A Small Molecule Fluorogenic Probe for the Detection of Sphingosine in Living Cells

ABSTRACTThe single-chained sphingolipid sphingosine is an essential structural lipid and signaling molecule. Abnormal sphingosine metabolism is observed in several diseases, including cancer, diabetes, and Alzheimer’s. Despite its biological importance, there are a lack of tools for detecting sphingosine in living cells. This is likely due to the broader challenge of developing highly selective and live-cell compatible affinity probes for hydrophobic lipid species. In this work, we have developed a small molecule fluorescent turn-on probe for labeling sphingosine in living cells. This probe utilizes a selective reaction between sphingosine and salicylaldehyde esters to fluorescently label sphingosine molecules. We demonstrate that this probe exhibits a dose-dependent response to sphingosine and is able to detect endogenous pools of sphingosine. Using our probe, we successfully detected sphingosine accumulation in live Niemann-Pick type C1 (NPC1) patient cells, a lipid transport disorder in which increased sphingosine mediates disease progression. This work provides a simple and accessible method for the detection of sphingosine and should facilitate study of this critical signaling lipid in biology and disease.

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Recent advances in 1,8-naphthalimide-based small-molecule fluorescent probes for organelles imaging and tracking in living cells

Coordination Chemistry Reviews ◽

10.1016/j.ccr.2021.214019 ◽

2021 ◽

Vol 444 ◽

pp. 214019

Author(s):

Haitao Yu ◽

Yan Guo ◽

Wencheng Zhu ◽

Kaden Havener ◽

Xujun Zheng

Keyword(s):

Small Molecule ◽

Fluorescent Probes ◽

Living Cells ◽

Recent Advances

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Small-molecule FRET probes for protein kinase activity monitoring in living cells

Biochemical and Biophysical Research Communications ◽

10.1016/j.bbrc.2010.06.026 ◽

2010 ◽

Vol 397 (4) ◽

pp. 750-755 ◽

Cited By ~ 17

Author(s):

Angela Vaasa ◽

Marje Lust ◽

Anna Terrin ◽

Asko Uri ◽

Manuela Zaccolo

Keyword(s):

Protein Kinase ◽

Small Molecule ◽

Kinase Activity ◽

Living Cells ◽

Activity Monitoring ◽

Protein Kinase Activity

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Dynamic Imaging of Small Molecule Induced Protein–Protein Interactions in Living Cells with a Fluorophore Phase Transition Based Approach

Analytical Chemistry ◽

10.1021/acs.analchem.8b03476 ◽

2018 ◽

Vol 90 (24) ◽

pp. 14287-14293 ◽

Cited By ~ 7

Author(s):

Chan-I Chung ◽

Qiang Zhang ◽

Xiaokun Shu

Keyword(s):

Phase Transition ◽

Small Molecule ◽

Protein Interactions ◽

Living Cells ◽

Dynamic Imaging ◽

Protein Protein Interactions

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A novel lysosome-targeted fluorogenic probe based on 5-triazole-quinoline for the rapid detection of hydrogen sulfide in living cells

Organic & Biomolecular Chemistry ◽

10.1039/c7ob02881d ◽

2018 ◽

Vol 16 (5) ◽

pp. 712-716 ◽

Cited By ~ 15

Author(s):

Yandong Dou ◽

Xiaoxu Gu ◽

Shasha Ying ◽

Shen Zhu ◽

Shian Yu ◽

...

Keyword(s):

Hydrogen Sulfide ◽

Rapid Detection ◽

Living Cells ◽

The Novel ◽

Signaling Molecule ◽

Fluorogenic Probe

A fluorogenic probe based on the novel fluorophore 5-triazole-quinoline was developed for the detection of hydrogen sulfide, an endogenous signaling molecule associated with the development of various diseases.

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One-pot synthesis of a hydrogen peroxide-selective fluorogenic probe and its application in Parkinson's disease in vitro and vivo models

Materials Advances ◽

10.1039/d0ma00318b ◽

2020 ◽

Vol 1 (5) ◽

pp. 1448-1454 ◽

Cited By ~ 1

Author(s):

Yao Lu ◽

Bo Peng ◽

Xinghan Qiu ◽

Xin Li ◽

Zheng Li ◽

...

Keyword(s):

Parkinson’S Disease ◽

Hydrogen Peroxide ◽

Parkinson's Disease ◽

Multicomponent Reaction ◽

Living Cells ◽

Phosphate Ester ◽

One Pot ◽

Fluorogenic Probe ◽

Abnormal Level

An abnormal level of hydrogen peroxide in neurons is strongly implicated in the progression of Parkinson’s disease. A one-pot multicomponent reaction has been utilized to synthesise phosphate ester-based probe for imaging of H2O2 in living cells and Drosophila PD model.

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