Photophysical Behavior of Angelicins and Thioangelicins: Semiempirical Calculations and Experimental Study

Photochemistry and Photobiology

Volumn 68, Issue 2, 1998, Pages 164-172

  Elisei, F ^a   Aloisi, G G ^a   Dall'Acqua, F ^b   Latterini, L ^a   Masetti, F ^a   Rodighiero, P ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000829155     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02484.x     Document Type: Article

References (35)

1. Bordin, F., F. Dall'Acqua and A. Guiotto (1991) Angelicins, angular analogs of psoralens: chemistry, photochemical, photobiological and phototherapeutic properties. Pharmacol. Ther. 52, 331-363.
2. Dall'Acqua, F., D. Vedaldi, A. Guiotto, P. Rodighiero, F. Carlassare, F. Baccichetti and F. Bordin (1981) Methylangelicins: new potential agents for the photochemotherapy of psoriasis. Structure-activity study on the dark and photochemical interaction with DNA. J. Med. Chem. 24, 806-811.
3. Dall'Acqua, F., D. Vedaldi, F. Baccichetti, G. Rodighiero and A. Gennaro (1984) QSAR on furocumarins, agents for the photochemotherapy of psoriasis. In Design of bioactive compounds (Edited by Kuchar). Prous, Barcelona, p. 87-95.
4. Cristofolini, M., G. Recchia, S. Boi, F. Piscioli, F. Bordin, F. Baccichetti, F. Carlassare, M. Tamaro, B. Pani, N. Babudri, A. Guiotto, P. Rodighiero, D. Vedaldi and F. Dall'Acqua (1990) 6-Methylangelicins: new monofunctional photochemotherapeutic agents for psoriasis. Br. J. Dermatol. 122, 513-524.
5. Morita, A., A. Takashima, M. Nagai and F. Dall'Acqua (1990) Treatment of mycosis fungoides and parapsoriasis en plaque with topical PUVA using monofunctional furocoumarin derivative, 4,6,4′-trimethylangelicin. J. Dermatol. 17, 545-549.
6. Vedaldi, D., G. Miolo, S. Caffieri, G. Piazza, P. Rodighiero and F. Dall'Acqua (1997) Trimethylthioangelicin, a new furocoumarin derivative with potential photochemotherapeutic properties. First Italian-Swiss Meeting on Medicinal Chemistry, Turin (Italy), Acts, B36.
7. Rodighiero, P., G. Pastorini, A. Chillin and A. Marotto (1998) Synthesis of methylderivatives of linear and angular thienocoumarins and thiopyranocoumarins. J. Heterocycl. Chem. 35, 1.
8. Averbeck, D., L. Dubertret, M. Crow, T. G. Truscott, F. Dall'Acqua, P. Rodighiero, D. Vedaldi and E. J. Land (1984) Photophysical, photochemical and photobiological studies of 4′-methylangelicins, potential agents for photochemotherapy. Il Farmaco 39, 57-69.
9. Crow, M., T. G. Truscott, F. Dall'Acqua, A. Guiotto, D. Vedaldi and E. J. Land (1984) Methylangelicins: possible correlation between photophysical properties of the triplet excited state and photobiological activity. Photochem. Photobiophys. 7, 359-365.
10. Andreoni, A., R. Cubeddu, F. Dall'Acqua, C. N. Knox and T. G. Truscott (1985) Fluorescence lifetimes of furocoumarins. Psoralens. Chem. Phys. Lett. 114, 329.
11. Knox, C. N., E. J. Land and T. G. Truscott (1988) Triplet state properties and triplet-state-oxygen interactions of some linear and angular furocoumarins. J. Photochem. Photobiol. B Biol. 1, 315-321 and references therein.
12. Bensasson, R. V., E. J. Land and T. G. Truscott (1993) Excited States and Free Radicals in Biology and Medicine. Oxford University Press, Oxford.
13. Elisei, F., G. G. Aloisi, C. Lattarini, L. Latterini, F. Dall'Acqua and A. Guiotto (1996) Photophysical properties of some methyl-substituted angelicins: fluorometric and flash photolytic studies. Photochem. Photobiol. 64, 67-74.
14. Lai, T.-I., B. T. Lim and E. C. Lim (1982) Photophysical properties of biologically important molecules related to proximity effects: psoralens. J. Am. Chem. Soc. 104, 7631-7635.
15. Lim, E. C. (1986) Proximity effect in molecular photophysics: dynamical consequences of pseudo-Jahn-Teller interaction. J. Phys. Chem. 90, 6770-6777.
16. Murov, S. V., I. Carmichael and G. L. Hug (1993) Handbook of Photochemistry, pp. 283-287. Marcel Dekker, New York.
17. Eaton, D. F. (1989) Luminescence spectroscopy. In Handbook of Organic Photochemistry, Vol. 1 (Edited by J. C. Scaiano), pp. 231-239. CRC Press, Boca Raton, FL, and references therein.
18. Beechem, J. M., E. Gratton, M. Ameloot, J. R. Kutson and L. Brand (1988) Fluorescence Spectroscopy, Vol. 1. Principles and Techniques (Edited by J. R. Lakowicz). Plenum Press, New York and references therein.
19. Romani, A., F. Elisei, F. Masetti and G. Favaro (1992) pH-induced effects on the photophysics of dipyridyl ketones. J. Chem. Soc. Faraday Trans. 88, 2147-2154.
20. Görner, H., F. Elisei and G. G. Aloisi (1992) Photoinduced electron transfer between styrylanthracenes and electron donors and acceptors in acetonitrile. J. Chem. Soc., Faraday Trans. 88, 29-34.
21. Carmichael, I. and G. L. Hug (1986) Triplet-triplet absorption spectra of organic molecules in condensed phase. J. Chem. Phys. Ref. Data 15, 1-204.
22. Latterini, L. (1996) Studio fotofisico e fotochimico di molecole aromatiche mediante tecniche stazionarie e pulsate. Dottorato Thesis, University of Perugia, Italy.
23. Becker, R. S., J. Seixas de Melo, A. L. Maçanita and F. Elisei (1996) Comprehensive evaluation of the absorption, photophysical, energy transfer, structural and theoretical properties of α-oligothiophenes with one to seven rings. J. Phys. Chem. 100, 18683-18695.
24. g) sensitization. J. Photochem. Photobiol. A Chem. 79, 11-17.
25. Dewar, M. J. S. and W. Thiel (1977) Ground states of molecules. 38. The MNDO method. Approximations and parameters. J. Am. Chem. Soc. 99, 4899-4907.
26. Ridley, J. E. and M. C. Zerner (1976) Triplet states via intermediate neglect of differential overlap: benzene, pyridine and diazines. Theor. Chim. Acta 42, 223-236.
27. Bacon, A. D. and M. C. Zerner (1979) An intermediate neglect of differential overlap theory for transition metal complexes: Fe, Co and Cu chlorides. Theor. Chim. Acta 53, 21-54.
28. Zerner, M. C., G. H. Loew, R. F. Kirchner and U. T. Müller-Westerhoff (1980) An intermediate neglect of differential overlap technique for spectroscopy of transition-metal complexes. Ferrocene. J. Am. Chem. Soc. 102, 589-599.
29. Birks, J. B. (1970) Photophysics of Aromatic Molecules. Wiley Interscience, London.
30. Wilkinson, F., W. P. Helman and A. B. Ross (1995) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Chem. Phys. Ref. Data 24, 663-1021.
31. g), in organic and aqueous media: a time-resolved luminescence study. J. Am. Chem. Soc. 109, 3091-3097.
32. Gorman, A. A., G. Lovering and M. A. J. Rodgers (1978) A pulse radiolysis study of the triplet sensitized production of singlet oxygen: determination of energy transfer efficiencies. J. Am. Chem. Soc. 100, 4527-4532.
33. Rodgers, M. A. J. (1987) Singlet oxygen quantum yields. Am. Chem. Soc. Symp. Ser. 339, 76-97.
34. Redmond, R. W. and S. Braslawsky (1988) Time-resolved thermal lensing and phosphorescence studies of photosensitized singlet molecular oxygen formation. Influence of the electronic configuration of the sensitizer on sensitization efficiency. Chem. Phys. Lett. 148, 523-529.
35. El-Sayed, M. A. (1964) Vanishing first-and second-order intramolecular heavy-atom effects on (π* → n) phosphorescence in carbonyls. J. Chem. Phys. 41, 2462-2467 and references therein.