An Aza-Cope Reactivity-Based Fluorescent Probe for Imaging Formaldehyde in Living Cells

Formaldehyde (FA) is a reactive carbonyl species (RCS) produced in living systems that has been implicated in epigenetics as well as in the pathologies of various cancers, diabetes, and heart, liver, and neurodegenerative diseases. Traditional methods for biological FA detection rely on sample destr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-09, Vol.137 (34), p.10886-10889
Main Authors: Brewer, Thomas F, Chang, Christopher J
Format: Article
Language:English
Subjects:
Aza Compounds - analysis
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Cell Survival
Fluorescent Dyes - analysis
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Formaldehyde - analysis
HEK293 Cells
Humans
MCF-7 Cells
Molecular Structure
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Summary:Formaldehyde (FA) is a reactive carbonyl species (RCS) produced in living systems that has been implicated in epigenetics as well as in the pathologies of various cancers, diabetes, and heart, liver, and neurodegenerative diseases. Traditional methods for biological FA detection rely on sample destruction and/or extensive processing, resulting in a loss of spatiotemporal information. To help address this technological gap, we present the design, synthesis, and biological evaluation of a fluorescent probe for live-cell FA imaging that relies on a FA-induced aza-Cope rearrangement. Formaldehyde probe-1 (FAP-1) is capable of detecting physiologically relevant concentrations of FA in aqueous buffer and in live cells with high selectivity over potentially competing biological analytes. Moreover, FAP-1 can visualize endogenous FA produced by lysine-specific demethylase 1 in a breast cancer cell model, presaging the potential utility of this chemical approach to probe RCS biology.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b05340