Carboxylated 2'-amino LNA oligonucleotides for cellular uptake

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Solution Overview

Problem

Current oligonucleotides face challenges in achieving improved efficacy and specificity, particularly in cellular uptake and therapeutic applications, due to limitations in potency and stability, especially when interacting with RNA targets in living cells.

Innovation Solution

The development of oligonucleotides incorporating carboxylated 2'-amino LNA nucleotide units, such as carboxyalkylated and carboxyarylated derivatives, which enhance potency and specificity by modifying the 2'-amino group of LNA nucleotides, allowing for improved cellular uptake and therapeutic efficacy.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional oligonucleotides are used, then manufacturing and operation are simple, but potency and cellular uptake are insufficient

Engineering Contradiction:
ImprovepotencyVSAvoidnucleotide structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing carboxylated 2'-amino LNA nucleotide units at specific positions within the oligonucleotide sequence rather than uniformly modifying all nucleotides. This localized modification at the 2'-amino group with carboxylated substituents enhances potency and cellular uptake while maintaining manageable structural complexity in the overall oligonucleotide design.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by modifying the chemical structure of LNA nucleotides through carboxylation at the 2'-amino group. This chemical parameter modification (adding carboxylated substituents) transforms the physical-chemical properties of the nucleotide, improving cellular uptake and potency while maintaining the fundamental oligonucleotide structure.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If oligonucleotides are modified to improve cellular uptake, then potency increases, but specificity may be compromised

Engineering Contradiction:
Improvecellular uptake efficiencyVSAvoidspecificity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent maintains specificity by applying carboxylation modifications only at the 2'-amino group of LNA nucleotides while preserving the complementary base pairing regions. This localized modification approach ensures that cellular uptake is enhanced without compromising the sequence-specific recognition and binding to target RNA molecules.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent segments the oligonucleotide into functionally distinct regions: carboxylated 2'-amino LNA units for cellular uptake and stability, and unmodified or differently modified nucleotides for specific target recognition. This segmentation allows independent optimization of uptake efficiency and binding specificity.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP3992288A1Carboxylated 2'-amino-LNA nucleotides and oligonucleotides comprising the same
Publication Date: 2022.05.04 BIONTECH DELIVERY TECHNOLOGIES GMBH
  • EP3992288A1 patent drawingFigure 1
  • EP3992288A1 patent drawingFigure 1
  • EP3992288A1 patent drawingFigure 2A~2B

AI summary

The invention proves an oligonucleotide comprising one or more carboxylated 2'- amino-LNA nucleotide units. The invention also provides a method of transfecting cells with the oligonucleotide, a method of treating a human or animal by therapy using the oligonucleotide, and a pharmaceutical composition comprising the oligonucleotide.