A new quinoline based probe with large Stokes shift and high sensitivity for formaldehyde and its bioimaging applications

Abstract

As a common reactive metabolite in living organisms, abnormal levels of formaldehyde may cause diseases such as cancer and Alzheimer's disease. Therefore, it is important to develop a sensitive and efficient method to understand the role of formaldehyde in physiology and pathology. Herein, a new fluorescent probe 4-phenyl-2-(trifluoromethyl) quinolin-7-hydrazino (QH-FA) was prepared for the detection of formaldehyde in near-total aqueous media with hydrazine as the reaction site and quinoline derivatives as the fluorophore. After reacting with formaldehyde, the hydrazine group formed methylenehydrazine and the fluorescence was significantly enhanced (223-fold) with large Stokes shift of 140 nm. Furthermore, the response of QH-FA to formaldehyde could be finished with in only 10 min with good selectivity, and can distinguish formaldehyde from other aldehydes. More remarkably, the estimated limit of detection of QH-FA is 8.1 nM, which is superior to those of previously reported formaldehyde fluorescent probes. At the end, we detected formaldehyde in cells and zebrafish using QH-FA in a near-total aqueous system and obtained fluorescence images by confocal microscopy.