The hydroxylation of the salicylate anion by a Fenton reaction and T-radiolysis: a consideration of the respective mechanisms

Free Radical Biology & Medicine
Z MaskosW H Koppenol

Abstract

The yield of 2,3- and 2,5-dihydroxybenzoates (dHB's) from the reaction of .OH radicals with salicylate (SA) ions has been measured as a function of pH and in the presence of oxidants. Under steady-state radiolysis conditions, the production of these products occurs via the reactions .OH + SA----HO-SA. (radical adduct) HO-SA. H+.OH+----2-carboxyphenoxyl radical (SA.) + H2O HO-SA. + SA.----2,3-/2,5-dHB + SA The addition of the oxidants O2, Fe3+ edta, or Fe(CN)63- increases the relative yield of 2,5-dHB/2,3-dHB from about 0.2 to 1. A model to account for this effect is presented. Steady-state radiolyses of 3- and 4-hydroxybenzoate give dihydroxybenzoate products consistent with the phenol group being an ortho-para director in the electrophilic attack of the hydroxyl radical on the aromatic ring. A comparison of product distributions from the reaction of ferrous edta with hydrogen peroxide using salicylate as a scavenger strongly suggests that the same hydroxyl radical adducts are formed as in the radiation experiments.

Citations

Sep 2, 1998·European Journal of Drug Metabolism and Pharmacokinetics·E SamN Verbeke
Dec 1, 1995·Toxicology Letters·C C Winterbourn
Jan 1, 1991·Free Radical Biology & Medicine·B HalliwellM Ingelman-Sundberg
Jan 1, 1991·Free Radical Biology & Medicine·Z Maskos, W H Koppenol
Jan 1, 1991·Free Radical Biology & Medicine·C C Winterbourn
Dec 1, 1992·Free Radical Biology & Medicine·A GhiselliA Ferro-Luzzi
Oct 1, 1993·Free Radical Biology & Medicine·S GoldsteinG Czapski
Jan 1, 1993·Free Radical Biology & Medicine·A L SagoneW B Davis
Jan 1, 1996·Free Radical Biology & Medicine·O I Aruoma
Jun 6, 2000·Mutation Research·J Termini
Nov 11, 1999·Toxicology Letters·D E StevensonJ E Klaunig
Mar 28, 1997·Journal of Chromatography. B, Biomedical Sciences and Applications·D R McCabeI N Acworth
May 27, 2008·Plant Physiology·Ayako NishizawaShigeru Shigeoka
Feb 6, 2004·Chemical & Pharmaceutical Bulletin·Shinji AbeToshiaki Tamaki
Feb 4, 2012·The Arabidopsis Book·D'Maris Amick DempseyDaniel F Klessig
Nov 30, 2011·Radiation Physics and Chemistry·Vicky J TangJamie R Milligan
Jul 22, 2014·Chemical Research in Toxicology·Pedro Sanchez-CruzAntonio E Alegría
Mar 15, 2005·Clinical and Experimental Immunology·K SchroecksnadelD Fuchs
Jul 18, 2015·Bioorganic & Medicinal Chemistry Letters·Rosivaldo S Borges, Steven L Castle
Mar 23, 2005·Medical Hypotheses·Christian MurrDietmar Fuchs
Sep 30, 2006·Journal of Hazardous Materials·Rani VargheseCharuvila T Aravindakumar
Apr 5, 2016·Ageing Research Reviews·Brett R Ipson, Alfred L Fisher
Aug 1, 1992·Archives of Biochemistry and Biophysics·Z MaskosW H Koppenol
Aug 1, 1992·Archives of Biochemistry and Biophysics·Z MaskosW H Koppenol
Feb 6, 2015·Chemical Research in Toxicology·Fatima I AdamWillem H Koppenol
Feb 12, 2008·Journal of Inorganic Biochemistry·Wolfhardt FreinbichlerLaura Della Corte
Oct 12, 2011·International Archives of Allergy and Immunology·Daniela ZaknunDietmar Fuchs

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.