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Quinone-derived π-extended phenazines as new fluorogenic probes for live-cell imaging of lipid droplets

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    Rights statement: Copyright © 2018 de Moliner, King, Dias, de Lima, de Simone, da Silva Júnior and Vendrell. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

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https://www.frontiersin.org/articles/10.3389/fchem.2018.00339/full
Original languageEnglish
JournalFrontiers in chemistry
DOIs
Publication statusPublished - 13 Aug 2018

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 behaviour 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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