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Naphthalimide Scaffold Provides Versatile Platform for Selective Thiol Sensing and Protein Labeling
Pengcheng Zhou1, Juan Yao1, Guodong Hu1
1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.
ACS Chemical Biology
|January 28, 2016
Summary
Researchers developed a new fluorescent probe, 4-methylsulfonyl-N-n-butyl-1,8-naphthalimide (MSBN), for highly selective thiol detection. This probe enables sensitive imaging of thiols in live cells and protein thiol labeling for redox regulation studies.
Area of Science:
- Biochemistry
- Cell Biology
- Chemical Biology
Background:
- Cellular redox regulation relies on reversible thiol modifications.
- Accurate detection and labeling of thiols are crucial for studying these modifications.
Purpose of the Study:
- To discover and characterize a novel fluorogenic probe for selective thiol detection.
- To demonstrate the probe's utility in live-cell imaging and protein thiol modification analysis.
Main Methods:
- Synthesis of 4-methylsulfonyl-N-n-butyl-1,8-naphthalimide (MSBN) based on the 1,8-naphthalimide scaffold.
- Utilizing nucleophilic aromatic substitution for thiol-probe reaction, leading to fluorescence restoration.
- Developing a mass-tagged variant (MSBN-TPP) for discriminating redox states of proteins like thioredoxin.
Main Results:
- MSBN exhibits high selectivity for thiols, with a >100-fold fluorescence increase upon reaction.
- The probe successfully imaged thiols in live cells and labeled protein thiols with a turn-on signal.
- MSBN-TPP differentiated reduced and oxidized thioredoxin, highlighting its application in redox state analysis.
Conclusions:
- MSBN is a versatile and selective fluorogenic probe for thiol detection and imaging.
- The naphthalimide scaffold allows for facile probe development for thiol-based bioconjugation and modification studies.
- MSBN provides a valuable tool for investigating cellular redox regulation and protein thiol modifications.
