Effects of Singlet Oxygen on the Biological Activity of DNA and Its Involvement in Single Strand-Break Formation

  • Heribert Wefers
  • Paolo Di Mascio
  • Hong-Phuc Do-Thi
  • Dietrich Schulte-Frohlinde
  • Helmut Sies
Part of the Basic Life Sciences book series (BLSC, volume 49)


The formation of singlet molecular oxygen (1O2) has been shown to occur during photoexcitation of a variety of biological and also clinically applied compounds, such as porphyrins, psoralens and tetracyclines (see, for example references 1–3), but also occurs during enzymatic reactions including cyclooxygenase4 and chloroperoxidase.5 Regarding the biological consequences of 1O2 formation, DNA is of particular interest. 1O2 is known to react with guanine 6,7; however, results on biologically active DNA were conflicting, in particular regarding 1O2-dependent strand-break formation under neutral conditions, i.e. without alkaline treatment. 8-11 Here we emphasize two aspects of 1O2-mediated damage. First, the effect of 1O2 on the transforming activity of pBR322 and M1 3 DNA in E. coli is presented. Second, two different sources of 1O2 are employed for investigation of strand-break formation; these are microwave discharge and the thermodissociable endoperoxide of disodium 3,3′-(1,4-naphthylidene)dipropionate (NDPO2).


Singlet Oxygen Alkaline Treatment Rose Bengal Transforming Activity Cyanuric Acid 
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  1. 1.
    T.J. Dougherty, Photosensitization of malignant tumors, Seminars in Surgical Oncology 2:24 (1986).PubMedCrossRefGoogle Scholar
  2. 2.
    W. Poppe, and L.I. Grossweiner, Photodynamic sensitization by 8-methoxypsoralen via the singlet oxygen mechanism, Photochem. and Photobiol. 22:217 (1975).CrossRefGoogle Scholar
  3. 3.
    T. Hasan, and A.U. Khan, Phototoxicity of the tetracyclines: Photosensitized emission of singlet delta dioxygen, Proc. Natl. Acad. Sci. USA 83:4604 (1986).PubMedCrossRefGoogle Scholar
  4. 4.
    E. Cadenas, H. Sies, W. Nastainczyk, and V. Ullrich, Singlet oxygen formation detected by low-level chemiluminescence during enzymatic reduction of prostaglandin G2 to H2, Hoppe-Seyler’s Z. Physiol. Chemie 364:519 (1983).CrossRefGoogle Scholar
  5. 5.
    J.R. Kanofsky, Singlet oxygen production by chloroperoxidase-hydrogen peroxide-halide systems, J.Biol.Chem. 259:5596 (1984).PubMedGoogle Scholar
  6. 6.
    F.R. Hallett, B.P. Hallett, and W. Snipes, Reactions between singlet oxygen and the constituents of nucleic acids, Biophys. J. 10:305 (1970).PubMedCrossRefGoogle Scholar
  7. 7.
    J. Cadet, C. Decarroz, S.Y. Wang, and W.R. Midden, Mechanisms and products of photosensitized degradation of nucleic acids and related model compounds, Israel Journal of Chemistry 2 3:420 (1983).Google Scholar
  8. 8.
    E. Boye, and J. Moan, The photodynamic effect of hematoporphyrin on DNA Photochem.Photobiol. 31:223 (1980).CrossRefGoogle Scholar
  9. 9.
    R.J. Fiel, N. Datta-Gupta, E.H. Mark, and J.C. Howard, Induction of DNA damage by porphyrin photosensitizers, Cancer Research 41:3543 (1981).PubMedGoogle Scholar
  10. 10.
    A.W.M. Nieuwint, J.M. Aubry, F. Arwert, H. Kortbeek, S. Herzberg, and H. Joenje, Inability of chemically generated singlet oxygen to break the DNA backbone, Free Rad. Res. Comms. 1:1 (1985).CrossRefGoogle Scholar
  11. 11.
    H. Wefers, D. Schulte-Frohlinde, and H. Sies, Loss of transforming activity of plasmid DNA (pBR322) in E.coli caused by singlet molecular oxygen, FEBS Lett. 211:49 (1987).PubMedCrossRefGoogle Scholar
  12. 12.
    E.A. Ogryzlo, in: Singlet Oxygen (H.H. Wassermann and R.W. Murray, eds), pp. 35–56, Academic Press, New York (1979).Google Scholar
  13. 13.
    W.R. Midden, and S. Yi Wang, Singlet oxygen generation for solution kinetics: clean and simple, J. Am. Chem. Soc. 105:4129 (1983).CrossRefGoogle Scholar
  14. 14.
    P. Di Mascio and H. Sies, Detection and quantification of singlet oxygen generated by thermolysis of a water-soluble endoperoxide, J. Am. Chem. Soc, submitted (1988).Google Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • Heribert Wefers
    • 1
  • Paolo Di Mascio
    • 1
  • Hong-Phuc Do-Thi
    • 2
  • Dietrich Schulte-Frohlinde
    • 2
  • Helmut Sies
    • 1
  1. 1.Institut für Physiologische Chemie IUniversität DüsseldorfDeutschland
  2. 2.Max-Planck-Institut für StrahlenchemieMülheim a. d. RuhrDeutschland

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