Polymers for Fluorescence Imaging of Formaldehyde in Living Systems via the Hantzsch Reaction.

Abstract

Formaldehyde (FA) has been detected via the Hantzsch reaction for many decades. However, the Hantzsch reaction has been rarely used to detect FA in biological systems due to the disadvantages of small-molecule probes (including toxicity and poor water solubility). In this study, polymeric fluorescent probes were developed to resolve these issues associated with small molecules, and FA in living systems was successfully detected via the Hantzsch reaction. These water-soluble polymers were easily scaled-up (∼25 g) by radical polymerization using commercial monomers. These polymers exhibited similar, albeit better, sensitivity to FA compared to water-soluble small molecules, primarily indicative of the advantages of polymers for the detection of FA via the Hantzsch reaction. The polymer structures were highly biocompatible with the probes; thus, these polymers can effectively detect endogenous FA in cells or zebrafish in a safe manner. This result confirmed the superiority of polymers in safety as biocompatible materials. This study highlights a straightforward method for exploring probes for the detection of FA in living systems. It offers functional polymers for bioimaging and extends the application scope of the Hantzsch reaction, reflecting the utility of a broad study of organic reactions in interdisciplinary fields as well as possible key implications in organic chemistry, analytical chemistry, and polymer chemistry.