A Design of Fluorescent Probes for Superoxide Based on a Nonredox Mechanism

Maeda, Hatsuo; Yamamoto, Keijiro; Nomura, Yoko; Kohno, Iho; Hafsi, Leila; Ueda, Nasuo; Yoshida, Shoko; Fukuda, Masako; Fukuyasu, Yuka; Yamauchi, Yuji; Itoh, Norio

doi:10.1021/ja047018k

Cited by 189 publications

(134 citation statements)

References 9 publications

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“…Other commonly used fluorescent dyes are based on rhodamine, ethidine and the phenoxazine backbones, well known examples include Amplex Red and Amplex Ultra Red which are based on phenoxazine (resourfin). Commonly used chemiluminescent based indicators include lucigenin as a specific detector for O 2¯• while luminol has mostly been used as an indicator for general ROS production.Based on redox active substituents in the benzene ring and using the nucleophilic character of some reactive species, the development of a new generation of dyes with potentially improved characteristics has been described [31][32][33][34][35][36][37][38][39][40].Because of the quite complex chemistry of all of these dyes, great care has to be taken in designing biological experiments and in their interpretation. For example, there is evidence that DCF may produce secondary radicals induced by its own oxidation [41].…”

Section: Dyesmentioning

confidence: 99%

Redox regulation of calcium ion channels: Chemical and physiological aspects

et al. 2011

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a b s t r a c tReactive oxygen species (ROS) are increasingly recognized as second messengers in many cellular processes. While high concentrations of oxidants damage proteins, lipids and DNA, ultimately resulting in cell death, selective and reversible oxidation of key residues in proteins is a physiological mechanism that can transiently alter their activity and function. Defects in ROS producing enzymes cause disturbed immune response and disease.Changes in the intracellular free Ca 2+ concentration are key triggers for diverse cellular functions. Ca 2+ homeostasis thus needs to be precisely tuned by channels, pumps, transporters and cellular buffering systems. Alterations of these key regulatory proteins by reversible or irreversible oxidation alter the physiological outcome following cell stimulation. It is therefore necessary to understand which proteins are regulated and if this regulation is relevant in a physiological-and/or pathophysiological context. Because ROS are inherently difficult to identify and to measure, we first review basic oxygen redox chemistry and methods of ROS detection with special emphasis on electron paramagnetic resonance (EPR) spectroscopy. We then focus on the present knowledge of redox regulation of Ca 2+ permeable ion channels such as voltage-gated (CaV) Ca 2+ channels, transient receptor potential (TRP) channels and Orai channels.© 2011 Elsevier Ltd. All rights reserved. Basic redox chemistry of oxygenMany chemical processes are linked to the exchange of electrons between two or more molecular entities. The transfer of one (or more) electron(s) is associated with oxidation (loss of electron) and reduction (gain of electron) of the components. Such reactions are also known as redox reactions. The processes of reactive oxygen species (ROS) formation and elimination are exclusively of redox nature.Molecular oxygen is the precursor of all ROS. It contains two unpaired electrons in separate (antibonding) orbitals in its outer electron sphere and is thus, by definition, a radical. Radicals have at least one unpaired electron in their orbital system and usually show high reactivity; transition metal ions also may have unpaired electrons, but are not called radicals. Although having radical character, molecular oxygen is chemically rather inert (luckily!), because high * Corresponding authors at: Institut für Biophysik, Gebäude 58, Universität des Saarlandes, D-66421 Homburg/Saar, Germany. Tel.: +49 6841 1626453; fax: +49 6841 1626060.E-mail addresses: ivan.bogeski@uks.eu (I. Bogeski), barbara.niemeyer@uks.eu (B.A. Niemeyer).

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Section: Dyesmentioning

confidence: 99%

Redox regulation of calcium ion channels: Chemical and physiological aspects

et al. 2011

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“…We have made initial progress in the development of small-molecule ratiometric probes [37] and reversible redox sensors [38]. Finally, although this review has focused specifically on NO and H 2 O 2 indicators, new fluorogenic reagents for peroxynitrite [39], hypochlorous acid [40], superoxide [41], highly reactive oxygen species [42], and global nitrative stress [43] have also been reported recently. The continuing interplay between chemical design and biological inquiry presages a rich future for studying the oxidation biology of the cell and its contributions to human health and disease.…”

Section: Small Molecule Fluorescent Probes For Hydrogen Peroxidementioning

confidence: 99%

Fluorescent probes for nitric oxide and hydrogen peroxide in cell signaling

Miller

Chang

2007

Current Opinion in Chemical Biology

161

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Nitric oxide (NO) and hydrogen peroxide (H 2 O 2 ) have emerged as essential small molecules for cellular signal transduction owing in large part to their ability to mediate oxidative posttranslational modifications (PTMs). Inventing new ways to track these small, diffusible, and reactive species with spatial and temporal resolution is a key challenge in elucidating their chemistry in living systems. Recent progress in the development of fluorescent probes that respond selectively to NO and H 2 O 2 produced at cell signaling levels offers a promising approach to interrogating their physiological production, accumulation, trafficking, and function.

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“…Furthermore, CL is an effective method in research on ROS, because of the associated instantaneous nature of CL and the short lifetime of ROS radicals (11)(12)(13)(14)(15)(16). Goto et al (17) successfully investigated the CL mechanism of the alkalineearth metal peroxides (MgO 2 , BaO 2 ) with CL reagents (luminol and lucigenin), and demonstrated that the hydroxyl ( • OH) and • O 2 − were released chiefly on the MgO 2 and BaO 2 , respectively, with CL.…”

Section: Ros As Hydrogen Peroxide (H 2 O 2 ) Superoxide Anion ( • Omentioning

confidence: 99%

Study on the generation mechanism of reactive oxygen species on calcium peroxide by chemiluminescence and UV‐visible spectra

Zhang

Zhao

et al. 2007

Luminescence

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In the present work, the generation mechanism of reactive oxygen species (ROS) on calcium peroxide (CaO 2 ) was studied. A very intense chemiluminescence (CL) signal was observed when adding an aqueous solution of luminol or 2-methyl-6-(4-methoxyphenyl)-3,7-dihydroimidazo[1,2α]-pyrazin-3-one hydrochloride (MCLA) to a suspension of CaO 2 . The ROS released on CaO 2 were thought to be oxidizing agents leading to CL, and were characterized by CL, UV-visible (UV-vis) spectra and the effective scavengers of the special ROS. ( 1 O 2 ) in the process. Obviously, the release of the ROS on CaO 2 is the main factor that contributed to the effect of CaO 2 , but the details have not been clarified and needed further research.Chemiluminescence (CL) is a powerful analytical technique that has excellent sensitivity, and a wide linear dynamic range and requires relatively simple and inexpensive instrumentation. Furthermore, CL is an effective method in research on ROS, because of the associated instantaneous nature of CL and the short lifetime of ROS radicals (11-16). Goto et al. (17) successfully investigated the CL mechanism of the alkalineearth metal peroxides (MgO 2 , BaO 2 ) with CL reagents (luminol and lucigenin), and demonstrated that the hydroxyl ( • OH) and • O 2 − were released chiefly on the MgO 2 and BaO 2 , respectively, with CL. According to our literature search, corresponding reports about CaO 2 have not so far been made.

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A Design of Fluorescent Probes for Superoxide Based on a Nonredox Mechanism

Cited by 189 publications

References 9 publications

Redox regulation of calcium ion channels: Chemical and physiological aspects

Redox regulation of calcium ion channels: Chemical and physiological aspects

Fluorescent probes for nitric oxide and hydrogen peroxide in cell signaling

Study on the generation mechanism of reactive oxygen species on calcium peroxide by chemiluminescence and UV‐visible spectra

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