Amino acid chloramine damage to proliferating cell nuclear antigen in mammalian cells

In Vivo

Volumn 26, Issue 4, 2012, Pages 501-518

  Salama, Samir A ^a,b,d   Snapka, Robert M ^a,b,c  

^a THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b OHIO STATE UNIVERSITY   (United States)

^c OHIO STATE UNIVERSITY   (United States)

^d Al Azhar University   (Egypt)

Author keywords

Amino acid chloramines; HOCl; Inflammation; PCNA; Protein damage

Indexed keywords

ARGININE DERIVATIVE; CYCLINE; CYSTEINE; EPITOPE; GLYCINE DERIVATIVE; HISTIDINE DERIVATIVE; METHIONINE; METHIONINE SULFOXIDE; PROLINE DERIVATIVE; SULFENAMIDE DERIVATIVE; SULFINAMIDE; SULFONAMIDE; TAURINE DERIVATIVE; TOSYLCHLORAMIDE SODIUM; TYROSINE;

ANIMAL CELL; ARTICLE; CELL DAMAGE; CELL NUCLEUS; CELL PROLIFERATION; CONTROLLED STUDY; CROSS LINKING; ELECTROPHORETIC MOBILITY; HUMAN; HUMAN CELL; INTERSTITIAL FLUID; MAMMAL CELL; MASS SPECTROMETRY; NONHUMAN; WESTERN BLOTTING;

EID: 84865105736     PISSN: 0258851X     EISSN: 17917549     Source Type: Journal    
DOI: None     Document Type: Article

References (66)

1. Klebanoff SJ: Myeloperoxidase: friend and foe. J Leukoc Biol 77: 598-625, 2005.
2. Winterbourn CC: Reconciling the chemistry and biology of reactive oxygen species. Nat Chem Biol 4: 278-286, 2008.
3. Hansson GK and Nilsson J: Introduction: atherosclerosis as inflammation: a controversial concept becomes accepted. J Intern Med 263: 462-463, 2008. (Pubitemid 351533559)
4. Mantovani A, Allavena P, Sica A and Balkwill F: Cancer-related inflammation. Nature 454: 436-444, 2008.
5. McGeer PL, Rogers J and McGeer EG: Inflammation, antiinflammatory agents and Alzheimer disease: the last 12 years. J Alzheimers Dis 9: 271-276, 2006. (Pubitemid 44253320)
6. Wilms H, Zecca L, Rosenstiel P, Sievers J, Deuschl G and Lucius R: Inflammation in Parkinson's diseases and other neurodegenerative diseases: cause and therapeutic implications. Curr Pharm Des 13 : 1925-1928, 2007. (Pubitemid 47017994)
7. Weiss SJ and LoBuglio AF: Phagocyte-generated oxygen metabolites and cellular injury. Lab Invest 47 : 5-18, 1982. (Pubitemid 12098892)
8. Pattison DI, Hawkins CL and Davies MJ: What Are the Plasma Targets of the Oxidant Hypochlorous Acid? A Kinetic Modeling Approach. Chem Res Toxicol 22 : 807-817, 2009.
9. Pattison DI and Davies MJ: Kinetic analysis of the role of histidine chloramines in hypochlorous acid mediated protein oxidation. Biochem 44: 7378-7387, 2005. (Pubitemid 40656681)
10. Pattison DI and Davies MJ: Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: implications for the prevention of hypochlorous-acid-mediated damage. Biochem 45 : 8152-8162, 2006. (Pubitemid 43993236)
11. Peskin AV and Winterbourn CC: Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. Free Radical Biol Med 30 : 572-579, 2001. (Pubitemid 32162964)
12. Midwinter RG, Peskin AV, Vissers MC and Winterbourn CC: Extracellular oxidation by taurine chloramine activates ERK via the epidermal growth factor receptor. J Biol Chem 279: 32205- 32211, 2004.
13. Midwinter RG, Cheah FC, Moskovitz J, Vissers MC and Winterbourn CC: IkappaB is a sensitive target for oxidation by cell-permeable chloramines: inhibition of NF-kappaB activity by glycine chloramine through methionine oxidation. Biochem J 396: 71-78, 2006. (Pubitemid 43764498)
14. Robaszkiewicz A, Bartosz G and Soszynski M: Effect of Nchloroamino acids on the erythrocyte. Free Radical Res 42 : 30- 39, 2008.
15. Yang J, Ji R, Cheng Y, Sun JZ, Jennings LK and Zhang C: Larginine chlorination results in the formation of a nonselective nitric-oxide synthase inhibitor. J Pharmacol Exp Ther 318: 1044- 1049, 2006.
16. Zhang C, Reiter C, Eiserich JP, Boersma B, Parks DA, Beckman JS, Barnes S, Kirk M, Baldus S, Darley-Usmar VM and White CR: L-Arginine chlorination products inhibit endothelial nitric oxide production. J Biol Chem 276 : 27159- 27165, 2001.
17. Peskin AV, Midwinter RG, Harwood DT and Winterbourn CC: Chlorine transfer between glycine, taurine, and histamine: reaction rates and impact on cellular reactivity. Free Radical Biol Med 38 : 397-405, 2005.
18. Thomas EL, Grisham MB and Jefferson MM: Cytotoxicity of chloramines. Methods Enzymol 132: 585-593, 1986.
19. Sizeneva IP, Kondrashova NB and Val'tsifer VA: Spontaneous decomposition of industrially manufactured sodium hypochlorite solutions. Russ J Appl Chem 78: 541-545, 2005. (Pubitemid 40960546)
20. Morris JC: The acid ionization constant of hypochlorous acid from 5 to 35 degrees. J Phys Chem 70 : 3798-3805, 1966.
21. Dypbukt JM, Bishop C, Brooks WM, Thong B, Eriksson H, and Kettle AJ: A sensitive and selective assay for chloramine production by myeloperoxidase. Free Radic Biol Med 39: 1468- 1477, 2005.
22. Thomas EL, Grisham MB and Jefferson MM: Preparation and characterization of chloramines. Methods Enzymol 132 : 569- 585, 1986.
23. Bae SI, Zhao R, and Snapka RM: PCNA damage caused by antineoplastic drugs. Biochem Pharmacol 76 : 1653-1668, 2008.
24. Naryzhny SN, Desouza LV, Siu KW and Lee H: Characterization of the human proliferating cell nuclear antigen physico-chemical properties: aspects of double trimer stability. Biochem Cell Biol 84: 669-676, 2006. (Pubitemid 46121590)
25. Zhang P, Zhang SJ, Zhang Z, Woessner JF Jr. and Lee MY: Expression and physicochemical characterization of human proliferating cell nuclear antigen. Biochem 34 : 10703-10712, 1995.
26. Englert RP and Shacter E: Distinct modes of cell death induced by different reactive oxygen species: amino acyl chloramines mediate hypochlorous acid-induced apoptosis. J Biol Chem 277: 20518-20526, 2002. (Pubitemid 34967351)
27. Test ST, Lampert MB, Ossanna PJ, Thoene JG and Weiss SJ: Generation of nitrogen-chlorine oxidants by human phagocytes. J Clin Invest 74 : 1341-1349, 1984. (Pubitemid 15206830)
28. Weiss SJ: Tissue destruction by neutrophils. New Eng J Med 320 : 365-376, 1989.
29. Summers FA, Morgan PE, Davies MJ and Hawkins CL: Identification of plasma proteins that are susceptible to thiol oxidation by hypochlorous acid and N-chloramines. Chem Res Toxicol 21: 1832-1840, 2008.
30. Lampert MB and Weiss SJ: The chlorinating potential of the human monocyte. Blood 62: 645-651, 1983. (Pubitemid 13001698)
31. Weiss SJ, Klein R, Slivka A and Wei M: Chlorination of taurine by human neutrophils. Evidence for hypochlorous acid generation. J Clin Invest 70: 598-607, 1982. (Pubitemid 12054584)
32. Sloop CH, Dory L and Roheim PS: Interstitial fluid lipoproteins. J Lipid Res 28: 225-237, 1987. (Pubitemid 17042840)
33. Zurovsky Y, Mitchell G and Hattingh J: Composition and viscosity of interstitial fluid of rabbits. Exp Physiol 80: 203-207, 1995.
34. Brosnan JT: Interorgan amino acid transport and its regulation. J Nutr 133 : 2068S-2072S, 2003.
35. Waterval WA, Scheijen JL, Ortmans-Ploemen MM, Habets-van der Poel CD and Bierau J: Quantitative UPLC-MS/MS analysis of underivatised amino acids in body fluids is a reliable tool for the diagnosis and follow-up of patients with inborn errors of metabolism. Clin Chim Acta 407: 36-42, 2009.
36. Wiig H, Reed RK, and Tenstad O: Interstitial fluid pressure, composition of interstitium, and interstitial exclusion of albumin in hypothyroid rats. Am J Physiol Heart Circ Physiol 278: H1627-H1639, 2000. (Pubitemid 30395576)
37. Kanayama A, Inoue J, Sugita-Konishi Y, Shimizu M and Miyamoto Y: Oxidation of IkappaBalpha at methionine 45 is one cause of taurine chloramine-induced inhibition of NF-kappa B activation. J Biol Chem 277: 24049-24056, 2002. (Pubitemid 34951917)
38. Le DT, Liang X, Fomenko DE, Raza AS, Chong CK, Carlson BA, Hatfield DL and Gladyshev VN: Analysis of methionine/ selenomethionine oxidation and methionine sulfoxide reductase function using methionine-rich proteins and antibodies against their oxidized forms. Biochem 47: 6685-6694, 2008. (Pubitemid 351874295)
39. Sroussi HY, Berline J and Palefsky JM: Oxidation of methionine 63 and 83 regulates the effect of S100A9 on the migration of neutrophils in vitro . J Leukoc Biol 81: 818-824, 2007. (Pubitemid 46393560)
40. Neumann NP: Oxidation with hydrogen peroxide. In: Methods in Enzymology. C.H.W. Hirs, S.N. Timasheff (eds.). New York, Academic Press Inc., 25(Part B): 393-400, 1972.
41. Oien DB, Canello T, Gabizon R, Gasset M, Lundquist BL, Burns JM and Moskovitz J: Detection of oxidized methionine in selected proteins, cellular extracts and blood serums by novel anti-methionine sulfoxide antibodies. Arch Biochem Biophys 485 : 35-40, 2009.
42. Wenz F, Azzam EI, and Little JB: The response of proliferating cell nuclear antigen to ionizing radiation in human lymphoblastoid cell lines is dependent on p53. Rad Research 149: 32-40, 1998. (Pubitemid 28022893)
43. Zhao R, Hammitt R, Thummel RP, Liu Y, Turro C and Snapka RM: Nuclear targets of photodynamic tridentate ruthenium complexes. Dalton Trans pp. 10926-10931, 2009.
44. Hawkins CL and Davies MJ: Hypochlorite-induced oxidation of proteins in plasma: formation of chloramines and nitrogencentred radicals and their role in protein fragmentation. Biochem J 340(Pt 2) : 539-548, 1999. (Pubitemid 29286577)
45. Krishna TS, Kong XP, Gary S, Burgers PM and Kuriyan J: Crystal structure of the eukaryotic DNA polymerase processivity factor PCNA. Cell 79: 1233-1243, 1994.
46. Pattison DI, Hawkins CL and Davies MJ: Hypochlorous acidmediated protein oxidation: how important are chloramine transfer reactions and protein tertiary structure? Biochem 46: 9853-9864, 2007. (Pubitemid 47328591)
47. Montaner B, O'Donovan P, Reelfs O, Perrett CM, Zhang X, Xu YZ, Ren X, MacPherson P, Frith D and Karran P: Reactive oxygen-mediated damage to a human DNA replication and repair protein. EMBO Rep 8 : 1074-1079, 2007. (Pubitemid 350042344)
48. Winterbourn CC and Brennan SO: Characterization of the oxidation products of the reaction between reduced glutathione and hypochlorous acid. Biochem J 326(Pt 1) : 87-92, 1997. (Pubitemid 27386921)
49. Klamt F and Shacter E: Taurine chloramine, an oxidant derived from neutrophils, induces apoptosis in human B lymphoma cells through mitochondrial damage. J Biol Chem 280: 21346-21352, 2005. (Pubitemid 40805697)
50. Roos G, Landberg G, Huff JP, Houghten R, Takasaki Y and Tan EM: Analysis of the epitopes of proliferating cell nuclear antigen recognized by monoclonal antibodies. Lab Invest 68: 204-210, 1993. (Pubitemid 23084293)
51. Bergt C, Fu X, Huq NP, Kao J and Heinecke JW: Lysine residues direct the chlorination of tyrosines in YXXK motifs of apolipoprotein A-I when hypochlorous acid oxidizes high density lipoprotein. J Biol Chem 279 : 7856-7866, 2004. (Pubitemid 38294672)
52. Weisshart K, Friedl S, Taneja P, Nasheuer HP, Schlott B, Grosse F and Fanning E: Partial proteolysis of simian virus 40 T antigen reveals intramolecular contacts between domains and conformation changes upon hexamer assembly. J Biol Chem 279 : 38943-38951, 2004. (Pubitemid 39296055)
53. Hawkins CL and Davies MJ: Hypochlorite-induced damage to proteins: formation of nitrogen-centred radicals from lysine residues and their role in protein fragmentation. Biochem J 332(Pt 3) : 617-625, 1998. (Pubitemid 28306685)
54. Heinecke JW: Oxidative stress: new approaches to diagnosis and prognosis in atherosclerosis. Am J Cardiol 91: 12A-16A, 2003.
55. Stocker R and Keaney JF, Jr.: Role of oxidative modifications in atherosclerosis. Physiol Rev 84: 1381-1478, 2004. (Pubitemid 39302636)
56. Wu BJ, Kathir K, Witting PK, Beck K, Choy K, Li C, Croft KD, Mori TA, Tanous D, Adams MR, Lau AK and Stocker R: Antioxidants protect from atherosclerosis by a heme oxygenase- 1 pathway that is independent of free radical scavenging. J Exp Med 203: 1117-1127, 2006.
57. Fu X, Wang Y, Kao J, Irwin A, d'Avignon A, Mecham RP, Parks WC and Heinecke JW: Specific sequence motifs direct the oxygenation and chlorination of tryptophan by myeloperoxidase. Biochem 45: 3961-3971, 2006.
58. Hoshi T and Heinemann S: Regulation of cell function by methionine oxidation and reduction. J Physiol 531: 1-11, 2001. (Pubitemid 32178022)
59. Schenck HL, Dado GP and Gellman SH: Redox-triggered secondary structure changes in the aggregated states of a designed methionine-rich peptide. J Am Chem Soc 118 : 12487- 12494, 1996.
60. Fu X, Mueller DM and Heinecke JW: Generation of intramolecular and intermolecular sulfenamides, sulfinamides, and sulfonamides by hypochlorous acid: a potential pathway for oxidative cross-linking of low-density lipoprotein by myeloperoxidase. Biochem 41: 1293-1301, 2002. (Pubitemid 34083782)
61. Hawkins CL, Pattison DI and Davies MJ: Hypochlorite-induced oxidation of amino acids, peptides and proteins. Amino Acids 25: 259-274, 2003. (Pubitemid 38041264)
62. Hazell LJ, van den Berg JJ and Stocker R: Oxidation of lowdensity lipoprotein by hypochlorite causes aggregation that is mediated by modification of lysine residues rather than lipid oxidation. Biochem J 302(Pt 1): 297-304, 1994. (Pubitemid 24256368)
63. Shacter E: Quantification and significance of protein oxidation in biological samples. Drug Metab Rev 32: 307-326, 2000.
64. Harwood DT, Kettle AJ, and Winterbourn CC: Production of glutathione sulfonamide and dehydroglutathione from GSH by myeloperoxidase-derived oxidants and detection using a novel LC-MS/MS method. Biochem J 399: 161-168, 2006. (Pubitemid 44505417)
65. Raftery MJ, Yang Z, Valenzuela SM and Geczy CL: Novel intraand inter-molecular sulfinamide bonds in S100A8 produced by hypochlorite oxidation. J Biol Chem 276: 33393-33401, 2001.
66. Hawkins CL and Davies MJ: Reaction of HOCl with amino acids and peptides: EPR evidence for rapid rearrangement and fragmentation reactions of nitrogen-centred radicals. J Chem Soc Perkin Trans 2 1998: 1937-1946, 1998.