A boronate-based ratiometric fluorescent probe for fast selective detection of peroxynitrite

Li, Qi; Zhou, Yang

doi:10.1016/j.tetlet.2017.12.004

Cited by 29 publications

(10 citation statements)

References 27 publications

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“…Experimental results showed that only H 2 O 2 induced a strong fluorescence enhancement, while other ROS generating agents, KO 2 , NaOCl, NaOtBu, ONOO – , TBHP, TBAB, TBAF, ascorbic acid, BSA, glutamic acid, proline, leucine, and tryptophan, showed insignificant changes (Figure B). In some cases, peroxynitrite (ONOO – ) reacts with the boronate ester group and transform to other fluorescent products. , But, some reports also show that ONOO – does not have much significant reaction with the boronate ester group. , Our derivative VBD also not significantly react with ONOO – . The tremendous selectivity of our probe toward H 2 O 2 is due to the H 2 O 2 specific boronate deprotection reaction.…”

Section: Resultsmentioning

confidence: 99%

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Vanillin Benzothiazole Derivative Reduces Cellular Reactive Oxygen Species and Detects Amyloid Fibrillar Aggregates in Alzheimer’s Disease Brain

Gharai

Khan

Mallesh

et al. 2023

ACS Chem. Neurosci.

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The misfolding of amyloid beta (Aβ) peptides into Aβ fibrillary aggregates is a major hallmark of Alzheimer's disease (AD), which responsible for the excess production of hydrogen peroxide (H 2 O 2 ), a prominent reactive oxygen species (ROS) from the molecular oxygen (O 2 ) by the reduction of the Aβ-Cu(I) complex. The excessive production of H 2 O 2 causes oxidative stress and inflammation in the AD brain. Here, we have designed and developed a dual functionalized molecule VBD by using π-conjugation (C�C) in the backbone structure. In the presence of H 2 O 2 , the VBD can turn into fluorescent probe VBD-1 by cleaving of the selective boronate ester group. The fluorescent probe VBD-1 can undergo intramolecular charge transfer transition (ICT) by a πconjugative system, and as a result, its emission increases from the yellow (532 nm) to red (590 nm) region. The fluorescence intensity of VBD-1 increases by 3.5-fold upon binding with Aβ fibrillary aggregates with a high affinity (K d = 143 ± 12 nM). Finally, the VBD reduces the cellular toxic H 2 O 2 as proven by the CCA assay and DCFDA assay and the binding affinity of VBD-1 was confirmed by using in vitro histological staining in 8-and 18-month-old triple transgenic AD (3xTg-AD) mice brain slices.

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Section: Resultsmentioning

confidence: 99%

“…In some cases, peroxynitrite (ONOO − ) reacts with the boronate ester group and transform to other fluorescent products. 58,59 But, some reports also show that ONOO − does not have much significant reaction with the boronate ester group. 60,61 Our derivative VBD also not significantly react with ONOO − .…”

Section: Uv−visible and Fluorescence Spectroscopymentioning

confidence: 99%

Vanillin Benzothiazole Derivative Reduces Cellular Reactive Oxygen Species and Detects Amyloid Fibrillar Aggregates in Alzheimer’s Disease Brain

Gharai

Khan

Mallesh

et al. 2023

ACS Chem. Neurosci.

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“…Yang et al designed and developed an ONOO À ratiometric fluorescent probe 1 (Figure 3) by combining a fluorophore (2-(2-hydroxy-3-methoxyphenyl)benzothiazole; HMBT) with an arylboronate moiety. [43] In PBS/ethanol buffer (6 : 4, v/v, pH 8.0), probe 1 has its largest emission peak at 405 nm. Upon reaction with ONOO À , the arylboronate moiety in this probe turned phenolic, generating a 483 nm emission band at the ketone…”

Section: Fluorescent Probes Based On Oxidation Of Benzeneboronic Acid...mentioning

confidence: 99%

“…Yang et al. designed and developed an ONOO − ratiometric fluorescent probe 1 (Figure 3) by combining a fluorophore (2‐(2‐hydroxy‐3‐methoxyphenyl)benzothiazole; HMBT) with an arylboronate moiety [43] . In PBS/ethanol buffer (6 : 4, v / v , pH 8.0), probe 1 has its largest emission peak at 405 nm.…”

Section: Ratiometric Fluorescent Probes For Onoo−mentioning

confidence: 99%

Recent Progress of Small‐Molecule Ratiometric Fluorescent Probes for Peroxynitrite in Biological Systems

Zhai

et al. 2022

Chemistry A European J

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Peroxynitrite (ONOO À ) as a major reactive oxygen species plays important roles in cellular signal transduction and homeostatic regulation. Precise detection of ONOO À in biological systems is vital for exploring its physiological and pathological function. Among numerous detection methods, fluorescence imaging technology using fluorescent probes offers some advantages, including simple operation, high sensitivity and selectivity, as well as real-time and nondestructive detection. In particular, ratiometric fluorescent probes, in which the built-in calibration of the two emission bands prevents interference from the biological environment, have been extensively employed to monitor the fluctuation of bioactive species. In this review, we will discuss smallmolecule ratiometric fluorescent probes for ONOO À in live cells or in vivo, which involves chemical structures, response mechanisms, and biological applications. Moreover, the challenges and future prospects of ONOO À -responsive ratiometric fluorescent probe are also proposed.

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“…The emission color red shifts from blue to green when the nal product of 4-hydroxy-1,8-naphthalimide is yielded. Compounds 20-22 are excited-state intramolecular proton transfer (ESIPT)-based uorescent probes for sensing H 2 O 2 and ONOO − [52][53][54]. After the quinone-form product is generated through oxidative hydrolysis of the arylboronate group, the ESIPT process turns on and the keto-form nal product is generated and exhibits a strong uorescent signal.…”

Section: Arylboronate-based Probesmentioning

confidence: 99%

Boronates as hydrogen peroxide–reactive warheads in the design of detection probes, prodrugs, and nanomedicines used in tumors and other diseases

Chen

Liang

et al. 2022

Drug Deliv. and Transl. Res.

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Hydrogen peroxide (H 2 O 2 ) has always been a topic of great interests attributed to its vital role in biological process. H 2 O 2 is known as a major reactive oxygen species (ROS) which involves in numerous physiological processes such as cell proliferation, signal transduction, differentiation, and even pathogenesis. A plenty of diseases development such as chronic disease, in ammatory disease, and organ dysfunction are found to be relevant to abnormality of H 2 O 2 production. Thus, imminent and feasible strategies to modulate and detect H 2 O 2 level in vitro and in vivo have gained great importance.To date, the boronate-based chemical structure probes have been widely used to address the problems from the above aspects because of the rearranged chemical bonding which can detect and quantify ROS including hydrogen peroxide (H 2 O 2 ) and peroxynitrite (ONOO − ). This present article discusses boronatebased probes based on the chemical structure difference as well as reactivities to H 2 O 2 and ONOO − . In this review, we also focus on the application of boronate-based probes in the eld of cell imaging, prodrugs nanoplatform, nanomedicines and electrochemical biosensors for disease diagnosis and treatment. In a nutshell, we outline the recent application of boronate-based probes and represent the prospective potentiality in biomedical domain in the future.

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A boronate-based ratiometric fluorescent probe for fast selective detection of peroxynitrite

Cited by 29 publications

References 27 publications

Vanillin Benzothiazole Derivative Reduces Cellular Reactive Oxygen Species and Detects Amyloid Fibrillar Aggregates in Alzheimer’s Disease Brain

Vanillin Benzothiazole Derivative Reduces Cellular Reactive Oxygen Species and Detects Amyloid Fibrillar Aggregates in Alzheimer’s Disease Brain

Recent Progress of Small‐Molecule Ratiometric Fluorescent Probes for Peroxynitrite in Biological Systems

Boronates as hydrogen peroxide–reactive warheads in the design of detection probes, prodrugs, and nanomedicines used in tumors and other diseases

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