Reaction‐Based and Single Fluorescent Emitter Decorated Ratiometric Nanoprobe to Detect Hydrogen Peroxide

Abstract

A novel reaction-based cross-linked polymeric nanoprobe with a self-calibrating ratiometric fluorescence readout to selectively detect H2O2 is reported. The polymeric nanoprobe is fabricated by using hydrophobic H2O2-reactive boronic ester groups, crosslinker units, and environmentally sensitive 3-hydroxyflavone fluorophores through a miniemulsion polymerization. On treatment with H2O2, the boronic esters in the polymer are cleaved to form hydrophilic alcohols and subsequently lead to a hydrophobic-hydrophilic transition. Covalently linked 3-hydroxyflavones manifest the change in polarity as a ratiometric transition from green to blue, accompanied by a 500-fold increase in volume. Furthermore, this nanoprobe has been used for ratiometric sensing of glucose by monitoring the H2O2 generated during the oxidation of glucose by glucose oxidase, and thus successfully distinguished between normal and pathological levels of glucose.

Tuning of hydrogen peroxide-responsive polymeric micelles of biodegradable triblock polycarbonates as a potential drug delivery platform with ratiometric fluorescence signaling

“…These features suggest that the nanoprobe has potential as a dual-function drug delivery nanocarrier with stimuli-responsive sensing and drug release. 46 However, the limited swelling of the crosslinked nanoparticles prevents efficient drug release from the expanding interstices of the nanoparticles, especially when larger molecules are used as therapeutic agents. It is also noted that the crosslinked nanoparticle formulation, although robust, is still restricted by the difficulty encountered when anchoring targeting ligands to the particle surface, inconvenient drug loading, and the lack of metabolic biodegradation pathways, which reduce its feasibility for further biomedical applications.…”

“…Covalently labeled 3-HF fluorophores are programmed to report the drug release event with a ratiometric green-to-blue fluorescence response, signaling the liberation of buried 3-HFs from the hydrophobic micellar core (prefer to undergo excited state intramolecular proton transfer (ESIPT) emission) to the fully hydrated medium (prefer to undergo excited-state intramolecular charge transfer (ESICT) emission). 46,51 The chemical composition of the ABA-type triblock amphiphilic polymers HP-3HF-Alk n PC and HP-3HF-ArPC is shown in Fig. 2.…”

Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy

“…The 9-membered macrocyclic polyamine 9 ([9]­aneN 3 ) was treated with (Boc) 2 O to give 23 , which was then reacted with 4-(bromomethyl)­phenylboronic acid 24a to afford 25a (Scheme ). After removing the Boc groups of 25a by treatment with trifluoroacetic acid (TFA) to give 12a as the 2TFA salt, the reaction of 12a with bicyclohexyl-1,1′-diol 26 gave 15a . The synthesis of the m -isomer 15b was carried out in a similar manner .…”

A Fluorogenic Molecule for Probing Islet Amyloid Using Flavonoid as a Scaffold Design

“…The ratio of the intensities of these two bands strongly depends on the polarity of the environment . Because of these unique features, 3-HF and its derivatives have been widely applied in studies of polymers, reverse micelles, and proteins. − Along these lines, flavonoid was considered as an ideal scaffold for the design of our fluorescent probes. In addition, the conjugated 4′-methoxybenzene motif of the stilbene derivative is another well-known molecular skeleton with high binding affinity for amyloid fibrils .…”

“…30 The ratio of the intensities of these two bands strongly depends on the polarity of the environment. 31 Because of these unique features, 3-HF and its derivatives have been widely applied in studies of polymers, 32 reverse micelles, 33 and proteins. 34−36 Along these lines, flavonoid was considered as an ideal scaffold for the design of our fluorescent probes.…”