Oxidative modification of citrate synthase by peroxyl radicals and protection with novel antioxidants

References

• Lenaz G, Baracca A, Fato R, Genova ML, Solaini G.New insights into structure and function of mitochondria and their role in aging and disease. Antioxid Redox Signal 2006;8:417–37.
   PubMed Web of Science ®Google Scholar
• Turrens JF. Superoxide production by the mitochondrial respiratory chain. Biosci Rep 1997;17:3–8.
   PubMed Web of Science ®Google Scholar
• Tahara EB, Barros MH, Oliveira GA, Netto LE, Kowaltowski AJ. Dihydrolipoyl dehydrogenase as a source of reactive oxygen species inhibited by caloric restriction and involved in Saccharomyces cerevisiae aging. FASEB J 2007;21:274–83.
   PubMed Web of Science ®Google Scholar
• Starkov AA, Fiskum G, Chinopoulos C, Lorenzo BJ, Browne SE, Patel MS, et al. Mitochondrial alpha-ketoglutarate dehydrogenase complex generates reactive oxygen species. J Neurosci 2004;24:7779–88.
   PubMed Web of Science ®Google Scholar
• Tretter L, Adam-Vizi V. Alpha-ketoglutarate dehydrogenase: a target and generator of oxidative stress. Philos Trans R Soc Lond B Biol Sci 2005;360:2335–45.
   PubMed Web of Science ®Google Scholar
• Adam-Vizi V. Production of reactive oxygen species in brain mitochondria: contribution by electron transport chain and non-electron transport chain sources. Antioxid Redox Signal 2005;7:1140–9.
   PubMed Web of Science ®Google Scholar
• Lenaz G. The mitochondrial production of reactive oxygen species: mechanisms and implications in human pathology. IUBMB Life 2001;52:159–64.
   PubMed Web of Science ®Google Scholar
• Bulteau AL, Ikeda-Saito M, Szweda LI. Redox-dependent modulation of aconitase activity in intact mitochondria. Biochemistry 2003;42:14846–55.
   PubMed Web of Science ®Google Scholar
• Sadek HA, Humphries KM, Szweda PA, Szweda LI. Selective inactivation of redox-sensitive mitochondrial enzymes during cardiac reperfusion. Arch Biochem Biophys 2002;406:222–8.
   PubMed Web of Science ®Google Scholar
• Tretter L, Adam-Vizi V. Inhibition of Krebs cycle enzymes by hydrogen peroxide: a key role of α-ketoglutarate dehydrogenase in limiting NADH production under oxidative stress. J Neurosci 2000;20:8972–79.
   PubMed Web of Science ®Google Scholar
• Remington SJ. Structure and mechanism of citrate synthase. Curr Top Cell Regul 1992;33:209–29.
   PubMedGoogle Scholar
• Sharma AB, Sun J, Howard LL, Williams AG Jr, Mallet RT. Oxidative stress reversibly inactivates myocardial enzymes during cardiac arrest. Am J Physiol Heart Circ Physiol 2007;292:H198–206.
   PubMed Web of Science ®Google Scholar
• Sheeran FL, Pepe S. Energy deficiency in the failing heart: linking increased reactive oxygen species and disruption of oxidative phosphorylation rate. Biochim Biophys Acta 2006;1757:543–52.
   PubMed Web of Science ®Google Scholar
• Flueraru M, Chichirau A, Chepelev LL, Willmore WG, Durst T, Charron M, et al. Cytotoxicity and cytoprotective activity in naphthalenediols depends on their tendency to form naphthoquinones. Free Radic Biol Med 2005;39:1368–77.
   PubMed Web of Science ®Google Scholar
• Flueraru M, So R, Willmore WG, Poulter MO, Durst T, Charron M, et al. Cytotoxicity and cytoprotective activity of naphthalenediols in rat cortical neurons. Chem Res Toxicol 2006;19:1221–7.
   PubMed Web of Science ®Google Scholar
• Reisch AS, Elpeleg O. Biochemical assays for mitochondrial activity: assays of TCA cycle enzymes and PDHc. Methods Cell Biol 2007;80:199–222.
   PubMed Web of Science ®Google Scholar
• Marin-Garcia J, Ananthakrishnan R, Goldenthal M. Human mitochondrial function during cardiac growth and development. Mol Cell Biochem 1998;179:21–6.
   PubMed Web of Science ®Google Scholar
• Drahota Z, Milerova M, Stieglerova A, Houstek J, Ostadal B. Developmental changes of cytochrome c oxidase and citrate synthase in rat heart homogenate. Physiol Res 2004;53:119–22.
   PubMed Web of Science ®Google Scholar
• Navarro A, Sanchez Del Pino MJ, Gomez C, Peralta JL, Boveris A. Behavioral dysfunction, brain oxidative stress, and impaired mitochondrial electron transfer in aging mice. Am J Physiol Regul Integr Comp Physiol 2002;282:R985–92.
   PubMed Web of Science ®Google Scholar
• Vitorica J, Cano J, Satrustegui J, Machado A. Comparison between developmental and senescent changes in enzyme activities linked to energy metabolism in rat heart. Mech Ageing Dev 1981;16:105–16.
   PubMed Web of Science ®Google Scholar
• Freitas JJ, Pompeia C, Miyasaka CK, Curi RJ. Walker-256 tumor growth causes oxidative stress in rat brain. J Neurochem 2001;77:655–63.
   PubMed Web of Science ®Google Scholar
• Rooyackers OE, Adey DB, Ades PA, Nair KS. Effect of age on in vivo rates of mitochondrial protein synthesis in human skeletal muscle. Proc Natl Acad Sci USA 1996;93:15364–9.
   PubMed Web of Science ®Google Scholar
• Niki E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol 1990;186:100–8.
   PubMed Web of Science ®Google Scholar
• Terao K, Niki E. Damage to biological tissues induced by radical initiator 2,2’-azobis(2-amidinopropane) dihydrochloride and its inhibition by chain-breaking antioxidants. Free Radic Biol Med 1986;2:193–201.
   Google Scholar
• Książek K, Bręborowicz A, Jörres A, Witowski J. Oxidative stress contributes to accelerated development of the senescent phenotype in human peritoneal mesothelial cells exposed to high glucose. Free Radic Biol Med 2007;42:636–41.
   PubMed Web of Science ®Google Scholar
• Książek K, Passos JF, Olijslagers S, von Zglinicki T. Mitochondrial dysfunction is a possible cause of accelerated senescence of mesothelial cells exposed to high glucose. Biochem Biophys Res Commun 2008;366:793–9.
   PubMed Web of Science ®Google Scholar
• Hussain HH, Babic G, Durst T, Wright JS, Flueraru M, Chichirau A, et al. Development of novel antioxidants: design, synthesis, and reactivity. J Org Chem 2003;68:7023–32.
   PubMed Web of Science ®Google Scholar
• Ragot JP, Steeneck C, Alcaraz M-L, Taylor RJK. The synthesis of 1,8-dihydroxynaphthalene-derived natural products: palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin A and novel analogs. Perkin Trans 1 1999;8:1073–82.
   Google Scholar
• Foti MC, Johnson ER, Vinqvist MR, Wright JS, Barclay LRC, Ingold KU. Naphthalene diols: a new class of antioxidants. Intramolecular hydrogen bonding in catechols, naphthalene diols and their aryloxyl radicals. J Org Chem 2002;67:5190–6.
   PubMed Web of Science ®Google Scholar
• Frezza C, Cipolat S, Scorrano L. Organelle isolation: functional mitochondria from mouse liver, muscle and cultured fibroblasts. Nat Protoc 2007;2:287–95.
   PubMed Web of Science ®Google Scholar
• Searle AJF, Tomasi A. Hydroxyl free radical production in iron-cysteine solutions and protection by zinc. Inorg Biochem 1982;17:161–6.
   Web of Science ®Google Scholar
• Videla LA, Salim-Hanna M, Lissi EA. Inactivation of yeast alcohol dehydrogenase by alkylperoxyl radicals. Characteristics and influence of nicotinamide-adenine dinucleotides. Biochem Pharmacol 1992;44:1443–52.
   PubMed Web of Science ®Google Scholar
• Srere PA. Citrate synthase. Methods Enzymol 1969;13:3–11.
   Google Scholar
• Laboratory protocol: citrate synthase. Oroboros Instruments, Innsbruck, Austria, 2006 April 10. Available at: http://www.oroboros.at/, accessed 2007 Sep 12.
   Google Scholar
• Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–5.
   PubMed Web of Science ®Google Scholar
• Weber G, Young LB. Fragmentation of bovine serum albumin by pepsin. I. The origin of the acid expansion of the albumin molecule. J Biol Chem 1964;239:1415–23.
   PubMed Web of Science ®Google Scholar
• Jiménez I, Lissi EA, Speisky H. Free-radical-induced inactivation of lysozyme and carbonyl residue generation in protein are not necessarily associated. Arch Biochem Biophys 2000;381:247–52.
   PubMed Web of Science ®Google Scholar
• Viner RI, Krainev AG, Williams TD, Schoneich C, Bigelow DJ. Identification of oxidation-sensitive peptides within the cytoplasmic domain of the sarcoplasmic reticulum Ca2+-ATPase. Biochemistry 1997;36:7706–16.
   PubMed Web of Science ®Google Scholar
• Lissi EA, Salim-Hanna M, Faure M, Videla LA. 2,2′-Azo-bis-amidinopropane as a radical source for lipid peroxidation and enzyme inactivation studies. Xenobiotica 1991;221:995–1.
   Web of Science ®Google Scholar
• Chao CC, Ma YS, Stadtman ER. Modification of protein surface hydrophobicity and methionine oxidation by oxidative systems. Proc Natl Acad Sci USA 1997;94:2969–74.
   PubMed Web of Science ®Google Scholar
• Kang JH, Kim KS, Choi SY, Kwon HY, Won MH, Kang T-C. Protective effects of carnosine, homocarnosine and anserine against peroxyl radical-mediated Cu,Zn-superoxide dismutase modification. Biochim Biophys Acta 2002;1570:89–96.
   PubMed Web of Science ®Google Scholar
• Mayo JC, Tan DX, Sainz RM, Lopez-Burillo S, Reiter RJ. Oxidative damage to catalase induced by peroxyl radicals: functional protection by melatonin and other antioxidants. Free Radic Res 2003;37:543–53.
   PubMed Web of Science ®Google Scholar
• Batandier C, Guigas B, Detaille D, El-Mir M-Y, Fontaine E, Rigoulet M, et al. The ROS production induced by a reverse-electron flux at respiratory-chain complex 1 is hampered by metformin. J Bioenerg Biomembr 2006;38:33–42.
   PubMed Web of Science ®Google Scholar
• McEvily AJ, Harrison JH. Subunit equilibria of porcine heart citrate synthase. Effects of enzyme concentration, pH, and substrates. J Biol Chem 1986;261:2593–8.
   PubMed Web of Science ®Google Scholar
• Friguet B, Szweda LI, Stadtman ER. Susceptibility of glucose-6-phosphate dehydrogenase modified by 4-hydroxy-2-nonenal and metal-catalyzed oxidation to proteolysis by the multicatalytic protease. Arch Biochem Biophys 1994;311:168–73.
   PubMed Web of Science ®Google Scholar
• Ruan K, Li J, Liang R, Xu C, Yu Y, Lange R, et al. A rare protein fluorescence behavior where the emission is dominated by tyrosine: case of the 33-kDa protein from spinach photosystem II. Biochem Biophys Res Commun 2002;293:593–7.
   PubMed Web of Science ®Google Scholar
• Zaidi A, Leclere-L’Hostis E, Marden MC, Poyart C, Leclerc L. Heme as an optical probe for studying the interactions between calmodulin and the Ca2+-ATPase of the human erythrocyte membrane. Biochim Biophys Acta 1995;1236:114–18.
   PubMed Web of Science ®Google Scholar
• Andersson U, Leighton B, Young ME, Blomstrand E, Newsholme EA. Inactivation of aconitase and oxoglutarate dehydrogenase in skeletal muscle in vitro by superoxide anions and/or nitric oxide. Biochem Biophys Res Commun 1998;249:512–16.
   PubMed Web of Science ®Google Scholar
• Shacter E. Quantification and significance of protein oxidation in biological samples. Drug Metab Rev 2000;32:307–26.
   PubMed Web of Science ®Google Scholar
• Srere PA. The sulfhydryl groups of citrate-condensing enzyme. Biochem Biophys Res Commun 1965;18:87–91.
   PubMed Web of Science ®Google Scholar
• Giulivi C, Davies KJ. Dityrosine: a marker for oxidatively modified proteins and selective proteolysis. Methods Enzymol 1994;233:363–71.
   PubMed Web of Science ®Google Scholar
• DiMarco T, Giulivi C. Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples. Mass Spectrom Rev 2007;26:108–20.
   PubMed Web of Science ®Google Scholar
• Fukunaga Y, Katsuragi Y, Izumi T, Sakiyama F. Fluorescence characteristics of kynurenine and N’-formylkynurenine. Their use as reporters of the environment of tryptophan 62 in hen egg-white lysozyme. J Biochem 1982;92:129–41.
   PubMed Web of Science ®Google Scholar
• Zhang H, Andrekopoulos C, Joseph J, Crow J, Kalyanaraman B. The carbonate radical anion-induced covalent aggregation of human copper, zinc superoxide dismutase and α-synuclein intermediacy of tryptophan- and tyrosine-derived oxidation products. Free Radic Biol Med 2004;36:1355–65.
   PubMed Web of Science ®Google Scholar
• Wiegand G, Remington SJ. Citrate synthase: structure, control, and mechanism. Annu Rev Biophys Biophys Chem 1986;15:97–117.
   PubMedGoogle Scholar
• Stadtman ER. Protein oxidation and aging. Free Radic Res 2006;40:1250–8.
   PubMed Web of Science ®Google Scholar
• Hagerman AE, Rice ME, Ritchard NT. Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16 (4→8) catechin (procyanidin). J Agric Food Chem 1998;46:2590–5.
   Web of Science ®Google Scholar
• Fiuza SM, Gomes C, Teixeira LJ, Girão da Cruz MT, Cordeiro MNDS, Milhazes N, et al. Phenolic acid derivatives with potential anticancer properties—a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. Bioorg Med Chem 2004;12:3581–9.
   PubMed Web of Science ®Google Scholar
• Nakagawa Y, Moldeus P, Moore G. Propyl gallate-induced DNA fragmentation in isolated rat hepatocytes. Arch Toxicol 1997;72:33–7.
   PubMed Web of Science ®Google Scholar
• Johnson JK, Srivastava DK. Interaction of ligands with pig heart citrate synthase: conformational changes and catalysis. Arch Biochem Biophys 1991;287:250–6.
   PubMed Web of Science ®Google Scholar
• Ghosh S, Pulinilkunnil T, Yuen G, Kewalramani G, An D, Qi D, et al. Cardiomyocyte apoptosis induced by short-term diabetes requires mitochondrial GSH depletion. Am J Physiol Heart Circ Physiol 2005;289:H768–76.
   PubMed Web of Science ®Google Scholar
• Hu C, Kitts DD. Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro. Mol Cell Biochem 2001;218:147–55.
   PubMed Web of Science ®Google Scholar
• Lee M-J, Wang Z-Y, Li H, Chen L, Sun Y, Gobbo S, et al. Analysis of plasma and urinary tea polyphenols in human subjects. Cancer Epidemiol Biomarkers Prev 1995;4:393–9.
   PubMed Web of Science ®Google Scholar
• Roginsky V, Alegria AE. Oxidation of tea extracts and tea catechins by molecular oxygen. J Agric Food Chem 2005;53:4529–35.
   PubMed Web of Science ®Google Scholar
• Elbling L, Weiss RM, Teufelhofer O, Uhl M, Knasmueller S, Schulte-Hermann R, et al. Green tea extract and (-)-epigallocatechin-3-gallate, the major tea catechin, exert oxidant but lack antioxidant activities. FASEB J 2005;19:807–9.
   PubMed Web of Science ®Google Scholar
• Dashwood WM, Orner GA, Dashwood RH. Inhibition of beta-catenin/Tcf activity by white tea, green tea, and epigallocatechin-3-gallate (EGCG): minor contribution of H2O2 at physiologically relevant EGCG concentrations. Biochem Biophys Res Commun 2002;296:584–8.
   PubMed Web of Science ®Google Scholar
• Wroblewski K, Muhandiram R, Chakrabartty A, Bennick A. The molecular interaction of human salivary histatins with polyphenolic compounds. Eur J Biochem 2001;268:4384–97.
   PubMedGoogle Scholar
• Hagerman AE, Roger TD, Davies MJ. Radical chemistry of epigallocatechin gallate and its relevance to protein damage. Arch Biochem Biophys 2003;414:115–20.
   PubMed Web of Science ®Google Scholar
• Sutherland BA, Shaw OM, Clarkson AN, Jackson DM, Sammut IA, Appleton I. Neuroprotective effects of (-)-epigallocatechin gallate following hypoxia-ischemia-induced brain damage: novel mechanisms of action. FASEB J 2005;19:258–60.
   PubMed Web of Science ®Google Scholar