Photobiological Properties of 1′-Thieno-4,6,4′-trimethylangelicin

Photochemistry and Photobiology

Volumn 68, Issue 2, 1998, Pages 157-163

  Bordin, F ^a   Marzano, C ^a   Baccichetti, F ^a   Carlassare, F ^a   Vedaldi, D ^a   Falcomer, S ^b   Lora, S ^c,d   Rodighiero, P ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

^c Reparto Applicazioni   (Italy)

^d Istituto di Fotochimica e Radiazioni d'Alta Energia   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1' THIENO 4,6,4' TRIMETHYLANGELICIN; 1'-THIENO-4,6,4'-TRIMETHYLANGELICIN; 4,4',6 TRIMETHYLANGELICIN; 4,4',6-TRIMETHYLANGELICIN; PHOTOSENSITIZING AGENT; PSORALEN DERIVATIVE;

ANIMAL; ARTICLE; CELL CULTURE; CELL DIVISION; COMPARATIVE STUDY; DNA DAMAGE; DRUG EFFECT; EHRLICH ASCITES TUMOR; HELA CELL; HUMAN; MOUSE; PHOTOCHEMOTHERAPY;

ANIMALS; CARCINOMA, EHRLICH TUMOR; CELL DIVISION; DNA DAMAGE; HELA CELLS; HUMANS; MICE; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PSORALENS; TUMOR CELLS, CULTURED;

EID: 0032133870     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02483.x     Document Type: Article

References (31)

1. Ben-Hur, E. and P. S. Song (1984) The photochemistry and photobiology of furocoumarins (psoralens). Adv. Radiat. Biol. 11, 131-171.
2. Pathak, M. A. and T. B. Fitzpatrick (1992) The evolution of photochemotherapy with psoralens and UVA (PUVA): 200 BC to 1992 AD. J. Photochem. Photobiol. B Biol. 14, 3-22.
3. Edelson, R. L., C. L. Berger, F. P. Gasparro, B. Jegasothy, P. Heald, B. Wintroub, E. Vonderheid, R. Knobler, K. Wolff, G. Plewig et al. (1987) Treatment of cutaneous T-cell lymphoma by extracorporeal photochemotherapy. N. Engl. J. Med. 316, 297-303.
4. Gasparro, F. P. (1994) Extracorporeal Photochemoterapy-Clinical Aspects and the Molecular Basis for Efficacy. Landes Press, Georgetown, TX.
5. Venturini, S., M. Tamaro, C. Monti-Bragadin, F. Bordin, F. Baccichetti and F. Carlassare (1980) Comparative mutagenicity of linear and angular furocoumarins in Escherichia coli strains deficient in known repair functions. Chem.-Biol. Interact. 30, 203-207.
6. Gunther, E. J., T. M. Yeasky, F. P. Gasparro and P. M. Glazer (1995) Mutagenesis by 8-MOP and 5-methylangelicin photoadducts in mouse fibroblasts: mutations at cross-linkable sites induced by monoadducts as well cross-links. Cancer Res. 55, 1283-1288.
7. Hook, G. J., J. A. Heddle and R. R. Marshall (1983) On the types of chromosomal aberrations induced by 8-methoxypsoralen. Cytogenet. Cell Genet. 35, 100-103.
8. Rodighiero, G., F. Dall'Acqua and D. Averbeck (1988) New psoralens and angelicin derivatives. In Psoralen DNA Photobiology, Vol. I (Edited by F. P. Gasparro), pp. 37-114. CRC Press, Boca Raton, FL.
9. Bordin, F., F. Dall'Acqua and A. Guiotto (1991) Angelicins, angular analogs of psoralens: chemistry, photochemical, photobiological and photochemotherapeutic properties. Pharmacol. Ther. 52, 331-363.
10. Baccichetti, F., F. Carlassare, F. Bordin, A. Guiotto, P. Rodighiero, D. Vedaldi, M. Tamaro and F. Dall'Acqua (1984) 4,4′,6-Trimethylangelicin, a new very photoreactive and nonskin-phototoxic monofunctional furocoumarin. Photochem. Photobiol. 39, 525-529.
11. Chen, X., J. Kagan, G. Miolo, F. Dall'Acqua, D. Averbeck and E. Bisagni (1994) Photosensitized cross-linking and cleavage of pBR322 and M13 DNA: comparison of 4,4′,6-trimethylangelicin and 3-carbethoxypsoralen. J. Photochem. Photobiol. B Biol. 22, 51-57.
12. Bordin, F., C. Marzano, C. Gatto, F. Carlassare, P. Rodighiero and F. Baccichetti (1994) 4,6,4′-Trimethylangelicin induces inter-strand cross-links in mammalian cell DNA. J. Photochem. Photobiol. B Biol. 26, 197-201.
13. Vedaldi, D., F. Dall'Acqua, S. Caffieri, F. Baccichetti, F. Carlassare, F. Bordin, A. Chilin and A. Guiotto (1991) 4,4′,5′-Trimethyl-8-azapsoralen, a new photoactive and non skin-phototoxic bifunctional bioisoster of psoralen. Photochem. Photobiol. 53, 143-148.
14. Pani, B., M. Tamaro, F. Baccichetti, F. Carlassare, M. Simonato and F. Bordin (1992) Aspects of genotoxic activity of some 8-azapsoralen derivatives. Med. Biol. Environ. 20, 117-124.
15. Baccichetti, F., F. Bordin, M. Simonato, L. Toniolo, C. Marzano, P. Rodighiero, A. Chilin and F. Carlassare (1992) Photobiological activity of certain new methylazapsoralens. Il Farmaco 47, 1529-1541.
16. Jakobs, A. E. and J. Piette (1994) Photobiological activity of sulphur and selenium analogues of psoralen. J. Photochem. Photobiol. B 22, 9-15.
17. Jakobs, A. E. and J. Piette (1995) 1-Thiomethoxsalen and 1-thiopsoralen: synthesis, photobiological properties, and site specific reaction of thiopsoralens with DNA. J. Med. Chem. 38, 869-874.
18. Collet, M., E. Sage and J. Piette (1997) Photoreaction of sulfur and selenium analogs of psoralen with DNA: sequence and mutation specificity in the Escherichia coli lacZ gene. J. Photochem. Photobiol. B Biol. 66, 214-223.
19. Vedaldi, D., S. Caffieri, S. Frank, F. Dall'Acqua, A. E. Jakobs and J. Piette (1995) Sulphur and selenium analogues of psoralens as novel potential photochemotherapeutic agents. Il Farmaco 50, 527-536.
20. Rodighiero, P., A. Guiotto, A. Chilin, F. Bordin, F. Baccichetti, F. Carlassare, D. Vedaldi, S. Caffieri, A. Pozzan and F. Dall'Acqua (1996) Angular furoquinolinones, psoralen analogues: novel antiproliferative agents for skin diseases. Synthesis, biological activity, mechanism of action and computer-aided studies. J. Med Chem. 29, 1293-1302.
21. Bordin, F., C. Marzano, F. Carlassare, P. Rodighiero, A. Guiotto, S. Caffieri and F. Baccichetti (1996) Photobiological properties of a new tetramethylfuroquinolinone. J. Photochem. Photobiol. B Biol. 34, 159-168.
22. Marzano, C., E. Severin, B. Pani, A. Guiotto and F. Bordin (1997) DNA damage and cytotoxicity induced in mammalian cells by a tetramethylfuroquinolinone derivative. Environ. Mol. Mutagen. 29, 256-264.
23. Mosti, L., P. Schenone, G. Menozzi, G. Romussi, F. Baccichetti, F. Carlassare and F. Bordin (1984) Synthesis and photobiological activity of N,N-disubstituted 4-amino-3-chloro-2H-thieno[2,3-h]-1-benzopyran-2-ones, 7-thioisosters of 4-amino-3-chloroangelicins. Il Farmaco Ed. Sci. 34, 81-94.
24. Rodigheiro, P., G. Pastorini, A. Chilin and A. Marotto (1998) Synthesis of methyl derivatives of linear and angular thienocoumarins and thiopyranocoumarins. J. Heterocyclic Chem. 35, in press.
25. Guiotto, A., P. Rodighiero, P. Manzini, G. Pastorini, F. Bordin, F. Baccichetti, F. Carlassare, D. Vedaldi, F. Dall'Acqua, M. Tamaro, G. Recchia and M. Cristofolini (1984) 6-Methylangelicins: a new series of potential photochemotherapeutic agents for the treatments of psoriasis. J. Med. Chem. 27, 959-967.
26. Burton, K. (1956) A study of the conditions and mechanism of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid. Biochemistry 62, 315-323.
27. Kohn, K. W. (1991) Principles and practice of DNA filter elution. Pharmacol. Ther. 49, 55-77.
28. Kagan, J., X. Chen, T. P. Wang and P. Forlot (1992) Psoralens cleave pBR322 DNA under ultraviolet radiation. Photochem. Photobiol. 56, 185-193.
29. Schoonderwoerd, S. A., G. M. J. Beijersbergen van Henegouwen, C. C. M. Persons, S. Caffieri and F. Dall'Acqua (1991) Photobinding of methoxypsoralen, 4,6,4′-trimethylangelicin and chloropromazine to Wistar rat epidermal biomacromolecules in vivo. J. Photochem. Photobiol. 10, 257-268.
30. Papadopoulo, D., D. Averbeck and E. Moustacchi (1987) The fate of 8-methoxypsoralen-photoinduced DNA inter-strand cross-links in Fanconi's anemia cells of defined genetic complementation groups. Mutal. Res. 184, 271-280.
31. Laquerbe, A., E. Moustacchi and D. Papadopoulo (1995) Genotoxic potential of psoralen cross-links versus monoadducts in normal human lymphoblasts. Mutat. Res. 346, 173-179.