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DOI: 10.1039/A701079F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 1725-1730

The synthesis and photophysical properties of polyether substituted phthalocyanines of potential use in photodynamic therapy

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Sarah Foley, Gurnos Jones, Raffaelle Liuzzi, David J. McGarvey, Martin H. Perry and T. George Truscott

Abstract

The synthesis, photophysical properties and singlet oxygen yields of a range of polyether substituted metallo and free-base phthalocyanines are reported and discussed in the context of the potential use of these compounds as alternatives to haematoporphyrin derivatives (HpD) in the photodynamic therapy (PDT) of cancer. The triplet states of the phthalocyanines have been studied in benzene and methanol using nanosecond laser flash photolysis and pulse radiolysis. Triplet state absorption maxima occur at ca. 510 to 525 nm and the quantum yields of triplet formation (ϕT) lie in the range 0.14 to 0.32. Triplet state lifetimes are in the range 26 to 155 µs. Energy transfer from the triplet state (T1) of the phthalocyanines to ground state molecular oxygen O23Σg- to produce singlet oxygen O21ωg is efficient and evidence is presented for the establishment of an equilibrium in perdeuterated benzene, eqn. (a).Singlet oxygen quantum yields (ϕΔ), determined by time resolved near infrared luminescence, are comparable with the triplet yield suggesting a high proportion of quenching encounters result in the formation of singlet oxygen.The photophysical properties of the metallophthalocyanines are dependent on the relative atomic mass and the magnetic properties of the central metal ion.

References

  1. F. H. Moser and A. L. Thomas, The Phthalocyanines, Vol I and II, CRC Press, Inc., Boca Raton, 1968 Search PubMed.
  2. C. Prinze, L. C. Penning, T. M. A. R. Dubbelman and J. Van Steveninck, Cancer Res., 1992, 52, 117.
  3. B. W. Henderson, S. M. Waldow, T. S. Mang, W. R. Potter, P. B. Malone and T. J. Dougherty, Cancer Res., 1988, 45, 572.
  4. G. A. Kostenich, I. N. Zhuravkin, A. V. Furmanchuk and E. A. Zhavrid, J. Photochem. Photobiol., B: Biol., 1993, 7, 187 CrossRef.
  5. I. Rosenthal, C. Murali Krishna, P. Riesz and E. Ben-Hur, Radiation Res, 1986, 107, 136 Search PubMed.
  6. I. Rosenthal and E. Ben-Hur, Int. J. Radiat. Biol., 1995, 67, 85 CrossRef CAS.
  7. K. R. Weishaupt, C. J. Gomer and T. J. Dougherty, Cancer Res., 1976, 36, 2326 CAS.
  8. E. Zenkevich, E. Sagun, V. Knyukshto, R. Bonnett, S. P. Songea and M. Kassem, J. Photochem. Photobiol., B: Biol., 1996, 133, 171 CrossRef CAS.
  9. D. Wöhrle, N. Isklander, G. Graschew, H. Sinn, E. A. Freidrich, W. Maier-Borst, J. Stern and P. Schlag, Photochem. Photobiol., 1990, 51, 351 CAS.
  10. K. R. Adams, M. C. Berenbaum, R. Bonnett, A. N. Nizhnik, A. Salgado and M. A. Valles, J. Chem. Soc., Perkin Trans. 1, 1992, 1465 RSC.
  11. J. Moan, J. Photochem. Photobiol., B: Biol., 1990, 5, 521 CrossRef CAS.
  12. M. J. Cook, A. J. Dunn, S. D. Howe, A. J. Thomson and K. J. Harrison, J. Chem. Soc., Perkin Trans. 1, 1989, 2453 Search PubMed.
  13. I. Carmichael and G. L. Hug, J. Phys. Chem. Ref. Data, 1986, 15, 1.
  14. R. Bonnett, A. A. Charalambides, E. J. Land, R. S. Sinclair, D. Tait and T. G. Truscott, J. Chem. Soc., Faraday Trans 1, 1980, 76, 852 RSC.
  15. B. D. Rhiter, M. E. Kenney, W. E. Ford and M. A. J. Rodgers, J. Am. Chem. Soc, 1990, 112, 8064 CrossRef.
  16. P. A. Firey, W. E. Ford, J. R. Sounik, M. E. Kennedy and M. A. J. Rodgers, J. Am. Chem. Soc, 1988, 110, 7626 CrossRef CAS.
  17. W. E. Ford, B. D. Rhiter, M. E. Kenney and M. A. J. Rodgers, Photochem. Photobiol, 1989, 50, 277 CAS.
  18. A. A. Gorman, I. R. Gould, I. Hamblett and M. C. Standen, J. Am. Chem. Soc., 1984, 106, 6956 CrossRef CAS.
  19. M. A. J. Rodgers, J. Am. Chem. Soc., 1983, 105, 6201 CrossRef CAS.
  20. J. H. Tinkler, S. M. Tavender, A. W. Parker, D. J. McGarvey, L. Mulroy and T. G. Truscott, J. Am. Chem. Soc., 1996, 118, 1756 CrossRef CAS.
  21. J. Butler, B. W. Hodgson, B. M. Hoey, E. J. Land, J. S. Lea, E. J. Lindey, F. A. P. Rushton and A. J. Swallow, Radiat. Phys. Chem., 1989, 34, 633.
  22. R. V. Bensasson, E. J. Land and T. G. Truscott, Flash photolysis and pulse radiolysis: Contributions to the chemistry of biology and medicine, Pergamon Press, Oxford, 1983 Search PubMed.
  23. R. Bensasson and E. J. Land, Trans. Faraday Soc., 1971, 67, 1904 RSC.
  24. M. Nemoto, H. Kokbun and M. Koizumi, Bull. Chem. Soc. Jpn., 1969, 42, 1223 CAS.
  25. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, Inc.New York, 1993 Search PubMed.
  26. Y. Usui, H. Koike and Y. Hurimura, Bull. Chem. Soc. Jpn., 1987, 60, 3373 CAS.
  27. F. Wilkinson, J. Phys. Chem. Ref. Data, 1993, 22, 113 CAS.
  28. J. N. Chacon, J. McLearie and R. S. Sinclair, Photochem. Photobiol., 1987, 46, 647.
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