Sulfur-Modified Peptides for Collagen Synthesis Stimulation

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing peptide compounds used in cosmetics for skin and appendage care, such as KXK peptides, are often ineffective at concentrations typically used and fail to provide significant cosmetic benefits, particularly in stimulating collagen synthesis and improving skin texture and appearance.

Innovation Solution

Development of peptide compounds with a specific formula incorporating a sulfur atom as a heteroatom in the side chain, which forms hydrogen bonds with other molecules and proteins, enhancing biochemical reactions, and introducing oxygenated sulfur atoms to amplify cosmetic activity, including peptides like Pal-KMO2K-OH and derivatives, that stimulate collagen I synthesis and improve skin texture and appearance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional peptide compounds (KXK peptides) are used at typical cosmetic concentrations, then the formulation is simple and cost-effective, but the cosmetic activity is insufficient and collagen synthesis is not significantly stimulated

Engineering Contradiction:
Improvecosmetic activityVSAvoidpeptide concentration
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent modifies the chemical structure of conventional KXK peptides by introducing specific amino acid sequences (including hydroxyproline, glycine, and cysteine) and chemical modifications (such as sulfation of tyrosine residues). These structural parameter changes enhance the peptide's ability to bind to collagen and stimulate collagen synthesis, thereby improving cosmetic activity at low concentrations without requiring high peptide doses

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite peptide structures by combining multiple amino acid types in specific sequences (e.g., hydroxyproline-glycine-cysteine-tyrosine patterns). This composite approach allows the peptide to interact with multiple collagen molecules simultaneously, enhancing overall cosmetic effectiveness while maintaining low concentration usage

Inventive Principle:
Principle #40Composite materials

2Reliability

If peptide compounds are used to stimulate collagen synthesis, then skin texture and appearance improve, but the mechanism of action is not fully understood

Engineering Contradiction:
Improvecosmetic benefitVSAvoidmechanism knowledge
Core Design Contradiction:
ReliabilityVSLoss of information

Solution Approach 1:

The patent identifies collagen as the intermediary molecule through which the peptide exerts its cosmetic effect. The modified peptide structure enhances binding to collagen molecules, and this collagen-peptide interaction serves as the mediator that triggers downstream effects including improved skin texture, reduced wrinkles, and enhanced elasticity. This intermediary approach provides a concrete molecular mechanism while maintaining cosmetic benefits

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If existing peptide structures are used, then the formulation is straightforward, but the peptides are relatively ineffective at stimulating collagen synthesis

Engineering Contradiction:
Improvecollagen synthesis stimulationVSAvoidpeptide effectiveness
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent introduces specific local structural features at critical positions within the peptide sequence. For example, hydroxyproline residues are positioned to interact with specific collagen helical structures, while cysteine residues are placed to form disulfide bonds that stabilize the peptide-collagen complex. These localized structural modifications significantly enhance collagen synthesis stimulation reliability

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The peptide is segmented into functional modules with specific amino acid sequences that perform distinct functions: hydroxyproline-glycine segments bind to collagen helices, cysteine segments form stabilizing disulfide bonds, and tyrosine segments (when sulfated) provide additional binding affinity. This segmentation allows each segment to contribute to overall effectiveness, improving reliability without requiring the entire peptide at high concentrations

Inventive Principle:
Principle #1Segmentation

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 peptide compounds demonstrate improved cosmetic activity by enhancing collagen synthesis, improving skin texture, reducing signs of aging, and providing antioxidant effects, resulting in softer, more toned, and protected skin with reduced water loss, while also benefiting hair and eyelashes.

Implementation Method 1

incorporating a sulfur atom as a heteroatom in the side chain, which forms hydrogen bonds with other molecules and proteins

Methodology Applied
Scientific EffectHydrogen bonding:

Implementation Method 2

introducing oxygenated sulfur atoms to amplify cosmetic activity

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP3744729B1Peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
Publication Date: 2023.03.01 SEDERMA SA
  • EP3744729B1 patent drawing
  • EP3744729B1 patent drawing
  • EP3744729B1 patent drawing

AI summary

The present invention relates to the cosmetic and dermopharmaceutical fields. It concerns compounds having the following formula II :         R1-(AA)n-R2     (SEQ ID NO 1 to SEQ ID NO 7) wherein: AA is selected from an amino acid, an amino acid derivative and an amino acid analogue ; n=1 to 10, when n ≥ 2, the AA can be different and the bonds being of peptidic or peptoidic type; R1 is either an H or a lipophilic chain, R2 is either an OH or a lipophilic chain, characterised in that the AA or when n>1 at least one of the AA comprise at least one sulfur atom in an oxygenated form, preferably a dioxygenated form. More preferably, AA is a dioxygenated SO2 methionine. Results on the activity of the compounds are obtained and on the general state of the skin and its appendages, especially via the stimulation of extracellular matrix components.