An arylboronate-based fluorescent probe for selective and sensitive detection of peroxynitrite and its applications for fluorescence imaging in living cells

Zhang, Jian; Li, Yaping; Zhao, Jingjing; Guo, Wei

doi:10.1016/j.snb.2016.06.054

Cited by 50 publications

(12 citation statements)

References 55 publications

(26 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To date, a number of fluorescent probes have been developed for the selective detection of ONOO – , and a few of these probes with a mitochondria-targeting capability have been successfully applied for the sensing and imaging of ONOO – in mitochondria. − However, no fluorescent ONOO – probes are yet available for the real-time monitoring of ONOO – -induced mitophagy. To achieve the goal of mitochondrial ONOO – sensing and subsequent mitophagy monitoring, 2-methoxy-4-( N -methyl)aminophenol (AP) and triphenylphosphonium groups were integrated into 1,8-naphthalimide as an ONOO – receptor and mitochondria-targeting group, respectively.…”

Section: Resultsmentioning

confidence: 99%

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

et al. 2021

View full text Add to dashboard Cite

Visualizing and modulating the mitophagy process is essential for understanding the role of mitophagy in cellular homeostasis, physiology, and pathology. To overcome the sensing limitation of available mitophagy probes to only lysosome fusion or degradation, a molecular logic gate probe showing multiple fluorescence responses to different mitophagy stages was proposed in this study to sense the oxidative stress-induced mitophagy via a dual-channel mode. This new fluorescent molecular logic gate probe, Mito-PN, was composed by integrating a peroxynitrite-responsive 1,8-naphthalimide with an acidity-activatable rhodamine spirolactam and possesses the mitochondria-targeting capability due to its triphenylphosphonium group. This probe is able to sense both the mitophagy initiation triggered by peroxynitrite and lysosome fusion at different fluorescence wavelengths. It can be rapidly activated by mitochondrial peroxynitrite to turn on the green fluorescence of naphthalimide, and subsequent lysosome/mitophagosome fusion activates the probe with protons to generate red fluorescence. Moreover, our preliminary results demonstrate that the fluorescence response of Mito-PN to peroxynitrite-induced mitophagy can be discriminated from the mitophagy stimulated by carbonyl cyanide m-chlorophenyl hydrazone, which further proves the specific mitophagy tracking ability of Mito-PN. Overall, this research offers a potentially powerful tool for studying the role played by peroxynitrite in mitophagy and provides a versatile strategy for monitoring oxidative stress-related pathological processes.

show abstract

Section: Resultsmentioning

confidence: 99%

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

et al. 2021

View full text Add to dashboard Cite

show abstract

“…In this strategy, the boronic moiety is introduced indirectly via transformation of an aromatic hydroxyl group (phenol) into a good leaving group in a reaction with trifluoromethanesulfonic anhydride (Demicheli et al, 2016 ; Zhang J. et al, 2016 ) or N -phenyl-bis(trifluoromethanesulfonimide) (Albers et al, 2008 ; Srikun et al, 2010 ; Kim E. J. et al, 2014 ) in the presence of amines like DMAP (4-dimethylaminopyridine) (Demicheli et al, 2016 ), DIPEA (N,N-diisopropylethylamine) (Rios et al, 2016 ), or pyridine (Li et al, 2020 ) in anhydrous solvent under inert atmosphere at room temperature. Subsequently, the triflate derivative is substituted in a Pd(dppf)Cl 2 -assisted reaction with bis(pinacolato)diboron in the presence of potassium acetate, and refluxed under anaerobic conditions ( Scheme 3A ) (Miller et al, 2007 ; Albers et al, 2008 ; Srikun et al, 2010 ).…”

Section: Synthetic Approaches To Boronate-based Molecular Probesmentioning

confidence: 99%

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

et al. 2020

View full text Add to dashboard Cite

Boronate-based molecular probes are emerging as one of the most effective tools for detection and quantitation of peroxynitrite and hydroperoxides. This review discusses the chemical reactivity of boronate compounds in the context of their use for detection of biological oxidants, and presents examples of the practical use of those probes in selected chemical, enzymatic, and biological systems. The particular reactivity of boronates toward nucleophilic oxidants makes them a distinct class of probes for redox biology studies. We focus on the recent progress in the design and application of boronate-based probes in redox studies and perspectives for further developments.

show abstract

“… 1,2 It features a relatively higher reactivity and thus shorter lifetime in physiological and pathological processes. 3–5 Excessive ONOO − will cause critical damage to cellular biomolecules, such as tyrosine residues or proteins containing thiols, DNA, and unsaturated fatty-acid-containing lipids by oxidation or nitrification, leading to diseases including cancer, diabetes, Alzheimer's disease, Parkinson's disease, Huntington's disease, inflammatory diseases, etc. 6,7 Recent research 8–10 has revealed that ONOO − is also involved in cellular signal transduction as well as cell apoptosis.…”

Section: Introductionmentioning

confidence: 99%

An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO⁻ in living cells

Nie

Zhang

et al. 2018

RSC Adv.

View full text Add to dashboard Cite

Based on ESIPT, we designed and synthesized a naphthalimide chemosensor N-CBT for selectively visualizing endo/exogenous peroxynitrite (ONOO À ) in living cells. The incorporation of 2benzothiazoleacetonitrile offers N-CBT a rare pre-existing eight-membered ring hydrogen bonding configuration, which is able to generate two types of emission of naphthalimide. Confirmed by calculation results, fast proton transfer from the hydroxyl group to the carbonyl group occurs along with excited-state energy transfer via the intramolecular H-bond, leading to a tautomeric transformation from the excited enol form to the excited keto form. In aqueous solution, the formation of intermolecular hydrogen bonding with water perturbs ESIPT and destroys the stable planar construction. By breaking the cyano carbon-carbon double bond in the presence of ONOO À , green fluorescence can be regenerated efficiently. As a result, 34-fold fluorescence enhancement at 518 nm was observed in response, and it showed a good linear relationship in the range of 1 to 14 mM with a detection limit of 37 nM. Subsequently, N-CBT was applied in visualizing cellular ONOO À , and it demonstrated great potential in selectively visualizing endo/exogenous peroxynitrite (ONOO À ) in living cells.

show abstract

An arylboronate-based fluorescent probe for selective and sensitive detection of peroxynitrite and its applications for fluorescence imaging in living cells

Cited by 50 publications

References 55 publications

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO⁻ in living cells

Contact Info

Product

Resources

About

An arylboronate-based fluorescent probe for selective and sensitive detection of peroxynitrite and its applications for fluorescence imaging in living cells

Cited by 50 publications

References 55 publications

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

Activity-Based Fluorescent Molecular Logic Gate Probe for Dynamic Tracking of Mitophagy Induced by Oxidative Stress

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO− in living cells

Contact Info

Product

Resources

About

An ESIPT based naphthalimide chemosensor for visualizing endogenous ONOO⁻ in living cells