title: An Aza-Cope Reactivity-Based Fluorescent Probe for Imaging Formaldehyde in Living Cells.
abstract: 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.
authors: Department of Chemistry, ‡Department of Molecular and Cell Biology, and §Howard Hughes Medical Institute, University of California, Berkeley , Berkeley, California 94720, United States.
authors: Thomas F
authors: TF
authors: Brewer
authors: Department of Chemistry, ‡Department of Molecular and Cell Biology, and §Howard Hughes Medical Institute, University of California, Berkeley , Berkeley, California 94720, United States.
authors: Christopher J
authors: CJ
authors: Chang
mesh_terms: D001372:Aza Compounds / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D002470:Cell Survival; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D005557:Formaldehyde / Q000032:analysis*; D057809:HEK293 Cells; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure
chemical_list: D001372:Aza Compounds; D005456:Fluorescent Dyes; D005557:Formaldehyde