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A Reductant-resistant And Metal-free Fluorescent Probe For Nitroxyl Applicable To Living Cells.

Kodai Kawai, N. Ieda, Kazuyuki Aizawa, T. Suzuki, N. Miyata, H. Nakagawa
Published 2013 · Chemistry, Medicine

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Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO) and has characteristic biological and pharmacological effects distinct from those of NO. However, studies of its biosynthesis and activities are restricted by the lack of versatile HNO detection methods applicable to living cells. Here, we report the first metal-free and reductant-resistant HNO imaging probe available for use in living cells, P-Rhod. It consists of a rhodol derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent rhodol derivative. P-Rhod showed high selectivity for HNO in the presence of various biologically relevant reductants, such as glutathione and ascorbate, in comparison with previous HNO probes. We show that P-Rhod can detect not only HNO enzymatically generated in the horseradish peroxidase-hydroxylamine system in vitro but also intracellular HNO release from Angeli's salt in living cells. These results suggest that P-Rhod is suitable for detection of HNO in living cells.
This paper references
G.G. Stokes (1890)
An unexpected Bis-ligation of S-nitrosothiols.
J. Zhang (2009)
Page 8 of 10 ACS Paragon Plus Environment Journal of the American Chemical Society 1 2 3 4 5 6 7 8
J. M. Fukuto (2013)
A comparison of the chemistry associated with the biological signaling and actions of nitroxyl (HNO) and nitric oxide (NO).
J. Fukuto (2013)
Exploration of the "traceless" reductive ligation of S-nitrosothiols.
J. Zhang (2009)
β-Galactosidase fluorescence probe with improved cellular accumulation based on a spirocyclized rhodol scaffold.
Mako Kamiya (2011)
Water-soluble triarylphosphines as biomarkers for protein S-nitrosation.
Erika Bechtold (2010)
Construction of a library of rhodol fluorophores for developing new fluorescent probes.
T. Peng (2010)
Fluorescent rhodol derivatives: versatile, photostable labels and tracers.
J. Whitaker (1992)
Cell surface engineering by a modified Staudinger reaction.
E. Saxon (2000)
Detection of nitroxyl (HNO) by a prefluorescent probe
Meredith R. Cline (2011)
ACS Paragon Plus Environment Journal of the American Chemical Society 1 2 3 4 5 6 7
J. C. Irvine (2008)
Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex.
Joel Rosenthal (2010)
Nitroxyl anion exerts redox-sensitive positive cardiac inotropy in vivo by calcitonin gene-related peptide signaling
N. Paolocci (2001)
Nitroxyl (HNO): the Cinderella of the nitric oxide story.
J. Irvine (2008)
Nitric oxide: physiology, pathophysiology, and pharmacology.
S. Moncada (1991)
HKGreen-3: a rhodol-based fluorescent probe for peroxynitrite.
T. Peng (2010)
Generation of nitroxyl by heme protein-mediated peroxidation of hydroxylamine but not N-hydroxy-L-arginine.
Sonia Donzelli (2008)
The physiological chemistry and biological activity of nitroxyl (HNO): the neglected, misunderstood, and enigmatic nitrogen oxide.
J. Fukuto (2005)
The mode of decomposition of Angeli's salt (Na2N2O3) and the effects thereon of oxygen, nitrite, superoxide dismutase, and glutathione.
S. Liochev (2003)
Physical and structural properties of [Cu(BOT1)Cl]Cl, a fluorescent imaging probe for HNO.
M. Royzen (2013)
Mechanisms of inhibition of aldehyde dehydrogenase by nitroxyl, the active metabolite of the alcohol deterrent agent cyanamide.
E. Demaster (1998)
Photocontrollable peroxynitrite generator based on N-methyl-N-nitrosoaminophenol for cellular application.
N. Ieda (2012)
Comparison of the NO and HNO donating properties of diazeniumdiolates: primary amine adducts release HNO in Vivo.
K. Miranda (2005)
Reactive nitrogen species in the chemical biology of inflammation.
P. Dedon (2004)
A biochemical rationale for the discrete behavior of nitroxyl and nitric oxide in the cardiovascular system
K. Miranda (2003)
Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex.
Y. Zhou (2011)
Reduced glutathione-resisting ¹⁹F NMR sensors for detecting HNO.
Narufumi Kitamura (2012)
Reductive phosphine-mediated ligation of nitroxyl (HNO).
J. Reisz (2009)
Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation.
J. Reisz (2011)

This paper is referenced by
Selective Conversion of P=O-Bridged Rhodamines into P=O-Rhodols: Solvatochromic Near-Infrared Fluorophores.
Marek Grzybowski (2017)
A FRET-based ratiometric two-photon fluorescent probe for dual-channel imaging of nitroxyl in living cells and tissues.
X. Zhu (2016)
Chapter 4 – Fluorescence Technique
F. Villamena (2017)
A highly sensitive and reductant-resistant fluorescent chemodosimeter for the rapid detection of nitroxyl
C. Liu (2015)
A FRET-based ratiometric fluorescent probe for nitroxyl detection in living cells.
Huatang Zhang (2015)
A Fast and Selective Near-Infrared Fluorescent Sensor for Multicolor Imaging of Biological Nitroxyl (HNO)
Alexandra T. Wrobel (2014)
A fluoran-based fluorescent probe via a strategy of blocking the intramolecular photoinduced electron transfer (PET) process
Kun Huang (2017)
Detection and quantification of nitric oxide–derived oxidants in biological systems
Matías N. Möller (2019)
A benzothiazole-rhodol based luminophor: ESIPT-induced AIE and an application for detecting Fe2+ ion.
J. Guan (2019)
Design and Synthesis of Near-infrared Fluorescent Probes for Imaging of Biological Nitroxyl
Y. Tan (2015)
Single probe giving different signals towards reactive oxygen species and nitroxyl
W. Li (2018)
A highly sensitive and rapidly responding fluorescent probe based on a rhodol fluorophore for imaging endogenous hypochlorite in living mice.
Y. Zhang (2018)
A Water-Soluble Copper(II) Complex for the Selective Fluorescence Detection of Nitric Oxide/Nitroxyl and Imaging in Living Cells.
Xiaolong Sun (2016)
Kinetic and mechanistic studies on the reaction of the vitamin B12 complex aquacobalamin with the HNO donor Angeli's salt: Angeli's salt and HNO react with aquacobalamin.
Harishchandra Subedi (2014)
Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum
X. Jin (2016)
Small Molecule Control of Protein Function through Staudinger Reduction
J. Luo (2016)
Phosphine-Based HNO Detection
Z. Miao (2017)
Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems.
Vivian S. Lin (2015)
Glutathione sulfinamide serves as a selective, endogenous biomarker for nitroxyl after exposure to therapeutic levels of donors.
Gail M Johnson (2014)
Rhodols - synthesis, photophysical properties and applications as fluorescent probes.
Yevgen M Poronik (2019)
Surfactant-modulated discriminative sensing of HNO and H 2 S with a Cu 2+ -complex-based fluorescent probe
Hai-juan Lv (2016)
A ratiometric fluorescent probe based on a Bodipy-Coumarin conjugate for sensing of nitroxyl in living cells
K. Zheng (2016)
Achieving Reversible Sensing of Nitroxyl by Tuning the Ligand Environment of Azamacrocyclic Copper(II) Complexes.
Sunghee Kim (2016)
A near-infrared fluorescent probe for imaging of nitroxyl in living cells.
Z. Liu (2020)
A reductive ligation based fluorescent probe for S-nitrosothiols.
Di Zhang (2014)
Proline-based Phosphoramidite Reagents for the Reductive Ligation of S-Nitrosothiols
Chung-Min Park (2016)
An isophorone-fused near-infrared fluorescent probe with a large Stokes shift for imaging endogenous nitroxyl in living cells and zebrafish.
Chao Wei (2019)
Recent progress in the development of fluorescent, luminescent and colorimetric probes for detection of reactive oxygen and nitrogen species.
Xiaoqiang Chen (2016)
Two-photon red-emissive fluorescent probe for imaging nitroxyl (HNO) in living cells and tissues.
Baoli Dong (2017)
A Super-Resolution Probe To Monitor HNO Levels in the Endoplasmic Reticulum of Cells.
F. Ali (2017)
Specific Reactions of RSNO/HSNO/HNO and Their Applications in the Design of Fluorescent Probes.
M. Xian (2020)
Phosphine based fluorescent probes for nitroxyl detection and their reactivity toward S-nitrosothiols
Zhengrui Miao (2016)
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