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Development of Photoactivated Fluorescent N-Hydroxyoxindoles and Their Application for Cell-Selective Imaging.
Jinping Lai1, An Yu1, Letao Yang1
1Department of Chemistry and Chemical Biology, Institute for Advanced Materials, Devices and Nanotechnology (IAMDN), Rutgers University, Piscataway, NJ, 08854, USA.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 24, 2016
Summary
Researchers developed novel photoactivatable fluorescent N-hydroxyoxindoles from o-nitrophenyl ethanol (ONPE) for enhanced biological imaging. These small, biocompatible probes offer superior photoactivation efficiency and fluorescence, overcoming limitations of conventional dyes.
Area of Science:
- Chemical Biology
- Molecular Imaging
- Organic Synthesis
Background:
- Photoactivatable fluorophores are crucial for high-resolution biological studies.
- Conventional fluorophores face limitations like low efficiency, cytotoxicity, and complex synthesis.
Purpose of the Study:
- To develop novel, efficient, and biocompatible photoactivatable fluorophores.
- To overcome the limitations of existing conventional dyes.
Main Methods:
- Synthesis of N-hydroxyoxindoles via intramolecular photocyclization of substituted o-nitrophenyl ethanol (ONPE).
- Evaluation of photoactivation efficiency, fluorescence enhancement, and biocompatibility.
- Structure-activity relationship analysis for property optimization.
- Proof-of-concept imaging in cancer (Hela) and neural stem cells (hNSCs).
Main Results:
- Achieved ultra-high fluorescence enhancement (up to 800-fold) with excellent photoactivation efficiency.
- Developed small-sized oxindole fluorophores with exceptional biocompatibility (water as the only byproduct).
- Established a structure-activity relationship guiding future probe development.
- Demonstrated selective cell imaging using a new ONPE probe (365-405 nm uncaging, 515/620 nm ex/em).
Conclusions:
- Novel ONPE-derived N-hydroxyoxindoles represent a promising class of photoactivatable fluorophores.
- These probes offer significant advantages in efficiency, size, and biocompatibility for biological imaging.
- The established structure-property correlations facilitate the rational design of advanced fluorescent probes.
