Direct oxidation of boronates by peroxynitrite: mechanism and implications in fluorescence imaging of peroxynitrite. Free Radic Biol Med 2009 Nov 15;47(10):1401-7
Date
08/19/2009Pubmed ID
19686842Pubmed Central ID
PMC3375817DOI
10.1016/j.freeradbiomed.2009.08.006Scopus ID
2-s2.0-70350028730 (requires institutional sign-in at Scopus site) 289 CitationsAbstract
In this study, we show that boronates, a class of synthetic organic compounds, react rapidly and stoichiometrically with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives as major products. Using a stopped-flow kinetic technique, we measured the second-order rate constants for the reaction with ONOO(-), hypochlorous acid (HOCl), and hydrogen peroxide (H(2)O(2)) and found that ONOO(-) reacts with 4-acetylphenylboronic acid nearly a million times (k=1.6x10(6) M(-1) s(-1)) faster than does H(2)O(2) (k=2.2 M(-1) s(-1)) and over 200 times faster than does HOCl (k=6.2x10(3) M(-1) s(-1)). Nitric oxide and superoxide together, but not alone, oxidized boronates to the same phenolic products. Similar reaction profiles were obtained with other boronates. Results from this study may be helpful in developing a novel class of fluorescent probes for the detection and imaging of ONOO(-) formed in cellular and cell-free systems.
Author List
Sikora A, Zielonka J, Lopez M, Joseph J, Kalyanaraman BAuthors
Balaraman Kalyanaraman PhD Professor in the Biophysics department at Medical College of WisconsinJacek M. Zielonka PhD Assistant Professor in the Biophysics department at Medical College of Wisconsin
MESH terms used to index this publication - Major topics in bold
Boronic AcidsCarbon Dioxide
Fluorescence
Fluorescent Dyes
Glutathione
Hydrogen Peroxide
Kinetics
Oxidation-Reduction
Peroxynitrous Acid
Time Factors