Neutral Cyanine Label Compounds That Suppress Self-Association
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Solution Overview
Problem
Fluorescently labeled biological substances using cyanine dyes suffer from self-association, leading to decreased fluorescence quantum yield and intensity in various states such as solution, membrane, or dot blot.
Innovation Solution
A compound represented by General Formula (1) with specific structural features, including a polymethine chain with indoline and indolenine rings, ethyleneoxy groups, and a linking group that avoids aromatic hydrocarbon and charged groups, enhancing fluorescence intensity in these states.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If cyanine dyes are used for fluorescence labeling, then fluorescence labeling capability is achieved, but self-association occurs leading to decreased fluorescence quantum yield
Solution Approach 1:
The patent modifies the chemical structure of cyanine dyes by introducing macrocyclic constraints and specific substituent patterns (Formula 1 structure with indoline/indolenine rings and polymethine chains) to change the physical and chemical parameters of the dye molecules. This structural parameter change prevents self-association while maintaining fluorescence properties, thereby resolving the contradiction between fluorescence intensity and quantum yield stability.
2Reliability
If macrocyclic cyanine dyes are used to suppress self-association, then stability is improved, but fluorescence intensity remains insufficient in membrane and dot blot states
Solution Approach 1:
The patent applies local quality modification by introducing specific functional groups (ethyleneoxy groups, carboxy groups) at particular positions on the cyanine dye structure (Formula 1). These localized structural modifications enhance water solubility and prevent aggregation in different states (solution, membrane, dot blot) while maintaining high fluorescence intensity, thus resolving the contradiction between stability and fluorescence intensity across different applications.
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 in solutions, membranes, and dot blots, suppressing self-association and maintaining binding properties to biological substances, particularly suitable for near-infrared fluorescence detection.
Implementation Method 1
fluorescently labeled biological substances obtained by labeling a biological molecule with a fluorescent compound
Implementation Method 2
fluorescence detection by near-infrared light excitation
Data Source
AI summary
There are provided a compound of Formula (1) and a labeled biological substance having the compound.R1 to R6, R11 to R13, and R22 to R29 represent specific groups, and n is an integer of 1 to 3.One selected from R1, R2, R5, R22 to R25 and one selected from R3, R4, R6, and R26 to R29 are bonded through a linking group LL.The linking group LL represents a linking group having 1 to 100 atoms, which does not have any one of an aromatic hydrocarbon ring, a sulfo group, or a phosphono group.R1, . . . , R6, R22, . . . , or R29 includes a structure represented by —(CH2—CH2—O)m—, where m is 1 to 50.The above-described compound is a neutral compound and contains at least one substituent capable of being bonded to a carboxy group or a biological substance.