Trigonal Peptide Agonists Acid Stability

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Solution Overview

Problem

Current peptides for treating metabolic disorders, such as diabetes and obesity, face challenges in stability and solubility, especially in acidic conditions and when combined with antimicrobial preservatives, limiting their efficacy and duration of action.

Innovation Solution

Development of novel trigonal GLP-1/glucagon/GIP receptor agonists derived from exendin-4, with specific amino acid substitutions and modifications, such as replacing Tyr10 and Tyr13 with Leu, and incorporating a lipophilic residue at position 14, enhancing solubility, stability, and receptor activation, including high activity on both glucagon and GIP receptors while maintaining GLP-1 receptor activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current peptides are used for treating metabolic disorders, then they can provide therapeutic effects, but they exhibit poor stability and solubility especially in acidic conditions and when combined with antimicrobial preservatives

Engineering Contradiction:
ImprovestabilityVSAvoiddegradation in acidic conditions
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the amino acid sequence of exendin-4 through specific substitutions (Tyr10→Leu, Tyr13→Leu, Met14→Lys) to alter the peptide's physicochemical properties. These changes improve stability in acidic conditions and resistance to degradation by antimicrobial preservatives like m-cresol and phenol, while maintaining biological activity at all three receptors.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by making targeted modifications at specific positions (10, 13, and 14) of the exendin-4 sequence. The substitutions at these local positions confer acid stability and preservative resistance without compromising the overall structure-function relationship, allowing the peptide to maintain its trigonal agonist activity.

Inventive Principle:
Principle #3Local quality

2Duration of action of moving object

If current peptides are used for treating metabolic disorders, then they can provide therapeutic effects, but they have limited duration of action

Engineering Contradiction:
Improveduration of actionVSAvoidresistance to degradation
Core Design Contradiction:
Duration of action of moving objectVSReliability

Solution Approach 1:

The patent applies parameter changes by modifying the amino acid sequence of exendin-4 through specific substitutions (Tyr10→Leu, Tyr13→Leu, Met14→Lys) to alter the peptide's physicochemical properties. These changes improve stability in acidic conditions and resistance to degradation by antimicrobial preservatives like m-cresol and phenol, while maintaining biological activity at all three receptors.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If amino acid substitutions are made to improve stability, then solubility and stability improve, but receptor activation activity may be compromised

Engineering Contradiction:
ImprovestabilityVSAvoidreceptor activation activity
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by modifying the amino acid sequence of exendin-4 through specific substitutions (Tyr10→Leu, Tyr13→Leu, Met14→Lys) to alter the peptide's physicochemical properties. These changes improve stability in acidic conditions and resistance to degradation by antimicrobial preservatives like m-cresol and phenol, while maintaining biological activity at all three receptors.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by making targeted modifications at specific positions (10, 13, and 14) of the exendin-4 sequence. The substitutions at these local positions confer acid stability and preservative resistance without compromising the overall structure-function relationship, allowing the peptide to maintain its trigonal agonist activity.

Inventive Principle:
Principle #3Local quality

Data Source

PatentEP3548508B1New compounds as peptidic trigonal GLP1/glucagon/GIP receptor agonists
Publication Date: 2021.10.27 SANOFI SA(FR)
  • EP3548508B1 patent drawingFigure 1
  • EP3548508B1 patent drawingFigure 2
  • EP3548508B1 patent drawingFigure 3

AI summary

The present invention relates to trigonal GLP-1 / glucagon / GIP receptor agonists and their medical use, for example in the treatment of disorders of the metabolic syndrome, including diabetes and obesity, as well as for reduction of excess food intake.