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Chiral, J-Aggregate-Forming Dyes for Alternative Signal Modulation Mechanisms in Self-Immolative Enzyme-Activatable
Jagoda Sloniec-Myszk1, Ute Resch-Genger1, Andreas Hennig1,2
1BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, 12489 Berlin, Germany.
Abstract:
Enzyme-activatable optical probes are important for future advances in cancer imaging, but may easily suffer from low signal-to-background ratios unless not optimized. To address this shortcoming, numerous mechanisms to modulate the fluorescence signal have been explored. We report herein newly synthesized probes based on self-immolative linkers containing chiral J-aggregate-forming dyes. Signal modulation by formation of chiral J-aggregates is yet unexplored in optical enzyme probe design. The comprehensive characterization of the probes by absorption, CD, fluorescence, and time-resolved fluorescence spectroscopy revealed dye-dye interactions not observed for the free dyes in solution as well as dye-protein interactions with the enzyme. This suggested that J-aggregate formation is challenging to achieve with current probe design and that interactions of the dyes with the enzyme may interfere with achieving high signal-to-background ratios. The detailed understanding of the interactions provided herein provides valuable guidelines for the future design of similar probes.
Insights
Newly developed chiral J-aggregate probes for enzyme-activatable optical imaging show promise but face challenges. Dye interactions, not J-aggregate formation, impacted signal-to-background ratios, guiding future probe design.
Area of Science:
- Chemical Biology
- Biomedical Imaging
- Organic Chemistry
Background:
- Enzyme-activatable optical probes are crucial for cancer imaging.
- Low signal-to-background ratios limit current probe performance.
- Novel mechanisms are needed to optimize probe signal modulation.
Purpose of the Study:
- To synthesize and characterize novel optical probes utilizing self-immolative linkers and chiral J-aggregate-forming dyes.
- To explore the potential of chiral J-aggregate formation for signal modulation in enzyme probe design.
- To investigate dye-dye and dye-protein interactions influencing probe performance.
Main Methods:
- Synthesis of novel self-immolative probes incorporating chiral J-aggregate-forming dyes.
- Comprehensive characterization using absorption, circular dichroism (CD), fluorescence, and time-resolved fluorescence spectroscopy.
- Analysis of dye-dye and dye-protein interactions with the target enzyme.
Main Results:
- The synthesized probes exhibited dye-dye interactions not seen in free dyes.
- Dye-protein interactions with the enzyme were observed.
- Achieving J-aggregate formation proved challenging with the current probe design.
- Interactions interfered with optimal signal-to-background ratios.
Conclusions:
- Chiral J-aggregate formation is difficult to achieve in current enzyme probe designs.
- Dye-enzyme interactions significantly impact signal-to-background ratios.
- Understanding these interactions provides critical guidelines for future optical probe development.
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