CoChat
Sign Up
Cited by 78Redox biology and oxidative stressNitric Oxide and Endothelin EffectsNeutrophil, Myeloperoxidase and Oxidative Mechanisms

Mechanistic Studies of Peroxynitrite-Mediated Tyrosine Nitration in Membranes Using the Hydrophobic Probe N-t- BOC- l -tyrosine tert -Butyl Ester

Bartesaghi, Silvina, Valez, Valeria, Trujillo, Madia, Peluffo, Gonzalo, Romero, Natalia, Zhang, Hao, Kalyanaraman, Balaraman, Radi, Rafael·2006·Biochemistry
DOI 10.1021/bi060363x
Open this paper in CoChat — free account

Abstract

Most of the mechanistic studies of tyrosine nitration have been performed in aqueous solution. However, many protein tyrosine residues shown to be nitrated in vitro and in vivo are associated to nonpolar compartments. In this work, we have used the stable hydrophobic tyrosine analogue N-t-BOC-L-tyrosine tert-butyl ester (BTBE) incorporated into phosphatidylcholine (PC) liposomes to study physicochemical and biochemical factors that control peroxynitrite-dependent tyrosine nitration in phospholipid bilayers. Peroxynitrite leads to maximum 3-nitro-BTBE yields (3%) at pH 7.4. In addition, small amounts of 3,3'-di-BTBE were formed at pH 7.4 (0.02%) which increased over alkaline pH; at pH 6, a hydroxylated derivative of BTBE was identified by HPLC-MS analysis. BTBE nitration yields were similar in dilauroyl- and dimyristoyl-PC and were also significant in the polyunsaturated fatty acid-containing egg PC. *OH and *NO2 scavengers inhibited BTBE nitration. In contrast to tyrosine in the aqueous phase, the presence of CO2 decreased BTBE nitration, indicating that CO3*- cannot permeate to the compartment where BTBE is located. On the other hand, micromolar concentrations of hemin and Mn-tccp strongly enhanced BTBE nitration. Electron spin resonance (ESR) detection of the BTBE phenoxyl radical and kinetic modeling of the pH profiles of BTBE nitration and dimerization were in full agreement with a free radical mechanism of oxidation initiated by ONOOH homolysis in the immediacy of or even inside the bilayer and with a diffusion coefficient of BTBE phenoxyl radical 100 times less than for the aqueous phase tyrosyl radical. BTBE was successfully applied as a hydrophobic probe to study nitration mechanisms and will serve to study factors controlling protein and lipid nitration in biomembranes and lipoproteins.

Integrity signals

Registry

Crossref · 10.1021/bi060363x

Cites

15 of 15 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

  • Tyrosines for which the aromatic ring is closer to the surface of a protein, in which there is a neighboring negative charge, and those in hydrophobic regions are more likely to be nitrated.

    “Tyrosines for which the aromatic ring is closer to the surface of a protein, in which there is a neighboring negative charge, and those in hydrophobic regions are more likely to be nitrated (66, 877).”

    From Sources of Vascular Nitric Oxide and Reactive Oxygen Species and Their Regulation (2019) · cites this paper as [66]

Cites

Flagged first, then by citations

Cited by

Sorted by citations

Related

Authors
Bartesaghi, S., Valez, V., Trujillo, M., Peluffo, G., Romero, N., Zhang, H., Kalyanaraman, B., & Radi, R.
Affiliations
  • Universidad de la República de Uruguay (UY)
  • Departamento de Bioquímica and Center for Free Radical and Biomedical Research, Facultad de Medicina, Universidad de la República, Montevideo 11800, Uruguay, and Biophysics Research Institute and Free Radical Research Center, Medical College of Wisconsin, Milwaukee, Wisconsin 53226
ORCID
Venue
Biochemistry
Publisher
American Chemical Society (ACS)
Published
2006-05-13
Volume
45
Issue
22
Pages
6813-6825
ISSN
  • 0006-2960 (ISSN-L)
  • 1520-4995
DOI
10.1021/bi060363x
OpenAlex
W2076839694
Cited by
78
References
15
Citations by year
2026: 1 · 2025: 1 · 2023: 1 · 2022: 3 · 2021: 1 · 2020: 1 · 2019: 2 · 2018: 3 · 2017: 4 · 2016: 4 · 2015: 4 · 2014: 5 · 2013: 8 · 2012: 7
FWCI
2.45
Type
journal article
Language
en
Open access
closed
Locations
  • Biochemistry (publishedVersion)
  • PubMed (publishedVersion)
Funders
National Heart, Lung, and Blood Institute (R01HL063119)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
  • Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
  • Life Sciences › Immunology and Microbiology › Immunology › Neutrophil, Myeloperoxidase and Oxidative Mechanisms
Keywords
peroxynitrite, tyrosine nitration, hydrophobic probes, phosphatidylcholine liposomes, radical mechanism, phenoxyl radicals, pH dependence, hemin, dimyristoylphosphatidylcholine, egg phosphatidylcholine, dimerization, nitration kinetics, electron spin resonance
MeSH terms
Carbon Dioxide, Chromatography, High Pressure Liquid, Fatty Acids, Unsaturated, Lipid Bilayers, Liposomes, Membranes, Nitrogen, Oxidation-Reduction, Phosphatidylcholines, Spectrum Analysis, Tyrosine, Molecular Probes, Dimerization, Peroxynitrous Acid, Hydrophobic and Hydrophilic Interactions

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review