Journal
ANALYTICAL CHEMISTRY
Volume 93, Issue 34, Pages 11729-11735Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.analchem.1c01842
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Funding
- National Natural Science Foundation of China [52073163, 51773111, 21672130, 51273107, 51273175]
- Natural Science Foundation of Shandong Province, China [ZR2017ZC0227]
- Fundamental Research Funds of Shandong University [2017JC011, 2018JC030]
- Special Fund of Taishan Scholars Project of Shandong Province, China [tsqn201909012]
- Program of Qilu Young Scholars of Shandong University
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In this study, a reliable strategy based on pH-sensitive intramolecular spirocyclization was developed to design and synthesize a single fluorescent probe (SFP) CMHCH for targeting lipid droplets and lysosomes simultaneously and selectively, enabling real-time monitoring of lipophagy.
Lipid droplets (LDs) and lysosomes are crucial for maintaining intracellular homeostasis. But single fluorescent probes (SFPs) capable of simultaneous and discriminative visualizing of two organelles above and their interaction in living cells are still challenging due to the lack of rational design strategies. To break this bottleneck, herein, we develop a reliable strategy based on a pH-sensitive intramolecular spirocyclization. As a proof of concept, an SFP CMHCH, which possesses a switchable hemicyanine/spiro-oxazine moiety induced by pH, has been designed and synthesized. In acidic environments, the ring-open form CMHCH exhibits red-shift emission and low IogP value, whereas the ringclosed form CMHC displays blue-shift emission and high IogP value in neutral or basic environments. Thus, the distinct different hydrophilicity/hydrophobicity and absorption/emission properties of these two forms enable targeting LDs and lysosomes simultaneously and discriminatingly. Very importantly, the dynamic process of lipophagy can be directly monitored with CMHCH. The success of CMHCH indicated that the spirocyclization strategy is efficient for constructing SFPs to LDs and lysosomes.
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