Water-soluble cationic boronate probe based on coumarin imidazolium scaffold: Synthesis, characterization, and application to cellular peroxynitrite detection

Grzelakowska, Aleksandra; Modrzejewska, Julia; Kolińska, Jolanta; Szala, Marcin; Zielonka, Monika; Dębowska, Karolina; Zakłos‐Szyda, Małgorzata; Sikora, Adam; Zielonka, Jacek

doi:10.1016/j.freeradbiomed.2021.12.260

Cited by 22 publications

(11 citation statements)

References 63 publications

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“…However, only the presence of ONOO − led to the formation of MpC‐H as a specific product for peroxynitrite. The appearance of the specific minor product ( MpC‐H ) did not occur in the presence of MPO/H 2 O 2 /NO 2 − , which is consistent with the previously reported data for the ortho ‐mito‐phenylboronic acid probe [40] and cationic boronate probe based on a coumarin–imidazolium scaffold [22]. Conversely, MPO in the presence of nitrite led to nitration of the primary MpC‐OH coumarin, formed in the oxidation of MpC‐BA by H 2 O 2, giving MpC‐OHNO 2 (Figure 4a,b).…”

Section: Resultssupporting

confidence: 91%

Pro‐fluorescent probe with morpholine moiety and its reactivity towards selected biological oxidants

Modrzejewska,

Grzelakowska,

Szala

et al. 2024

Luminescence

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Biologial oxidants participate in many processes in the human body. Their excessive production causes organelle damage, which may result in the accumulation of cytotoxic mediators and cell degradation and may manifest itself in various diseases. Peroxynitrite (ONOO−), hypochlorous acid (HOCl), hydrogen peroxide (H2O2), and peroxymonocarbonate (HOOCO2−) are important oxidants in biology, toxicology, and various pathologies. Derivatives of coumarin, containing an oxidant‐sensitive boronate group, have been recently developed for the fluorescent detection of inflammatory oxidants. Here, we report the synthesis and characterization of 4‐[2‐(morpholin‐4‐yl)‐2‐oxoethyl]‐2‐oxo‐2H‐chromen‐7‐yl boronic acid (MpC‐BA) as a fluorescent probe for the detection of oxidants, with better solubility in water, high stability and fast response time toward peroxynitrite and hypochlorous acid. The effectiveness of the MpC‐BA probe for the detection of peroxynitrite was measured by adding bolus ONOO− or using the co‐generating superoxide and nitrogen oxide system. MpC‐BA is oxidized by ONOO− to 7‐hydroxy‐4‐[2‐(morpholin‐4‐yl)‐2‐oxoethyl]‐2H‐chromen‐2‐one (MpC‐OH). However, peroxynitrite‐specific product (MpC‐H) is formed in the minor reaction pathway. MpC‐OH is also yielded in the reaction of MpC‐BA with HOCl, and the subsequent formation of a chlorinated MpC‐OH gives a specific product for HOCl (MpC‐OHCl). H2O2 slowly oxidizes MpC‐BA. However, the addition of NaHCO3 increased the MpC‐OH formation rate. We conclude that MpC‐BA is potentially an improved fluorescent probe detecting peroxynitrite and hypochlorite in biological settings. Complementation of the fluorescence measurements by HPLC‐based identification of chlorinated and reduced coumarin(s) will help identify the oxidants detected.

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Section: Resultssupporting

confidence: 91%

Pro‐fluorescent probe with morpholine moiety and its reactivity towards selected biological oxidants

Modrzejewska,

Grzelakowska,

Szala

et al. 2024

Luminescence

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“…5 was successfully applied in the fluorescent imaging of endogenous and exogenous ONOO - in living cells, zebrafish, and live tissues from a high-fat diet-induced obese mouse model. In 2022, Radosław et al synthesized probe 6 with mitochondrial targeting function by introducing imidazolium into probe 5 (Figure 4 ) 29 . Compared with 5 , the fluorescence emission peaks of 6 showed a certain degree of red shift ( F 450 nm / F 385 nm to F 481 nm / F 405 nm ).…”

Section: Small-molecule-based Fluorescent Probes For Detection Of Ono...mentioning

confidence: 99%

Recent advances in fluorescent probes of peroxynitrite: Structural, strategies and biological applications

Sun¹,

Cao²,

Lu³

et al. 2023

Theranostics

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Peroxynitrite (ONOO - ), owing to its high oxidative and nitrating stress, is associated with several physiological processes in addition to various pathological processes, including those related to neurodegenerative diseases and cancer. Detection of ONOO - at the cellular level is of great significance to understand its pathogenesis. To this end, a variety of fluorescent probes based on small molecules and nanoparticles (NPs) have been engineered and applied as excellent tools for imaging of ONOO - in cells as well as in their diverse biological applications. In this review, we highlight representative cases of fluorescent probes based on recognition mechanism and emphasize their response type (ratiometric, two-photon, long-wavelength/near-infrared, and targeting) in ONOO - detection in the last five years. We further discuss their design strategy, sensing mechanism, and application in bio-imaging and describe NP-based probes according to diverse nanoplatforms.

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“…It has been proposed, that the reaction between ONOO − and boronic acid leads to the formation of ONOO − adduct, followed by the heterolytic (major pathway) or homolytic (minor pathway) O-O bond cleavage, resulting in the formation of phenols (major pathway) and minor radical-derived products ( Sikora et al, 2011 ). It has been proposed, that the formation of the products of both major and minor pathways in a specific ratio can be used as a “peroxynitrite fingerprint” ( Sikora et al, 2011 ; Zielonka et al, 2015 ; Zielonka et al, 2016a ; Szala et al, 2020 ; Grzelakowska et al, 2021 ; Zielonka et al, 2021 ; Grzelakowska et al, 2022 ). This strategy has been applied to unambiguously determine the identity of the product of HNO reaction with O 2 ( Smulik et al, 2014 ).…”

Section: Hno Chemistrymentioning

confidence: 99%

The Chemistry of HNO: Mechanisms and Reaction Kinetics

et al. 2022

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Azanone (HNO, also known as nitroxyl) is the protonated form of the product of one-electron reduction of nitric oxide (•NO), and an elusive electrophilic reactive nitrogen species of increasing pharmacological significance. Over the past 20 years, the interest in the biological chemistry of HNO has increased significantly due to the numerous beneficial pharmacological effects of its donors. Increased availability of various HNO donors was accompanied by great progress in the understanding of HNO chemistry and chemical biology. This review is focused on the chemistry of HNO, with emphasis on reaction kinetics and mechanisms in aqueous solutions.

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Water-soluble cationic boronate probe based on coumarin imidazolium scaffold: Synthesis, characterization, and application to cellular peroxynitrite detection

Cited by 22 publications

References 63 publications

Pro‐fluorescent probe with morpholine moiety and its reactivity towards selected biological oxidants

Pro‐fluorescent probe with morpholine moiety and its reactivity towards selected biological oxidants

Recent advances in fluorescent probes of peroxynitrite: Structural, strategies and biological applications

The Chemistry of HNO: Mechanisms and Reaction Kinetics

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