Facile and Highly Selective Ratiometric Fluorescence Probe Based on Benzo[5]helicene for the Detection of Hypochlorous Acid

Abstract

In physiological processes, hypochlorous acid can regulate in vitro signaling molecules as one kind of reactive oxygen species (ROS). Serious diseases, such as cardiovascular disorders, neurodegenerative diseases, Alzheimer’s disease, and cancers are usually concerned with the abnormal levels of hypochlorous acid in human bodies. Herein, we report a new probe DPH-BP for HClO, which consists of a benzo[5]­helicene-pyridine fluorophore and benzyl-benzeneboronic acid pinacol ester as HClO reaction sites. The structural motifs combined with chromogenic media and fluorescence become a single-molecule sensor response in aqueous solutions. In the presence of HClO, this probe shows a remarkable blue shift of fluorescence from 536 to 452 nm in an aqueous solution and obvious fluorescence color change from yellow to blue. In the same conditions, almost no response can be recorded with the other common ROS/RNS, such as H2O2, TBHP, •OH, t-BuO•, ONOO–, and O2 •–. As we have designed, the oxidation of phenylboronic ester by HClO induces the cleavage of the benzyl in DPH-BP, which has been proven by 1H NMR spectra and density functional theory calculations. To the best of our knowledge, this is the first report of the analysis of HClO using the oxidation of benzyl-benzeneboronic acid pinacol ester.

Quinoline-based fluorescent probe for the detection and monitoring of hypochlorous acid in a rheumatoid arthritis model

“…5A inset), indicating the fast response of HQ to HOCl. [41][42][43][44][45][46][47] Effects of pH on HQ's emission and its uorescence response to HOCl were also investigated in the presence and absence of HOCl. As shown in Fig.…”

Phosphorescent and Test Strips Detection Properties of ClO− Probes Based on Iridium(III) Complexes with Pivaloyl Unit as Recognition Site

“…[5b,7] As one of reactive oxygen species (ROS), hypochlorous acid/hypochlorite (HClO/ClO À ) in organism is usually generated through enzyme-catalyzed oxidation reaction between chloride and hydrogen peroxide in activated phagocytes under the assistance of myeloperoxidase (MPO). [8,9] It is a double-edged sword for organisms, because it not only plays an important role in many biological processes as an important intracellular signaling molecule, [10] but also is associated with pathogenesis of various diseases, [11] so the hypochlorous acid. For instance, it is found that the abnormal accumulation of HClO can cause extensive oxidative stress [12] and oxidative damage in human neurodegenerative diseases and further induce a series of diseases including atherosclerosis, [13] rheumatoid rheumatism, [14] cancer, [15] reperfusion injury, [16] ischemia and so on.…”

“…In recent years, many new progress about the application of ROS in disinfection has also been reported [5b,7] . As one of reactive oxygen species (ROS), hypochlorous acid/hypochlorite (HClO/ClO − ) in organism is usually generated through enzyme‐catalyzed oxidation reaction between chloride and hydrogen peroxide in activated phagocytes under the assistance of myeloperoxidase (MPO) [8,9] . It is a double‐edged sword for organisms, because it not only plays an important role in many biological processes as an important intracellular signaling molecule, [10] but also is associated with pathogenesis of various diseases, [11] so the hypochlorous acid.…”

Pagoda[n]arenes (n = 4, 5): Extremely Strong Binders for the Tropylium Cation

“…There was no interaction between 2,6-dimethoxyanthracene and G because of almost no change in fluorescence. To quantitatively study the binding affinity, fluorescence titration experiments were performed to determine the association constants ( K a ) . Pagoda­[ n ]­arenes showed strong blue fluorescence, and the electron deficient tropylium could quench the fluorescence effectively.…”