Photosensitization: Reaction Pathways

  • Johan E. Van Lier
Part of the NATO ASI Series book series (NSSA, volume 216)

Abstract

Thousands of naturally occurring and synthetic dyes can function as photosensitizers and inflict biological damage in the presence of light (Spikes, 1989 and references cited). The action is initiated by the absorption of a photon to yield an excited sensitizer and is followed by many competing dark reactions which ultimately result in the alteration of vital biomol-ecules. Reactions of the excited sensitizer can involve electron or hydrogen transfer, usually with a reducing substrate (Type I reaction) or interaction with oxygen (Type II reaction) (Foote, 1976 and references cited). The latter usually involves energy transfer to yield singlet molecular oxygen. Both Types I and Π pathways may compete, with the predominant route being determined by such factors as oxygen and substrate concentrations, the proximity of the sensitizer to the substrate as well as the nature of the sensitizers and the substrate. Both pathways ultimately lead to the formation of oxidized products and radical chain reactions resulting in extensive biological damage. Living organisms contain many enzymic and nonenzymic antioxidant mechanisms to protect against reactive oxygen species and the inability to control the latter has been defined as oxidative stress (Sies, 1986).

Keywords

MeOH Tryptophan NADH Myeloma Porphyrin 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary Reading

References

  1. Amesz, J. (1973) The function of plastoquinone in photosynthetic electron transport. Biochem.Biophys.Acta, 301, 35–51.PubMedCrossRefGoogle Scholar
  2. Beckwith, A.L J., A.G. Davies, I.G.E. Davison, A. Maccoll and M.H. Mruzek (1989) The mechanisms of the rearrangements of allylic hydroperoxides: 5α-Hydroperoxy-3β-hydroxycholest-6-ene and 7α-hy-droperoxy-3β-hydroxy-cholest-5-ene. J. Chem. Soc. Perkin. Trans. II, 815–824.Google Scholar
  3. Bernauer, Κ. and S. Fallab (1961) Phthalocyanine in wasseriger Losung I. Helv. Chim. Acta, 44, 1287–1292.CrossRefGoogle Scholar
  4. Bruce, J.M. (1967) Light-induced reactions of quinones. Quart. Rev., 21, 405–428.CrossRefGoogle Scholar
  5. Firey, P.A., T.W. Jones, G. Jori and M.A.J. Rodgers (1988) Photoexcitation of zinc phthalocyanine in mouse myeloma cells: the observation of triplet states but not of singlet oxygen. Photochem. Photobiol. 48, 357–360.PubMedCrossRefGoogle Scholar
  6. Foote, C.S. (1976) Photosensitized oxidation and singlet oxygen: Consequences in biological systems. In Free Radicals in Biology (Edited by W.A. Pryor ), Vol. II, pp. 85–133. Academic Press, New York.Google Scholar
  7. Girotti, A.W. (1990) Photodynamic lipid peroxidation in biological systems. Photochem. Photobiol., 51,497– 509.Google Scholar
  8. Hartley, J.A.,K.ReszkaandJ.W.Lown (1988) Photosensitization by antitumor agents. 7. Correlation between anthracenedione-photosensitized DNA damage, NADH oxidation and oxygen consumption following visible light illumination. Photochem. Photobiol., 48, 19–25.Google Scholar
  9. Langlois, R., H. Ali, Ν. Brasseur, R. Wagner and J.E. van Lier (1986) Biological activities of phthalocyanines. IV. Type II sensitized photooxidation of L-tryptophan and cholesterol. Photochem. Photobiol., 44, 117–125.PubMedCrossRefGoogle Scholar
  10. Lee, P.C.C. and M.A.J. Rodgers (1987) Laser flash photokinetic studies of rose bengal sensitized photodynamic interactions of nucleotides and DNA. Photochem. Photobiol., 45, 79–86.PubMedCrossRefGoogle Scholar
  11. Schenck, G.O. (1963) Photosensitization. Ind. and Eng. Chem., 55, 40–43.CrossRefGoogle Scholar
  12. Sevanian, A. and L.L. McLeod (1987) Cholesterol autoxidation in phospholipid membrane bilayers. Lipids 22, 627–636.PubMedCrossRefGoogle Scholar
  13. Sies, H. (1986) Biochemistry of oxidative stress. Angew Chem. Int. Ed. Engl. 25, 1058–1071.CrossRefGoogle Scholar
  14. Smith, L.L. (1981) Cholesterol Autoxidation. Plenum Press, New York.Google Scholar
  15. Smith, L.L. (1987) Cholesterol autoxidation 1981–1986. Chem. Phys. Lipids 44, 87–125.PubMedCrossRefGoogle Scholar
  16. Smith, L.L. and B.H. Johnson (1989) Biological activities of oxysterols. Free Rad. Biol. Med. 7, 285–332.PubMedCrossRefGoogle Scholar
  17. Spikes, J.D. (1989) Photosensitization. In The Science of Photobiology (Edited by K.C. Smith ), pp. 79–111. Plenum Press, New York.Google Scholar
  18. Turro,N.J. (1978) Singlet oxygen and chemiluminescent organic reactions. In Modern Molecular Photochemistry (Edited by Ν. J. Turro) pp. 579–614. Benjamin/Cummings, London.Google Scholar
  19. van Lier, J.E. (1990) Phthalocyanines as sensitizers forPDT of cancer. In Photodynamic Therapy of Neoplastic Disease (Edited by D. Kessel ), Vol. I, pp. 279–291. CRC Press, Boca Raton, FL.Google Scholar
  20. Wagner, J.R., J. Cadet and G.J. Fisher (1984) Photo-oxidation of thymine sensitized by 2-methyl-l,4-naphthoquinone: Analysis of products including three novel photo-dimers. Photochem. Photobiol. 40, 589–597.CrossRefGoogle Scholar
  21. Wagner, J.R., H. Ali, R. Langlois, N. Brasseur and J.E. van Lier (1987) Biological activities of phthalocyanines. VI. Photooxidation of L-tryptophan by selectively sulfonated gallium phthalocyanines: singlet oxygen yields and effect of aggregation. Photochem. Photobiol., 45, 587–594.PubMedCrossRefGoogle Scholar
  22. Wagner, J.R., J.E. van Lier and L. J. Johnston (1990) Quinone sensitized electron transfer photooxidation of nucleic acids: chemistry of thymine and thymidine radical cations in aqueous solution. Photochem. Photobiol. 52, 333–345.PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • Johan E. Van Lier
    • 1
  1. 1.MRC Group in the Radiation Sciences, Faculty of MedicineUniversity of SherbrookeSherbrookeCanada

Personalised recommendations