A reversible fluorescent probe based on C=N isomerizationfor the selective detection of formaldehyde in living cells and in vivo

Xinyu Song【宋新宇】^a,b, XiaoyueHan【韩潇玥】^b,d, Fabiao Yu】于法标^b,c*, Jinjin Zhang^a,c,Lingxin Chen【陈令新】^b,c* & Changjun Lv【吕长俊】^a,c*

Formaldehyde (FA) is an endogenously produced reactivecarbonyl species (RCS) through biological metabolic processes whoseconcentration is closely related to human health and disease. Noninvasive andreal-time detection of FA concentration in organisms is very important forrevealing the physiological and pathological functions of FA. Herein, we designand synthesize a reversible fluorescent probe BOD-NH₂ for thedetection of FA in living cells and invivo. The probe is composed of two moieties: the BODIPY fluorophore and theprimary amino group response unit. The probe can proceed intracellular aldiminecondensation reaction with FA and form imine (C=N) which will result in C=N isomerizationand rotation to turn-off thefluorescence of the probe. It is important that the probe can providereversible response to FA. The probe BOD-NH₂ has been successfullyapplied to detecting and imaging FA in cytoplasm of living cells. BOD-NH₂is capable to detect level fluctuations of endogenous and exogenous FA indifferent types of living cells. The probe can be used to visualize the FAconcentration in fresh hippocampus. And the probe can further qualitativelyevaluate the FA concentrations in ex vivo-dissected organs. Moreover, BOD-NH₂is also capable of imaging in mice. The above applications make our new probe apotential chemical tool for the study of physiological and pathologicalfunctions of FA in cells and in vivo.

The article was first published on 01 Dec 2017
Analyst, 2017, Accepted Manuscript
http://dx.doi.org/10.1039/C7AN01488K