Cyanine Labeling Compound With PEG Linker for High Quantum Yield

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Solution Overview

Problem

Cyanine dyes used for fluorescence labeling exhibit low binding properties to biological molecules, leading to insufficient fluorescence intensity, and self-association interactions result in decreased quantum yield.

Innovation Solution

A compound represented by General Formula (1) with specific structural features, including polymethine chains, PEG groups, and nitrogen-containing rings, which enhance binding to biological substances and suppress self-association, ensuring high fluorescence intensity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If cyanine dyes are used for fluorescence labeling, then fluorescence labeling can be performed, but self-association between dyes occurs and fluorescence quantum yield decreases

Engineering Contradiction:
Improvefluorescence intensityVSAvoidfluorescence quantum yield
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

A PEG-based linker acts as an intermediary between the cyanine dye and the biological molecule. This linker suppresses self-association of the cyanine dye while maintaining binding to the biological molecule, thereby preserving fluorescence quantum yield and enabling high fluorescence intensity labeling.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If cyanine dyes with PEG groups are used to suppress self-association, then fluorescence quantum yield improves, but binding property to biological molecules decreases

Engineering Contradiction:
Improvefluorescence quantum yieldVSAvoidbinding property
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The fluorescent labeling compound is segmented into distinct functional modules: a cyanine dye moiety for fluorescence emission, a PEG-based linker for suppressing self-association and providing flexibility, and a biological molecule-binding moiety for specific binding. This segmentation allows each module to optimize its specific function without compromising the others.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention creates a composite fluorescent labeling compound combining cyanine dye, PEG linker, and biological molecule-binding groups. This composite structure integrates the fluorescence properties of cyanine dye with the self-association suppression of PEG and the binding capability for biological molecules, achieving both high fluorescence quantum yield and strong binding property.

Inventive Principle:
Principle #40Composite materials

3Illumination intensity

If conventional cyanine dyes are used, then labeling can be achieved, but sufficient fluorescence intensity cannot be obtained due to low binding property

Engineering Contradiction:
Improvefluorescence intensityVSAvoidbinding property
Core Design Contradiction:
Illumination intensityVSStrength

Solution Approach 1:

The invention creates a composite fluorescent labeling compound combining cyanine dye, PEG linker, and biological molecule-binding groups. This composite structure integrates the fluorescence properties of cyanine dye with the self-association suppression of PEG and the binding capability for biological molecules, achieving both high fluorescence quantum yield and strong binding property.

Inventive Principle:
Principle #40Composite materials

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 compound achieves excellent fluorescence intensity and binding properties, particularly in near-infrared fluorescence labeling, improving sensitivity and reducing interference in multicolor Western blotting and bioimaging applications.

Implementation Method 1

a cyanine dye is known as a fluorescent dye that is used for fluorescence labeling

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

the absorption and emission waveforms of a plurality of dyes

Methodology Applied
Scientific EffectAbsorption (EM radiation): Absorption (EM radiation)

Data Source

PatentUS12559476B2Compound and labeled biological substance using the same
Publication Date: 2026.02.24 FUJIFILM CORP
  • US12559476B2 patent drawing
  • US12559476B2 patent drawing
  • US12559476B2 patent drawing

AI summary

A compound of Formula (1) and a labeled biological substance having the compound.Z1 and Z2 represent a specific 6-membered ring, and at least one of Z1 or Z2 is a benzene ring having a specific substituent at an ortho position with respect to a nitrogen atom to which L1 or L2 is bonded, or a specific nitrogen-containing 6-membered ring in which a ring-constituting atom located at the ortho position is a nitrogen atom. The compound has at least one structure represented by —(CH2—CH2—O)m—R21 on a heterocyclic ring, and has at least one substituent capable of being bonded to a carboxy group or a biological substance at a specific position, and in a case where at least one of Z1 or Z2 is the specific nitrogen-containing 6-membered ring, the specific substituents may be bonded to each other to form a ring.