6
Views
4
CrossRef citations to date
0
Altmetric
Original Article

Aminothiols Linked to Quinoline and Acridine Chromophores Efficiently Decrease 7,8-dihydro-8-oxo-2′-deoxyguanosine Formation in γ-irradiated DNA

, , , , &
Pages 259-266 | Received 03 Nov 1993, Accepted 19 Apr 1994, Published online: 03 Jul 2009

References

  • Adams G.E., McNaughton B.S., Michael B.D. The pulse radiolysis of sulphur compounds. Part I. Cysteamine and cystamine. The Chemistry of Ionization and Excitation, G.R.A. Johnson, G. Scholes. Taylor & Francis, London 1967; 281–293, In
  • Berger M., Anselmino C., Mouret J.-F., Cadet J. High performance liquid chromatography-electrochemical assay for monitoring the formation of 8-oxo-7,8-dihydroadenine and its related 2′-deoxyribonucleoside. Journal of Liquid Chromatography 1990; 13: 929–940
  • Berger M., Cadet J. Isolation and characterization of the radiation-induced degradation products of 2′-deoxyguanosine in oxygen-free aqueous solutions. Zeitschrift für Naturforschung 1985; 40b: 1519–1531
  • Berger M., de Hazen M., Neijjari A., Fournier J., Guignard J., Pezerat H., Cadet J. Radical oxidation reactions of the purine moiety of 2′-deoxyribonucleosides and DNA by iron-containing minerals. Carcinogenesis 1993; 14: 41–46
  • Bolte J., Demuynck C., Lhomme M.F., Lhomme J., Barbet J., Roques B.P. Synthetic models related to DNA intercalating molecules: comparison between quinacrine and chloroquine in their ring-ring interaction with adenine and thymine. Journal of the American Chemistry Society 1982; 104: 760–765
  • Bothe E., Schulte-Frohlinde D. Release of Ky+ and H+ from poly (U) in aqueous solutions upon gamma and electron irradiation. Rate of strand break formation in poly (U). Zeitschrift für Naturforschung 1982; 37c: 1191–1204
  • Cadet J. Oxidation deamination, ultraviolet radiation, psoralens. DNA Adducts, K. Hemminki. IARC, Lyon 1993, (in press)
  • Cadet J., Berger M., Demonchaux P., Lhomme J. Modifying effects of cysteine and aromatic sulf-hydryl and disulfide agents on the radiation-induced decomposition of thymidine. Radiation Physics and Chemistry 1988; 32: 197–202
  • Cadet, J., Ravanat, J.-L., Buchko, G.W., Yeo, H., Ames, B.N. Singlet oxygen DNA damage: HPLC and MS analysis of damage products. Methods in Enzymology, in press, 1994
  • Cho B.P., Kadlubar F.F., Culp S.J., Evans F.E. 15N nuclear magnetic resonance studies on the tautomerism of 8-hydroxy-2′-deoxyguanosine, and other C8-substituted guanine nucleosides. Chemical Research in Toxicology 1990; 3: 445–452
  • Constant J.F., Fkyerat A., Demeunynck M., Laval J., O'connor T.R., Lhomme J. Design of molecules which specifically cleave abasic sites in DNA. Anti-Cancer Drug Design 1990; 5: 59–62
  • Constant J.F., O'Connor T.R., Lhomme J., Laval J. 9-[(19-(aden-9-yl)-4,8-diazadecyl)amino]-6-chloro-2-methoxy-acridine incises DNA at apurinic sites. Nucleic Acids Research 1988; 16: 2691–2703
  • Culp S.J., Cho B.P., Kadlubar F.F., Evans F.E. Structural and conformational analyses of 8-hydroxy-2′-deoxyguanosine. Chemical Research in Toxicology 1989; 2: 416–422
  • Demonchaux P., Laayoun A., Demeunynck M., Lhomme J. Synthesis of N-acridinyl and N-quinolinyl derivatives of radioprotective amino-thiols. Tetrahedron 1989; 45: 6455–6466
  • Devasagayam T.P., Steenken S., Obendorf M.S.W., Schulz W.A., Sies A. Formation of 8-hydroxy (deoxy) guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 1991; 25: 6283–6289
  • Dizdaroglu M. Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on gamma-irradiation in aqueous solution. Biochemistry 1985; 24: 4476–4481
  • Fahey R.C., Vojnovic B., Michael B.D. The effects of counter-ion condensation and co-ion depletion upon the rates of chemical repair of poly (U) radicals by thiols. International Journal of Radiation Biology 1991a; 59: 885–899
  • Fahey R.C., Prise K.M., Stratford M.R.L., Watfa R.R., Michael B.D. Rates for repair of pBR322 DNA radicals by thiols as measured by the gas explosion technique: evidence that counter-ion and coion depletion are significant at physiological ionic strength. International Journal of Radiation Biology 1991b; 59: 901–917
  • Fischer-Nielsen A., Poulsen H.E., Loft S. 8-Hydroxy-deoxyguanosine in vitro: effects of glutathione, ascorbate and 5-aminosalicylic acid. Free Radical Biology and Medicine 1992; 13: 121–126
  • Fkyerat A., Demeunynck M., Constant J.F., Michon P., Lhomme J. A new class of artificial nucleases that recognize and cleave apurinic sites in DNA with great selectivity and efficiency. Journal of the American Chemical Society 1993; 115: 9952–9959
  • Floyd R.A., Watson J.J., Wong P.K., Altmiller D.H., Rickard R.C. Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radical Research Communications 1986; 1: 163–172
  • Frankenberg D., Michael B.D., Frankenberg-Schwager M., Harbich R. Fast kinetics of the oxygen effect for DNA double-strand breakage and cell killing in irradiated yeast. International Journal of Radiation Biology 1990; 57: 485–501
  • Harris J.W., Philipps T.L. Radiobiological and biochemical studies of thiophosphate radioprotective compounds related to cysteamine. Radiation Research 1971; 46: 362–379
  • Held K.D., Harrop H.A., Michael B.D. Effects of oxygen and sulphydryl-containing compounds on irradiated transforming DNA. I. Action of dithiothreitol. International Journal of Radiation Biology 1981; 40: 613–622
  • Held K.D., Harrop H.A., Michael B.D. Effects of oxygen and sulphydryl-containing compounds on irradiated transforming DNA. II. Glutathione, cysteine and cysteamine. International Journal of Radiation Biology 1984a; 45: 615–626
  • Held K.D., Harrop H.A., Michael B.D. Effects of oxygen and sulphydryl-containing compounds on irradiated transforming DNA. III. Reaction rates. International Journal of Radiation Biology 1984b; 45: 627–636
  • Howards-Flanders P. Effect of oxygen on the radio-sensitivity of phage in the presence of SH Compounds. Nature 1960; 186: 485–487
  • Hutchinson F. Sulfhydryl groups and the oxygen effect on irradiated dilute solutions of enzymes and nucleic acids. Radiation Research 1961; 14: 721–731
  • Kasai H., Nishimura S. Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance. Oxidative Stress, Oxidants and Antioxidants, H. Sies. Academic, New York 1991; 99–116, In
  • Kasai H., Yamaizumi Z., Berger M., Cadet J. Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin. A non-singlet oxygen mediated reaction. Journal of the American Chemical Society 1992; 114: 9692–9694
  • Kieffer J. Biological Radiation Effects. Springer, Berlin 1990; 55–87
  • Lin T.S., Cheng J.C., Ishiguro K., Sartorelli A.C. 8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of the differentiation of Friend crythioleukemia cells. Journal of Medicinal Chemistry 1985; 28: 1194–1198
  • Liphard M., Bothe E., Schulte-Frohlinde D. The influence of glutathione on single-strand breakage in single-stranded DNA irradiated in aqueous solution in the abbsence and presence of oxygen. International Journal of Radiation Biology 1990; 58: 589–602
  • Michael B.D., Harrop H.A. Timescale and mechanism of radiosensitization and radioprotection at the cellular level. Radiation Sensitizer: Their Use in the Clinical Management of Cancer, L.W. Brady. Masson, New York 1980; 14–21, In
  • Mouret J.-F., Berger M., Anselmino C., Polverelli M., Cadet J. Etude comparative de l'oxydation radicalaire de l'ADN et de ses nucléosides par les radicaux hydroxyles et les ions ferryles issus de la réaction de Fenton. Journal de Chimie Physique 1991; 88: 1053–1061
  • Murray D., van Ankeren S.C., Milas L., Meyer R.E. Radioprotective action of aminothiols in vitro and in vivo: comparison between effects on DNA damage and cell survival. Pharmacology and Therapeutics 1988; 39: 151–153
  • Murray D., Prager A., Milas L. Radioprotection of cultured mammalian cells by the aminothiols WR-1065 and WR-255591: correlation between protection against DNA double strand breaks and cell killing. Radiation Research 1989; 120: 154–163
  • O'Neill P. Pulse radiolytic study of the interaction of thiols and ascorbate with OH-adducts of dGMP and dG. Implications for DNA repair processes. Radiation Research 1983; 96: 198–210
  • Prise K.M., Davies S., Stratford M.R.L., Michael B.D. The role of non protein sulphydryls in determining the chemical repair rates of free radical precursors of DNA damage and cell killing in Chinese hamster V79 cells. International Journal of Radiation Biology 1992; 62: 297–306
  • Quintiliani M., Badiello R., Tamba M., Esfandi A., Gorin G. Pulse radiolysis of glutathione. International Journal of Radiation Biology 1977; 32: 195–204
  • Rao P.J.K., Bothe E., Schulte-Frohlinde D. Reaction of dithiothreitol and para-nitroacetophenone with different radical precursors of ·OH radical-induced strand break formation of single-stranded DNA in anoxic aqueous solution. International Journal of Radiation Biology 1992; 61: 577–591
  • Smoluk G.D., Fahey R.C., Ward J.F. Interaction of glutathione and other low-molecular-weight thiols with DNA: evidence for counterion condensation and co-ion depletion neat DNA. Radiation Research 1988; 114: 3–10
  • Steenken S. Purine bases, nucleosides and nucleotides: aqueous solution chemistry and transformation of their radical cation and e- and ·OH adducts. Chemical Reviews 1989; 89: 503–520
  • Tahsildar H.I., Biaglow J.E., Kligerman M.M., Varnes M.E. Factors influencing the oxidation of the radio-protector WR-1065. Radiation Research 1988; 113: 243–251
  • von Sonntag C. The Chemical Basis of Radiation Biology. Taylor & Francis, London 1987
  • Ward J.F. Chemical aspects of DNA radioprotection. Radioprotection and Anticarcinogens, O.F. Nygaard, M.G. Simic. Academic, New York 1983; 73–85, In
  • Ward J.F., Mora-Arellano V.O. Pulse radiolysis studies of WR-1065. International Journal of Radiation Oncology, Biology and Physics 1984; 10: 1533–1536
  • Zeng S., Newton G.L., Gonick G., Fahey R.C., Ward J.F. Radioprotection of DNA by thiols: relationship between the net charge on a thiol and its ability to protect DNA. Radiation Research 1988; 114: 11–27

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.