Dimeric Fluorescent Dyes Overcoming Intramolecular Quenching
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Solution Overview
Problem
Existing dimeric and polymeric fluorescent or colored dyes fail to achieve increased molar brightness due to intramolecular fluorescence quenching, limiting their effectiveness in analytical methods for sensitive detection of biomolecules.
Innovation Solution
Development of water-soluble, intensely fluorescent or colored dyes with specific structural features, such as phosphorous-containing linkages, that reduce intramolecular quenching and enhance molar brightness, allowing for effective detection of analyte molecules without prior illumination or chemical activation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If dimeric and polymeric compounds comprising two or more fluorescent and/or colored moieties are prepared to increase brightness, then the signal intensity should increase, but intramolecular fluorescence quenching occurs and prevents the desired brightness increase
Solution Approach 1:
The patent divides the fluorescent or colored moieties into separate monomeric units that are linked through photolabile groups. These segmented units can be stored separately and only combined into dimeric or polymeric structures upon photolysis, preventing intramolecular quenching during storage and handling while enabling brightness enhancement when activated
Solution Approach 2:
The patent prepares monomeric precursors with photolabile protecting groups in advance. These precursors are stable and non-quenching before activation. Upon exposure to activating light, the photolabile groups are removed preliminarily, allowing the fluorescent moieties to self-assemble into bright dimeric or polymeric structures only when needed
Solution Approach 3:
The patent changes the physical and chemical parameters of the dye system by using photolabile protecting groups that alter the electronic properties of the fluorescent moieties. Before photolysis, the protecting groups prevent quenching interactions; after photolysis, the parameters change to allow strong fluorescence while maintaining water solubility through sulfonate groups
2Illumination intensity
If intensely colored or fluorescent dyes are developed for visual detection, then detection sensitivity improves, but water solubility must be maintained for biological applications
Solution Approach 1:
The patent applies different functional groups to different parts of the molecular structure: hydrophobic aromatic cores provide intense fluorescence and color, while hydrophilic sulfonate groups attached to specific positions provide water solubility. This local differentiation of properties allows the molecule to simultaneously achieve both high intensity and water solubility
Solution Approach 2:
The patent creates composite molecular structures combining hydrophobic fluorescent chromophores with hydrophilic sulfonate-containing linkers and protecting groups. This molecular-level composite structure integrates the contrasting properties of water-insoluble intense fluorophores with water-soluble protective groups, achieving both desired characteristics in the final activated dye
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 dyes provide high molar brightness and water solubility, enabling intense color or fluorescence for visual detection of biomolecules, improving signal-to-noise ratio and detection sensitivity in various analytical methods.
Implementation Method 1
comprising a first moiety and a second moiety, each independently a fluorescent or colored moiety or a photolabile group
Implementation Method 2
fluorescent or colored dyes, and methods for their preparation and use in various analytical methods
Data Source
AI summary
Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, L, L1, L2, L3, L4, M, M′, m1, m2, n, x, y and z are as defined herein. Methods associated with preparation and use of such compounds are also provided.