Glutathione suppresses the autoxidation of 2',5'-dihydroxy-4-chlorobiphenyl

[1]  N. Osheroff,et al.  Quinone-induced enhancement of DNA cleavage by human topoisomerase IIalpha: adduction of cysteine residues 392 and 405. , 2007, Biochemistry.

[2]  L. Robertson,et al.  Metabolic Activation of PCBs to Carcinogens in Vivo - A Review. , 2008, Environmental toxicology and pharmacology.

[3]  Giovanni Colonna,et al.  Modeling of the Bacterial Mechanism of Methicillin-Resistance by a Systems Biology Approach , 2009, PloS one.

[4]  V. Roginsky,et al.  Kinetics of oxidation of hydroquinones by molecular oxygen. Effect of superoxide dismutase , 2000 .

[5]  T. Fujita,et al.  PCBs: structure–function relationships and mechanism of action , 1985, Environmental health perspectives.

[6]  P. Dumas,et al.  Analysis of HO-PCBs and PCP in blood plasma from individuals with high PCB exposure living on the Chukotka Peninsula in the Russian Arctic. , 2004, Journal of environmental monitoring : JEM.

[7]  P. Rich.  Electron transfer reactions between quinols and quinones in aqueous and aprotic media , 1981 .

[8]  W. Karasov,et al.  Oxidative Stress Induced in PCB 126-Exposed Northern Leopard Frogs, Rana pipiens , 2007, Journal of toxicology and environmental health. Part A.

[9]  L. Kaminsky,et al.  Metabolism of dichlorobiphenyls by hepatic microsomal cytochrome P-450. , 1980, Biochemical pharmacology.

[10]  H. Neels,et al.  Distribution of PCBs, their hydroxylated metabolites, and other phenolic contaminants in human serum from two European countries. , 2010, Environmental science & technology.

[11]  R. Tate.  Microbial Transformation and Degradation of Toxic Organic Chemicals , 1996 .

[12]  D. Leibfritz,et al.  Free radicals and antioxidants in normal physiological functions and human disease. , 2007, The international journal of biochemistry & cell biology.

[13]  Stefan Hoops,et al.  Enzyme kinetics and computational modeling for systems biology. , 2009, Methods in enzymology.

[14]  A. E. Alegria,et al.  Oxidation of tea extracts and tea catechins by molecular oxygen. , 2005, Journal of agricultural and food chemistry.

[15]  R. Letcher,et al.  Hydroxylated and methylsulfone‐containing metabolites of polychlorinated biphenyls in the plasma and blubber of bowhead whales (Balaena mysticetus) , 2003, Environmental toxicology and chemistry.

[16]  A. Davison,et al.  Multiple actions of superoxide dismutase: why can it both inhibit and stimulate reduction of oxygen by hydroquinones? , 1990, Free radical biology & medicine.

[17]  E. Cadenas,et al.  Effect of superoxide dismutase on the autoxidation of various hydroquinones--a possible role of superoxide dismutase as a superoxide:semiquinone oxidoreductase. , 1988, Free radical biology & medicine.

[18]  P. S. Samper Ots,et al.  Superoxidase dismutase (SOD) topical use in oncologic patients: treatment of acute cutaneous toxicity secondary to radiotherapy , 2008, Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico.

[19]  H. Sadeghi-aliabadi,et al.  Molecular cytotoxic mechanisms of catecholic polychlorinated biphenyl metabolites in isolated rat hepatocytes. , 2007, Chemico-biological interactions.

[20]  P. van Bladeren,et al.  Glutathione conjugate mediated toxicities. , 1990, Toxicology and applied pharmacology.

[21]  Andres Martinez,et al.  Atmospheric PCB congeners across Chicago. , 2010, Atmospheric environment.

[22]  H. Lehmler,et al.  Production of DNA strand breaks in vitro and reactive oxygen species in vitro and in HL-60 cells by PCB metabolites. , 2001, Toxicological sciences : an official journal of the Society of Toxicology.

[23]  Yukiko Matsuoka,et al.  Using process diagrams for the graphical representation of biological networks , 2005, Nature Biotechnology.

[24]  A. Weissberger,et al.  Oxidation Processes. XI.1 The Autoxidation of Durohydroquinone , 1938 .

[25]  J. Segura-Aguilar,et al.  On the mechanism of the Mn3(+)-induced neurotoxicity of dopamine:prevention of quinone-derived oxygen toxicity by DT diaphorase and superoxide dismutase. , 1989, Chemico-biological interactions.

[26]  W. Bors,et al.  The kinetics and thermodynamics of quinone–semiquinone–hydroquinone systems under physiological conditions , 1999 .

[27]  P. O'Brien.  Molecular mechanisms of quinone cytotoxicity. , 1991, Chemico-biological interactions.

[28]  L. Campbell,et al.  Detection of hydroxylated polychlorinated biphenyls (OH-PCBs) in the abiotic environment: surface water and precipitation from Ontario, Canada. , 2007, Environmental science & technology.

[29]  G. Oakley,et al.  Analysis of polychlorinated biphenyl-DNA adducts by 32P-postlabeling. , 1996, Carcinogenesis.

[30]  G. Buettner.  The pecking order of free radicals and antioxidants: lipid peroxidation, alpha-tocopherol, and ascorbate. , 1993, Archives of biochemistry and biophysics.

[31]  E. Cadenas,et al.  Effect of superoxide dismutase on the autoxidation of substituted hydro- and semi-naphthoquinones. , 1990, Chemico-biological interactions.

[32]  A. Weissberger,et al.  Oxidation processes; quinone catalysis in the autoxidation of hydroquinones. , 1947, Journal of the American Chemical Society.

[33]  A. Wójtowicz,et al.  Comparison of the actions of 4-chlorobiphenyl and its hydroxylated metabolites on estradiol secretion by ovarian follicles in primary cells in culture. , 2005, Reproductive toxicology.

[34]  Garry R. Buettner,et al.  Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide. , 2010, Free radical biology & medicine.

[35]  L. Robertson,et al.  Investigation of mechanism(s) of DNA damage induced by 4-monochlorobiphenyl (PCB3) metabolites. , 2010, Environment international.

[36]  I. Martin,et al.  Reduced mitochondrial SOD displays mortality characteristics reminiscent of natural aging , 2007, Mechanisms of Ageing and Development.

[37]  N. Kikuchi,et al.  CellDesigner 3.5: A Versatile Modeling Tool for Biochemical Networks , 2008, Proceedings of the IEEE.

[38]  W. Williams.  Microbial reductive dechlorination of polychlorinated biphenyls in heat treated and bromoethanesulfonate treated anaerobic sediment slurries , 1994 .

[39]  G. Oakley,et al.  Oxidative DNA damage induced by activation of polychlorinated biphenyls (PCBs): implications for PCB-induced oxidative stress in breast cancer. , 1996, Chemical research in toxicology.

[40]  M. Erickson,et al.  Applications of polychlorinated biphenyls , 2011, Environmental science and pollution research international.

[41]  I. Fridovich,et al.  Superoxide dismutase: the first twenty years (1968-1988). , 1988, Free radical biology & medicine.

[42]  J. Goldstone,et al.  Uncoupling of cytochrome P450 1A and stimulation of reactive oxygen species production by co-planar polychlorinated biphenyl congeners. , 2006, Aquatic toxicology.

[43]  J S Bus,et al.  A proposed mechanism of benzene toxicity: formation of reactive intermediates from polyphenol metabolites. , 1981, Toxicology and applied pharmacology.

[44]  E. Cadenas,et al.  Reductive addition of glutathione to p-benzoquinone, 2-hydroxy-p-benzoquinone, and p-benzoquinone epoxides. Effect of the hydroxy- and glutathionyl substituents on p-benzohydroquinone autoxidation. , 1988, Chemico-biological interactions.

[45]  M. Trush,et al.  Oxidation of hydroquinone by copper: chemical mechanism and biological effects. , 1993, Archives of biochemistry and biophysics.

[46]  John R. Green,et al.  The Influence of Hydroxyl Ion Concentration on the Autoxidation of Hydroquinone , 1941 .

[47]  L. Kaminsky,et al.  Metabolism of monochlorobiphenyls by hepatic microsomal cytochrome P-450. , 1980, Biochemical pharmacology.

[48]  H. Lehmler,et al.  Semiquinone Radicals from Oxygenated Polychlorinated Biphenyls: Electron Paramagnetic Resonance Studies , 2008, Chemical research in toxicology.

[49]  U. Bauer,et al.  Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase. , 1996, Chemical research in toxicology.

[50]  R. Gupta,et al.  Detection of PCB adducts by the 32P-postlabeling technique. , 1996, Chemical research in toxicology.

[51]  A. Sobel,et al.  The Journal of Biological Chemistry. , 2009, Nutrition reviews.

[52]  S. Safe,et al.  Binding of polychlorinated biphenyls classified as either phenobarbitone-, 3-methylcholanthrene- or mixed-type inducers to cytosolic Ah receptor. , 1982, Chemico-biological interactions.

[53]  A. Weissberger,et al.  Oxidation Processes. XII.1 The Autoxidation of Hydroquinone and of the Mono-, Di- and Trimethylhydroquinones , 1938 .

[54]  S. Safe,et al.  Structure-dependent induction of CYP2B by polychlorinated biphenyl congeners in female Sprague-Dawley rats. , 1995, Biochemical pharmacology.

[55]  Mudita Singhal,et al.  COPASI - a COmplex PAthway SImulator , 2006, Bioinform..

[56]  E. Hassoun,et al.  Assessment of the roles of antioxidant enzymes and glutathione in 3,3′,4,4′,5-pentachlorobiphenyl (PCB 126)-induced oxidative stress in the brain tissues of rats after subchronic exposure , 2010, Toxicological and environmental chemistry.

[57]  J F Brown,et al.  Determination of PCB Metabolic, Excretion, and Accumulation Rates for Use as Indicators of Biological Response and Relative Risk. , 1994, Environmental science & technology.

[58]  L. Robertson,et al.  2-(4'-CHLOROPHENYL)-1,4-BENZOQUINONE INCREASES THE FREQUENCY OF MICRONUCLEI AND SHORTENS TELOMERES. , 2008, Environmental toxicology and pharmacology.

[59]  M. Duffel,et al.  Oxidation of 4-chlorobiphenyl metabolites to electrophilic species by prostaglandin H synthase. , 2009, Chemical research in toxicology.

[60]  C. Filesi,et al.  Novel mechanisms of natural antioxidant compounds in biological systems: involvement of glutathione and glutathione-related enzymes. , 2005, The Journal of nutritional biochemistry.

[61]  Freya Q. Schafer,et al.  Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. , 2001, Free radical biology & medicine.

[62]  Samuel C. Pierce,et al.  Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP‐2 uvrA , 2009, Environmental and molecular mutagenesis.

[63]  F. Fonnum,et al.  Hydroxylated polychlorinated biphenyls increase reactive oxygen species formation and induce cell death in cultured cerebellar granule cells. , 2009, Toxicology and applied pharmacology.

[64]  I. Fridovich,et al.  Superoxide dismutases enhance the rate of autoxidation of 3-hydroxyanthranilic acid. , 1990, Archives of biochemistry and biophysics.

[65]  R. Letcher,et al.  Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls , 2000 .

[66]  I. Fridovich.  Biological effects of the superoxide radical. , 1986, Archives of biochemistry and biophysics.

[67]  N. H. Williams,et al.  Outer-sphere electron-transfer reactions of ascorbate anions , 1982 .

[68]  L. Barrie,et al.  Arctic contaminants: sources, occurrence and pathways. , 1992, The Science of the total environment.

[69]  A. Canada,et al.  Superoxide dismutase: its role in xenobiotic detoxification. , 1989, Pharmacology & therapeutics.

[70]  A. Ross,et al.  Reactivity of HO2/O−2 Radicals in Aqueous Solution , 1985 .

[71]  E. Bertini,et al.  Analysis of glutathione: implication in redox and detoxification. , 2003, Clinica chimica acta; international journal of clinical chemistry.

[72]  M. Toborek,et al.  PCB-induced oxidative stress in endothelial cells: modulation by nutrients. , 2002, International journal of hygiene and environmental health.

[73]  R. Dietz,et al.  Hydroxylated and methyl sulfone PCB metabolites in adipose and whole blood of polar bear (Ursus maritimus) from East Greenland. , 2004, The Science of the total environment.

[74]  U. Bauer,et al.  Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl. , 1996, Chemical research in toxicology.

[75]  A. Kettle,et al.  Oxidation of hydroquinone by myeloperoxidase. Mechanism of stimulation by benzoquinone. , 1992, The Journal of biological chemistry.

[76]  C. Winterbourn.  Inhibition of autoxidation of divicine and isouramil by the combination of superoxide dismutase and reduced glutathione. , 1989, Archives of biochemistry and biophysics.

[77]  P. Eyer.  Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. , 1991, Chemico-biological interactions.

[78]  Kazuo T. Suzuki,et al.  Reaction of para-hydroxybenzoic acid esters with singlet oxygen in the presence of glutathione produces glutathione conjugates of hydroquinone, potent inducers of oxidative stress , 2006, Free radical research.

[79]  J. Luvalle,et al.  Oxidation processes; the mechanism of autoxidation reactions in the presence of foreign catalysts and inhibitors. , 1947, Journal of the American Chemical Society.

[80]  I. Fridovich,et al.  Pulse radiolytic investigations of superoxide catalyzed disproportionation. Mechanism for bovine superoxide dismutase. , 1973, Journal of the American Chemical Society.

[81]  G. Buettner,et al.  In the absence of catalytic metals ascorbate does not autoxidize at pH 7: ascorbate as a test for catalytic metals. , 1988, Journal of biochemical and biophysical methods.

[82]  K. Norén,et al.  Methylsulfonyl metabolites of PCBs and DDE in human tissues. , 1997, Environmental health perspectives.

[83]  B. S. Neporent,et al.  On The Mechanism of , 1975 .

[84]  I. Yamazaki,et al.  ELECTRON PARAMAGNETIC RESONANCE OF UNDISSOCIATED P-BENZOSEMIQUINONES. , 1965, Journal of the American Chemical Society.

[85]  L. Sayre,et al.  Ligand dependence in the copper-catalyzed oxidation of hydroquinones. , 2005, Archives of biochemistry and biophysics.

[86]  E. Rideal,et al.  THE INFLUENCE OF HYDROGEN CONCENTRATION ON THE AUTO-OXIDATION OF HYDROQUINONE. A NOTE ON THE STABILITY OF THE QUINHYDRONE ELECTRODE , 1924 .

[87]  R P Mason,et al.  Redox cycling and sulphydryl arylation; their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes. , 1988, Chemico-biological interactions.

[88]  Snell A. Mills,et al.  A summary of the 209 PCB congener nomenclature. , 2007, Chemosphere.

[89]  M. Stratford,et al.  Oxidative metabolism of combretastatin A-1 produces quinone intermediates with the potential to bind to nucleophiles and to enhance oxidative stress via free radicals. , 2007, Chemical research in toxicology.

[90]  J. Pedersen.  On the application of electron paramagnetic resonance in the study of naturally occurring quinones and quinols. , 2002, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[91]  S. Dutt,et al.  Superoxide dismutase: an industrial perspective , 2011, Critical reviews in biotechnology.

[92]  W. T. Dixon,et al.  Electron spin resonance spectra of radicals derived from arylhydroquinones , 1972 .

[93]  K. Hornbuckle,et al.  Polychlorinated biphenyls (PCBs): sources, exposures, toxicities. , 2010, Environmental science & technology.

[94]  J. Gunn,et al.  Protecting against Antimicrobial Effectors in the Phagosome Allows SodCII To Contribute to Virulence in Salmonella enterica Serovar Typhimurium , 2010, Journal of bacteriology.

[95]  T. Tsukatani,et al.  Metabolism of Benzoquinone by Yeast Cells and Oxidative Characteristics of Corresponding Hydroquinone: Application to Highly Sensitive Measurement of Yeast Cell Density by Using Benzoquinone and a Chemiluminescent Probe , 2004, Bioscience, biotechnology, and biochemistry.

[96]  R. Mason,et al.  Characterization of a glutathione conjugate of the 1,4-benzosemiquinone-free radical formed in rat hepatocytes. , 1988, The Journal of biological chemistry.

[97]  L. Robertson,et al.  Sulfhydryl binding and topoisomerase inhibition by PCB metabolites. , 2002, Chemical research in toxicology.

[98]  Hiroaki Kitano,et al.  CellDesigner: a process diagram editor for gene-regulatory and biochemical networks , 2003 .

[99]  H. Lehmler,et al.  Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones , 2009, Proceedings of the National Academy of Sciences.

[100]  A. Bergman,et al.  Selective retention of hydroxylated PCB metabolites in blood. , 1994, Environmental health perspectives.

[101]  T. I. Apak,et al.  Hydroxylated polychlorinated biphenyls are substrates and inhibitors of human hydroxysteroid sulfotransferase SULT2A1. , 2006, Chemical research in toxicology.

[102]  J. Bolton,et al.  Role of quinones in toxicology. , 2000, Chemical research in toxicology.

[103]  S. Safe,et al.  Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses, and implications for risk assessment. , 1994, Critical reviews in toxicology.

[104]  D. Burgin.  PCBs: Recent Advances in Environmental Toxicology and Health Effects , 2002 .

[105]  I. Fridovich,et al.  Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). , 1969, The Journal of biological chemistry.

[106]  S. Parkin,et al.  Chlorination increases the persistence of semiquinone free radicals derived from polychlorinated biphenyl hydroquinones and quinones. , 2008, The Journal of organic chemistry.

[107]  J. Pedersen.  Electron spin resonance studies of oxidative processes of quinones and hydroquinones in alkaline solution; formation of primary and secondary semiquinone radicals , 1973 .

[108]  R. Munday.  Autoxidation of naphthohydroquinones: Effects of pH, naphthoquinones and superoxide dismutase , 2000, Free radical research.

[109]  Mudita Singhal,et al.  Bioinformatics Original Paper Copasi—a Complex Pathway Simulator , 2022 .