A fluorescent redox sensor with tuneable oxidation potential

Kierat, Radoslaw M.; Thaler, B.; Krämer, Roland

doi:10.1016/j.bmcl.2009.03.171

Cited by 26 publications

(19 citation statements)

References 18 publications

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“…In contrast, quasi-reversible probes, while reacting with the oxidants irreversibly, produce products that can be reduced back to probes by cellular thiols or other nonenzymatic and/or enzymatic reductants [70, 82, 236, 237]. Many redox couples have been used for the design of such probes, including quinone-hydroquinone [238, 239], flavin-dihydroflavin [240], sulfhydryl-disulfide [241, 242], nitroxide-hydroxylamine [243, 244], selenium, and tellurium-based redox systems [245–248]. The fluorescent properties of such probes are affected by the redox state of the redox couple, which is controlled by both the rates of oxidation of the probe and of the reduction of the product.…”

Section: Probes Used For Cellular Oxidantsmentioning

confidence: 99%

Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Zielonka

Kalyanaraman

2018

Free Radical Biology and Medicine

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Reactive oxygen species (ROS) have been implicated in both pathogenic cellular damage events and physiological cellular redox signaling and regulation. To unravel the biological role of ROS, it is very important to be able to detect and identify the species involved. In this review, we introduce the reader to the methods of detection of ROS using luminescent (fluorescent, chemiluminescent, and bioluminescent) probes and discuss typical limitations of those probes. We review the most widely used probes, state-of-the-art assays, and the new, promising approaches for rigorous detection and identification of superoxide radical anion, hydrogen peroxide, and peroxynitrite. The combination of real-time monitoring of the dynamics of ROS in cells and the identification of the specific products formed from the probes will reveal the role of specific types of ROS in cellular function and dysfunction. Understanding the molecular mechanisms involving ROS may help with the development of new therapeutics for several diseases involving dysregulated cellular redox status.

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Section: Probes Used For Cellular Oxidantsmentioning

confidence: 99%

Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Zielonka

Kalyanaraman

2018

Free Radical Biology and Medicine

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“…In another design, rhodamine was linked to two different hydroquinones,t hus demonstrating the possibility of tuning the redox potential. [30] 1,4-Benzoquinone/rhodamine (Rh-Q) and 2-methoxy-1,4-benzoquinone/rhodamine (Rh-QOMe) probes undergo,r espectively,s ixfold and fourfold decreases in fluorescence upon oxidation by an excess of [Cu(phen) 2 ] 2+ (phen = 1,10-phenanthroline), and these changes were rapidly reversed by addition of cysteine.W hile they were efficiently internalized by HeLa cells,n oo xidation could be observed in cellulo even upon oxidative stimulation, probably because of the reduction of the probe by intracellular GSH. However,the authors speculate that this can be addressed by lowering the probes redox potential by varying the hydroquinone moiety.…”

Section: Methodsmentioning

confidence: 99%

“…Quinones RF-1 [29] n.a. 490/503 > 50-fold increase HEK 29 -H 2 O 2 Rh-Q, Rh-QOMe [30] n. [32] O 2 C À 491 (800) TP / 515…”

Section: Raw2647 Cells-h 2 O 2 E Po Kbr and Gstmentioning

confidence: 99%

Reversible Fluorescent Probes for Biological Redox States

2015

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The redox chemistry of the cell is key to its function and health, and the development of chemical tools to study redox biology is important. While fluxes in oxidative state are essential for healthy cell function, a chronically elevated oxidative capacity is linked to disease. It is therefore essential that probes of biological redox states distinguish between these two conditions by the reversible sensing of changes over time. In this review, we discuss the current progress towards such probes, and identify key directions for future research in this nascent field of vital biological interest.

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“…1) are a widely occurring structural component incorporated into numerous interesting molecules usually evaluated for biological purposes. Examples can be found in the field of fluorescent molecular probes [1][2][3][4][5][6][7][8][9] and bioactive compounds. [10][11][12][13][14][15][16][17] As shown in Figure 1, the synthetic strategy leading to unsymmetrical diacylated alkanediamines involves a mono acylated alkanediamine (B) as precursor.…”

Section: Introductionmentioning

confidence: 99%

Efficient monoacylation of symmetrical secondary alkanediamines and synthesis of unsymmetrical diacylated alkanediamines. A new L-proline-based organocatalyst

Moulat¹,

Martínez²,

Salom‐Roig³

2020

Arkivoc

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A simple procedure was developed for the monoacylation of several unprotected alkanediamines with carboxylic acids by using PyBOP-HOBt as coupling agent in the presence of DIEA at room temperature. Yields were moderate with primary alkanediamines and good to excellent with linear or cyclic secondary ones. To illustrate the utility of these monoacylated products, six unsymmetrical diacylated alkanediamines were synthesized. In addition, one of these compounds was evaluated as organocatalyst in an asymmetric aldol reaction.

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A fluorescent redox sensor with tuneable oxidation potential

Cited by 26 publications

References 18 publications

Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Reversible Fluorescent Probes for Biological Redox States

Efficient monoacylation of symmetrical secondary alkanediamines and synthesis of unsymmetrical diacylated alkanediamines. A new L-proline-based organocatalyst

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