CDR Histidine Substitution in Polypeptides for Intestinal Stability

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Solution Overview

Problem

Therapeutic polypeptides, such as immunoglobulin chain variable domains, are unstable in the intestinal tract, limiting their oral administration and affecting their stability and binding affinity, particularly in the presence of proteases and inflammatory conditions.

Innovation Solution

Substituting lysine and arginine residues in the complementarity determining regions (CDRs) of immunoglobulin chain variable domains with histidine residues to enhance intestinal stability while maintaining binding affinity, suitable for oral administration and resistance to proteases.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If amino acid substitutions are made in CDR regions to enhance intestinal stability, then protease resistance is improved, but binding affinity to target antigen deteriorates

Engineering Contradiction:
Improveintestinal stabilityVSAvoidbinding affinity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent applies local quality by making specific amino acid substitutions only in non-CDR regions (framework regions) of the immunoglobulin variable domain, while leaving the CDR regions unchanged. This localized approach allows the polypeptide to gain intestinal stability from the substitutions in framework regions without compromising the binding affinity determined by the intact CDR regions.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent segments the immunoglobulin variable domain into functional regions (CDRs for binding and framework regions for structural stability) and applies modifications only to the framework regions. This segmentation allows independent optimization of binding affinity (maintained in CDRs) and intestinal stability (improved in framework regions through substitutions).

Inventive Principle:
Principle #1Segmentation

2Reliability

If additional cysteine bridges are introduced to increase proteolytic stability, then intestinal stability is improved, but recombinant production levels deteriorate

Engineering Contradiction:
Improveproteolytic stabilityVSAvoidrecombinant production levels
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent changes the amino acid sequence parameters by substituting specific residues in framework regions with amino acids that enhance protease resistance (such as replacing protease cleavage sites). This parameter change approach improves proteolytic stability without introducing additional cysteine bridges that would complicate the protein structure and reduce recombinant production efficiency.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If conventional small molecule oral dosage forms are used for polypeptide delivery, then oral administration is enabled, but intestinal stability deteriorates

Engineering Contradiction:
Improveoral administration capabilityVSAvoidintestinal stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent extracts the polypeptide from the conventional small molecule dosage form context and applies direct amino acid sequence modifications to the polypeptide itself. This extraction from the formulation approach and implementation of molecular-level modifications enables the polypeptide to inherently resist intestinal proteases while maintaining oral administrability.

Inventive Principle:
Principle #2Taking out (Extraction)

Data Source

PatentEP3277713B1polypeptides
Publication Date: 2025.09.10 SORRISO PHARMACEUTICALS INC
  • EP3277713B1 patent drawingFigure 1
  • EP3277713B1 patent drawingFigure 2A~2B
  • EP3277713B1 patent drawingFigure 3A~3B

AI summary

There is provided inter alia a polypeptide comprising an immunoglobulin chain variable domain comprising three complementarity determining regions (CDR1 -CDR3) and four framework regions, wherein: (a) at least one lysine residue in CDR1, CDR2 and/or CDR3 has been substituted with at least one histidine residue, and/or (b) at least one arginine residue in CDR1, CDR2 and/or CDR3 has been substituted with at least one histidine residue; wherein the polypeptide has increased intestinal stability relative to a corresponding polypeptide not having said histidine substitutions.