Quinone-Derived π-Extended Phenazines as New Fluorogenic Probes for Live-Cell Imaging of Lipid Droplets.

Frontiers in Chemistry
Fabio de MolinerMarc Vendrell

Abstract

We describe a new synthetic methodology for the preparation of fluorescent π-extended phenazines from the naturally-occurring naphthoquinone lapachol. These novel structures represent the first fluorogenic probes based on the phenazine scaffold for imaging of lipid droplets in live cells. Systematic characterization and analysis of the compounds in vitro and in cells led to the identification of key structural features responsible for the fluorescent behavior of quinone-derived π-extended phenazines. Furthermore, live-cell imaging experiments identified one compound (P1) as a marker for intracellular lipid droplets with minimal background and enhanced performance over the lipophilic tracker Nile Red.

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Citations

Sep 21, 2018·Materials·Tkhe Kyong FamMayeul Collot
Jul 23, 2019·Bioorganic & Medicinal Chemistry·Zhiming ChengEufrânio N da Silva Júnior
Jun 26, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Gleiston G DiasEufrânio N da Silva Júnior
Jul 13, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Bingli LuWeiying Lin

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Methods Mentioned

BETA
light microscopy
column chromatography
dynamic light scattering
X-ray
fluorescence microscopy
fluorescence imaging

Software Mentioned

WINGX
Enraf
HKL DENZO - SCALEPACK
ChemBioDraw Ultra
SHELXS
COLLECT
Bruker Data Analysis
ORTEP
- COLLECT
SHELXL

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