Ternary copper complexes and manganese (III) tetrakis(4-benzoic acid) porphyrin catalyze peroxynitrite-dependent nitration of aromatics

Chemical Research in Toxicology
G Ferrer-SuetaR Radi

Abstract

Peroxynitrite is a powerful oxidant formed in biological systems from the reaction of nitrogen monoxide and superoxide and is capable of nitrating phenols at neutral pH and ambient temperature. This peroxynitrite-mediated nitration is catalyzed by a number of Lewis acids, including CO2 and transition-metal ion complexes. Here we studied the effect of ternary copper-(II) complexes constituted by a 1,10-phenanthroline and an amino acid as ligands. All the complexes studied accelerate both the decomposition of peroxynitrite and its nitration of 4-hydroxyphenylacetic acid at pH > 7. The rate of these reactions depends on the copper complex concentration in a hyperbolic plus linear manner. The yield of nitrated products increases up to 2.6-fold with respect to proton-catalyzed nitration and has a dependency on the concentration of copper complexes which follows the same function as observed for the rate constants. The manganese porphyrin complex, Mn(III)tetrakis(4-benzoic acid)porphyrin [Mn(tbap)], also promoted peroxynitrite-mediated nitration with an even higher yield (4-fold increase) than the ternary copper complexes. At pH = 7.5 +/- 0.2 the catalytic behavior of the copper complexes can be linearly correlated with the pKa of th...Continue Reading

References

Nov 1, 1992·Chemical Research in Toxicology·W H KoppenolJ S Beckman
Jan 1, 1995·Free Radical Biology & Medicine·D BartlettW H Koppenol
Aug 12, 1993·Nature·J S BeckmanW H Koppenol
Mar 1, 1996·Chemical Research in Toxicology·B AlvarezR Radi

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Citations

Aug 8, 2009·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Ga Young ParkKenneth D Karlin
Jun 4, 2008·Pathology Oncology Research : POR·Carmen Mejia, Lena Ruiz-Azuara
Aug 6, 2000·Free Radical Biology & Medicine·J P Crow
Feb 22, 2001·Free Radical Biology & Medicine·R RadiA Cayota
Jun 12, 2003·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Leobardo ReyesLucía Macías
May 27, 2008·Antioxidants & Redox Signaling·Madia TrujilloRafael Radi
May 28, 2013·Antioxidants & Redox Signaling·Huaxin ShengDavid S Warner
Mar 27, 1999·FEBS Letters·G E ArteelH Sies
Oct 15, 2010·Free Radical Research·Laura CastroRafael Radi
Jan 16, 2007·Chemico-biological Interactions·Adolfo Rivero-MüllerMiloslav Dobrota
Aug 19, 2007·Basic & Clinical Pharmacology & Toxicology·Marco Leal-GarcíaHéctor Sumano
Jul 1, 2014·Redox Report : Communications in Free Radical Research·Nicolás CampoloRafael Radi
Aug 17, 2012·Communicative & Integrative Biology·Kazuma Murakami, Takahiko Shimizu
Nov 4, 2011·Journal of the American Chemical Society·Liang QiaoHubert H Girault
Nov 2, 2001·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·S PfeifferB Mayer
Apr 18, 2003·The Journal of Biological Chemistry·Gerardo Ferrer-SuetaRafael Radi
Jun 6, 2003·Biochemical Pharmacology·Alvaro Marín-HernándezRafael Moreno-Sánchez
Mar 10, 2009·ACS Chemical Biology·Gerardo Ferrer-Sueta, Rafael Radi
Feb 6, 2018·Chemical Reviews·Gerardo Ferrer-SuetaRafael Radi

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