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

被引:238
作者
Brewer, Thomas F. [1 ]
Chang, Christopher J. [1 ,2 ,3 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Howard Hughes Med Inst, Berkeley, CA 94720 USA
关键词
HISTONE DEMETHYLATION; DNA METHYLATION; START SITES; URINE; BLOOD; CHROMATOGRAPHY; MECHANISM; HEADSPACE; MOLECULE; REVERSAL;
D O I
10.1021/jacs.5b05340
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 neuro-degenerative 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.
引用
收藏
页码:10886 / 10889
页数:4
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