Imaging of Formaldehyde in Live Cells and Daphnia magna via Aza-Cope Reaction Utilizing Fluorescence Probe With Large Stokes Shifts

Abstract

Formaldehyde (FA), a highly reactive carbonyl species, plays significant role in physiological and pathological functions. However, elevated FA will lead to cognitive impairments, memory loss and various neurodegenerative diseases due to its potent DNA and protein cross-linking mechanisms. In this work, a fluorescence probe, BD-CHO, based on benz-2-oxa-1, 3- diazole (BD) skeleton, was designed and synthesized for detection of FA via Aza-Cope reaction with high selectivity and large Stokes shifts (about 118 nm). BD-CHO was successfully applied to monitor the changes FA level in living cells, and kidney tissues of mice. Importantly it was the first time that BD-CHO was used for visualizing exogenous FA changes in Daphnia magna through fluorescence microscopy, demonstrating its potential application for studies of biological processes associated with FA.

Sensitized Lanthanide Photoluminescence Based Sensors–a Review

“…Upon reaction with formaldehyde, bipheny‐l,4‐carboxaldehyde was generated, which sensitized Tb 3+ in the cholate (TbCh) hydrogel, leading to the generation of green luminescence as shown in Scheme 6. The LOD of formaldehyde was about 100 n m , which is quite low compared to many other methods [45,46] . This protocol is not only highly sensitive but also selective towards the detection of formaldehyde among many other potentially interfering molecules such as acetaldehyde, acetone, alanine, serine, cysteine, glutathione, hydrogen peroxide and glucose ( Figure 5).…”

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

“…353,354 The use of the reagent as turn-on probe with a 100-fold enhancement of fluorescence within 2.5 h for 1 mM formaldehyde was reported (Figure 46). 354 The groups of Lin and Peng reported the synthesis of turnon probes PDB-FA 144a and BD-CHO 144b, based on NBD as a fluorophore, 355,356 in a three-step procedure from commercial 4-chlorobenzoxadiazole. The probes showed 55-fold (PDB-FA) and 255-fold enhancement (BD-CHO) upon exposure to excess formaldehyde after 2 h at pH 7.4.…”

Reaction-based fluorescent and chemiluminescent probes for formaldehyde detection and imaging

“…6). [50][51][52][53][54][55][56][57][58] These probes have been used to detect FA with high sensitivity and selectivity in various samples, such as air, aqueous sample, serum, real food and living cells.…”