Quinone-induced protein modifications: Kinetic preference for reaction of 1,2-benzoquinones with thiol groups in proteins

Free Radical Biology and Medicine

Volumn 97, Issue , 2016, Pages 148-157

  Li, Yuting ^a,b   Jongberg, Sisse ^b   Andersen, Mogens L ^b   Davies, Michael J ^c   Lund, Marianne N ^b,c  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Plant phenols; Protein modification; Quinone protein adduct; Rate constants; Thiols

Indexed keywords

ALPHA LACTALBUMIN; ARGININE; BENZOQUINONE DERIVATIVE; BOVINE SERUM ALBUMIN; GUANIDINE; HUMAN SERUM ALBUMIN; NITROGEN; NUCLEOPHILE; QUINONE DERIVATIVE; THIOL GROUP; 4-METHYLBENZOQUINONE; AMINE; ANTIOXIDANT; CYSTEINE; POLYPHENOL; THIOL DERIVATIVE;

ADDUCTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HUMAN; KINETICS; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; NUCLEOPHILICITY; OBSERVED RATE CONSTANT; PRIORITY JOURNAL; PROTEIN MODIFICATION; TANDEM MASS SPECTROMETRY; ULTRAVIOLET RADIATION; ULTRAVIOLET SPECTROPHOTOMETRY; ANIMAL; BOVINE; CHEMISTRY; DRUG EFFECTS; METABOLISM; OXIDATION REDUCTION REACTION; PROTEIN PROCESSING;

AMINES; ANIMALS; ANTIOXIDANTS; BENZOQUINONES; CATTLE; CHROMATOGRAPHY, LIQUID; CYSTEINE; HUMANS; OXIDATION-REDUCTION; POLYPHENOLS; PROTEIN PROCESSING, POST-TRANSLATIONAL; SERUM ALBUMIN, BOVINE; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFHYDRYL COMPOUNDS; TANDEM MASS SPECTROMETRY;

EID: 84973304277     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2016.05.019     Document Type: Article

References (51)

1. S. Bittner When quinones meet amino acids: chemical, physical and biological consequences Amino Acids 30 2006 205 224
2. V. Nair, R.S. Menon, A.T. Biju, and K.G. Abhilash 1,2-Benzoquinones in Diels-Alder reactions, dipolar cycloadditions, nucleophilic additions, multicomponent reactions and more Chem. Soc. Rev. 41 2012 1050 1059
3. J. Kroll, H.M. Rawel, and S. Rohn Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds Food Sci. Technol. Res. 9 2003 205 218
4. C. Le Bourvellec, and C.M.G.C. Renard Interactions between polyphenols and macromolecules: quantification methods and mechanisms Crit. Rev. Food Sci. Nutr. 52 2012 213 248
5. D. Del Rio, A. Rodriguez-Mateos, J.P.E. Spencer, M. Tognolini, G. Borges, and A. Crozier Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases Antiox. Redox Signal. 18 2013 1818 1892
6. J.L. Bolton, M.A. Trush, T.M. Penning, G. Dryhurst, and T.J. Monks Role of quinones in toxicology Chem. Res. Toxicol. 13 2000 135 160
7. V.M. Totlani, and D.G. Peterson Epicatechin carbonyl-trapping reactions in aqueous Maillard systems: identification and structural elucidation J. Agric. Food Chem. 54 2006 7311 7318
8. M. Kim, S.J. Lim, H.-J. Lee, and C.W. Nho Cassia tora seed extract and its active compound aurantio-obtusin inhibit allergic responses in IgE-mediated mast cells and analphylactic models J. Agric. Food Chem. 63 2015 9037 9046
9. T.J. Monks, R.P. Hanzlik, G.M. Cohen, D. Ross, and D.G. Graham Quinone chemistry and toxicity Toxicol. Appl. Pharmacol. 112 1992 2 16
10. K. Morita, H. Arimochi, and Y. Ohnishi In vitro cytotoxicity of 4-methylcatechol in murine tumor cells: induction of apoptotic cell death by extracellular pro-oxidant action J. Pharmacol. Exp. Ther. 306 2003 317 323
11. A. Ghosh, A. Choudbury, A. Das, N.S. Chatterjee, T. Das, R. Chowdbury, and et al. Cigarette smoke induces p-benzoquinone-albumin adduct in blood serum: implications on structure and ligand binding properties Toxicology 292 2012 78 89
12. A. Srinivasan, L. Robertson, and G. Ludewig Sulfhydryl binding and topoisomerase inhibition by PCB metabolites Chem. Res. Toxicol. 15 2002 497 505
13. C.H. Tsai, P.H. Lin, S. Waidyanatha, and S.M. Rappaport Characterization of metabolic activation of pentachlorophenol to quinones and semiquinones in rodent liver Chem. Biol. Interact. 134 2001 55 71
14. P.J. O'Brien Molecular mechanisms of quinone cytotoxicity Chem. Biol. Interact. 80 1991 1 41
15. T. Satoh, S.R. McKercher, and S.A. Lipton Nrf2/ARE-mediated antioxidant actions of pro-electrophilic drugs Free Radic. Biol. Med. 65 2013 645 657
16. V.K. Tandon, and S. Kumar Recent development on naphtoquinone derivatives and their therapeutic applications as anticancer agents Expert Opin. Ther. Pat. 23 2013 1087 1108
17. S.S. Lau, C.L. Kuhlman, S.B. Bratton, and T.J. Monks Role of hydroquinone-thiol conjugates in benzene-mediated toxicity Chem. Biol. Interact. 184 2010 212 217
18. A.W. Boots, G.R. Haenen, G.J. den Hartog, and A. Bast Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants Biochim. Biophys. Acta- Mol. Cell Biol. Lipids 1583 2002 279 284
19. J.R. Rees, and A. Pirie Possible reactions of 1,2-naphthaquinone in the eye Biochem. J. 102 1967 853 863
20. A.L. Waterhouse Wine phenolics Ann. N.Y. Acad. Sci. 957 2002 21 36
21. S. Jongberg, N.E. Gislason, M.N. Lund, L.H. Skibsted, and A.L. Waterhouse Thiol-quinone adduct formation in myofibrillar proteins detected by LC-MS J. Agric. Food Chem. 59 2011 6900 6905
22. S. Jongberg, M.A. Tørngren, A. Gunvig, L.H. Skibsted, and M.N. Lund Effect of green tea or rosemary extract on protein oxidation in Bologna type sausages prepared from oxidatively stressed pork Meat Sci. 93 2013 538 546
23. S. Jongberg, L.S. Terkelsen, R. Miklos, and M.N. Lund Green tea extract impair meat emulsion properties by disturbing protein disulfide cross-linking Meat Sci. 100 2015 2 9
24. A.A. Fisher, M.T. Labenski, S. Malladi, V. Gokhale, M.E. Bowen, R.S. Milleron, and et al. Quinone electrophiles selectively adduct "electrophile binding motifs" within cytochrome c Biochemistry 46 2007 11090 11100
25. A.A. Fisher, M.T. Labenski, S. Malladi, J.D. Chapman, S.B. Bratton, T.J. Monks, and et al. The frequency of 1,4-benzoquinone-lysine adducts in cytochrome c correlate with defects in apoptosome activation Toxicol. Sci 122 2011 64 72
26. J. Yin, R.V. Hedegaard, L.H. Skibsted, and M.L. Andersen Epicatechin and epigallocatechin gallate inhibit formation of intermediary radicals during heating of lysine and glucose Food Chem. 146 2014 48 55
27. P.V. Guerra, and V.A. Yaylayan Interaction of flavanols with amino acids: postoxidative reactivity of the B-ring of catechin with Glycine J. Agric. Food Chem. 62 2014 3831 3836
28. J.R. Whitaker, A.G. Voragen, and D.W. Wong Handbook of Food Enzymology 2003 Taylor and Francis Group LLC Abingdon, UK
29. A. Aitken, and M. Learmonth Protein determination by UV absorption J.M. Walker, The Protein Protocols Handbook 1996 Springer, Science & Business Media New York, US 3 6
30. G.N.L. Jameson, J. Zhang, R.F. Jameson, and W. Linert Kinetic evidence that cysteine reacts with dopaminoquinone via reversible adduct formation to yield 5-cysteinyl-dopamine: an important precursor of neuromelanin Org. Biomol. Chem. 2 2004 777 782
31. F. Scholz Electroanalytical Methods: Guide to Experiments and Applications 2009 Springer Science & Business Media New York, US
32. S. Shahrokhian, and S. Rastgar Investigation of the electrochemical behavior of catechol and 4-methylcatechol in the presence of methyl mercapto thiadiazol as a nucleophile: application to electrochemical synthesis J. Appl. Electrochem. 40 2010 115 122
33. L. Turell, R. Radi, and B. Alvarez The thiol pool in human plasma: the central contribution of albumin to redox processes Free Radic. Biol. Med. 65 2013 244 253
34. W. Pierpoint o-Quinones formed in plant extracts. Their reactions with amino acids and peptides Biochem. J. 112 1969 609 616
35. D. Nematollahi, and M. Hesari Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives J. Electroanal. Chem. 577 2005 197 203
36. D. Metodiewa, A.K. Jaiswal, N. Cenas, E. Dickancaité, and J. Segura-Aguilar Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product Free Radic. Biol. Med. 26 1999 107 116
37. W. Bors, C. Michel, and S. Schikora Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: a pulse radiolysis study Free Radic. Biol. Med. 19 1995 45 52
38. N. Watanabe, D.A. Dickinson, R.-M. Liu, and H.J. Forman Quinones and glutathione metabolism Methods Enzymol. 378 2004 319 340
39. C. Hansson, G. Agrup, H. Rorsman, A.-M. Rosengren, E. Rosengren, and L.-E. Edholm Analysis of cysteinyldopas, dopa, dopamine, noradrenaline and adrenaline in serum and urine using high-performance liquid chromatography and electrochemical detection J. Chromatogr. 162 1979 7 22
40. V. Cheynier, J. Rigaud, and M. Moutounet Oxidation kinetics of transcaffeoyltartrate and its glutathione derivatives in grape musts Phytochemistry 29 1990 1751 1753
41. A.W. Boots, N. Kubben, G.R. Haenen, and A. Bast Oxidized quercetin reacts with thiols rather than with ascorbate: implication for quercetin supplementation Biochem. Biophys. Res. Commun. 308 2003 560 565
42. T.A. McDonald, K. Yeowell-O'Connell, and S.M. Rappaport Comparison of protein adducts of benzene oxide and benzoquinone in the blood and bone marrow of rats and mice exposed to [14C/13C6] benzene Cancer Res. 54 1994 4907 4919
43. D.C.S. Tse, R.L. McCreery, and R.N. Adams Potential oxidative pathways of brain catecholamines J. Med. Chem. 19 1976 37 40
44. G. Ferrer-Sueta, B. Manta, H. Botti, R. Radi, M. Trujillo, and A. Denicola Factors affecting protein thiol reactivity and specificity in peroxide reduction Chem. Res. Toxicol. 24 2011 434 450
45. C.C. Winterbourn, and D. Metodiewa Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide Free Radic. Biol. Med. 27 1999 322 328
46. M.D. Person, D.E. Mason, D.C. Liebler, T.J. Monks, and S.S. Lau Alkylation of cytochrome c by (glutathion-S-yl)-1,4-benzoquinone and iodoacetamide demonstrates compound-dependent site specificity Chem. Res. Toxicol. 18 2005 41 50
47. T.A. Gerken Amino group environments and metal binding properties of carbon-13 reductively methylated bovine a-lactalbumin Biochemistry 23 1984 4688 4697
48. S. Hoff, M.N. Lund, M.A. Petersen, B.M. Jespersen, and M.L. Andersen Influence of malt roasting on the oxidative stability of sweet wort J. Agric. Food Chem. 60 2012 5652 5659
49. J.L. Bolton, and G.R. Thatcher Potential mechanisms of estrogen quinone carcinogenesis Chem. Res. Toxicol. 21 2008 93 101
50. Y.J. Surh, J.K. Kundu, and H.K. Na Nrf2 as a master redox switch in turning on the cellular signaling involved in the induction of cytoprotective genes by some chemopreventive phytochemicals Planta Med. 74 2008 1526 1539
51. T. Suzuki, and M. Yamamoto Molecular basis of the Keap1-Nrf2 system Free Radic. Biol. Med. 88 2015 93 100