pH-Dependent Fluorescent Dyes for Rapid Wound pH Sensing

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Solution Overview

Problem

Existing pH sensors for wound infections are slow and lack sensitivity, stability, and specificity, particularly in detecting pH changes relevant to wound healing and infection, necessitating a more accurate and immediate point-of-care method.

Innovation Solution

Development of pH-dependent dyes with specific absorption and fluorescence properties, including absorption maxima outside biological interference, high photostability, and a pKa range of 4 to 7, enabling ratiometric measurements and sensitive detection of pH changes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If standard bacterial cultures and testing are used for wound infection detection, then diagnostic accuracy can be achieved, but the method is slow (up to 48 hours) and requires laboratory infrastructure away from the patient

Engineering Contradiction:
Improvediagnostic accuracyVSAvoiddetection time
Core Design Contradiction:
Measurement precisionVSLoss of time

Solution Approach 1:

The patent replaces the mechanical/laboratory-based bacterial culture system with an optical detection system using fluorescent dyes. The dye-based pH sensing mechanism enables rapid detection of wound infection through fluorescence emission, eliminating the need for time-consuming bacterial cultivation while maintaining diagnostic accuracy.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

Solution Approach 2:

The patent utilizes pH parameter changes as a biomarker for wound infection detection. By monitoring pH variations in wound exudate using fluorescent dyes, the system achieves rapid detection without requiring direct bacterial identification, thus reducing detection time while maintaining accuracy.

Inventive Principle:
Principle #35Parameter changes

2Measurement precision

If classic pH indicators like litmus or phenolphthalein are used, then pH detection is possible, but the sensitivity and accuracy are insufficient for biological samples

Engineering Contradiction:
ImprovepH detection accuracyVSAvoidsensitivity
Core Design Contradiction:
Measurement precisionVSDifficulty of detecting and measuring

Solution Approach 1:

The patent employs fluorescent dyes that undergo significant color and fluorescence intensity changes in response to pH variations. These dyes provide enhanced sensitivity and accuracy compared to classic indicators, enabling reliable pH detection in biological samples through optimized fluorescence emission characteristics.

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The patent utilizes dyes with specific pKa values (6.5-7.5) that undergo protonation/deprotonation transitions at physiological pH ranges. This parameter change enables sensitive detection of pH variations in wound exudate, achieving both accuracy and sensitivity requirements for biological applications.

Inventive Principle:
Principle #35Parameter changes

3Measurement precision

If fluorescence-based pH sensing is used, then measurement sensitivity is improved, but the dyes require specific optical properties and photostability to function effectively

Engineering Contradiction:
Improvemeasurement sensitivityVSAvoiddye requirements
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The patent selects dyes with specific optical parameters including absorption maxima in the 500-650 nm range and pKa values of 6.5-7.5. These parameter optimizations enable the dyes to function effectively in biological samples, achieving high measurement sensitivity while maintaining manageable complexity through standardized dye selection criteria.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs commercially available fluorescent dyes that can be easily incorporated into wound dressings. These dyes provide sufficient photostability and optical properties for the application without requiring complex custom synthesis, reducing overall system complexity while maintaining high measurement sensitivity.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

4Reliability

If SNARF dyes are used for intracellular pH measurement, then photostability and ratiometric measurement capability are improved, but the pKa range (7.5-7.9) is too high for wound infection detection

Engineering Contradiction:
ImprovephotostabilityVSAvoidpKa range suitability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent modifies the pKa parameter of the dye system by selecting dyes with pKa values of 6.5-7.5, which are optimized for detecting the pH changes occurring during wound healing and infection. This parameter adjustment maintains the photostability and ratiometric measurement capabilities while achieving suitability for wound infection detection applications.

Inventive Principle:
Principle #35Parameter changes

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 dyes provide sensitive, rapid, and accurate pH detection suitable for wound infection diagnosis, allowing real-time monitoring and potential drug release, with high turn-on-ratio and photostability, suitable for biological and medical applications.

Implementation Method 1

The pH can therefore also be used to monitor the healing process of a wound... the pH will return to acidic during the wound healing... the pH of a wound therefore drops during the healing process

Methodology Applied
Scientific EffectProtonation/Deprotonation: Chemical Bonding

Implementation Method 2

fluorescent dyes whose fluorescence intensity or fluorescence wavelength depends on the pH can be used. Optical measurement via fluorescence is often even more accurate, as emitted light is measured more sensitively than absorption

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP4711422A1Dyes with ph-dependent absorption and fluorescence
Publication Date: 2026.03.18 ATTO TEC
  • EP4711422A1 patent drawingFigure 1
  • EP4711422A1 patent drawingFigure 2
  • EP4711422A1 patent drawingFigure 3

AI summary

The present invention relates to dyes with pH-dependent absorption and fluorescence for pH detection and their applications in biology, medicine and theranostic. In particular, the present invention relates to compounds of the general formulae (I) - (IV), that show pH dependent absorption and fluorescence spectra as well as pH dependent fluorescence quantum yield, methods for their preparation and their application as pH-sensors and labeling groups for the detection of analytes.