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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Photostable polymorphic organic cages for targeted live cell imaging.

Dana Al Kelabi¹, Avishek Dey¹, Lukman O Alimi¹

¹Smart Hybrid Materials (SHMs) Laboratory, Advanced Membranes and Porous Materials Center, King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Kingdom of Saudi Arabia niveen.khashab@kaust.edu.sa.

Chemical Science

|July 8, 2022

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A novel organic cage, OC1, offers improved cell permeability and photostability for live cell imaging. This self-assembled fluorophore selectively targets mitochondria, advancing fluorescent microscopy for single-molecule visualization.

Area of Science:

Biochemistry
Cell Biology
Materials Science

Background:

Fluorescent microscopy is crucial for studying cellular dynamics.
Current organic fluorophores have limitations like poor solubility and photostability.
Targeting specific organelles remains a challenge in live cell imaging.

Purpose of the Study:

To develop a novel organic fluorophore with enhanced properties for live cell imaging.
To investigate the structure-activity relationship of a tautomeric organic cage (OC1).
To demonstrate OC1's selective targeting of mitochondria.

Main Methods:

Synthesis and characterization of the tautomeric organic cage OC1.
Structure-activity relationship study focusing on keto-enol tautomerization.

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Live cell imaging experiments to assess cell permeability, photostability, and organelle targeting.

Main Results:

OC1 exhibits high cell permeability and photostability.
Keto-enol tautomerization is key to OC1's strong fluorescence via self-assembly.
OC1 passively diffuses into cells and selectively targets mitochondria without endosomal/lysosomal uptake.

Conclusions:

OC1 represents a significant advancement over traditional organic fluorophores.
Self-assembled, biocompatible fluorophores can passively target organelles for advanced imaging.
This approach enables single-molecule level visualization of cellular processes in live samples.