Formaldehyde (FA), a highly reactive carbonyl species, is widely known for its ability to cross-link proteins for tissue fixation. While exposure can occur through natural and anthropogenic sources, FA is also produced at high concentrations (100–400 µM) endogenously through a variety of enzymatic reactions and vital processes such as epigenetics and one-carbon metabolism. Elevated levels of FA may contribute to a number of disease states, including neurodegenerative, cardiovascular, and liver diseases. Commonly used detection methods for FA are sensitive, but lack spatial and temporal resolution. For improved detection methods suitable for live-cell imaging, a reaction-based trigger utilizing the 2-aza-Cope reaction was developed and conjugated to phenolic fluorophores. Upon reacting with FA, the trigger undergoes an E1cB elimination to release the free fluorophore allowing for a dose-dependent fluorescent turn-on for FA. The utility of the trigger allows for the creation of FA probes with a variety of excitation wavelengths for multi-analyte imaging, as well as subcellular organelle-targetable FA probes. These newly developed detection methods are being applied in cells to study upregulated or inhibited biological processes that may change FA concentration and contribute to disease progression.

Fluorescent probes for imaging formaldehyde in living cells

253rd National Meeting (2017)

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