Fluorogenic Probe Using a Mislow–Evans Rearrangement for Real‐Time Imaging of Hydrogen Peroxide

Abstract

Hydrogen peroxide (H2O2) mediates the biology of wound healing, apoptosis, inflammation, etc. H2O2 has been fluorometrically imaged with protein‐ or small‐molecule‐based probes. However, only protein‐based probes have afforded temporal insights within seconds. Small‐molecule‐based electrophilic probes for H2O2 require many minutes for a sufficient response in biological systems. Here, we report a fluorogenic probe that selectively undergoes a [2,3]‐sigmatropic rearrangement (seleno‐Mislow‐Evans rearrangement) with H2O2, followed by acetal hydrolysis, to produce a green fluorescent molecule in seconds. Unlike other electrophilic probes, the current probe acts as a nucleophile. The fast kinetics enabled real‐time imaging of H2O2 produced in endothelial cells in 8 seconds (much earlier than previously shown) and H2O2 in a zebrafish wound healing model. This work may provide a platform for endogenous H2O2 detection in real time with chemical probes.

Spying on the Polarity Dynamics during Wound Healing of Zebrafish by Using Rationally Designed Carbon Dots

“…Several groups have reported reactive oxygen species (ROSs) to be critical signaling molecules for wound healing. [13,14,42,43] The PPh-CDs we prepared were shown to display not only low toxicity, NIR emission, a strong response www.advancedsciencenews.com www.advhealthmat.de to a slight change in polarity, and chemical stability, but also a lack of reactivity with ROSs. Hence, we set out to use these CDs to determine whether cell polarity is closely related to wound healing.…”

AIE-active organic resonance molecules for highly sensitive dynamic explosive detection

“…Conjugated organic molecules with unique optical and electronic properties play an important role in the development of high-performance organic optoelectronic devices, including organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and chemo/bio sensors. [1][2][3][4][5][6][7][8][9] Organic molecules possessing resonance effects, defined as organic resonance molecules, have attracted considerable attention owing to their spectacular optoelectronic properties and promising device performance, such as the dynamic charge redistribution for modulating the optoelectronic properties by resonance variation in response to the external environmental stimuli. [10][11][12][13] Recently, we presented a design strategy for resonance variation-based dynamic adaption to realize self-adaptive resonance variation for dynamic and selective tuning of organic materials.…”