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Two-photon uncaging with fluorescence reporting: evaluation of the o-hydroxycinnamic platform
Nathalie Gagey1, Pierre Neveu, Chouaha Benbrahim
1Ecole Normale Supérieure, Département de Chimie, UMR CNRS-ENS-Université Paris 6 8640 PASTEUR, 24 rue Lhomond, 75231 Paris Cedex 05, France.
Journal of the American Chemical Society
|July 31, 2007
Summary
This study introduces o-hydroxycinnamic caging groups for efficient fluorescence reporting. These novel compounds enable precise uncaging and quantitative substrate delivery with both one- and two-photon excitation, even in living organisms.
Area of Science:
- Organic Chemistry
- Photochemistry
- Biomedical Optics
Background:
- Designing effective caging groups is crucial for controlled release of molecules in biological systems.
- Fluorescence reporting upon uncaging offers a powerful tool for monitoring substrate delivery.
- Existing caging strategies often lack efficiency or versatility in excitation modes.
Purpose of the Study:
- To evaluate the o-hydroxycinnamic platform for developing efficient caging groups.
- To investigate the fluorescence reporting capabilities upon one- and two-photon excitation.
- To establish structure-property relationships for optimizing caging group design.
Main Methods:
- Synthesis of model o-hydroxycinnamate caging groups via one-step coupling.
- Photophysical characterization including one-photon absorption, fluorescence emission, and quantum yield determination.
- Measurement of uncaging cross-sections using two-photon excitation and fluorescence-based techniques.
- In vivo evaluation in zebrafish embryos to assess uncaging efficiency in a biological context.
Main Results:
- Model cinnamates are easily synthesized and exhibit tunable near-UV absorption.
- Quantitative substrate release and fluorescent coproduct generation were observed upon photolysis.
- One-photon uncaging quantum yields are in the 10% range.
- Two-photon uncaging cross-sections are in the 1-10 GM range at 750 nm, comparable to state-of-the-art caging groups.
- In vivo uncaging was confirmed in zebrafish embryos, demonstrating applicability in living systems.
Conclusions:
- The o-hydroxycinnamic platform is highly effective for designing versatile caging groups.
- These caging groups provide efficient fluorescence reporting for quantitative substrate delivery.
- The developed compounds show promise for diverse applications requiring one- and two-photon uncaging.
