Vinyl-Modified Silicon Rhodamine Dyes for Stable Targeted Labeling
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Solution Overview
Problem
Existing silicon-rhodamine (SiR) dyes face challenges in maintaining photophysical properties such as absorption and emission wavelengths, quantum yield, and photostability when modified to target specific biological components, leading to significant changes in their characteristics.
Innovation Solution
The introduction of a vinyl group attached to the Si atom in SiR dyes, allowing for derivatization through a thiol-ene reaction, results in functionalized or conjugated SiR dyes that maintain similar photophysical properties and improve specific binding affinity for biologically relevant targets.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If the xanthene moiety of SiR dye is modified to target specific biological components, then specific binding affinity is improved, but photophysical properties (absorption and emission wavelengths, quantum yield, and photostability) deteriorate
Solution Approach 1:
The patent applies local quality by introducing a vinyl group specifically at the silicon atom position (position 10) of the SiR dye core, while keeping the xanthene moiety unchanged. This localized modification enables derivatization at a specific site without affecting the photophysical properties determined by the xanthene core structure, thereby resolving the contradiction between improving binding affinity and maintaining photophysical stability
Solution Approach 2:
The patent segments the dye molecule into distinct functional regions: the SiR core (with vinyl group) maintains photophysical properties, while separate targeting moieties (attached via the vinyl group) provide specific binding affinity. This segmentation allows independent optimization of each function without compromising the other
2Adaptability or versatility
If SiR dye is functionalized to improve binding affinity for biological targets, then adaptability is improved, but photostability deteriorates
Solution Approach 1:
The vinyl group serves as an intermediary between the SiR core and targeting moieties. It provides a reactive handle for attaching various biological targets while acting as a buffer that isolates the photostable SiR core from potential destabilizing interactions with the attached moieties, thus maintaining photostability while enabling functionalization
3Adaptability or versatility
If modifications are made to SiR dye to target specific biological components, then versatility is improved, but absorption and emission wavelengths change significantly
Solution Approach 1:
The vinyl group is pre-installed at the silicon atom position during SiR core synthesis, before attachment of various targeting moieties. This preliminary action creates a standardized interface that ensures consistent photophysical properties across different conjugates, as the vinyl group's position and chemistry are fixed and do not vary with different targets
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 modified SiR dyes exhibit enhanced photostability and binding affinity, providing a versatile platform for targeted biological applications while retaining desirable fluorescence characteristics.
Implementation Method 1
The vinyl group can be derivatized, e.g., using a thiol-ene reaction, to provide functionalized or conjugated SiR dyes
Implementation Method 2
Silicon-rhodamine (SiR) dyes can provide bright fluorescence at far red wavelengths
Data Source
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AI summary
Silicon-substituted rhodamine compounds are disclosed herein. Also described herein are SiR dyes comprising at least one vinyl group attached to the Si atom (10 position) of the SiR dye. Derivatives, functionalized versions, conjugates, kits, related synthetic methods and uses of SiR compounds also are provided. Silicon-rhodamine (SiR) dyes can provide bright fluorescence at far red wavelengths and exhibit good photostability. The compounds described herein can be useful for fluorescent labeling and detection of biological samples.