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Original

Cationic peptides containing tyrosine protect against radiation-induced oxidative DNA damage

, , &
Pages 421-433 | Received 19 Jan 2006, Accepted 24 Apr 2006, Published online: 03 Jul 2009

References

  • Adams G E, Aldrich J E, Bisby R H, Cundall R B, Redpath J L, Willson R L. Selective free radical reactions with proteins and enzymes: reactions of inorganic radical anions with amino acids. Radiation Research 1972; 49: 278–289
  • Angelov D, Beylot B, Spassky A. Origin of the heterogenous distribution of the yield of guanyl radical in UV laser photolyzed DNA. Biophysical Journal 2005; 88: 2766–2778
  • Ayene I S, Koch C J, Kirsch R E. Simulation of the cellular oxygen effect with an SV40 DNA model system using DNA strand breaks as an end point. Radiation Research 1996; 146: 501–509
  • Baeza I, Gariglio P, Rangel L M, Chavez P, Cervantes L, Arguello C, Wong C, Montanez C. Electron microscopy and biochemical properties of polyamine compacted DNA. Biochemistry 1987; 26: 6387–6392
  • Becker D, Sevilla M D. The chemical consequences of radiation damage to DNA. Advances in Radiation Biology 1993; 17: 121–180
  • Begusova M, Giliberto S, Gras J, Sy D, Charlier M, Spotheim-Maurizot M. DNA radiolysis in DNA-protein complexes: a stochastic simulation of attack by hydroxyl radicals. International Journal of Radiation Biology 2003; 79: 385–391
  • Bloomfield V A. DNA condensation. Current Opinion in Structural Biology 1996; 6: 334–341
  • Cadet J, Berger M, Douki T, Ravanat J -L. Oxidative damage to DNA: formation, measurement, and biological significance. Reviews in Physiology and Biochemical Pharmacology 1997; 131: 1–87
  • Candeias L P, Steenken S. Reaction of HO• with guanine derivatives in aqueous solution: Formation of two different redox-active OH-adduct radicals and their unimolecular transformation reactions. Properties of G(-H)•. Chemistry 2000; 6: 475–484
  • Chapman J D, Reuvers A P, Borsa J, Greenstock C L. Chemical radioprotection and radiosensitization of mammalian cells growing in vitro. Radiation Research 1973; 56: 291–306
  • Chiu S, Oleinick N L. Radioprotection of cellular chromatin by the polyamines spermine and putrescine: Preferential action against formation of DNA-protein crosslinks. Radiation Research 1998; 149: 543–549
  • Colson A O, Besler B, Close D M, Sevilla M D. Ab initio molecular orbital calculations of DNA bases and their radical ions in various protonation states: Evidence for proton transfer in GC base pair radical anions. Journal of Physical Chemistry 1992; 96: 661–668
  • Conwell C C, Hud N V. Evidence that both kinetic and thermodynamic factors govern DNA toroid dimensions. Effects of magnesium (II) on DNA condensation by hexamine cobalt (III). Biochemistry 2004; 43: 5380–5387
  • Daban J -R. High concentration of DNA in condensed chromatin. Biochemical and Cellular Biology 2003; 81: 91–99
  • Debije M G, Razskazovskiy Y, Bernhard W A. The yield of strand breaks resulting from direct-type effects in crystalline DNA X-irradiated at 4 K and room temperature. Journal of the American Chemical Society 2001; 123: 2917–2918
  • Douki T, Martini R, Ravanat J -L, Turesky R J, Cadet J. Measurement of 2,6-diamino-4-hydroxy-5-formamidopyrimidine and 8-oxo-7,8-dihydroguanine in isolated DNA exposed to gamma radiation in aqueous solution. Carcinogenesis 1997; 18: 2385–2391
  • Douki T, Cadet J. Modification of DNA bases by photosensitized one electron oxidation. International Journal of Radiation Biology 1999; 75: 571–581
  • Douki T, Bretonniere Y, Cadet J. Protection against radiation-induced degradation of DNA bases by polyamines. Radiation Research 2000; 153: 29–35
  • Duarte V, Gasparutto D, Jaquinod M, Cadet J. In vitro DNA synthesis opposite oxazolone and repair of this DNA damage using modified oligonucleotides. Nucleic Acids Research 2000; 28: 1555–1563
  • Faucitano A, Buttafava A, Martinotti F, Pedralynoy G. ESR study of the direct radiolysis of DNA, DNA-histones and DNA-intercalator complexes. Radiation Physics and Chemistry 1992; 40: 357–364
  • Haraguchi K, Delaney M O, Wiederholt C J, Sambandam A, Hantosi Z, Greenberg M M. Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues. Journal of the American Chemical Society 2002; 124: 3263–3269
  • He S, Arscott P G, Bloomfield V A. Condensation of DNA by multivalent cations: Experimental studies of condensation kinetics. Biopolymers 2000; 53: 329–341
  • Hosford M E, Muller J G, Burrows C J. Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation. Journal of the American Chemical Society 2004; 126: 9540–9541
  • Houée-Levin C, Sicard-Roselli C. Radiation chemistry of proteins. Radiation chemistry present status and future prospects, C Jonah, B Rao. Elsevier, New York 2001; 553–584
  • Johansen M E, Muller J G, Xu X, Burrows C J. Oxidatively induced DNA protein cross linking between single stranded binding protein and oligodeoxynucleotides containing 8-oxo-7,8-dihydro-2′-deoxyguanosine. Biochemistry 2005; 44: 5660–5671
  • Jones G D, Lea J S, Symons M C, Taiwo F A. Structure and mobility of electron gain and loss centers in proteins. Nature 1987; 330: 772–773
  • Kaneda K, Sekiguchi J, Shida T. Role of the tryptophan residue in the vicinity of the catalytic center of exonuclease III family AP endonucleases: AP site recognition mechanism. Nucleic Acids Research 2006; 34: 1552–1563
  • Kurbanyan K, Nguyen K L, To P, Rivas E V, Lueras A MK, Kosinski C, Steryo M, Gonzalez A, Mah D A, Stemp E DA. DNA protein cross linking via guanine oxidation: Dependence upon protein and photosensitizer. Biochemistry 2003; 42: 10269–10281
  • Luger K, Maeder A M, Richmond R K, Sargent D F, Richmond T J. Crystal structure of the nucleosome core particle at 2.8 Å resolution. Nature 1997; 389: 251–260
  • Lutze L H, Winegar R A. pHAZE. A shuttle vector system for the detection and analysis of ionizing radiation induced mutations. Mutation Research 1990; 245: 305–310
  • Lutze L H, Cleaver J E, Morgan W F, Winegar R A. Mechanisms involved in rejoining DNA double-strand breaks induced by ionizing radiation and restriction enzymes. Mutation Research 1993; 299: 225–232
  • Mascotti D P, Lohman T M. Thermodynamic extent of counterion release upon binding oligolysines to single stranded nucleic acids. Proceedings of the National Academy of Sciences of the USA 1990; 87: 3142–3146
  • Milligan J R, Aguilera J A, Ward J F. Variation of single strand break yield with scavenger concentration for plasmid DNA irradiated in aqueous solution. Radiation Research 1993; 133: 151–157
  • Milligan J R, Ward J F. Yield of single-strand breaks due to attack on DNA by scavenger-derived radicals. Radiation Research 1994; 137: 295–299
  • Milligan J R, Ng J Y, Wu C C, Aguilera J A, Ward J F, Kow Y W, Wallace S S, Cunningham R P. Methylperoxyl radicals as intermediates in the damage to DNA irradiated in aqueous dimethyl sulfoxide with gamma rays. Radiation Research 1996; 146: 436–443
  • Milligan J R, Aguilera J A, Paglinawan R A, Ward J F. Mechanism of DNA damage by thiocyanate radicals. International Journal of Radiation Biology 2000; 76: 1305–1314
  • Milligan J R, Aguilera J A, Ly A, Tran N Q, Hoang O, Ward J F. Repair of oxidative DNA damage by amino acids. Nucleic Acids Research 2004a; 31: 6258–6263
  • Milligan J R, Tran N Q, Ly A, Ward J F. Peptide repair of oxidative DNA damage. Biochemistry 2004b; 43: 5102–5108
  • Morimoto S, Hatta H, Fujita S, Matsuyama T, Ueno T, Nishimoto S. Hydroxyl radical induced cross linking of thymine and lysine: Identification of the primary structure and mechanism. Bioorganic and Medicinal Chemistry Letters 1998; 8: 865–870
  • Morin B, Cadet J. Chemical aspects of the benzophenone photosensitized formation of two lysine 2′-deoxyguanosine cross links. Journal of the American Chemical Society 1995; 117: 12408–12415
  • Neta P, Huie R E, Ross A B. Rate constants for reactions of inorganic radicals in aqueous solution. Journal of Physical and Chemical Reference Data 1988; 17: 1027–1084
  • Newton G L, Aguilera J A, Ward J F, Fahey R C. Polyamine induced compaction and aggregation of DNA. A major factor in radioprotection of chromatin under physiological conditions. Radiation Research 1996; 145: 776–780
  • Newton G L, Ly A, Tran N Q, Ward J F, Milligan J R. Radioprotection of plasmid DNA by oligolysines. International Journal of Radiation Biology 2004; 80: 643–651
  • Porschke D, Ronnenberg J. The reaction of aromatic peptides with double helical DNA. Quantitative characterisation of a two step reaction scheme. Biophysical Chemistry 1981; 13: 283–290
  • Rabow L, Venkataraman R, Kow Y W. Mechanism of action of Escherichia coli formamidopyrimidine N-glycosylase: Role of K155 in substrate binding and product release. Progress in Nucleic Acid Research and Molecular Biology 2001; 68: 223–234
  • Rauk A, Yu D, Taylor J, Shustov G V, Block D A, Armstrong D A. Effects of structure on alpha C-H bond enthalpies of amino acid residues. Relevance to H transfers in enzyme mechanisms and in protein oxidation. Biochemistry 1999; 38: 9089–9096
  • Razskazovskiy Y, Debije M G, Bernhard W A. Strand breaks produced in X-irradiated crystalline DNA: Influence of base sequence. Radiation Research 2003; 159: 663–639
  • Roots R, Holley W, Chatterjee A, Irizarry M, Kraft G. The formation of strand breaks in DNA after high-LET irradiation: A comparison of data from in vitro and cellular systems. International Journal of Radiation Biology 1990; 58: 55–69
  • Schafer F Q, Buettner G R. Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radicals in Biology and Medicine 2001; 30: 1191–1212
  • Seidel C AM, Schulz A, Sauer M HM. Nucleobase specific quenching of fluorescent dyes. I. Nucleobase one electron redox potentials and their correlation with static and dynamic quenching efficiencies. Journal of Physical Chemistry 1996; 100: 5541–5553
  • Shukla L I, Adhikary A, Pazdro R, Becker D, Sevilla M D. Formation of 8-oxo-7,8-dihydroguanine-radicals in gamma-irradiated DNA by multiple one-electron oxidations. Nucleic Acids Research 2004; 32: 6565–6574
  • Spinks J WT, Woods R J. Introduction to radiation chemistry3rd ed. Wiley, New York 1990
  • Spotheim-Maurizot M, Ruiz S, Sabattier R, Charlier M. Radioprotection of DNA by polyamines. International Journal of Radiation Biology 1995; 68: 571–577
  • Stanbury D M. Reduction potentials involving inorganic free radicals in aqueous solution. Advances in Inorganic Chemistry 1989; 33: 69–138
  • Stivers J T, Jiang Y L. A mechanistic perspective on the chemistry of DNA repair glycosylases. Chemical Reviews 2003; 103: 2729–2759
  • Stuart-Audette M, Blouquit Y, Faraggi M, Sicard-Roselli C, Houée-Levin C, Jolles P. Re-evaluation of intramolecular long-range electron transfer between tyrosine and tryptophan in lysozymes. Evidence for the participation of other residues. European Journal of Biochemistry 2003; 270: 3565–3571
  • Stubbe J A, van der Donk W A. Protein radicals in enzyme catalysis. Chemical Reviews 1998; 98: 705–762
  • Swarts S G, Becker D, Sevilla M, Wheeler K T. Radiation-induced DNA damage as a function of hydration. II. Base damage from electron-loss centers. Radiation Research 1996; 145: 304–314
  • Udovicic L, Mark F, Bothe E. Yields of single-strand breaks in double-stranded calf thymus DNA irradiated in aqueous solution in the presence of oxygen and scavengers. Radiation Research 1994; 140: 166–171
  • van Holde K E. Chromatin. Springer, New York 1988
  • Vijayanathan V, Thomas T, Shirahata A, Thomas T J. DNA condensation by polyamines. A laser light scattering study of structural effects. Biochemistry 2001; 40: 13644–13651
  • von Sonntag C. The chemical basis of radiation biology. Taylor & Francis, Philadelphia 1987
  • Warters R L, Newton G L, Olive P L, Fahey R C. Radioprotection of human cell nuclear DNA by polyamines. Radiosensitivity of chromatin is influenced by tightly bound spermine. Radiation Research 1999; 151: 354–362
  • Webb C F, Jones G D, Ward J F, Moyer D J, Aguilera J A, Ling L L. Mechanisms of radiosensitization in bromodeoxyuridine substituted cells. International Journal of Radiation Biology 1993; 64: 695–705
  • Weiland B, Hüttermann J. Spin transfer from protein to DNA in X-irradiated dry DNA and hydrated chromatin. An electron spin resonance investigation of spectral components between 77 K and room temperature. International Journal of Radiation Biology 2000; 76: 1075–1084
  • Widom J, Baldwin R L. Cation induced toroidal condensation of DNA studies with Co(NH3)63+. Journal of Molecular Biology 1980; 144: 431–453
  • Zheng S, Newton G L, Ward J F, Fahey R C. Aerobic radioprotection of pBR322 by thiols: Effect of thiol net charge upon scavenging of hydroxyl radicals and repair of DNA radicals. Radiation Research 1992; 130: 183–193

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