ESIPT-based fluorescence probe for the ratiometric detection of superoxide

Wu, Linjing; Liu, Liyuan; Han, Hai; Xue, Tian; Odyniec, Maria L.; Feng, Lei; Sedgwick, Adam; He, Xiao; Bull, Steven D.; James, Tony D.

doi:10.1039/c8nj05656k

Cited by 31 publications

(14 citation statements)

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“…Hemicyanine-based fluorophore LW−OH was first prepared by retro-Knoevenagel reaction 35 followed by addition of a O 2 •− -reactive trifluoromethanesulfonate unit (triflate, OTf) to afford LW-OTf (for further discussion of the OTf counteranion see the ESI). 36,37 In the presence of O 2 •− triflate deprotection occurs, which leads to an increased NIRF signal by generation of fluorophore LW−OH. Subsequent reaction with ONOO − results in oxidative cleavage of the alkene linker of LW−OH to generate xanthene derivative LW-XTD, [38][39][40] capable of two-photon fluorescence (see ESI for further discussion hemicyanine-xanthene fluorescent turn-on mechanism and selectivity).…”

Section: Introductionmentioning

confidence: 99%

Fluorescent probe for the imaging of superoxide and peroxynitrite during drug-induced liver injury

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Fluorescent probe for the imaging of superoxide and peroxynitrite during drug-induced liver injury

et al. 2021

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“… a Adapted with permission from ref . Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC. …”

Section: Fluorescent Probes For Ros/rnsmentioning

confidence: 99%

Reaction-Based Fluorescent Probes for the Detection and Imaging of Reactive Oxygen, Nitrogen, and Sulfur Species

et al. 2019

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Conspectus This Account describes a range of strategies for the development of fluorescent probes for detecting reactive oxygen species (ROS), reactive nitrogen species (RNS), and reactive (redox-active) sulfur species (RSS). Many ROS/RNS have been implicated in pathological processes such as Alzheimer’s disease, cancer, diabetes mellitus, cardiovascular disease, and aging, while many RSS play important roles in maintaining redox homeostasis, serving as antioxidants and acting as free radical scavengers. Fluorescence-based systems have emerged as one of the best ways to monitor the concentrations and locations of these often very short lived species. Because of the high levels of sensitivity and in particular their ability to be used for temporal and spatial sampling for in vivo imaging applications. As a direct result, there has been a huge surge in the development of fluorescent probes for sensitive and selective detection of ROS, RNS, and RSS within cellular environments. However, cellular environments are extremely complex, often with more than one species involved in a given biochemical process. As a result, there has been a rise in the development of dual-responsive fluorescent probes (AND-logic probes) that can monitor the presence of more than one species in a biological environment. Our aim with this Account is to introduce the fluorescent probes that we have developed for in vitro and in vivo measurement of ROS, RNS, and RSS. Fluorescence-based sensing mechanisms used in the construction of the probes include photoinduced electron transfer, intramolecular charge transfer, excited-state intramolecular proton transfer (ESIPT), and fluorescence resonance energy transfer. In particular, probes for hydrogen peroxide, hypochlorous acid, superoxide, peroxynitrite, glutathione, cysteine, homocysteine, and hydrogen sulfide are discussed. In addition, we describe the development of AND-logic-based systems capable of detecting two species, such as peroxynitrite and glutathione. One of the most interesting advances contained in this Account is our extension of indicator displacement assays (IDAs) to reaction-based indicator displacement assays (RIAs). In an IDA system, an indicator is allowed to bind reversibly to a receptor. Then a competitive analyte is introduced into the system, resulting in displacement of the indicator from the host, which in turn modulates the optical signal. With an RIA-based system, the indicator is cleaved from a preformed receptor–indicator complex rather than being displaced by the analyte. Nevertheless, without a doubt the most significant result contained in this Account is the use of an ESIPT-based probe for the simultaneous sensing of fibrous proteins/peptides AND environmental ROS/RNS.

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“…Furthermore, because of the negligible self-reabsorption, the ESIPT-based organic lasers often exhibit better optical stability than traditional ones. In addition, ESIPT materials have other properties such as dual emission, an ultrafast process, − , and sensitivity to the surrounding environment that facilitate their widespread applications, such as organic optoelectronic materials, ,,, molecular logic gates, ultrasensitive sensing, − fluorescence imaging, , radiation scintillators, UV absorbers, and fundamental photophysical dynamics studies …”

Section: Fundamentals Of Esipt Processmentioning

confidence: 99%

Organic Lasers Harnessing Excited State Intramolecular Proton Transfer Process

2020

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Excited state intramolecular proton transfer (ESIPT) molecules are considered to be natural born laser materials because of their intrinsic four-level system. Organic lasers based on ESIPT materials, especially recently developed micro/nanolasers, have been drawing great attention in the past few decades due to their unique photophysical properties, such as ultralow threshold and high-quality value, as well as near-infrared (NIR) and wavelength tunable emission. These photophysical properties facilitate their widespread applications in lasing communication, ultrasensitive sensing, biological imaging, data storage and on-chip optical circuits. In this Review, first, the ESIPT process is introduced concisely. Second, recent advances of ESIPT-based organic lasers in solution, film and crystal states are reviewed. Finally, the current challenges and future development of ESIPT-based organic lasers are presented.

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ESIPT-based fluorescence probe for the ratiometric detection of superoxide

Abstract: A simple ESIPT-based fluorescence probe (HMBT-LW) was developed for the detection of superoxide (O2˙−).

Cited by 31 publications

References 24 publications

Fluorescent probe for the imaging of superoxide and peroxynitrite during drug-induced liver injury

Fluorescent probe for the imaging of superoxide and peroxynitrite during drug-induced liver injury

Reaction-Based Fluorescent Probes for the Detection and Imaging of Reactive Oxygen, Nitrogen, and Sulfur Species

Organic Lasers Harnessing Excited State Intramolecular Proton Transfer Process

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