Glutathione synthesis and its role in redox signaling

Lambeth, 2002, Nox/Duox family of nicotinamide adenine dinucleotide (phosphate) oxidases, Current Opinion in Hematology, 9, 11, 10.1097/00062752-200201000-00003 Turrens, 2003, Mitochondrial formation of reactive oxygen species, Journal of Physiology, 552, 335, 10.1113/jphysiol.2003.049478 McCord, 1970, The utility of superoxide dismutase in studying free radical reactions. II. The mechanism of the mediation of cytochrome c reduction by a variety of electron carriers, Journal of Biological Chemistry, 245, 1374, 10.1016/S0021-9258(18)63246-6 Wink, 1998, Chemical biology of nitric oxide: Insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide, Free Radical Biology and Medicine, 25, 434, 10.1016/S0891-5849(98)00092-6 Forman, 2010, Signaling functions of reactive oxygen species, Biochemistry, 49, 835, 10.1021/bi9020378 Forman, 2004, Redox signaling: thiol chemistry defines which reactive oxygen and nitrogen species can act as second messengers, American Journal of Physiology: Cell Physiology, 287, C246, 10.1152/ajpcell.00516.2003 Forman, 2008, The chemistry of cell signaling by reactive oxygen and nitrogen species and 4-hydroxynonenal, Archives of Biochemistry and Biophysics, 477, 183, 10.1016/j.abb.2008.06.011 Kampa, 2008, Human health effects of air pollution, Environmental Pollution, 151, 362, 10.1016/j.envpol.2007.06.012 Stjernschantz, 1984, The leukotrienes, Medical Biology, 62, 215 Jones, 2010, Redox sensing: orthogonal control in cell cycle and apoptosis signalling, Journal of Internal Medicine, 268, 432, 10.1111/j.1365-2796.2010.02268.x Jacob, 2006, Aspects of the biological redox chemistry of cysteine: from simple redox responses to sophisticated signalling pathways, Biological Chemistry, 387, 1385, 10.1515/BC.2006.174 Meister, 1988, Glutathione metabolism and its selective modification, Journal of Biological Chemistry, 263, 17205, 10.1016/S0021-9258(19)77815-6 Jones, 2006, Redefining oxidative stress, Antioxidants and Redox Signalling, 8, 1865, 10.1089/ars.2006.8.1865 Bock, 1987, The role of conjugation reactions in detoxication, Archives of Toxicology, 60, 22, 10.1007/BF00296941 Hayes, 2005, Glutathione transferases, Annual Review of Pharmacology and Toxicology, 45, 51, 10.1146/annurev.pharmtox.45.120403.095857 Ketterer, 1983, The role of glutathione in detoxication, Environmental Health Perspectives, 49, 59, 10.1289/ehp.834959 Murphy, 2002, Glutathione adducts of oxyeicosanoids, Prostaglandins and Other Lipid Mediators, 68–69, 471, 10.1016/S0090-6980(02)00049-7 Sies, 1989, Biochemistry of thiol groups: the role of glutathione, Naturwissenschaften, 76, 57, 10.1007/BF00396705 Chen, 2006, Mechanisms of cystic fibrosis transmembrane conductance regulator activation by S-nitrosoglutathione, Journal of Biological Chemistry, 281, 9190, 10.1074/jbc.M513231200 Zhang, 2009, Redox regulation of gamma-glutamyl transpeptidase, American Journal of Respiratory Cell and Molecular Biology, 41, 509, 10.1165/rcmb.2009-0169TR Meister, 1984, New developments in glutathione metabolism and their potential application in therapy, Hepatology, 4, 739, 10.1002/hep.1840040431 Griffith, 1981, Formation of gamma-glutamycyst(e)ine in vivo is catalyzed by gamma-glutamyl transpeptidase, Proceedings of the National Academy of Sciences of the United States of America, 78, 2777, 10.1073/pnas.78.5.2777 Huang, 1993, Catalytic and regulatory properties of the heavy subunit of rat kidney γ-glutamylcysteine synthetase, Journal of Biological Chemistry, 268, 19675, 10.1016/S0021-9258(19)36569-X Sun, 1996, Regulation of γ-glutamylcysteine synthetase by protein phosphorylation, Biochemical Journal, 320, 321, 10.1042/bj3200321 Zhang, 2007, Submicromolar concentrations of 4-hydroxynonenal induce glutamate cysteine ligase expression in HBE1 cells, Redox Rep, 12, 101, 10.1179/135100007X162266 Iles, 2005, Mechanisms of glutamate cysteine ligase (GCL) induction by 4-hydroxynonenal, Free Radical Biology and Medicine, 38, 547, 10.1016/j.freeradbiomed.2004.11.012 Yang, 2001, Cloning and characterization of the 5’-flanking region of the rat glutamate-cysteine ligase catalytic subunit, Biochemical Journal, 357, 447, 10.1042/0264-6021:3570447 Tan, 2008, NRF2 as a determinant of cellular resistance in retinoic acid cytotoxicity, Free Radical Biology and Medicine, 45, 1663, 10.1016/j.freeradbiomed.2008.09.010 Dickinson, 2002, 4-hydroxynonenal induces glutamate cysteine ligase through JNK in HBE1 cells, Free Radical Biology and Medicine, 33, 974, 10.1016/S0891-5849(02)00991-7 Zipper, 2000, Inhibition of ERK and p38 MAP kinases inhibits binding of Nrf2 and induction of GCS genes, Biochemical and Biophysical Research Communications, 278, 484, 10.1006/bbrc.2000.3830 Rushworth, 2006, Role of protein kinase C delta in curcumin-induced antioxidant response element-mediated gene expression in human monocytes, Biochemical and Biophysical Research Communications, 341, 1007, 10.1016/j.bbrc.2006.01.065 Kim, 2004, Insulin signaling regulates gamma-glutamylcysteine ligase catalytic subunit expression in primary cultured rat hepatocytes, Journal of Pharmacology and Experimental Therapeutics, 311, 99, 10.1124/jpet.104.070375 Wang, 2008, Essential roles of the PI3 kinase/Akt pathway in regulating Nrf2-dependent antioxidant functions in the RPE, Investigative Ophthalmology and Visual Science, 49, 1671, 10.1167/iovs.07-1099 Dickinson, 2003, Curcumin alters EpRE and AP-1 binding complexes and elevates glutamate-cysteine ligase gene expression, FASEB Journal, 17, 473, 10.1096/fj.02-0566fje Itoh, 1999, Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain, Genes and Development, 13, 76, 10.1101/gad.13.1.76 Cullinan, 2003, Nrf2 is a direct PERK substrate and effector of PERK-dependent cell survival, Molecular and Cellular Biology, 23, 7198, 10.1128/MCB.23.20.7198-7209.2003 Bloom, 2003, Journal of Biological Chemistry, 278, 44675, 10.1074/jbc.M307633200 Itoh, 2004, Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles, Free Radical Biology and Medicine, 36, 1208, 10.1016/j.freeradbiomed.2004.02.075 Giudice, 2010, Review of molecular mechanisms involved in the activation of the Nrf2-ARE signaling pathway by chemopreventive agents, Methods in Molecular Biology, 647, 37, 10.1007/978-1-60761-738-9_3 Levy, 2010, C-Myc is a Nrf2-interacting protein that negatively regulates phase II genes through their electrophile responsive elements, IUBMB Life, 62, 237, 10.1002/iub.314 Jain, 2007, GSK-3beta acts upstream of Fyn kinase in regulation of nuclear export and degradation of NF-E2 related factor 2, Journal of Biological Chemistry, 282, 16502, 10.1074/jbc.M611336200 Rojo, 2008, GSK-3beta down-regulates the transcription factor Nrf2 after oxidant damage: relevance to exposure of neuronal cells to oxidative stress, Journal of Neurochemistry, 105, 192, 10.1111/j.1471-4159.2007.05124.x Niture, 2011, Src subfamily kinases regulate nuclear export and degradation of transcription factor Nrf2 to switch off Nrf2-mediated antioxidant activation of cytoprotective gene expression, Journal of Biological Chemistry, 286, 28821, 10.1074/jbc.M111.255042 Rada, 2011, SCF/{beta}-TrCP promotes glycogen synthase kinase 3-dependent degradation of the Nrf2 transcription factor in a Keap1-independent manner, Molecular and Cellular Biology, 31, 1121, 10.1128/MCB.01204-10 Levy, 2009, The role of c-Jun phosphorylation in EpRE activation of phase II genes, Free Radical Biology and Medicine, 47, 1172, 10.1016/j.freeradbiomed.2009.07.036 Jeyapaul, 2000, Nrf2 and c-Jun regulation of antioxidant response element (ARE)-mediated expression and induction of gamma-glutamylcysteine synthetase heavy subunit gene, Biochemical Pharmacology, 59, 1433, 10.1016/S0006-2952(00)00256-2 Dhakshinamoorthy, 2000, Small maf (MafG and MafK) proteins negatively regulate antioxidant response element-mediated expression and antioxidant induction of the NAD(P)H:Quinone oxidoreductase1 gene, Journal of Biological Chemistry, 275, 40134, 10.1074/jbc.M003531200 Myhrstad, 2001, TCF11/Nrf1 overexpression increases the intracellular glutathione level and can transactivate the gamma-glutamylcysteine synthetase (GCS) heavy subunit promoter, Biochimica et Biophysica Acta, 1517, 212, 10.1016/S0167-4781(00)00276-1 Dhakshinamoorthy, 2005, Bach1 competes with Nrf2 leading to negative regulation of the antioxidant response element (ARE)-mediated NAD(P)H:quinone oxidoreductase 1 gene expression and induction in response to antioxidants, Journal of Biological Chemistry, 280, 16891, 10.1074/jbc.M500166200 Sankaranarayanan, 2004, Nrf3 negatively regulates antioxidant-response element-mediated expression and antioxidant induction of NAD(P)H:quinone oxidoreductase1 gene, Journal of Biological Chemistry, 279, 50810, 10.1074/jbc.M404984200 He, 2001, Identification of activating transcription factor 4 (ATF4) as an Nrf2-interacting protein. Implication for heme oxygenase-1 gene regulation, Journal of Biological Chemistry, 276, 20858, 10.1074/jbc.M101198200 Zhu, 2001, Functional characterization of transcription regulators that interact with the electrophile response element, Biochemical and Biophysical Research Communications, 289, 212, 10.1006/bbrc.2001.5944 Rahman, 1999, Molecular mechanism of the regulation of glutathione synthesis by tumor necrosis factor-alpha and dexamethasone in human alveolar epithelial cells, Journal of Biological Chemistry, 274, 5088, 10.1074/jbc.274.8.5088 Ofir, 1990, Phosphorylation of the C terminus of Fos protein is required for transcriptional transrepression of the c-fos promoter, Nature, 348, 80, 10.1038/348080a0 Binetruy, 1991, Ha-Ras augments c-Jun activity and stimulates phosphorylation of its activation domain, Nature, 351, 122, 10.1038/351122a0 Rinna, 2008, SHP-1 inhibition by 4-hydroxynonenal activates jun N-terminal kinase and glutamate cysteine ligase, American Journal of Respiratory Cell and Molecular Biology, 39, 97, 10.1165/rcmb.2007-0371OC Pimentel, 2011, Regulation of cell physiology and pathology by protein S-glutathionylation. Lessons learned from the cardiovascular system, Antioxidants and Redox Signalling Leisinger, 1995, Bacterial growth with chlorinated methanes, Environmental Health Perspectives, 103, 33, 10.1289/ehp.95103s433 Manevich, 2004, Activation of the antioxidant enzyme 1-CYS peroxiredoxin requires glutathionylation mediated by heterodimerization with pi GST, Proceedings of the National Academy of Sciences of the United States of America, 101, 3780, 10.1073/pnas.0400181101 Ralat, 2006, Direct evidence for the formation of a complex between 1-cysteine peroxiredoxin and glutathione S-transferase pi with activity changes in both enzymes, Biochemistry, 45, 360, 10.1021/bi0520737 Klomsiri, 2011, Cysteine-based redox switches in enzymes, Antioxidants and Redox Signalling, 14, 1065, 10.1089/ars.2010.3376 Li, 2001, Glutathiolation of proteins by glutathione disulfide S-oxide derived from S-nitrosoglutathione. Modifications of rat brain neurogranin/RC3 and neuromodulin/GAP-43, Journal of Biological Chemistry, 276, 3098, 10.1074/jbc.M008260200 Huang, 2002, Glutathionylation of proteins by glutathione disulfide S-oxide, Biochemical Pharmacology, 64, 1049, 10.1016/S0006-2952(02)01175-9 Townsend, 2009, Novel role for glutathione S-transferase pi. Regulator of protein S-Glutathionylation following oxidative and nitrosative stress, Journal of Biological Chemistry, 284, 436, 10.1074/jbc.M805586200 Gallogly, 2009, Mechanistic and kinetic details of catalysis of thiol-disulfide exchange by glutaredoxins and potential mechanisms of regulation, Antioxidants and Redox Signalling, 11, 1059, 10.1089/ars.2008.2291 Shelton, 2005, Glutaredoxin: role in reversible protein s-glutathionylation and regulation of redox signal transduction and protein translocation, Antioxidants and Redox Signalling, 7, 348, 10.1089/ars.2005.7.348 Kalinina, 2008, Involvement of thio-:peroxi-, and glutaredoxins in cellular redox-dependent processes, Biochemistry. Biokhimiia, 73, 1493, 10.1134/S0006297908130099 Mieyal, 2008, Molecular mechanisms and clinical implications of reversible protein S-glutathionylation, Antioxidants and Redox Signalling, 10, 1941, 10.1089/ars.2008.2089 Ho, 2007, Targeted disruption of the glutaredoxin 1 gene does not sensitize adult mice to tissue injury induced by ischemia/reperfusion and hyperoxia, Free Radical Biology and Medicine, 43, 1299, 10.1016/j.freeradbiomed.2007.07.025 Wu, 2011, Glutaredoxin 2 knockout increases sensitivity to oxidative stress in mouse lens epithelial cells, Free Radical Biology and Medicine, 51, 2108, 10.1016/j.freeradbiomed.2011.09.011 Qanungo, 2007, Glutathione supplementation potentiates hypoxic apoptosis by S-glutathionylation of p65-NFkappaB, Journal of Biological Chemistry, 282, 18427, 10.1074/jbc.M610934200 Findlay, 2005, Sulfiredoxin: a potential therapeutic agent?, Biomedicine and Pharmacotherapy, 59, 374, 10.1016/j.biopha.2005.07.003 Park, 2009, Deglutathionylation of 2-Cys peroxiredoxin is specifically catalyzed by sulfiredoxin, Journal of Biological Chemistry, 284, 23364, 10.1074/jbc.M109.021394 Fratelli, 2003, Identification of proteins undergoing glutathionylation in oxidatively stressed hepatocytes and hepatoma cells, Proteomics, 3, 1154, 10.1002/pmic.200300436 Hurd, 2005, Glutathionylation of mitochondrial proteins, Antioxidants and Redox Signalling, 7, 999, 10.1089/ars.2005.7.999 Pineda-Molina, 2001, Glutathionylation of the p50 subunit of NF-kappaB: a mechanism for redox-induced inhibition of DNA binding, Biochemistry, 40, 14134, 10.1021/bi011459o Reynaert, 2006, Dynamic redox control of NF-kappaB through glutaredoxin-regulated S-glutathionylation of inhibitory kappaB kinase beta, Proceedings of the National Academy of Sciences of the United States of America, 103, 13086, 10.1073/pnas.0603290103 Chantzoura, 2010, Glutaredoxin-1 regulates TRAF6 activation and the IL-1 receptor/TLR4 signalling, Biochemical and Biophysical Research Communications, 403, 335, 10.1016/j.bbrc.2010.11.029 Flescher, 1998, Oxidative stress suppresses transcription factor activities in stimulated lymphocytes, Clinical and Experimental Immunology, 112, 242, 10.1046/j.1365-2249.1998.00548.x Immenschuh, 2005, Peroxiredoxins, oxidative stress, and cell proliferation, Antioxidants and Redox Signalling, 7, 768, 10.1089/ars.2005.7.768 Wood, 2002, Dimers to doughnuts: redox-sensitive oligomerization of 2-cysteine peroxiredoxins, Biochemistry, 41, 5493, 10.1021/bi012173m Chae, 1999, Characterization of three isoforms of mammalian peroxiredoxin that reduce peroxides in the presence of thioredoxin, Diabetes Research and Clinical Practice, 45, 101, 10.1016/S0168-8227(99)00037-6 Woo, 2003, Reversing the inactivation of peroxiredoxins caused by cysteine sulfinic acid formation, Science, 300, 653, 10.1126/science.1080273 Fratelli, 2002, Identification by redox proteomics of glutathionylated proteins in oxidatively stressed human T lymphocytes, Proceedings of the National Academy of Sciences of the United States of America, 99, 3505, 10.1073/pnas.052592699 Park, 2011, Glutathionylation of peroxiredoxin I induces decamer to dimers dissociation with concomitant loss of chaperone activity, Biochemistry, 50, 3204, 10.1021/bi101373h Morinaka, 2011, Oligomeric peroxiredoxin-I is an essential intermediate for p53 to activate MST1 kinase and apoptosis, Oncogene, 30, 4208, 10.1038/onc.2011.139 Cao, 2009, Prdx1 inhibits tumorigenesis via regulating PTEN/AKT activity, EMBO Journal, 28, 1505, 10.1038/emboj.2009.101 Chen, 2010, S-glutathionylation uncouples eNOS and regulates its cellular and vascular function, Nature, 468, 1115, 10.1038/nature09599 Queiroga, 2010, Glutathionylation of adenine nucleotide translocase induced by carbon monoxide prevents mitochondrial membrane permeabilization and apoptosis, Journal of Biological Chemistry, 285, 17077, 10.1074/jbc.M109.065052 Forman, 2007, Use and abuse of exogenous H2O2 in studies of signal transduction, Free Radical Biology and Medicine, 42, 926, 10.1016/j.freeradbiomed.2007.01.011 Martinez-Ruiz, 2011, Nitric oxide signaling: classical, less classical, and nonclassical mechanisms, Free Radical Biology and Medicine, 51, 17, 10.1016/j.freeradbiomed.2011.04.010 Ignarro, 1982, Activation of purified guanylate cyclase by nitric oxide requires heme. Comparison of heme-deficient: heme-reconstituted and heme-containing forms of soluble enzyme from bovine lung, Biochimica et Biophysica Acta, 718, 49, 10.1016/0304-4165(82)90008-3 Wink, 1994, Reaction kinetics for nitrosation of cysteine and glutathione in aerobic nitric oxide solutions at neutral pH. Insights into the fate and physiological effects of intermediates generated in the NO/O2 reaction, Chemical Research in Toxicology, 7, 519, 10.1021/tx00040a007 Clancy, 1994, Nitric oxide reacts with intracellular glutathione and activates the hexose monophosphate shunt in human neutrophils: evidence for S-nitrosoglutathione as a bioactive intermediary, Proceedings of the National Academy of Sciences of the United States of America, 91, 3680, 10.1073/pnas.91.9.3680 Moro, 1994, Paradoxical fate and biological action of peroxynitrite on human platelets, Proceedings of the National Academy of Sciences of the United States of America, 91, 6702, 10.1073/pnas.91.14.6702 Chiueh, 1999, Neuroprotective properties of nitric oxide, Annals of the New York Academy of Sciences, 890, 301, 10.1111/j.1749-6632.1999.tb08007.x Liu, 2001, A metabolic enzyme for S-nitrosothiol conserved from bacteria to humans, Nature, 410, 490, 10.1038/35068596 Fernandez, 2003, S-nitrosoglutathione reductase activity of human and yeast glutathione-dependent formaldehyde dehydrogenase and its nuclear and cytoplasmic localisation, Cellular and Molecular Life Sciences, 60, 1013, 10.1007/s00018-003-3025-x Zeng, 2001, Metabolism of S-nitrosoglutathione by endothelial cells, American Journal of Physiology: Heart And Circulatory Physiology, 281, H432 Hogg, 1997, S-Nitrosoglutathione as a substrate for gamma-glutamyl transpeptidase, Biochemical Journal, 323, 477, 10.1042/bj3230477 Zhang, 2005, S-Nitrosothiols: cellular formation and transport, Free Radical Biology and Medicine, 38, 831, 10.1016/j.freeradbiomed.2004.12.016 Matsumoto, 2011, Membrane transfer of S-nitrosothiols, Nitric Oxide, 25, 102, 10.1016/j.niox.2011.02.006 Carver, 2005, S-nitrosothiol formation, Methods in Enzymology, 396, 95, 10.1016/S0076-6879(05)96010-2 Aracena, 2003, S-glutathionylation decreases Mg2+ inhibition and S-nitrosylation enhances Ca2+ activation of RyR1 channels, Journal of Biological Chemistry, 278, 42927, 10.1074/jbc.M306969200 Sanchez, 2005, Tachycardia increases NADPH oxidase activity and RyR2 S-glutathionylation in ventricular muscle, Journal of Molecular and Cellular Cardiology, 39, 982, 10.1016/j.yjmcc.2005.08.010 Bundgaard, 2010, beta(3) adrenergic stimulation of the cardiac Na+–K+ pump by reversal of an inhibitory oxidative modification, Circulation, 122, 2699, 10.1161/CIRCULATIONAHA.110.964619 Clavreul, 2006, S-glutathiolation by peroxynitrite of p21ras at cysteine-118 mediates its direct activation and downstream signaling in endothelial cells, FASEB Journal, 20, 518, 10.1096/fj.05-4875fje Klatt, 1999, Nitric oxide inhibits c-Jun DNA binding by specifically targeted S-glutathionylation, Journal of Biological Chemistry, 274, 15857, 10.1074/jbc.274.22.15857 Mohr, 1999, Nitric oxide-induced S-glutathionylation and inactivation of glyceraldehyde-3-phosphate dehydrogenase, Journal of Biological Chemistry, 274, 9427, 10.1074/jbc.274.14.9427 Velu, 2007, Human p53 is inhibited by glutathionylation of cysteines present in the proximal DNA-binding domain during oxidative stress, Biochemistry, 46, 7765, 10.1021/bi700425y Jahngen-Hodge, 1997, Regulation of ubiquitin-conjugating enzymes by glutathione following oxidative stress, Journal of Biological Chemistry, 272, 28218, 10.1074/jbc.272.45.28218 Zmijewski, 2009, S-glutathionylation of the Rpn2 regulatory subunit inhibits 26 S proteasomal function, Journal of Biological Chemistry, 284, 22213, 10.1074/jbc.M109.028902 Anathy, 2009, Redox amplification of apoptosis by caspase-dependent cleavage of glutaredoxin 1 and S-glutathionylation of Fas, Journal of Cell Biology, 184, 241, 10.1083/jcb.200807019 Huang, 2008, Inhibition of caspase-3 activity and activation by protein glutathionylation, Biochemical Pharmacology, 75, 2234, 10.1016/j.bcp.2008.02.026 Rinna, 2006, Stimulation of the alveolar macrophage respiratory burst by ADP causes selective glutathionylation of protein tyrosine phosphatase 1B, Free Radical Biology and Medicine, 41, 86, 10.1016/j.freeradbiomed.2006.03.010