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Volumn 41, Issue 2, 2013, Pages 315-321

Reactive intermediates: Molecular and MS-based approaches to assess the functional significance of chemical-protein adducts

Author keywords

bioactivation; chemical induced toxicities; covalent binding; drug metabolism; protein adducts; proteomics; reactive intermediates

Indexed keywords

ELECTROPHILE;

EID: 84875743156     PISSN: 01926233     EISSN: 15331601     Source Type: Journal    
DOI: 10.1177/0192623312467399     Document Type: Article
Times cited : (5)

References (47)
  • 1
    • 0037093336 scopus 로고    scopus 로고
    • Assay of advanced glycation endproducts (AGEs): Surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N- hydroxysuccinimidyl- carbamate and application to N-epsilon-carboxymethyl- lysine- and N-epsilon-(1-carboxyethyl)lysine-modified albumin
    • Ahmed N., Argirov O. K., Minhas H. S., Cordeiro C. A., Thornalley P. J.. Assay of advanced glycation endproducts (AGEs): Surveying AGEs by chromatographic assay with derivatization by 6-aminoquinolyl-N- hydroxysuccinimidyl- carbamate and application to N-epsilon-carboxymethyl- lysine- and N-epsilon-(1-carboxyethyl)lysine-modified albumin. Biochem J. 2002 ; 364: 1-14
    • (2002) Biochem J , vol.364 , pp. 1-14
    • Ahmed, N.1    Argirov, O.K.2    Minhas, H.S.3    Cordeiro, C.A.4    Thornalley, P.J.5
  • 2
    • 14044251043 scopus 로고    scopus 로고
    • Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity
    • Ahmed N., Dobler D., Dean M., Thornalley P. J.. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem. 2005 ; 280: 5724-32
    • (2005) J Biol Chem , vol.280 , pp. 5724-5732
    • Ahmed, N.1    Dobler, D.2    Dean, M.3    Thornalley, P.J.4
  • 4
    • 84862692196 scopus 로고    scopus 로고
    • Glycation and biomarkers of vascular complications of diabetes
    • Beisswenger P. W.. Glycation and biomarkers of vascular complications of diabetes. Amino Acids. 2012 ; 42: 1171-83
    • (2012) Amino Acids , vol.42 , pp. 1171-1183
    • Beisswenger, P.W.1
  • 5
    • 0032510747 scopus 로고    scopus 로고
    • Evidence of high levels of methylglyoxal in cultured Chinese hamster ovary cells
    • Chaplen F. W. R., Fahl W. E., Cameron D. C.. Evidence of high levels of methylglyoxal in cultured Chinese hamster ovary cells. Proc Natl Acad Sci USA. 1998 ; 95: 5533-38
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 5533-5538
    • Chaplen, F.W.R.1    Fahl, W.E.2    Cameron, D.C.3
  • 6
    • 63249117650 scopus 로고    scopus 로고
    • Methylglyoxal, protein binding and biological samples: Are we getting the true measure?
    • Dhar A., Desai K., Liu J., Wu L.. Methylglyoxal, protein binding and biological samples: Are we getting the true measure?. J Chromatogr B. 2009 ; 877: 1093-100
    • (2009) J Chromatogr B , vol.877 , pp. 1093-1100
    • Dhar, A.1    Desai, K.2    Liu, J.3    Wu, L.4
  • 7
    • 0033857113 scopus 로고    scopus 로고
    • Aldose reductase and the role of the polyol pathway in diabetic nephropathy
    • Dunlop M.. Aldose reductase and the role of the polyol pathway in diabetic nephropathy. Kidney Int Suppl. 2000 ; 77: S3-12
    • (2000) Kidney Int Suppl , vol.77 , pp. 3-12
    • Dunlop, M.1
  • 8
    • 79960976076 scopus 로고    scopus 로고
    • The frequency of 1,4-benzoquinone-lysine adducts in cytochrome c are associated with defects in apoptosome activation
    • Fisher A. A., Labenski M. T., Malladi S., Chapman J. D., Bratton S. B., Monks T. J., Lau S. S.. The frequency of 1,4-benzoquinone-lysine adducts in cytochrome c are associated with defects in apoptosome activation. Toxicol Sci. 2011 ; 122: 64-72
    • (2011) Toxicol Sci , vol.122 , pp. 64-72
    • Fisher, A.A.1    Labenski, M.T.2    Malladi, S.3    Chapman, J.D.4    Bratton, S.B.5    Monks, T.J.6    Lau, S.S.7
  • 10
    • 80052998418 scopus 로고    scopus 로고
    • Exploring the biology of lipid peroxidation-derived protein carbonylation
    • Fritz K. S., Petersen D. R.. Exploring the biology of lipid peroxidation-derived protein carbonylation. Chem Res Toxicol. 2011 ; 24: 1411-19
    • (2011) Chem Res Toxicol , vol.24 , pp. 1411-1419
    • Fritz, K.S.1    Petersen, D.R.2
  • 12
    • 33750284754 scopus 로고    scopus 로고
    • Interaction of alpha-synuclein and dopamine metabolites in the pathogenesis of Parkinson's disease: A case for the selective vulnerability of the substantia nigra
    • Galvin J. E.. Interaction of alpha-synuclein and dopamine metabolites in the pathogenesis of Parkinson's disease: A case for the selective vulnerability of the substantia nigra. Acta Neuropathol. 2006 ; 112: 115-26
    • (2006) Acta Neuropathol , vol.112 , pp. 115-126
    • Galvin, J.E.1
  • 13
    • 52049088770 scopus 로고    scopus 로고
    • Oxidative stress and covalent modification of protein with bioactive aldehydes
    • Grimsrud P. A., Xie H., Griffin T. H., Bernlohr D. A.. Oxidative stress and covalent modification of protein with bioactive aldehydes. J Biol Chem. 2008 ; 283: 21837-41
    • (2008) J Biol Chem , vol.283 , pp. 21837-21841
    • Grimsrud, P.A.1    Xie, H.2    Griffin, T.H.3    Bernlohr, D.A.4
  • 14
    • 17444383114 scopus 로고    scopus 로고
    • P-Mod: An algorithm and software to map modifications to peptide sequences using tandem MS data
    • Hansen B. T., Davey S. W., Ham A. J., Liebler D. C.. P-Mod: An algorithm and software to map modifications to peptide sequences using tandem MS data. J Proteome Res. 2005 ; 4: 358-368
    • (2005) J Proteome Res , vol.4 , pp. 358-368
    • Hansen, B.T.1    Davey, S.W.2    Ham, A.J.3    Liebler, D.C.4
  • 15
    • 59649103839 scopus 로고    scopus 로고
    • Filing and mining the reactive metabolite target protein database
    • Hanzlik R. P., Fang J., Koen Y. M.. Filing and mining the reactive metabolite target protein database. Chem Biol Interact. 2009 ; 179: 38-44
    • (2009) Chem Biol Interact , vol.179 , pp. 38-44
    • Hanzlik, R.P.1    Fang, J.2    Koen, Y.M.3
  • 17
    • 84859711529 scopus 로고    scopus 로고
    • Role of advanced glycation endproducts and glyoxalase i in diabetic peripheral neuropathy
    • Jack M., Wright D.. Role of advanced glycation endproducts and glyoxalase I in diabetic peripheral neuropathy. Transl Res. 2012 ; 159: 355-65
    • (2012) Transl Res , vol.159 , pp. 355-365
    • Jack, M.1    Wright, D.2
  • 18
    • 77952650680 scopus 로고    scopus 로고
    • Systems analysis of protein modification and cellular responses induced by electrophile stress
    • Jacobs A. T., Marnett L. J.. Systems analysis of protein modification and cellular responses induced by electrophile stress. Acc Chem Res. 2011 ; 43: 673-83
    • (2011) Acc Chem Res , vol.43 , pp. 673-683
    • Jacobs, A.T.1    Marnett, L.J.2
  • 19
    • 50849091949 scopus 로고    scopus 로고
    • Capillary gas chromatographic deter-mination of methylglyoxal from serum of diabetic patients by precolumn derivatization with 1,2-diaminopropane
    • Khuhawar M. Y., Zardari L. A., Laghari A. J.. Capillary gas chromatographic deter-mination of methylglyoxal from serum of diabetic patients by precolumn derivatization with 1,2-diaminopropane. J Chromatogr B: Anal Technol Biomed Life Sci. 2008 ; 873: 15-19
    • (2008) J Chromatogr B: Anal Technol Biomed Life Sci , vol.873 , pp. 15-19
    • Khuhawar, M.Y.1    Zardari, L.A.2    Laghari, A.J.3
  • 20
    • 79958064063 scopus 로고    scopus 로고
    • New site(s) of methylglyoxal-modified human serum albumin, identified by multiple reaction monitoring, alter warfarin binding and prostaglandin metabolism
    • Kimzey M. J., Yassine H. N., Riepel B. M., Tsaprailis G., Monks T. J., Lau S. S.. New site(s) of methylglyoxal-modified human serum albumin, identified by multiple reaction monitoring, alter warfarin binding and prostaglandin metabolism. Chem Biol Interact. 2011 ; 192: 122-28
    • (2011) Chem Biol Interact , vol.192 , pp. 122-128
    • Kimzey, M.J.1    Yassine, H.N.2    Riepel, B.M.3    Tsaprailis, G.4    Monks, T.J.5    Lau, S.S.6
  • 21
    • 66649108045 scopus 로고    scopus 로고
    • Protein electrophile binding motifs: Lysine rich proteins are preferential targets of quinones
    • Labenski M. T., Fisher A. A., Lo H-H., Monks T. J., Lau S. S.. Protein electrophile binding motifs: Lysine rich proteins are preferential targets of quinones. Drug Metab Disp. 2009 ; 37: 1211-18
    • (2009) Drug Metab Disp , vol.37 , pp. 1211-1218
    • Labenski, M.T.1    Fisher, A.A.2    Lo, H.-H.3    Monks, T.J.4    Lau, S.S.5
  • 22
    • 0035155780 scopus 로고    scopus 로고
    • Carcinogenicity of a nephrotoxic metabolite of the "non- genotoxic" carcinogen hydroquinone
    • Lau S. S., Monks T. J., Everitt J. I., Kleymenova E., Walker C. W.. Carcinogenicity of a nephrotoxic metabolite of the "non-genotoxic" carcinogen hydroquinone. Chem Res Toxicol. 2001 ; 14: 25-33
    • (2001) Chem Res Toxicol , vol.14 , pp. 25-33
    • Lau, S.S.1    Monks, T.J.2    Everitt, J.I.3    Kleymenova, E.4    Walker, C.W.5
  • 23
    • 33744496005 scopus 로고    scopus 로고
    • The poisons within: Application of toxicity mechanisms to fundamental disease processes
    • Liebler D. C.. The poisons within: Application of toxicity mechanisms to fundamental disease processes. Chem Res Toxicol. 2006 ; 19: 610-13
    • (2006) Chem Res Toxicol , vol.19 , pp. 610-613
    • Liebler, D.C.1
  • 24
    • 38949089246 scopus 로고    scopus 로고
    • Protein damage by reactive electrophiles: Targets and consequences
    • Liebler D. C.. Protein damage by reactive electrophiles: Targets and consequences. Chem Res Toxicol. 2008 ; 21: 117-28
    • (2008) Chem Res Toxicol , vol.21 , pp. 117-128
    • Liebler, D.C.1
  • 25
    • 0030581151 scopus 로고    scopus 로고
    • Induction of apoptotic program in cell-free extracts: Requirement for dATP and cytochrome c
    • Liu X., Kim C. N., Yang J., Jemmerson R., Wang X.. Induction of apoptotic program in cell-free extracts: Requirement for dATP and cytochrome c. Cell. 1996 ; 86: 147-57
    • (1996) Cell , vol.86 , pp. 147-157
    • Liu, X.1    Kim, C.N.2    Yang, J.3    Jemmerson, R.4    Wang, X.5
  • 26
    • 84857891632 scopus 로고    scopus 로고
    • On PAR with PARP: Cellular stress signaling through poly(ADP-ribose) and PARP-1
    • Luo X., Kraus W. L.. On PAR with PARP: Cellular stress signaling through poly(ADP-ribose) and PARP-1. Genes and Dev. 2012 ; 26: 417-32
    • (2012) Genes and Dev , vol.26 , pp. 417-432
    • Luo, X.1    Kraus, W.L.2
  • 27
    • 0031020476 scopus 로고    scopus 로고
    • A role for 4-hydroxynonenal, an aldehydic product of lipid peroxidation, in disruption of ion homeostasis and neuronal death induced by amyloid beta-peptide
    • Mark R. J., Lovell M. A., Markesbery W. R., Uchida K., Mattson M. P.. A role for 4-hydroxynonenal, an aldehydic product of lipid peroxidation, in disruption of ion homeostasis and neuronal death induced by amyloid beta-peptide. J Neurochem. 1997 ; 68: 255-64
    • (1997) J Neurochem , vol.68 , pp. 255-264
    • Mark, R.J.1    Lovell, M.A.2    Markesbery, W.R.3    Uchida, K.4    Mattson, M.P.5
  • 28
    • 10844229438 scopus 로고    scopus 로고
    • Increase in molecular rigidity of the protein conformation of brain Na+-K+-ATPase by modification with 4-hydroxy-2-nonenal
    • Miyake H., Kadoya A, Ohyashiki T.. Increase in molecular rigidity of the protein conformation of brain Na+-K+-ATPase by modification with 4-hydroxy-2-nonenal. Biol Pharm Bull. 2003 ; 26: 1652-56
    • (2003) Biol Pharm Bull , vol.26 , pp. 1652-1656
    • Miyake, H.1    Kadoya, A.2    Ohyashiki, T.3
  • 29
    • 0025785533 scopus 로고
    • Oxidative modification by low levels of HOOH can transform myoglobin to an oxidase
    • Osawa Y., Korzekwa K.. Oxidative modification by low levels of HOOH can transform myoglobin to an oxidase. Proc Natl Acad Sci USA. 1991 ; 88: 587-94
    • (1991) Proc Natl Acad Sci USA , vol.88 , pp. 587-594
    • Osawa, Y.1    Korzekwa, K.2
  • 31
    • 84866848255 scopus 로고    scopus 로고
    • 4-Hydroxy-2-nonenal, a reactive product of lipid peroxidation, and neurodegenerative diseases: A toxic combination illuminated by redox proteomics studies
    • Perluigi M., Coccia R., Butterfield D. A.. 4-Hydroxy-2-nonenal, a reactive product of lipid peroxidation, and neurodegenerative diseases: A toxic combination illuminated by redox proteomics studies. Antioxd Redox Signal. 2012 ; 17: 1590-1609
    • (2012) Antioxd Redox Signal , vol.17 , pp. 1590-1609
    • Perluigi, M.1    Coccia, R.2    Butterfield, D.A.3
  • 32
    • 0037986377 scopus 로고    scopus 로고
    • An integrated approach to identifying chemically induced post-translational modifications using comparative MALDI-MS and targeted HPLC-ESI-MS/MS
    • Person M. D., Monks T. J., Lau S. S.. An integrated approach to identifying chemically induced post-translational modifications using comparative MALDI-MS and targeted HPLC-ESI-MS/MS. Chem Res Toxicol. 2003 ; 16: 598-608
    • (2003) Chem Res Toxicol , vol.16 , pp. 598-608
    • Person, M.D.1    Monks, T.J.2    Lau, S.S.3
  • 33
    • 12144255851 scopus 로고    scopus 로고
    • Alkylation of cytochrome c by (glutathion-S-yl)-1,4-benzoquinone and iodoacetamide demonstrates compound dependent site specificity
    • Person M. D., Mason D. E., Liebler D. C., Monks T. J., Lau S. S.. Alkylation of cytochrome c by (glutathion-S-yl)-1,4-benzoquinone and iodoacetamide demonstrates compound dependent site specificity. Chem Res Toxicol. 2005 ; 18: 41-50
    • (2005) Chem Res Toxicol , vol.18 , pp. 41-50
    • Person, M.D.1    Mason, D.E.2    Liebler, D.C.3    Monks, T.J.4    Lau, S.S.5
  • 34
    • 0027422270 scopus 로고
    • An immunochemical approach of identifying and characterizing protein targets of reactive metabolites
    • Pohl L. R.. An immunochemical approach of identifying and characterizing protein targets of reactive metabolites. Chem Res Toxicol. 1993 ; 6: 786-93
    • (1993) Chem Res Toxicol , vol.6 , pp. 786-793
    • Pohl, L.R.1
  • 35
    • 79955945923 scopus 로고    scopus 로고
    • Glyoxalase in diabetes, obesity and related disorders
    • Rabbani N., Thornalley P. J.. Glyoxalase in diabetes, obesity and related disorders. Semin Cell Dev Biol. 2011 ; 22: 309-17
    • (2011) Semin Cell Dev Biol , vol.22 , pp. 309-317
    • Rabbani, N.1    Thornalley, P.J.2
  • 36
    • 77956393934 scopus 로고    scopus 로고
    • Alpha-synuclein, lipids and Parkinson's disease
    • Ruiperez V., Darios F., Davietov B.. Alpha-synuclein, lipids and Parkinson's disease. Prog Lipid Res. 2010 ; 49: 420-28
    • (2010) Prog Lipid Res , vol.49 , pp. 420-428
    • Ruiperez, V.1    Darios, F.2    Davietov, B.3
  • 37
    • 0021816377 scopus 로고
    • Immunological studies on the mechanism of halothane-induced hepatotoxicity; Immunohistochemical evidence for trifluoroacetylated hepatocytes
    • Satoh H., Fukuda Y., Anderson D. K., Ferrans V. J., Gillette J. R., Pohl L. R.. Immunological studies on the mechanism of halothane-induced hepatotoxicity; immunohistochemical evidence for trifluoroacetylated hepatocytes. J Pharmacol Exp Ther. 1985 ; 233: 857-62
    • (1985) J Pharmacol Exp Ther , vol.233 , pp. 857-862
    • Satoh, H.1    Fukuda, Y.2    Anderson, D.K.3    Ferrans, V.J.4    Gillette, J.R.5    Pohl, L.R.6
  • 38
    • 0242689518 scopus 로고
    • Human anti-endoplasmic reticulum antibodies in sera of patients with halothane-induced hepatitis are directed against a trifluoroacetylated carboxylesterase
    • Satoh H., Martin B. M., Schulick A.H, Christ D. D., Kenna J. G., Pohl L. R.. Human anti-endoplasmic reticulum antibodies in sera of patients with halothane-induced hepatitis are directed against a trifluoroacetylated carboxylesterase. Proc Natl Acad Sci USA. 1989 ; 86: 322-26
    • (1989) Proc Natl Acad Sci USA , vol.86 , pp. 322-326
    • Satoh, H.1    Martin, B.M.2    Schulick, A.H.3    Christ, D.D.4    Kenna, J.G.5    Pohl, L.R.6
  • 41
    • 80053004364 scopus 로고    scopus 로고
    • Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: A perspective based on the critical examination of trends in the top 200 drugs marketed in the United States
    • Stepan A. F., Walker D. P., Bauman J., Price D. A., Baillie T. A., Kalgutkar A. S., Aleo M. D.. Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: A perspective based on the critical examination of trends in the top 200 drugs marketed in the United States. Chem Res Toxicol. 2011 ; 24: 1345-410
    • (2011) Chem Res Toxicol , vol.24 , pp. 1345-1410
    • Stepan, A.F.1    Walker, D.P.2    Bauman, J.3    Price, D.A.4    Baillie, T.A.5    Kalgutkar, A.S.6    Aleo, M.D.7
  • 42
    • 4644231059 scopus 로고    scopus 로고
    • Advanced glycation and advanced lipoxidation: Possible role in initiation and progression of diabetic retinopathy
    • Stitt A. W., Frizzell N., Thorpe S. R.. Advanced glycation and advanced lipoxidation: Possible role in initiation and progression of diabetic retinopathy. Curr Pharm Des. 2004 ; 10: 3349-60
    • (2004) Curr Pharm des , vol.10 , pp. 3349-3360
    • Stitt, A.W.1    Frizzell, N.2    Thorpe, S.R.3
  • 43
    • 0030176306 scopus 로고    scopus 로고
    • Pharmacology of methylglyoxal: Formation, modification of proteins and nucleic acids, and enzymatic detoxification - A role in pathogenesis and antiproliferative chemotherapy
    • Thornalley P. J.. Pharmacology of methylglyoxal: Formation, modification of proteins and nucleic acids, and enzymatic detoxification - a role in pathogenesis and antiproliferative chemotherapy. Gen Pharmacol. 1996 ; 27: 565-73
    • (1996) Gen Pharmacol , vol.27 , pp. 565-573
    • Thornalley, P.J.1
  • 44
    • 69249114181 scopus 로고    scopus 로고
    • Highlights and hotspots of protein glycation in end-stage renal disease
    • Thornalley P. J., Rabbani N.. Highlights and hotspots of protein glycation in end-stage renal disease. Semin Dial. 2009 ; 22: 400-4
    • (2009) Semin Dial , vol.22 , pp. 400-404
    • Thornalley, P.J.1    Rabbani, N.2
  • 45
    • 0036183402 scopus 로고    scopus 로고
    • Structural insights into human serum albumin-mediated prostaglandin catalysis
    • Yang J. S., Petersen C. E., Ha C. E., Bhagavan N. V.. Structural insights into human serum albumin-mediated prostaglandin catalysis. Protein Sci. 2002 ; 11: 538-45
    • (2002) Protein Sci , vol.11 , pp. 538-545
    • Yang, J.S.1    Petersen, C.E.2    Ha, C.E.3    Bhagavan, N.V.4
  • 46
    • 0035918306 scopus 로고    scopus 로고
    • A mutational epitope for cytochrome c binding to the apoptosis protease activation factor-1
    • Yu T., Wang X., Purring-Koch C., Wei Y., McLendon G. L.. A mutational epitope for cytochrome c binding to the apoptosis protease activation factor-1. J Biol Chem. 2001 ; 276: 13034-38
    • (2001) J Biol Chem , vol.276 , pp. 13034-13038
    • Yu, T.1    Wang, X.2    Purring-Koch, C.3    Wei, Y.4    McLendon, G.L.5
  • 47
    • 0030745646 scopus 로고    scopus 로고
    • Apaf-1, a human protein homologous to C. elegans CED-4, participates in cytochrome c-dependent activation of caspase-3
    • Zou H., Henzel W. J., Liu X., Lutschg A., Wang X.. Apaf-1, a human protein homologous to C. elegans CED-4, participates in cytochrome c-dependent activation of caspase-3. Cell. 1997 ; 90: 405-413
    • (1997) Cell , vol.90 , pp. 405-413
    • Zou, H.1    Henzel, W.J.2    Liu, X.3    Lutschg, A.4    Wang, X.5


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