Issue 24, 2022

Photostable polymorphic organic cages for targeted live cell imaging

Abstract

Fluorescent microscopy is a powerful tool for studying the cellular dynamics of biological systems. Small-molecule organic fluorophores are the most commonly used for live cell imaging; however, they often suffer from low solubility, limited photostability and variable targetability. Herein, we demonstrate that a tautomeric organic cage, OC1, has high cell permeability, photostability and selectivity towards the mitochondria. We further performed a structure–activity study to investigate the role of the keto–enol tautomerization, which affords strong and consistent fluorescence in dilute solutions through supramolecular self-assembly. Significantly, OC1 can passively diffuse through the cell membrane directly targeting the mitochondria without going through the endosomes or the lysosomes. We envisage that designing highly stable and biocompatible self-assembled fluorophores that can passively diffuse through the cell membrane while selectively targeting specific organelles will push the boundaries of fluorescent microscopy to visualize intricate cellular processes at the single molecule level in live samples.

Graphical abstract: Photostable polymorphic organic cages for targeted live cell imaging

Supplementary files

Article information

Article type
Edge Article
Submitted
10 feb 2022
Accepted
01 jun 2022
First published
01 jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 7341-7346

Photostable polymorphic organic cages for targeted live cell imaging

D. Al Kelabi, A. Dey, L. O. Alimi, H. Piwoński, S. Habuchi and N. M. Khashab, Chem. Sci., 2022, 13, 7341 DOI: 10.1039/D2SC00836J

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