Detection and Quantification of Nitric Oxide-derived Oxidants in Biological Systems

Overview

Journal J Biol Chem

Specialty Biochemistry

Date 2019 Aug 15

PMID 31409645

Citations 57

Authors

Matias N Moller

Natalia Rios

Madia Trujillo

Rafael Radi

Ana Denicola

Beatriz Alvarez

Affiliations

Soon will be listed here.

Abstract

The free radical nitric oxide (NO) exerts biological effects through the direct and reversible interaction with specific targets ( soluble guanylate cyclase) or through the generation of secondary species, many of which can oxidize, nitrosate or nitrate biomolecules. The NO-derived reactive species are typically short-lived, and their preferential fates depend on kinetic and compartmentalization aspects. Their detection and quantification are technically challenging. In general, the strategies employed are based either on the detection of relatively stable end products or on the use of synthetic probes, and they are not always selective for a particular species. In this study, we describe the biologically relevant characteristics of the reactive species formed downstream from NO, and we discuss the approaches currently available for the analysis of NO, nitrogen dioxide (NO), dinitrogen trioxide (NO), nitroxyl (HNO), and peroxynitrite (ONOO/ONOOH), as well as peroxynitrite-derived hydroxyl (HO) and carbonate anion (CO) radicals. We also discuss the biological origins of and analytical tools for detecting nitrite (NO), nitrate (NO), nitrosyl-metal complexes, -nitrosothiols, and 3-nitrotyrosine. Moreover, we highlight state-of-the-art methods, alert readers to caveats of widely used techniques, and encourage retirement of approaches that have been supplanted by more reliable and selective tools for detecting and measuring NO-derived oxidants. We emphasize that the use of appropriate analytical methods needs to be strongly grounded in a chemical and biochemical understanding of the species and mechanistic pathways involved.

Citing Articles

Short-term Oral Nitrite Administration Decreases Arterial Stiffness in Both Trained and Sedentary Wistar Rats.

Souza T, Tardelli L, Nicoletti R, Jacomini A, Martins G, Pinheiro L Arq Bras Cardiol. 2024; 121(12):e20230783.

PMID: 39699451 PMC: 11634307. DOI: 10.36660/abc.20230783.

A systematic review and meta-analysis of nitric oxide-associated arginine metabolites in schizophrenia.

Zinellu A, Tommasi S, Carru C, Sotgia S, Mangoni A Transl Psychiatry. 2024; 14(1):439.

PMID: 39414767 PMC: 11484908. DOI: 10.1038/s41398-024-03157-7.

Induction and characterization of a rat model of endometriosis.

Chauhan J, Dubey P, Rai S, Tripathi A Sci Rep. 2024; 14(1):18827.

PMID: 39138257 PMC: 11322168. DOI: 10.1038/s41598-024-69440-1.

Reactive nitrogen species act as the enhancers of glutathione pool in embryonic axes of apple seeds subjected to accelerated ageing.

Marcin T, Katarzyna C, Urszula K Planta. 2024; 260(2):51.

PMID: 38995415 PMC: 11245430. DOI: 10.1007/s00425-024-04472-5.

The chemical biology of dinitrogen trioxide.

Moller M, Vitturi D Redox Biochem Chem. 2024; 8.

PMID: 38957295 PMC: 11218869. DOI: 10.1016/j.rbc.2024.100026.

References

Cassina A, Hodara R, Souza J, Thomson L, Castro L, Ischiropoulos H . Cytochrome c nitration by peroxynitrite. J Biol Chem. 2000; 275(28):21409-15. DOI: 10.1074/jbc.M909978199. View

Singh R, Hogg N, Mchaourab H, Kalyanaraman B . Physical and chemical interactions between nitric oxide and nitroxides. Biochim Biophys Acta. 1994; 1201(3):437-41. DOI: 10.1016/0304-4165(94)90073-6. View

Liochev S, Fridovich I . CO2, not HCO3-, facilitates oxidations by Cu,Zn superoxide dismutase plus H2O2. Proc Natl Acad Sci U S A. 2004; 101(3):743-4. PMC: 321751. DOI: 10.1073/pnas.0307635100. View

Akaike T, Yoshida M, Miyamoto Y, Sato K, Kohno M, Sasamoto K . Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/.NO through a radical reaction. Biochemistry. 1993; 32(3):827-32. DOI: 10.1021/bi00054a013. View

Bartesaghi S, Trujillo M, Denicola A, Folkes L, Wardman P, Radi R . Reactions of desferrioxamine with peroxynitrite-derived carbonate and nitrogen dioxide radicals. Free Radic Biol Med. 2004; 36(4):471-83. DOI: 10.1016/j.freeradbiomed.2003.10.011. View

Moller M, Denicola A . Acceleration of the autoxidation of nitric oxide by proteins. Nitric Oxide. 2019; 85:28-34. DOI: 10.1016/j.niox.2019.01.014. View

Kanski J, Schoneich C . Protein nitration in biological aging: proteomic and tandem mass spectrometric characterization of nitrated sites. Methods Enzymol. 2005; 396:160-71. DOI: 10.1016/S0076-6879(05)96016-3. View

Schopfer F, Cipollina C, Freeman B . Formation and signaling actions of electrophilic lipids. Chem Rev. 2011; 111(10):5997-6021. PMC: 3294277. DOI: 10.1021/cr200131e. View

Samouilov A, Zweier J . Development of chemiluminescence-based methods for specific quantitation of nitrosylated thiols. Anal Biochem. 1998; 258(2):322-30. DOI: 10.1006/abio.1998.2609. View

10.

Rosenthal J, Lippard S . Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex. J Am Chem Soc. 2010; 132(16):5536-7. PMC: 2866442. DOI: 10.1021/ja909148v. View

11.

Eich R, Li T, Lemon D, Doherty D, Curry S, Aitken J . Mechanism of NO-induced oxidation of myoglobin and hemoglobin. Biochemistry. 1996; 35(22):6976-83. DOI: 10.1021/bi960442g. View

12.

Pino N, Davis 3rd J, Yu Z, Chan J . NitroxylFluor: A Thiol-Based Fluorescent Probe for Live-Cell Imaging of Nitroxyl. J Am Chem Soc. 2017; 139(51):18476-18479. PMC: 7414788. DOI: 10.1021/jacs.7b11471. View

13.

Peng F, Li J, Guo T, Yang H, Li M, Sang S . Nitroproteins in Human Astrocytomas Discovered by Gel Electrophoresis and Tandem Mass Spectrometry. J Am Soc Mass Spectrom. 2015; 26(12):2062-76. DOI: 10.1007/s13361-015-1270-3. View

14.

Brito C, Naviliat M, Tiscornia A, Vuillier F, Gualco G, Dighiero G . Peroxynitrite inhibits T lymphocyte activation and proliferation by promoting impairment of tyrosine phosphorylation and peroxynitrite-driven apoptotic death. J Immunol. 1999; 162(6):3356-66. View

15.

Rios N, Piacenza L, Trujillo M, Martinez A, Demicheli V, Prolo C . Sensitive detection and estimation of cell-derived peroxynitrite fluxes using fluorescein-boronate. Free Radic Biol Med. 2016; 101:284-295. DOI: 10.1016/j.freeradbiomed.2016.08.033. View

16.

Zamojc K, Zdrowowicz M, Jacewicz D, Wyrzykowski D, Chmurzynski L . Fluorescent and Luminescent Probes for Monitoring Hydroxyl Radical under Biological Conditions. Crit Rev Anal Chem. 2015; 46(2):160-9. DOI: 10.1080/10408347.2015.1045118. View

17.

Viera L, Ye Y, Estevez A, Beckman J . Immunohistochemical methods to detect nitrotyrosine. Methods Enzymol. 1999; 301:373-81. DOI: 10.1016/s0076-6879(99)01101-5. View

18.

Samuni Y, Samuni U, Goldstein S . The use of cyclic nitroxide radicals as HNO scavengers. J Inorg Biochem. 2012; 118:155-61. DOI: 10.1016/j.jinorgbio.2012.10.002. View

19.

Alvarez M, Peluffo G, Folkes L, Wardman P, Radi R . Reaction of the carbonate radical with the spin-trap 5,5-dimethyl-1-pyrroline-N-oxide in chemical and cellular systems: pulse radiolysis, electron paramagnetic resonance, and kinetic-competition studies. Free Radic Biol Med. 2007; 43(11):1523-33. DOI: 10.1016/j.freeradbiomed.2007.08.002. View

20.

Forman H, Augusto O, Brigelius-Flohe R, Dennery P, Kalyanaraman B, Ischiropoulos H . Even free radicals should follow some rules: a guide to free radical research terminology and methodology. Free Radic Biol Med. 2014; 78:233-5. DOI: 10.1016/j.freeradbiomed.2014.10.504. View