Disulfide Cationic Lipid for Intracellular Nucleic Acid Release

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Solution Overview

Problem

Existing cationic lipids used for nucleic acid delivery exhibit low intracellular expression efficiency due to limitations in uptake, endosome escape, and nuclear membrane permeation, necessitating improved intracellular dynamics for enhanced delivery and expression.

Innovation Solution

A cationic lipid with a disulfide bond structure, represented by a specific formula, that facilitates intracellular release of nucleic acids by cleavage in a reductive environment, enhancing delivery efficiency and expression.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If known cationic lipids (DOTAP, DODAP) are used to form positively-charged liposome structures, then nucleic acid delivery to target cells is achieved, but intracellular expression efficiency remains low due to limitations in uptake, endosome escape, and nuclear membrane permeation

Engineering Contradiction:
Improvenucleic acid delivery efficiencyVSAvoidintracellular expression efficiency
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention modifies the chemical structure of cationic lipids by introducing a disulfide bond in place of traditional C-N or C-C bonds. This structural parameter change enables the lipid to respond to intracellular reductive environments, triggering conformational changes that enhance endosome escape and nuclear membrane permeation, thereby improving intracellular expression efficiency while maintaining delivery capability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The cationic lipid structure combines a hydrophobic tail region with a hydrophilic head region containing the disulfide bond and amine group. This composite structure allows the molecule to interact with both lipid membranes and nucleic acids, facilitating uptake, endosome escape, and nuclear permeation through its amphiphilic nature and redox-responsive disulfide linkage

Inventive Principle:
Principle #40Composite materials

2Duration of action of stationary object

If cationic lipids are designed for high stability in blood and accumulation in target tissues, then pharmacokinetics are improved, but intracellular dynamics (uptake, endosome escape, nuclear membrane permeation) need additional optimization for enhanced expression

Engineering Contradiction:
Improveblood stability and tissue accumulationVSAvoidintracellular expression per lipid membrane structure
Core Design Contradiction:
Duration of action of stationary objectVSProductivity

Solution Approach 1:

The cationic lipid molecule is segmented into distinct functional regions: a hydrophobic tail for membrane interaction, a disulfide bond for redox responsiveness, and a cationic head group for nucleic acid binding. This segmentation allows each region to perform its specific function optimally while the disulfide bond acts as a trigger for intracellular activation, enhancing expression efficiency without compromising blood stability

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The disulfide bond introduces dynamic behavior to the cationic lipid structure. In the oxidative extracellular environment, the lipid maintains a stable configuration for blood circulation and target accumulation. Upon entering the reductive intracellular environment, the disulfide bond undergoes reduction, triggering conformational changes that dynamically enhance endosome escape and nuclear membrane permeation capabilities

Inventive Principle:
Principle #15Dynamics

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 cationic lipid achieves high nucleic acid delivery efficiency and gene expression, particularly useful for cellular medicines by promoting intracellular release and improving intracellular dynamics.

Implementation Method 1

The disulfide bond contained in the cationic lipid of the present invention is cleaved in the intracellular reductive environment, thus promoting release of materials (nucleic acid) enclosed therein

Methodology Applied
Scientific EffectReductive cleavage: Reduction

Implementation Method 2

the amine moiety showing cationicity and a polyanion nucleic acid electrostatically interact to form a liposome or lipid membrane structure

Methodology Applied
Scientific EffectElectrostatic interaction: Electrostatics

Data Source

PatentEP4692059A1Cationic lipid having disulfide bond
Publication Date: 2026.02.11 NOF CORP
  • EP4692059A1 patent drawingFigure 1~2
  • EP4692059A1 patent drawingFigure 3~4
  • EP4692059A1 patent drawingFigure 5~7

AI summary

The present invention provides a cationic lipid represented by the following formula (1) (the symbols in the following formula (1) are as defined in the specification).