Fluorogenic Azide Compounds Near-Infrared Biomolecule Labeling
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Solution Overview
Problem
There is a need for near-infrared fluorogenic probes with emission maxima greater than 600 nm, as existing dyes employed in bioorthogonal chemistries have limitations in this range, particularly for labeling biomolecules in vitro or in vivo.
Innovation Solution
Development of fluorogenic azide compounds that form a covalent linkage with alkyne moieties of target biomolecules, utilizing a xanthene scaffold linked to an azido switch group, which undergoes photoinduced electron transfer to enhance fluorescence in the near-infrared range.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If existing dyes are employed in bioorthogonal chemistries, then labeling of biomolecules can be achieved, but emission maxima are limited below 600 nm
Solution Approach 1:
The patent modifies the chemical structure of fluorogenic probes by incorporating specific dye moieties (such as BODIPY, cyanine, and rhodamine derivatives) with extended conjugation systems, thereby changing the optical parameters to achieve emission wavelengths greater than 600 nm while maintaining bioorthogonal reactivity
Solution Approach 2:
The invention creates composite fluorogenic probes by combining reactive functional groups (azide, alkyne, tetrazine) with NIR-emitting dye structures, resulting in molecules that simultaneously exhibit bioorthogonal chemistry capabilities and near-infrared fluorescence properties
2Measurement precision
If fluorogenic probes are used for labeling biomolecules, then detection capability is improved, but extensive washing steps are required
Solution Approach 1:
The patent extracts the fluorogenic signal from the background by utilizing the unique spectral properties of NIR dyes, which emit in a wavelength range with minimal autofluorescence from biological samples, thereby enabling detection without extensive washing to remove background fluorescence
Solution Approach 2:
The reactive functional groups (azide, alkyne, tetrazine) act as intermediaries that form covalent bonds between the fluorogenic probe and the biomolecule, creating a stable linkage that eliminates the need for washing steps to remove unbound probe while maintaining high detection sensitivity
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
Enables effective labeling of biomolecules with enhanced fluorescence in the near-infrared range, facilitating advanced imaging and detection techniques without the need for extensive washing steps.
Implementation Method 1
utilizing a xanthene scaffold linked to an azido switch group, which undergoes photoinduced electron transfer to enhance fluorescence in the near-infrared range
Implementation Method 2
contacting the biomolecule with a fluorogenic azide compound, wherein the contacting results in covalent linkage of the compound with the alkyne moiety of the target biomolecule
Data Source
AI summary
The present disclosure provides fluorogenic azide compounds. Also provided are methods of using the subject compounds for labelling a target biomolecule that includes an alkyne. In some embodiments, the method includes contacting the biomolecule with a fluorogenic azide compound, wherein the contacting results in covalent linkage of the compound with the alkyne moiety of the target biomolecule.