Styryl Quinolinium Probes for Nucleoli Imaging

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Solution Overview

Problem

Current fluorescent dyes for selective nucleoli staining lack photochemical stability, ease of synthesis and purification, and rapid staining capabilities.

Innovation Solution

Development of a new family of styryl quinolinium compounds synthesized via an improved microwave-assisted process, which are used for selective nucleoli staining in both fixed and living cells.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorescent dyes are used for nucleoli staining, then staining capability is achieved, but photochemical stability is insufficient

Engineering Contradiction:
Improvephotochemical stabilityVSAvoidsynthesis and purification ease
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the chemical structure of fluorescent dyes by introducing specific substituents (e.g., hydroxyl, methoxy, fluorine, chlorine atoms) at defined positions on the styryl quinolinium core structure. These parameter changes in molecular composition enhance photochemical stability while maintaining staining capability through systematic structural optimization.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite fluorescent probe systems by combining styryl quinolinium core structures with various functional groups and substituents. This composite approach allows simultaneous optimization of photochemical stability, cellular uptake, and nucleoli binding properties through the synergistic effects of different molecular components.

Inventive Principle:
Principle #40Composite materials

2Speed

If rapid staining is achieved with current dyes, then imaging speed is improved, but photochemical stability deteriorates

Engineering Contradiction:
Improvestaining speedVSAvoidphotochemical stability
Core Design Contradiction:
SpeedVSReliability

Solution Approach 1:

The patent optimizes the balance between staining speed and photochemical stability by adjusting molecular parameters such as substituent types and positions. For example, introducing electron-donating or electron-withdrawing groups at specific positions modifies both the kinetics of nucleoli binding and the resistance to photodegradation, achieving simultaneous improvement in speed and stability.

Inventive Principle:
Principle #35Parameter changes

3Measurement precision

If selective nucleoli binding is achieved, then imaging specificity is improved, but synthesis complexity increases

Engineering Contradiction:
Improvestaining specificityVSAvoidsynthesis process complexity
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The patent divides the fluorescent dye molecule into distinct functional segments: a styryl quinolinium core responsible for fluorescence and a substituent module responsible for selective nucleoli binding. This segmentation allows independent optimization of each function and simplifies synthesis by enabling modular assembly of the molecular structure.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent achieves selective nucleoli binding through parameter changes in substituent positions and types (e.g., hydroxyl at position 4, methoxy at position 3, fluorine at positions 3 and 5) while maintaining a standardized synthetic route. This systematic parameter optimization enhances specificity without proportionally increasing synthesis complexity.

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 styryl quinolinium compounds demonstrate high photostability, rapid and specific binding to nucleoli, and are non-toxic to living cells, making them effective fluorescent probes for imaging rRNA.

Implementation Method 1

fluorescent probes for imaging, by rapid and selective stain of nucleoli in both fixed and living cells

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

improved microwave-assisted process

Methodology Applied
Scientific EffectMicrowave heating: Microwave Radiation

Data Source

PatentUS12202802B2Styryl quinolinium, process for their preparation and use thereof as fluorescent probes for imaging
Publication Date: 2025.01.21 BAR ILAN UNIV
  • US12202802B2 patent drawing
  • US12202802B2 patent drawing
  • US12202802B2 patent drawing

AI summary

The present invention is directed to styryl quinolinium compounds, a process for their synthesis and their use for selective nucleoli staining in cells, preferably in living cells and for imaging rRNA.