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Turn-on Coumarin Precursor: From Hydrazine Sensor to Covalent Inhibition and Fluorescence Detection of Rabbit Muscle
Sara Amer1, Uri Miles1, Michael Firer2,3
1Department of Chemical Sciences, Ariel University, 65 Ramat HaGolan Street, Ariel 4077625, Israel.
Molecules (Basel, Switzerland)
|May 25, 2024
Summary
New fluorescent sensors detect toxic hydrazine with high sensitivity. The pre-coumarin probes also react with primary amines and show potential for theranostic applications by targeting enzymes like ALDOA.
Area of Science:
- Chemical sensing
- Organic chemistry
- Biomedical applications
Background:
- Hydrazine is a toxic compound requiring sensitive detection methods.
- Previous work utilized pre-coumarin OFF-ON sensors for fluoride anions.
Purpose of the Study:
- Develop pre-coumarin sensors for hydrazine detection.
- Investigate sensor reactivity with primary amines.
- Explore theranostic potential of a coumarin precursor for enzyme targeting.
Main Methods:
- Adapting phenol protecting groups (propionate, levulinate, γ-bromobutanoate) to a pre-coumarin scaffold.
- Reacting probes with hydrazine and primary amines to observe fluorescence.
- Mechanistic studies including retro-Knoevenagel reaction analysis.
- Investigating the reaction of compound 3 with aldolase A (ALDOA) for theranostic purposes.
Main Results:
- Developed pre-coumarin probes for hydrazine detection with low micromolar limits of detection.
- Observed unexpected fluorescence from reactions with primary amines via phenol deprotection, cyclization, and coumarin formation.
- Compound 3 reacted with ALDOA, forming a fluorescent coumarin proportional to enzyme concentration, indicating theranostic potential.
Conclusions:
- The developed pre-coumarin sensors offer a sensitive method for hydrazine detection.
- The probes exhibit cross-reactivity with primary amines, leading to coumarin formation.
- Compound 3 demonstrates promise as a theranostic agent for enzyme-targeted fluorescence imaging and therapy.
