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Hemicyanine-Based Highly Water-Soluble Probe for Extracellular Nitroreductase
Shaoli Jiang1, Le Xu1, Yihong Zhong2
1Institute of Advanced Synthesis, Institute of Chemical Biology and Functional Molecules, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211816, China.
Chembiochem : a European Journal of Chemical Biology
|June 7, 2024
Summary
A new sensor, HCyS-NO2, detects extracellular nitroreductase (NTR) activity. This fluorescent probe distinguishes bacterial NTR activity without entering cells, aiding in studying extracellular reduction processes.
Area of Science:
- Biochemistry
- Microbiology
- Chemical Biology
Background:
- Nitroreductase (NTR) is crucial for nitro compound metabolism.
- Existing probes struggle to differentiate extracellular from intracellular NTR.
- Developing selective extracellular probes is vital for understanding bacterial processes.
Purpose of the Study:
- To develop a novel fluorescent sensor for detecting extracellular nitroreductase (NTR).
- To create a probe capable of distinguishing extracellular NTR activity from intracellular activity.
- To provide a tool for investigating extracellular reduction processes in bacteria.
Main Methods:
- Synthesized HCyS-NO2, a hemicyanine-based sensor with nitro and sulfo groups.
- Utilized the nitro group as a reporter, quenched fluorescence via intramolecular electron transfer (IET).
- Observed fluorescence restoration upon NTR-mediated reduction of the nitro group.
Main Results:
- HCyS-NO2 fluorescence is restored upon reduction by extracellular NTR.
- Sulfo groups enhance hydrophilicity and impart negative charges, preventing bacterial cell entry.
- The sensor successfully detected extracellular NTR activity in both gram-negative and gram-positive bacteria.
Conclusions:
- HCyS-NO2 is an effective and selective probe for extracellular NTR.
- The sensor enables monitoring of extracellular reduction without intracellular diffusion.
- This tool advances the study of bacterial nitro-compound metabolism and related processes.

