Reactions of nitrogen dioxide in aqueous model systems: Oxidation of tyrosine units in peptides and proteins

Prütz, Walter A.; Mönig, H.; Butler, J. A. V.; Land, Edward J.

doi:10.1016/0003-9861(85)90780-5

Cited by 337 publications

(193 citation statements)

References 25 publications

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“…Some reports describe chemical nitration of histones (30)(31)(32), whereas others demonstrate that nuclear staining for nitrotyrosine by immunohistochemistry is often observed in tissues and in NO-exposed cell cultures (33)(34)(35). Recently, Haqqani et al (36) described that histones are the most prominent nitrated proteins in the Mutatect tumor tissue as well as in the cultured Mutatect cells that are exposed to NO.…”

Section: Discussionmentioning

confidence: 99%

Histone H1.2 is a substrate for denitrase, an activity that reduces nitrotyrosine immunoreactivity in proteins

Irie

Saeki

Kamisaki

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

124

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Several reports have described an activity that modifies nitrotyrosinecontaining proteins and their immunoreactivity to nitrotyrosine Abs. Without knowing the product of the reaction, this new activity has been called a ''denitrase.'' In those studies, some nonspecific proteins, which have multiple tyrosine residues, e.g., albumin, were used as a substrate. Therefore, the studies were based on an unknown mechanism of reaction and potentially a high background. To solve these problems, one of the most important things is to find a more suitable substrate for assay of the enzyme. We developed an assay strategy for determining the substrate for denitrase combining 2D-gel electrophoresis and an on-blot enzyme assay. The resulting substrate from RAW 264.7 cells was Histone H1.2, an isoform protein of linker histone. Histone H1.2 has only one tyrosine residue in the entire molecule, which ensures the exact position of the substrate to be involved. It has been reported that Histones are the most prominent nitrated proteins in cancer tissues. It was also demonstrated that tyrosine nitration of Histone H1 occurs in vivo. These findings lead us to the idea that Histone H1.2 might be an intrinsic substrate for denitrase. We nitrated recombinant and purified Histone H1.2 chemically and subjected it to an on-blot enzyme assay to characterize the activity. Denitrase activity behaved as an enzymatic activity because the reaction was time dependent and was destroyed by heat or trypsin treatment. The activity was shown to be specific for Histone H1.2, to differ from proteasome activity, and to require no additional cofactors.

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Section: Discussionmentioning

confidence: 99%

Histone H1.2 is a substrate for denitrase, an activity that reduces nitrotyrosine immunoreactivity in proteins

Irie

Saeki

Kamisaki

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

124

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“…, oxo-metal complexes, lipid peroxyl radicals (33), and ⅐ NO 2 ) promote protein tyrosine oxidation and nitration (41). The typical mechanism of tyrosine nitration in biological systems is a two-step radical process: a one-electron oxidant leading to the formation of a tyrosyl radical (Equation 10), which then combines at diffusion-controlled rates with ⅐ NO 2 to yield 3-nitrotyrosine (Equation 11) (42).…”

Section: Peroxynitrite-mediated Protein Tyrosine Nitrationmentioning

confidence: 99%

Peroxynitrite, a Stealthy Biological Oxidant

Radí

2013

Journal of Biological Chemistry

726

444

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Peroxynitrite is the product of the diffusion-controlled reaction of nitric oxide and superoxide radicals. Peroxynitrite, a reactive short-lived peroxide with a pK a of 6.8, is a good oxidant and nucleophile. It also yields secondary free radical intermediates such as nitrogen dioxide and carbonate radicals. Much of nitric oxide-and superoxide-dependent cytotoxicity resides on peroxynitrite, which affects mitochondrial function and triggers cell death via oxidation and nitration reactions. Peroxynitrite is an endogenous toxicant but is also a cytotoxic effector against invading pathogens. The biological chemistry of peroxynitrite is modulated by endogenous antioxidant mechanisms and neutralized by synthetic compounds with peroxynitrite-scavenging capacity.

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“…Primary biological aerosols, or bioaerosols, including proteins, from different sources and with distinct properties are known to influence atmospheric cloud microphysics and public health (Lang-Yona et al, 2016;D'Amato et al, 2007;Pummer et al, 2015). Bioaerosols represent a diverse subset of atmospheric particulate matter that is directly emitted in form of active or dead organisms, or fragments, like bacteria, fungal spores, pollens, viruses and plant debris.…”

Section: Introductionmentioning

confidence: 99%

Light-induced protein nitration and degradation with HONO emission

et al. 2017

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Abstract. Proteins can be nitrated by air pollutants (NO 2 ), enhancing their allergenic potential. This work provides insight into protein nitration and subsequent decomposition in the presence of solar radiation. We also investigated lightinduced formation of nitrous acid (HONO) from protein surfaces that were nitrated either online with instantaneous gas-phase exposure to NO 2 or offline by an efficient nitration agent (tetranitromethane, TNM). Bovine serum albumin (BSA) and ovalbumin (OVA) were used as model substances for proteins. Nitration degrees of about 1 % were derived applying NO 2 concentrations of 100 ppb under VIS/UV illuminated conditions, while simultaneous decomposition of (nitrated) proteins was also found during long-term (20 h) irradiation exposure. Measurements of gas exchange on TNMnitrated proteins revealed that HONO can be formed and released even without contribution of instantaneous heterogeneous NO 2 conversion. NO 2 exposure was found to increase HONO emissions substantially. In particular, a strong dependence of HONO emissions on light intensity, relative humidity, NO 2 concentrations and the applied coating thickness was found. The 20 h long-term studies revealed sustained HONO formation, even when concentrations of the intact (nitrated) proteins were too low to be detected after the gas exchange measurements. A reaction mechanism for the NO 2 conversion based on the Langmuir-Hinshelwood kinetics is proposed.

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Reactions of nitrogen dioxide in aqueous model systems: Oxidation of tyrosine units in peptides and proteins

Cited by 337 publications

References 25 publications

Histone H1.2 is a substrate for denitrase, an activity that reduces nitrotyrosine immunoreactivity in proteins

Histone H1.2 is a substrate for denitrase, an activity that reduces nitrotyrosine immunoreactivity in proteins

Peroxynitrite, a Stealthy Biological Oxidant

Light-induced protein nitration and degradation with HONO emission

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