Cyanine Dye Structural Modification for Aggregation Control

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Solution Overview

Problem

Current fluorescent dyes used in aqueous systems tend to form dimers or aggregates, compromising their performance and exhibit poor chemical and photochemical stability, limiting their effectiveness in multiplex, multicolor analysis applications.

Innovation Solution

Development of new cyanine dye compounds with specific structural features, such as N-aryl substituents and negatively charged sulfonic groups, which reduce aggregation and enhance chemical and photochemical stability, allowing for improved fluorescence and selectivity in the visible or near-infrared region.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorescent dyes are used in aqueous systems, then they can be applied for labeling and detection, but they tend to form dimers or aggregates compromising their performance

Engineering Contradiction:
Improvefluorescence performanceVSAvoidaggregation tendency
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the chemical structure of cyanine dyes by introducing N-aryl substituents and sulfonate groups at specific positions (R14-R18), changing the physical and chemical parameters of the dye molecules. These structural parameter changes reduce the tendency to aggregate while maintaining fluorescence properties, directly resolving the contradiction between reliability and compositional stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite dye structures by combining multiple functional groups (N-aryl substituents, sulfonate groups at R14-R18 positions, and cyanine core) into a single molecular framework. This composite structure provides both anti-aggregation properties and enhanced fluorescence performance, simultaneously addressing both aspects of the contradiction.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional fluorescent dyes are used, then they can perform labeling functions, but they exhibit poor chemical and photochemical stability

Engineering Contradiction:
Improvelabeling functionVSAvoidchemical and photochemical stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent introduces specific structural parameters including N-aryl substituents and sulfonate groups at positions R14-R18, which change the chemical and photochemical properties of the dye. These parameter modifications enhance stability against degradation while preserving the labeling function, resolving the contradiction between reliability and compositional stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The accelerated stability testing described in the patent (comparing stability after prolonged storage versus rapid degradation conditions) allows for quick evaluation and optimization of dye stability. This method enables rapid identification of stable dye structures that maintain labeling functionality, effectively addressing the stability contradiction.

Inventive Principle:
Principle #21Skipping (Rushing through)

3Adaptability or versatility

If multiplex multicolor analysis is performed, then comprehensive detection is achieved, but dye aggregation and instability compromise the analysis quality

Engineering Contradiction:
Improvemultiplex analysis capabilityVSAvoidanalysis quality
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent develops cyanine dyes with universal structural features (N-aryl substituents and sulfonate groups at R14-R18) that provide multiple benefits simultaneously: reduced aggregation, enhanced chemical stability, improved photochemical stability, and maintained fluorescence. This multi-functional design enables reliable multiplex multicolor analysis by ensuring consistent performance across different dye molecules and experimental conditions.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 new cyanine dyes exhibit a low tendency to form aggregates, possess high photo- and chemical stability, and demonstrate stronger fluorescence and improved light absorption selectivity, making them suitable for advanced biological and chemical analysis applications.

Implementation Method 1

Fluorescent dyes are widely used for labeling, detecting, and quantifying components in a sample

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

demonstrate stronger fluorescence and improved light absorption selectivity

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentEP2758475B1Dyes for labelling molecular ligands
Publication Date: 2017.04.26 ILLUMINA CAMBRIDGE LTD
  • EP2758475B1 patent drawingFigure 1
  • EP2758475B1 patent drawingFigure 2
  • EP2758475B1 patent drawingFigure 3

AI summary

Cyanine dyes with improved fluorescence intensity and photostability.