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Rational Design of a Fluorogenic Probe for Sphingosine Based on Precisely Controlled Intramolecular Spirocyclization
Junjie Wang1, Nayan Zhang1, Rong Yun2
1Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, P. R. China.
Analytical Chemistry
|July 27, 2026
Summary
Researchers developed a new near-infrared fluorescent probe (CR-SE2) for sphingosine (Sph). This probe utilizes hydrophilicity-regulated ring-opening, enabling sensitive detection of Sph in biological samples and revealing links to aging.
Area of Science:
- Organic Chemistry
- Biochemistry
- Fluorescence Spectroscopy
Background:
- Coumarin-rhodamine (CR) derivatives exhibit near-infrared fluorescence (NIRF).
- Their intramolecular spirocyclization equilibrium is sensitive to substituent hydrophilicity/hydrophobicity.
- Hydrophobic substituents favor a closed, non-fluorescent state (OFF), while hydrophilic ones favor an open, fluorescent state (ON).
Purpose of the Study:
- To develop a novel design strategy for fluorogenic probes based on the CR scaffold.
- To create a sensitive and selective probe for sphingosine (Sph) detection.
- To investigate the correlation between Sph levels and aging in biological specimens.
Main Methods:
- Synthesis of coumarin-rhodamine (CR) derivatives.
- Design and synthesis of a sphingosine-specific fluorogenic probe (CR-SE2).
- Application of CR-SE2 to monitor Sph levels in senescent cells, mice, and tissue slices.
Main Results:
- The hydrophilicity of the 5'-substituent dictates the spirocyclization equilibrium of CR derivatives.
- CR-SE2 demonstrates a 'turn-on' NIR fluorescence response upon reaction with Sph, replacing its recognition moiety.
- CR-SE2 exhibits fast response, high sensitivity, and selectivity for Sph detection.
- Monitoring Sph levels in senescent cells and mice revealed a correlation between aging and Sph levels.
Conclusions:
- A generalizable strategy for developing hydrophilicity-regulated fluorogenic probes was established.
- The CR scaffold can be adapted to create probes for various biological and pathological processes.
- Sph levels are closely linked to aging, as evidenced by studies in biological specimens.
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