Faculty Collaboration Database

Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution. Biochemistry 2001 Jun 26;40(25):7675-86

Date

06/20/2001

Pubmed ID

11412121

DOI

10.1021/bi002958c

Scopus ID

2-s2.0-0035954378 (requires institutional sign-in at Scopus site)   75 Citations

Abstract

It has been reported that peroxynitrite will initiate both oxidation and nitration of tyrosine, forming dityrosine and nitrotyrosine, respectively. We compared peroxynitrite-dependent oxidation and nitration of a hydrophobic tyrosine analogue in membranes and tyrosine in aqueous solution. Reactions were carried out in the presence of either bolus addition or slow infusion of peroxynitrite, and also using the simultaneous generation of superoxide and nitric oxide. Results indicate that the level of nitration of the hydrophobic tyrosyl probe located in a lipid bilayer was significantly greater than its level of oxidation to the corresponding dimer. During slow infusion of peroxynitrite, the level of nitration of the membrane-incorporated tyrosyl probe was greater than that of tyrosine in aqueous solution. Evidence for hydroxyl radical formation from decomposition of peroxynitrite in a dimethylformamide/water mixture was obtained by electron spin resonance spin trapping. Mechanisms for nitration of the tyrosyl probe in the membrane are discussed. We conclude that nitration but not oxidation of a tyrosyl probe by peroxynitrite is a predominant reaction in the membrane. Thus, the local environment of target tyrosine residues is an important factor governing its propensity to undergo nitration in the presence of peroxynitrite. This work provides a new perspective on selective nitration of membrane-incorporated tyrosine analogues.

Author List

Zhang H, Joseph J, Feix J, Hogg N, Kalyanaraman B

Authors

Jimmy B. Feix PhD Professor in the Biophysics department at Medical College of Wisconsin
Neil Hogg PhD Associate Dean, Professor in the Biophysics department at Medical College of Wisconsin
Balaraman Kalyanaraman PhD Professor in the Biophysics department at Medical College of Wisconsin

MESH terms used to index this publication - Major topics in bold

Bicarbonates
Cyclic N-Oxides
Free Radicals
Hydroxyl Radical
Lipid Bilayers
Liposomes
Mass Spectrometry
Membranes, Artificial
Molsidomine
Nitrates
Nitrosation
Oxidation-Reduction
Solutions
Solvents
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Spin Labels
Tyrosine
Water