide has a length of 10 to 80 bases... improves affinity for AG02

Methodology Applied
Scientific EffectMolecular Binding: Adsorption

Data Source

PatentEP2891717B1oligonucleotide
Publication Date: 2020.04.29 KYOWA HAKKO KIRIN CO LTD
  • EP2891717B1 patent drawingFigure 1
  • EP2891717B1 patent drawingFigure 2
  • EP2891717B1 patent drawingFigure 3~4

AI summary

The present invention provides an oligonucleotide having improved affinity for AG02, and the like. The oligonucleotide has a nucleotide residue or a nucleoside residue represented by formula (I) {wherein X1 is an oxygen atom or the like, R1 is formula (IIA) (wherein R5A is halogen or the like, and R6A is a hydrogen atom or the like) or formula (IVA) (wherein Y3A is a nitrogen atom or the like, and Y4A is CH or the like), or the like, R2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R3 is a hydrogen atom or the like} at the 5' end thereof, and the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3.