Dissecting the Crosstalk between Bisulfite and Hypochlorous Acid in the Reaction-Based Fluorescence Detection with Dicyanovinyl-Based Probes

Abstract

Fluorescent probes bearing a reactive moiety of 1,1dicyanovinyl are known to detect several biological species including bisulfite and hypochlorous acid, which, however, possess a selectivity issue among those analytes. Structural modifications of the reactive group for optimal steric and electron effects based on theoretical calculations led us to address the selectivity issue, offering new reactive moieties that provide complete analyte selectivity, including that between bisulfite and hypochlorous acid, in cells as well as in solution.

Polarity-Driven Two-Photon Fluorescent Probe for Monitoring the Perturbation in Lipid Droplet Levels during Mitochondrial Dysfunction and Acute Pancreatitis

“…In the former case, the cationic to nonionic equilibria is driven by the polarity of the media, whereas in the latter case, the conversion is driven by exogenous/endogenous stimuli such as cysteine, SO 2 , esterase, and so forth. The reported probes are mostly hemicyanine dyes, where the electron-deficient vinyl bond is highly susceptible to intracellular nucleophiles and oxidants, such as GSH, HSO 3 – , H 2 S, Cys, HOCl, and so forth. , This raises a reliability concern on the data obtained with the known probes in long-term imaging conditions, which may facilitate nucleophilic reactions, causing signal alteration. The fluorescence property of hemicyanine-type donor–acceptor (D–A) dyes is also influenced by viscosity, which often results in signal crosstalk .…”

“…The reported probes for LD and mitochondria dual detection are mostly based on hemicyanine skeletons (Figure b). Such probes could be susceptible to intracellular biothiols and reactive oxygen species (ROS), , however, it is rarely investigated. This raises a reliability concern regarding the imaging data obtained with such probes.…”

Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO3– and HClO in Dried Foods and Living Cells

“…Fluorescence detection united with small-molecule probes is unceasingly promoted by thriving of fluorescence technology and dexterous molecular designing. − Nowadays, through the unremitting endeavors made by scientists, miscellaneous small-molecule probes based on coumarin, xanthene, flavonoid, hemicyanine, dicyanoisophorone, etc. have been created. − Promisingly, for deep biological applications, a series of fluorescent probes simultaneously reacting with RSS and ROS have also been put forward by researchers. − Nevertheless, seeking for admirable fluorescent probes with higher sensitivity, faster response time, and better brightness is always frustrated by tedious synthetic routes and hard purification processes. , Under such research background, it is desirable to tame easy-to-prepare fluorophores with compact structures and high performance. Concurrently, considering the above-mentioned pivotal functions of HSO 3 – and HClO, they have been tested by a series of small-molecule fluorescent probes owing to the designable reactive sites on the molecular skeletons. − However, fluorescence detection of HSO 3 – and HClO based on small molecules has been impeded by two points.…”