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Solvent-Dependent Excited State Properties of Psoralens

A Model to Their Antiproliferative Action

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Part of the book series: NATO ASI Series ((NSSA,volume 286))

Abstract

The singlet and the triplet excited states parameters of psoralen and derivatives, 4,6,4′-trimethylangelicin and 4,5′,8-trimethylpsoralen, show an extreme sensivity to solvent polarity in dioxane/water mixtures. The internal conversion rate constant is the non-radiative deactivation path dominating their photophysical behaviour. The minimum values of this radiationless rate constant correspond to a more allowed radiative transition and to a longer fluorescence wavelength. Thus, the singlet-triplet energy gap decreases and intersystem crossing is promoted. This work shows that dioxane/water mixtures can display the same solvent-induced changes in the electronic structure of psoralens during solvation as those induced by the biological microenvironment sensed by the drug localization in serum lipoproteins.

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References

  1. T.Sá e Melo, D.Averbeck, R.Bensasson, E.Land and C.Salet (1979) Some furocoumarins and analogs: xomparison of triplet properties in solution with photobiological activities in yeast, Photochem.Photobiol. 30:645–651.

    Article  PubMed  Google Scholar 

  2. P.Joshi and M.Pathak (1983) Production of singlet oxygen and superoxide radicals by psoralens and their biological signifiance, Biochem. Biophys. Research Comm. 638–646.

    Google Scholar 

  3. T.Sá e Melo, A.Maçanita, M.Prieto, M.Bazin, J.Ronfard-Haret and R.Santus (1988) Photophysical behaviour of 5-methoxypsoralen in dioxan-water mixtures, Photochem.Photobiol. 48:429–437.

    Article  PubMed  CAS  Google Scholar 

  4. T.Sá e Melo, L.Ribeiro, A.Maçanita, M.Bazin, J.Ronfard-Haret and R.Santus (1990) Photochemical processes of psoralen and derivatives (8MOP and 5MOP) in biological systems, Int.Conf. on Luminescence.

    Google Scholar 

  5. T.Sá e Melo, M.Bazin, J.Ronfard-Haret and R.Santus (1993) Quantification of the solvent effects on the triplet quantum yield of psoralen by the linear solvation energy relationship, Photochem.Photobiol. 58:19–27.

    Article  CAS  Google Scholar 

  6. C.Reichardt (1990) Solvents and solvent effects in Organic Chemistry, VCH Verlag, 2nd ed. Weinheim, Germany.

    Google Scholar 

  7. C.Knox, E.Land and T.Truscott (1988) Triplet state properties and triplet-state-oxygen interactions of some linear and angular furocoumarins, J.Photochem.Photobiol. 1:315–321.

    Article  CAS  Google Scholar 

  8. T.Lai, B.Lim and E.Lim (1982) Photophysical properties of biologically important molecules related to proximity effects Psoralens, J.Am.Chem.Soc. 104:7631–7635.

    Article  CAS  Google Scholar 

  9. P.Beaumont, B.Parsons, G.Phillips and J.Allen (1979) A laser flash photo-lysis study of the reactivities of the triplet states of 8-methoxypsoralen and 4,5′,8-trimethylpsoralen with nucleic acid bases in solution, Biochem: Biophys. Acta 562: 214–221.

    Article  CAS  Google Scholar 

  10. F.Bordin, C.Marzano, C.Gatto, F.Carlassare, F.Rodighiero, F.Baccichetti (1994) 4,6,4′-Trimethylan-gelicin induces interstrand cross-links in mammalian cell DNA, J.Photochem.Photobiol.B 26:197–201.

    Google Scholar 

  11. C.Knox, E.Land and T.Truscott (1986) Singlet oxygen generation by furocoumarin triplet states. Linear furocoumarins (psoralens), Photochem.Photobiol. 43, 359–363.

    Article  PubMed  CAS  Google Scholar 

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Sa e Melo, T., Sousa, C. (1996). Solvent-Dependent Excited State Properties of Psoralens. In: Kohen, E., Hirschberg, J.G. (eds) Analytical Use of Fluorescent Probes in Oncology. NATO ASI Series, vol 286. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-5845-3_43

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  • DOI: https://doi.org/10.1007/978-1-4615-5845-3_43

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7679-8

  • Online ISBN: 978-1-4615-5845-3

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