Photostable polymorphic organic cages for targeted live cell imaging

Dana Al Kelabi, Avishek Dey, Lukman Olawale Alimi, Hubert Marek Piwonski, Satoshi Habuchi, Niveen M. Khashab

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish (US)
JournalChemical Science
DOIs
StatePublished - Jun 1 2022

ASJC Scopus subject areas

  • Chemistry(all)

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