Skip to main content

Some Properties of Furocoumarin (FC) Excited States

  • Chapter
Primary Photo-Processes in Biology and Medicine

Abstract

Furocoumarins (psoralens) are natural or synthetic compounds (Fig.1) which can act as photosensitizers of biological systems.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  1. Hearst J.E. Psoralen photochemistry and nucleic acid structure, J. Invest. Dermatol. 77, 39–44 (1981).

    Article  Google Scholar 

  2. Avérbeck D. Photobiology of furocoumarins in“Trends in Photobiology” Edited by C. Hélène, M. Charlier, Th. Montenay-Garestier and G. Laustriat, Plenum Press 295–308 (1982).

    Google Scholar 

  3. Grekin D.A. and Epstein J.H., Psoralens, UVA (PUVA) and photocarcinogenesis, Photochem. Photobiol. 33, 957–960 (1981)

    Article  Google Scholar 

  4. Pathak M.A., Parrish J.A. and Fitzpatrick T.B., Psoralens in Photochemotherapy of skin diseases, II Farmaco 36, 449–491 (1981)

    Google Scholar 

  5. Parrish J.A. Phototherapy of psoriasis and other skin diseases in “The Science of Photomedicine” Ed. by J.D. Regan and J.A. Parrish, 511–531, Plenum 1982.

    Chapter  Google Scholar 

  6. Sa E Melo M.T.“Etude physico-chimique et photobiologique du mode d’action de certains médicaments antipsoriatiques (furocoumarins et anthraline) Thèse de Doctorat ès Sciences Physiques, Université de Paris VI (1983).

    Google Scholar 

  7. Moore T.A., Harter M.L. and Song P.S., Ultraviolet spectra of coumarins and psoralens, J. Mol. Spectrosc. 40, 144–157 (1971)

    Article  Google Scholar 

  8. Song P.S., Shin S.C. and Mantulin W.W., The electronic spec- tra of psoralens in their ground and triplet excited states, Bull. Chem. Soc. Jpn, 54, 315–316 (1981)

    Article  Google Scholar 

  9. Song P.S., The electronic spectroscopy of photoreceptors (other than rhodopsin) in “Photochemical and Photobiological Reviews”, Vol. 7, 77–139 Edited by Kendric C. Smith, Plenum (1983)

    Chapter  Google Scholar 

  10. Averbeck D., Bisagni E., Marquet J.P., Vigny P. and Gaboriau F., Photobiological activity in yeast of derivatives of psoralen substituted at the 3,4 and/or 4′,5′ reaction site, Photochem. Photobiol. 30, 547–555 (1979).

    Article  Google Scholar 

  11. Dall’Acqua F. and Rodighiero G., The dark interaction between furocoumarins and nucleic acids, Rend. Accad. Naz. Lincei (Roma) 40, 411–422 (1966).

    Google Scholar 

  12. Goyal G.L. and Grossweiner L.I., The effect of DNA binding on initial 8-methoxypsoralen photochemistry, Photochem. Photobiol. 29, 847–850 (1979).

    Article  Google Scholar 

  13. Decout J.L. and Lhomme J., Synthetic models related to DNA-Intercalating molecules. Interactions between 8-alkoxypsoralen and adenine, Photochem. Photobiol. 37, 155–161 (1983).

    Article  Google Scholar 

  14. Vigny P., Gaboriau F., Duquesne M., Bisagni E. and Averbeck D., Spectroscopie properties of psoralen derivatives substituted by carbethoxy group at the 3,4 and/or 41,5′ reaction site, Photochem. Photobiol. 30, 557–564 (1979).

    Article  Google Scholar 

  15. Gaboriau F., Etude spectroscopique comparée de l’interaction du 3-Carbethoxypsoralène et 8-Methoxypsoralène avec l’ADN. Thèse 3ème Cycle, Université de Paris V I (1980).

    Google Scholar 

  16. Mantulin W.W. and Song P.S., Excited states of skin-sensitizing coumarins and psoralens, spectroscopie studies, J. Am. Chem. Soc. 95, 5122–5129 (1973).

    Article  Google Scholar 

  17. Beaumont P.C., Parsons B.J., Navaratnam S., Phillips G.O. and Allen J.C., The reactivities of furocoumarin excited states with DNA in solution. A laser flash photolysis and fluorescence study., Biochim. Biophys. Acta, 608, 259–265 (1980).

    Article  Google Scholar 

  18. Salet C., Macedo De Sa e Melo T., Bensasson R. and Land E.J., Photophysical properties of aminomethyl psoralen in presence and absence of DNA, Biochim. Biophys. Acta, 607, 379–383 (1980)

    Article  Google Scholar 

  19. Andreoni A., Cubbeddu R., Dall’Acqua F., Knox C.N. and Truscott T.G., Fluorescence lifetimes of furocoumarins. Part I: Psoralens. Submitted to J.C.S. Faraday I.

    Google Scholar 

  20. Bensasson R.V., Rougee M., Ronfard-Haret J.C., unpublished results.

    Google Scholar 

  21. Anders A., Poppe W., Hertz-Maetzky C., Nieman E.G.and Hofer E., Investigations on the mechanism of photodynamic action of different posoralens with DNA, Biophys. Struct. Mech., 10, 11–30 (1983).

    Article  Google Scholar 

  22. Beaumont P.C., Parsons B.J., Navaratnam, Phillips G.O., A laser flash photolysis and fluorescence study of aminomethyltrimethylpsoralen in the presence and absence of DNA. Photobiochem. Photobiophys. 5, 359–364 (1983).

    Google Scholar 

  23. Selinger B.K.and Harris C.M., A critical appraisal of analytical methods in Time-resolved fluorescence spectroscopy in Biochemistry and Biology Edited by R.B. Cundall and R.E. Dale, 155–168, Plenum (1983).

    Google Scholar 

  24. Bensasson R.V., Land E.J. and Truscott T.G. in “Flash photolysis and pulse radiolysis”. Contributions to the Chemistry of Biology and Medicine, Pergamon (1983).

    Google Scholar 

  25. Craw M., Bensasson R.V., Ronfard-Haret J.C., Sa e Melo M.T. and Truscott T.G, Some photophysical properties of 3-Carbethoxypsoralen, 8-Methoxypsoralen and 5-Methoxypsoralen triplet states, Photochem. Photobiol. 37, 611–615 (1983).

    Google Scholar 

  26. Bensasson E.J., Chalvet O, Land E.J., Ronfard-Haret J.C., Triplet, radical anion and radical cation spectra of furocoumarins, Photochem. Photobiol. 39, 287–291 (1984)

    Article  Google Scholar 

  27. Bevilacqua R. and Bordin F., Photo-C4-cycloaddition of psoralen and pyrimidine bases: effects of oxygen and paramagnetic ions, Photochem. Photobiol. 17, 191–194 (1983).

    Article  Google Scholar 

  28. Ou C.N., Tsai C.H., Tapley K.J. and Song P.S., Photobinding of 8-Methoxypsoralen and 5,7-Dimethoxycoumarin to DNA and its effect on template activity, Biochemistry 17, 1047–1053 (1978).

    Article  Google Scholar 

  29. Cadet J., Decarroz C., Voituriez L., Gaboriau F. and Vigny P., Sensitized photoreactions of purine and pyrimidine 2′-deoxyribonucleosides by 8-Methoxypsoralen and 3-Carbethoxypsoralen in “Oxygen Radicals in Chemistry and Biology”. Edited by Bors W., Saran M. and Tait D. - Walter de Gruyter and Co, Berlin — New-York (1984).

    Google Scholar 

  30. Musajo L. and Rodighiero G., Photo-C4-cycloaddition reactions to the nucleic acids in Research Progress in Organic Biological and Medicinal Chemistry“ Vol.3 Part 1, chapter 10, 155–182 North Holland (1972).

    Google Scholar 

  31. Bensasson R.U., Land E.J. and Salet C., Triplet excited state of furocoumarins: reaction with nucleic acid bases and amino acids. Photochem. Photobiol. 27, 273–280 (1978).

    Article  Google Scholar 

  32. Voituriez L. and Cadet J. Personal communication.

    Google Scholar 

  33. Rodighiero G., Musajo L., Dall’Acqua F., Marciani S., Caporale G. and Liavatta L., Mechanism of skin photosensitization by furocoumarins. Photoreactivity of various furocoumarins with native DNA and with ribosomal RNA. Biochim. Biophys. Acta 217, 40–49 (1970).

    Article  Google Scholar 

  34. Straub K, Kanne D., Hearst J.E. and Rapoport H., Isolation and characterization of pyrimidine-psoralen photoadducts from DNA. J. Am. Chem. Soc. 103, 2347–2355 (1981).

    Article  Google Scholar 

  35. Kanne D., Straub K., Rapoport H. and Hearst J.E., The psoralen-DNA photoreaction. Characterization of the monoaddition products from 8-methoxypsoralen and 4,5′,8-trimethylpsoralen. Biochemistry 21, 861–871 (1982).

    Article  Google Scholar 

  36. Land E.J., Rushton F.A.P., Beddoes R.L., Bruce J.M., Cernik R.J., Dawson S.C. and Mills O.S., A (2 + 2) Photo-adduct of 8MOP and thymine: X Ray crystal structure: a model for the reaction of psoralens with DNA in the phototherapy of psoriasis. J.Chem. Soc. Chem. Comm., 22–23 (1982).

    Google Scholar 

  37. Cadet J., Voituriez L., Gaboriau F., Vigny P. and Della Negra S. Characterization of photocycloaddition products from reaction between thymidine and the mono-functional 3-carbethoxypsoralen. Photochem. Photobiol. 37, 363–371 (1983).

    Article  Google Scholar 

  38. Hearst J.E., Isaacs S.T., Kanne D., Rapoport H. and Straub K., The reactions of the psoralens with deoxyribonucleic acid. Quarterly Review of Biophysics 17, 1–44 (1984).

    Article  Google Scholar 

  39. Yoshikawa K., Mori N., Sakakibara S., Mizuno N. and Song P.S., Photoconjugation of 8-methoxypsoralen with singlet oxygen. Photochem. Photobiol. 29, 1127–1133 (1979).

    Article  Google Scholar 

  40. Ronfard-Haret J.C., Averbeck D., Bensasson R.V.,Bisagni E. and Land E.J., Some properties of the triplet excited state of the photosensitizing furocoumarin: 3-carbethoxypsoralen. Photochem. Photobiol. 35, 479–489 (1982).

    Google Scholar 

  41. Dubertret L., Averbeck D., Zajdela F., Bisagni E., Moustacchi E., Touraine R. and Latarjet R., Photochemo-therapy (PUVA) of 3-carbethoxypsoralen, a compound non-carcinogenic in mice. Brit. J. Dermatol. 101, 373–389 (1979).

    Article  Google Scholar 

  42. Averbeck D., Dubertret L., Craw M., Truscott T.G., Dall’Acqua F., Rodighiero P., Vedaldi D., Photophysical, photochemical and photobiological studies of 4’-methylangelicins, potential agents for photochemotherapy, Il Farmaco 57–69 (1984).

    Google Scholar 

  43. K. Wolff, T.B. Fitzpatrick, J.A. Parrish, F. Gschnait, B. Gilchrest, H. Honigsmann, M.A. Pathak and L. Tannenbaum. Photochemotherapy with orally administered methoxsalen. Arch. Dermatol., 112: 943 (1986).

    Article  Google Scholar 

  44. S. Cova, A. Longoni, A. Andreoni and R. Cubeddu. A. semiconductor detector for measuring ultra-weak fluorescence decays with 70 ps full-width at half maximum resolution. IEE J. Quantum Electron, 19: 630 (1983).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1985 Plenum Press, New York

About this chapter

Cite this chapter

Bensasson, R.V., Andreoni, A., Cubeddu, R., Dall’Acqua, F., Knox, C.N., Truscott, T.G. (1985). Some Properties of Furocoumarin (FC) Excited States. In: Bensasson, R.V., Jori, G., Land, E.J., Truscott, T.G. (eds) Primary Photo-Processes in Biology and Medicine. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-1224-6_14

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-1224-6_14

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-1226-0

  • Online ISBN: 978-1-4684-1224-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics