AIE-Active Conjugated Polyene Compounds for DNA Detection

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Solution Overview

Problem

Current fluorescent dyes for DNA detection and bioprobes suffer from aggregation-caused quenching, leading to reduced sensitivity and instability in aqueous environments, limiting their effectiveness in biological applications.

Innovation Solution

Development of water-soluble conjugated polyene compounds that exhibit aggregation-induced emission (AIE), which remain non-emissive in aqueous solutions but emit intensely when aggregated, allowing for enhanced fluorescence in bioprobes and sensors for DNA detection and potassium-ion sensing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorescent dyes are used in aqueous solutions for DNA detection, then they provide initial fluorescence signal, but aggregation-caused quenching reduces sensitivity and stability

Engineering Contradiction:
ImprovestabilityVSAvoidsensitivity
Core Design Contradiction:
ReliabilityVSMeasurement precision

Solution Approach 1:

The patent inverts the conventional fluorescent dye behavior by designing AIE-active molecules that are non-emissive in aqueous solutions but emit intensely when aggregated. This inversion resolves the contradiction by making the aggregated state (which causes quenching in conventional dyes) the emissive state, thereby simultaneously achieving high sensitivity and stability in biological applications

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The patent changes the photophysical parameters of the fluorescent molecules by developing AIE-active conjugated polyenes with specific molecular structures ( formulas I-IV) that exhibit aggregation-induced emission. This parameter change transforms the molecules from conventional ACQ-type fluorophores to AIE-type fluorophores, enabling them to maintain fluorescence in aggregated states and thus improving both sensitivity and stability

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If fluorescent dyes aggregate in aqueous environments, then they improve solubility, but aggregation-caused quenching reduces fluorescence intensity

Engineering Contradiction:
ImprovesolubilityVSAvoidfluorescence intensity
Core Design Contradiction:
Stability of the object's compositionVSIllumination intensity

Solution Approach 1:

The patent applies the inversion principle by designing molecules where aggregation leads to enhanced fluorescence rather than quenching. The AIE-active conjugated polyenes remain soluble in aqueous environments but exhibit intense fluorescence when aggregated, thus resolving the contradiction between solubility and fluorescence intensity

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The patent employs composite molecular structures combining hydrophilic groups (for solubility) with AIE-active conjugated polyene cores (for fluorescence). This composite design enables the molecules to maintain both water solubility and high fluorescence intensity in aggregated states, simultaneously satisfying both requirements

Inventive Principle:
Principle #40Composite materials

3Difficulty of detecting and measuring

If conventional fluorescent probes are used for bioprobes, then they provide detection capability, but self-quenching limits effectiveness in biological applications

Engineering Contradiction:
Improvedetection capabilityVSAvoideffectiveness
Core Design Contradiction:
Difficulty of detecting and measuringVSReliability

Solution Approach 1:

The patent inverts the detection mechanism by using AIE-active molecules that turn on fluorescence upon aggregation rather than remaining fluorescent in monomeric form. This inversion eliminates self-quenching issues and improves reliability of biological detection applications

Inventive Principle:
Principle #13The other way round (Inversion)

Solution Approach 2:

The patent converts the harmful aggregation-caused quenching effect into a beneficial detection mechanism. By designing AIE-active probes, the aggregation that previously caused quenching now serves as the trigger for fluorescence enhancement, thereby improving detection effectiveness in biological applications

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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

These AIE-active molecules provide sensitive and stable fluorescence, enabling efficient detection of biomacromolecules and G-quadruplex structures without self-quenching, improving sensitivity and stability in biological assays.

Implementation Method 1

water-soluble conjugated polyene compounds that exhibit aggregation induced emission, which remain non-emissive in aqueous solutions but emit intensely when aggregated

Methodology Applied
Scientific EffectAggregation-induced emission (AIE):

Implementation Method 2

Upon complexation with proteins and DNA, the fluorescence of the bioprobes can be enhanced/quenched and/or red/blue-shifted, thus enabling visual observation of the biomacromolecular species

Methodology Applied
Scientific EffectFluorescence enhancement: Fluorescence

Data Source

PatentUS8129111B2Fluorescent water-soluable conjugated polyene compounds that exhibit aggregation induced emission and methods of making and using same
Publication Date: 2012.03.06 THE HONG KONG UNIV OF SCI & TECH
  • US8129111B2 patent drawing
  • US8129111B2 patent drawing
  • US8129111B2 patent drawing

AI summary

The presently described subject matter is directed to water-soluble conjugated polyene compounds that exhibit aggregation induced emission, as well as to water dispersible, fluorescent, polymeric microparticles and/or nanoparticles comprising the water-soluble conjugated polyene compounds. Also provided are methods of making and using the compounds and particles. The described conjugated polyene compounds are useful as bioprobes for the detection biomacromolecules, as well as in the manufacture of sensors.