Photophysical Properties and Photobiological Activity of the Furanochromones Visnagin and Khellin

Photochemistry and Photobiology

Volumn 67, Issue 2, 1998, Pages 184-191

  Borges, Marta L ^a   Latterini, Loredana ^b   Elisei, Fausto ^b   Silva, Palmira F ^c   Borges, Rui ^d   Becker, Ralph S ^a,e   Maçanita, António L ^a,d  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^b UNIVERSITY OF PERUGIA   (Italy)

^c Center for Structural Chemistry   (Portugal)

^d UNIVERSITY OF LISBON   (Portugal)

^e UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESCHERICHIA COLI; FUNGI; FUSARIUM CULMORUM;

DRUG DERIVATIVE; KHELLIN; VISNAGIN;

ARTICLE; BIOLOGY; CHEMISTRY; DRUG EFFECT; ESCHERICHIA COLI; FUSARIUM; METHODOLOGY; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; SPECTROFLUOROMETRY;

CHEMISTRY, PHYSICAL; ESCHERICHIA COLI; FUSARIUM; KHELLIN; PHOTOBIOLOGY; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE;

EID: 0031988939     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb05185.x     Document Type: Article

References (30)

1. Becker, R. S., S. Chakravorti, C. A. Gartner and M. G. Miguel (1993) Photosensitizers: comprehensive photophysics/photochemistry and theory of coumarins, chromones, their homologues and thione analogues. J. Chem. Soc. Faraday Trans. 89, 1007.
2. Gallivan, J. B. and J. S. Brinen (1971) Solvent reordering of low lying triplet states in some aromatic carbonyls. Chem. Phys. Lett. 10, 455-459.
3. Rajadurai, S. and P. K. Das (1987) Reactivity and photophysical behavior of chromone triplet. A laser flash photolysis study. Can. J. Chem. 65, 2277-2285.
4. Adeleke, B. B., D. Weir, M. C. Depew and J. L. K. Wan (1984) An esr and CIDEP study of the photoreduction of chromone and chromanone and their organometallic radical adducts. Can. J. Chem. 62, 117-120.
5. Igarashi, M. Y., Y. Sakaguchi and Y. J. l'Haya (1991) Formation of alpha-keto alkyl radical in the photoreduction of chromone as studied by the laser flash photolysis-ESR technique. Chem Phys. Lett. 181, 187-192.
6. Martelli, P., L. Bovalini and G. G. Franchi (1984) Rapid separation and quantitative determination of khellin and visnagin in Ammi visnaga (L.) Lam. Fruits by high performance liquid chromatography. J. Chromatogr. 301, 297-302.
7. Trabalzini, L., P. Martelli, L. Bovalini, F. Dall' Acqua and E. Sage (1990) Photosensitization of DNA of defined sequence by furochromones, khellin and visnagin. Photochem. Photobiol. B Biol. 7, 317-336.
8. Morliere, P., H. Honigsmann, D. Averbeck, M. Dardolhon, G. Huppe, B. Ortel, R. Santus and L. Dubertret (1988) Phototherapeutic, photobiologic and photosensitizing properties of khellin. J. Invest. Dermatol. 90, 720-724.
9. Hudson, J. B. and G. H. N. Towers (1991) Therapeutic potential of plant photensitizers. Pharmacol. Ther. 49, 181-222.
10. Abysekera, B. F., Z. Abramowski and G. H. N. Towers (1983) Genotoxicity of the natural furochromones khellin and visnagin and the identification of a khellin-thymine photoadduct. Photobiochem. Photobiophys. 38, 311-315
11. Seixas de Melo, J. (1996), Fotofisica molecular de cumarinas e tiofenos. Ph.D. Thesis, Lisbon.
12. Elisei, F., G. G. Aloisi and U. Mazzucato (1990) Laser flash photolysis study of trans-styrylphenanthrene isomers and their exciplexes with amines. J. Phys. Chem. 94, 5818-5823.
13. Aloisi, G. G., F. Elisei and L. Latterini (1992) Triplet and radical ion properties of styrylnaphthalenes and their aza-derivatives: a laser flash photolytic study. J. Chem. Soc. Faraday Trans. 88, 2139-2145.
14. Burkey, T. J., M. Majewski and D. Griller (1986) Heats of formation of radicals and molecules by a photoacoustic technique. J. Am. Chem. Soc. 108, 2218-2221.
15. Maçanita, A. L., F. P. Costa, S. M. B. Costa, E. C. Melo and H. Santos (1989) The 9-anthroate chromophore as fluorescent probe for water. J. Phys. Chem. 93, 336-343.
16. Zachariasse, K., G. Duveneck and R. Busse (1984) Intramolecular excimer formation with 1.3-di(1-pyrenyl)propane. Decay parameters and influence of viscosity. J. Am. Chem. Soc. 106, 1045-1051.
17. Striker, G. (1982) Effective implementation of modulation functions. In Deconvolution and Reconvolution of Analytical Signals (Edited M. Bouchy), p. 329. University Press, Nancy, France.
18. Quantum Chemistry Program Exchange (1988) QCPE Program No. QCMP174. Department of Chemistry, Indiana University, Bloomington, IN.
19. Dewar, M. J. S., E. G. Zoebisch, E. F. Healy and J. P. Stewart (1985) AMI: a new purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
20. Becker, R. S., J. S 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. Chem. Phys. 100, 18683-18695
21. g) sensitization. J. Photochem. Photobiol. A Chem. 79, 11-17.
22. Wilkinson, F., W. P. Helman and A. B. Ross (1993) Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 1, 113.
23. Borges, M. L., O. C. Matos, I. Pais, J. S Melo, C. P. Ricardo, A. L. Maçanita and R. S. Becker (1995) Evaluation of a broad variety of coumarins, chromones, their furohomologues and thione analogs as phototoxins activated by UVA and visible light. Pestic. Sci. 44, 155.
24. Tuveson, R. W., G. Wang and R. S. Becker (1992) The phototoxicity of 8-methoxythionepsoralen and 6-methylthionecoumarin. Photochem. Photobiol. 56, 341-352.
25. Takemura, T., P. K. Das, G. Hug and R. S. Becker (1978) Visual pigments. 8. Hydrogen bonding effects on fluorescence properties of retinals. J. Am. Chem. Soc. 100, 2626-2630.
26. Becker, R. S. (1959) The nature and spectral effects of the interaction of certain polar solvents with benzophenone. J. Mol. Spectrosc. 3, 1-16.
27. Becker, R. S. (1969) Theory and Interpretation of Fluorescence and Phosphorescence. Wiley Interscience, New York.
28. Melo, T., A. L. Maçanita, M. J. Prieto, M. Bazin, J. C. Ronfard and R. Santus (1988) Photophysical behaviour of 5-methoxypsoralen in dioxane-water mixtures. Photochem. Photobiol. 47, 429-434.
29. Maçanita, A. L., F. P. Costa, S. M. B. Costa, E. C. Melo and H. Santos (1989) The 9-anthroate chromophore as a fluorescent probe to water. J. Phys. Chem. 93, 336-343.
30. Melo, E. C., S. M. B. Costa, A. L. Maçanita and H. Santos (1991) The use of the n-(9-anthroyloxy)stearic acids to probe the water content of SDS, DTAC and triton X-100 micelles. J. Colloid Interface Sci. 141, 439-453.