Photosensitization of DNA strand breaks by three phenothiazine derivatives

Chemical Research in Toxicology

Volumn 16, Issue 5, 2003, Pages 644-651

  Viola, Giampietro ^a   Latterini, Loredana ^b   Vedaldi, Daniela ^a   Aloisi, Gian Gaetano ^b   Dall'Acqua, Francesco ^a   Gabellini, Nadia ^a   Elisei, Fausto ^b   Barbafina, Arianna ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FLUPHENAZINE; OXYGEN; PERPHENAZINE; PHENOTHIAZINE DERIVATIVE; PLASMID DNA; THIORIDAZINE;

ARTICLE; DNA BINDING; DNA HELIX; DNA STRAND BREAKAGE; DRUG ACTIVITY; DRUG INTERACTION; DRUG STRUCTURE; ELECTRON TRANSPORT; FLUOROMETRY; INTERCALATION COMPLEX; IONIZATION; LINEAR DICHROISM; PHOTOSENSITIZATION;

EID: 0038582328     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025680t     Document Type: Article

References (33)

1. Greenhill, J. V., and McLelland, M. A. (1990) Photodecomposition of drugs. In Progress in Medicinal Chemistry (Ellis, G. P., and West, G. B., Eds.) Vol. 27, pp 51-121, Plenum Press, New York.
2. Beijersbergen van Henegouwen, G. M. J. (1997) Medicinal Photochemistry (phototoxic and phototherapeutic aspect of drugs). In Advances in Drug Research (Testa, B., and Mayer, U., Eds.) Vol. 29, pp 79-170, Academic Press, New York.
3. Dall'Acqua, F., and Viola, G. Cellular and molecular targets of psoralens (2001) In Photobiology for the 21st Century (Coohill, T., Ed.) pp 325-341, Valdenmar Publishing Company, Overland Park, Kansas.
4. Martinez, L., and Chignell, C. F. (1998) Photocleavage of DNA by the fluoroquinolone antibacterials. J. Photochem. Photobiol. B: Biol. 45, 51-59.
5. Artuso, T., Bernardou, J., Meunier, B., Piette, J., and Paillous, N. (1991) Mechanism of DNA cleavage mediated by photoexcited nonsteroidal antiinflamatory drugs. Photochem. Photobiol. 54, 205-213.
6. Artuso, T., Bernardou, J., Meunier, B., and Paillous, N. (1990) DNA strand breaks photosensitized by benoxaprofen and other non steroidal antiinflammatory agents. Biochem. Pharmacol. 39, 407-413.
7. Decupyer, J., Piette, J., Lopez, M., Merville, M., and Van de Vorst, A. (1984) Induction of inbreaks deoxyribonucleic acid by photoexcited promazine derivatives. Biochem. Pharmacol. 24, 4025-4031.
8. Ben Hur, E., Prager, A., Green, M. I., and Rosenthal, I. (1980) pH dependence of the phototoxic and photomutagenic effects of chlorpromazine. Chem.-Biol. Interact. 29, 223-233.
9. De Mol, N. J., Psthuma, R. M., and Mohn, G. R. (1983) Induction of repairable DNA damage in Escherichia Coli and interaction with DNA in vitro by the radical cation of chlorpromazine. Chem.Biol. Interact. 47, 223-237.
10. Kochevar, I. E., Chung, F. L., and Jeffrey, A. M. (1984) Photo-addition of Chlorpromazine to DNA. Chem.-Biol. Interact. 51, 273-284.
11. De Mol, N. J., and Busker, R. W. (1984) Irreversible binding of the chlorpromazine radical cation and of photoactivated chlor-promazine to biological macromolecule. Chem.-Biol. Interact. 52, 79-92.
12. Elisei, F., Latterini, L., Aloisi, G. G., Mazzucato, U., Viola, G., Miolo, G., Vedaldi, D., and Dall'Acqua, F. (2002) Excited-state properties and in vitro phototoxicity studies of three phenothiazine derivatives. Photochem. Photobiol. 75, 11-21.
13. Scatchard, G. (1949) The attraction ofproteins for small molecules and ions. Ann. N. Y. Acad. Sci. 51, 660-672.
14. McGhee, J. D., and von Hippel, P. H. (1974) Theorical aspect of DNA-protein interaction: cooperative and non cooperative binding of large ligands to a one-dimensional homogeneus lattice. J. Mol. Biol. 86, 469-489.
15. Beechem, J. M., Gratton, E., Ameloot, M., Kutson, J. R., and Brand, L. (1988) Fluorescence Spectroscopy (Lakowicz, J. R., Ed.) Vol. 1 Principles and Techniques, Plenum Press, New York, and references therein.
16. Wada, A., and Kozawa, S. (1964) Instrument for the studies of differential flow dichroism of polymer solution. J. Polim. Sci. 42, 853-864.
17. Ciulla, T. A., Van Camp, J. R., Rosenfeld, E., and Kochevar, I. E. (1989) Photosensitization of single-strand breaks in pBR322 DNA by rose bengal. Photochem. Photobiol. 49, 293-298.
18. Viola, G., Dall'Acqua, F., Gabellini, N., Moro, S., Vedaldi, D., and Ihmels, H. (2002) Indolo[2,3-b]-quinolizinium bromide: an efficient intercalator with DNA-photodamaging properties. ChemBioChem 3, 101-109.
19. Ihmels, H., Bringmann, G., Faulhaber, K., Messer, K., Sturm, C., Gabellini, N., Vedaldi, D., and Viola, G. (2001) Acridizinium salts as a novel class of DNA-binding and site-selective DNA- photodamaging chromophores Photochem. Photobiol. 74, 505-511.
20. Görner, H., Elisei, F., and Aloisi, G. G. (1992) Photoinduced electron transfer between styrylanthracenes and electron donors and acceptors in acetonitrile. J. Chem. Soc., Faraday Trans. 88, 29-34.
21. Romani, A., Elisei, F., Masetti, F., and Favaro, G. (1992) pH-induced effects on the photophysics of dipyridyl ketones. J. Chem. Soc., Faraday Trans. 88, 2147-2154.
22. Nordén, B., Kubista, M., and Kurucsev, T. (1992) Linear dichroism spectroscopy of nucleic acids. Q. Rev. Biophys. 25, 51-171.
23. Nordén, B., and Kurucsev, T. (1994) Analysing DNA complexes by circular and linear dichroism. J. Mol. Recognit. 7, 141-156.
24. Wasil, M., Halliwell, B., Grootveld, M., Moorhouse, C. P., Hutchison, D. C. S., and Baum, H. (1987) The specificity of thiourea, dimethylthiourea and dimethylsulphoxide as scavengers of hydroxyl radicals. Biochem. J. 243, 867-870.
25. Burrows, C. J., and Muller, J. G. (1998) Oxidative nucleobase modification leading to strand scission. Chem. Rev. 98, 1109- 1151.
26. Sanger, F., Nicklen, S., and Coulsen, A. R. (1977) DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. U.S.A. 74, 5463-5467.
27. Chen, L., Wood, P. D., Mnyusiwalla, A., Marlinga, J., and Johnston, L. J. (2001) Electron-transfer reactions in micelles: dynamics of psoralen and coumarin radical cations. J. Phys. Chem. B 105, 10927-10935.
28. Faraggi, M., Broitman, F., Trent, J. B., and Klapper, M. H. (1996) One-electron oxidation reactions of some purine and pyrimidine bases in aqueous solutions. Electrochemical and pulse radiolysis studies. J. Phys. Chem. 100, 14751-14761.
29. -) with pyrimidine and purine derivatives. J. Phys. Chem. A 102, 6259-6265.
30. De Mol, N. J., and Manders, J. P. A. C. M. (1983) Non covalent binding of some phenothiazines drugs to DNA. Int. J. Pharm. 16, 153-161.
31. Berhens, G., Kroneburg, G., and Schulte-Frohlinde, D. (1982) Model reactions for the degradation of DNA-4′ radicals in aqueous solution. Fast hydrolisis of α-alkoxyalkyl radical with a leaving group in β position followed by radical rearrangement and elimination reactions. Z. Naturforsch. C: J. Biosci. 37, 1205-1210.
32. Giese, B., Beirich-Graf, X., Burger, J., Kesselheim, C., Senn, M., and Schäfer, T. (1993) The mechanism of anaerobic, radical-induced DNA strand. Angew. Chem., Int. Ed. Engl. 32, 1742-1743.
33. Steenken, S., Jovanovic, S. V., Candeias, L. P., and Reynisson, J. (2001) Is "Frank" DNA-Strand Breakage via the Guanine Radical Thermodynamically and Sterically Possible. Chem. Eur. J. 7, 2829-2833 and references therein.