Supramolecular cationic tetraruthenated porphyrin induces single-strand breaks and 8-oxo-7,8-dihydro-2'-deoxyguanosine formation in DNA in the presence of light

Photochemistry and Photobiology

Volumn 63, Issue 3, 1996, Pages 272-277

  Onuki, Janice ^a   Ribas, Adrians V ^a   Medeiros, Marisa H G ^a   Araki, Koiti ^a   Toma, Henrique E ^a   Catalani, Luiz H ^a   Di Mascio, Paolo ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

8 OXO 7 HYDRODEOXYGUANOSINE; 8-OXO-7-HYDRODEOXYGUANOSINE; CATION; DEOXYGUANOSINE; DNA; DRUG DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOTOSENSITIZING AGENT; PORPHYRIN; SINGLE STRANDED DNA; TETRARUTHENATED PORPHYRIN;

ANIMAL; ARTICLE; BIOSYNTHESIS; CATTLE; DNA DAMAGE; DRUG EFFECT; LIGHT; METABOLISM; PHOTOCHEMOTHERAPY; RADIATION EXPOSURE;

ANIMALS; CATIONS; CATTLE; DEOXYGUANOSINE; DNA; DNA DAMAGE; DNA, SINGLE-STRANDED; LIGHT; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS;

ANIMALIA; BOS TAURUS;

EID: 0030111364     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1996.tb03024.x     Document Type: Article

References (41)

1. Henderson, B. W. and T. J. Dougherty (1992) How does photodynamic therapy work. Photoche. Photobiol. 55, 145-157.
2. Moan, J. and K. Berg (1992) Photochemotherapy of cancer: experimental research. Photochem. Photobiol. 55, 931-948.
3. Kessel, D. (1992) Photodynamic therapy and neoplastic disease. Oncol. Res. 4, 219-223.
4. Dougherty, T. J. (1986) Photosensitization of malignant tumors. Semin. Surg. Oncol. 2, 24-37.
5. Byrne, C. J., L. V. Marshallsay and A. D. Ward (1990) The composition of Photofrin II. J. Photochem. Photobiol. B Biol. 6, 12-27.
6. Agrez, M. V., R. E. Wharen, R. E. Anderson, E. R. Laws and D. M. Ilstrup (1983) Hematoporphyrin derivative, quantitative uptake in DMH induced murine colo-rectal carcinoma. J. Surg. Oncol. 24, 173-176.
7. Fiel. R. J., J. C. Howard, E. H. Mark and N. D. Gupta (1979) Interaction of DNA with a porphyrin ligand: evidence for intercalation. Nucleic Acids Res. 6, 3093-3118.
8. Strickland, J. A., L. G. Marzilli, K. M. Gay and W. D. Wilson (1988) Porphyrin and metalloporphyrin binding to DNA polymers: rate and equilibrium binding studies. Biochemistry 27. 8870-8878.
9. Marzilli, L. G. (1990) Medical aspects of DNA-porphyrin interactions. New J. Chem. 14, 409-420.
10. Fiel, R. J. (1989) Porphyrin-nucleic acid interactions; a review. J. Biomol. Struct. & Dyn. 6, 1259-1274.
11. Barton, J K. and A. L. Raphael (1984) Photoactivated stereo-specific cleavage of double-helical DNA by cobalt (III) complexes J Am. Chem. Soc. 106, 2466-2568.
12. Araki, K. and H. E. Toma, (1993), Synthesis and characterization of a multibridged porphyrin complex containing peripheral bis(bipyridine)ruthenium(II) groups J. Coord. Chem. 30, 9-17.
13. Araki, K. and H. E. Toma (1994) Luminescence, spectroelectrochemistry and photoelectrochemical properties of a tetraruthenated zinc porphyrin. J. Photochem. Photobiol. A Chem. 83. 245-250.
14. Di Mascio, P., H. Wefers. H.-P. Do-Thi, H. Lafleur and H. Sies (1989) Singlet molecular oxygen causes loss of biological activity in plasmid and bacteriophage DNA and induces single-strand breaks. Biochim. Biophys. Acta 1007, 151-157.
15. Khan, A. U., P. Di Mascio, M. H. G Medeiros and T. Wilson (1992) Spermine and spermidine protect plasmid DNA against single-strand breaks induced by singlet oxygen. Proc. Natl. Acad. Sci. USA 89, 11428-11430.
16. Gorman, A. A. and M. A. J. Rodgers (1989) Singlet oxygen. In CRC Handbook of Organic Photochemistry, Vol. II (Edited by J. C. Scaiano), pp. 229-247. CRC Press, Boca Raton. FL.
17. Pyle, A. M., J. P. Rehman. R. Meshoyrer, C. V. Kumar, N. J. Turro and J. K. Barton (1989) Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA. J. Am. Chem. Soc: 111, 3051-3058.
18. Paillous, N. and P. Vicendo (1993) Mechanisms of photosensitized DNA cleavage. J. Photochem. Phoiobiol. B Biol. 20. 203-209.
19. Subramanian, R. and C. F. Meares (1985) Photoinduced nicking of deoxyribonucleic acid by ruthenium(II) bleomycin in the presence of air. Biochem. Biophys. Res. Commun. 133, 1145-1151.
20. Subramanian, R. and C. F. Meares (1986) Photosensitization of cobalt bleomycin. J. Am. Chem. Soc. 108, 6427-6429.
21. -) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513-886.
22. Isabelle, V., C. Prevost, M. Spotheim-Maurizot, R Sabattier and M. Charlier (1995) Radiation-induced damages in single- and double-stranded DNA Int. J. Radiat. Biol. 67, 169-176.
23. Jovanovic, S. V. and M. G. Simic (1986) Mechanism of OH radical reaction with thymine and uracil derivatives. J. Am. Chem. Soc. 108, 5968-5972.
24. Cadet, J. and M. Berger (1985) Radiation-induced decomposition of purine bases within DNA and model compounds. Int. J. Radiat. Biol. 47, 127-143.
25. Gajewski, E., G. Rao, Z. Nackerdien and M. Dizdaroglu (1990) Modification of DNA bases in mammalian chromatin by radiation-generated free radicals. Biochemistry 29, 7876-7882.
26. Schulte-Frohlinde, D. and C. von Sonntag (1985) Radiolysis of DNA model systems in the presence of oxygen. In Oxidative Stress (Edited by H. Sies), pp. 11-40. Academic Press, New York.
27. - and OH adducts. Chem. Rev. 89, 503-520.
28. Schulte-Frohlinde, D. (1989) Studies of radiations effects on DNA in aqueous solution. I.C.R.U. News 2, 5-15.
29. Kelly, J. M., D. J. McConnell, C. OhUigin, A. B. Tossi, A. Kirsch-De Mesmaeker, A. Masschelein and J. Nasielski (1987) Ruthenium polypyridyl complexes; their interaction with DNA and their role as sensitisers for its photocleavage. J. Chem. Soc. Chem. Commun., 1821-1823.
30. Cadet, J. and R. Téoule (1978) Comparative study oxidation of nucleic acid components by hydroxyl radical, singlet oxygen and superoxide anion radicals. Photochem. Photobiol. 28, 661-667.
31. Kawanishi, S., S. Inoue and S. Sano (1986) Photodynamic guanine modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. J. Biol Chem. 261, 6090-6095.
32. Lee, P. C. C. and M. A. J. Rodgers (1987) Laser flash photokinetic studies of rose bengal sensitized photodynamic interactions of nucleotides and DNA. Photochem. Photobiol. 45, 79-86.
33. Piette, J. (1991) Biological consequences associated with DNA oxidation mediated by singlet oxygen. J. Photochem. Photobiol. B Biol. 11, 241-260.
34. Epe, B. (1991) Genotoxicity of singlet oxygen. Chem.-Biol. Interact. 80, 239-260.
35. Sies, H. (1993) Damage to plasmid DNA by singlet oxygen and its protection. Mutat. Res. 299, 183-191.
36. Cadet, J., C. Decarroz, S. Y. Wang and W. R. Midden (1983) Mechanisms and products of photosensitized degradation of nucleic acids and related model compounds. Isr. J. Chem. 23, 420-429.
37. Floyd, R. A., M. S. West, K. L. Eneff and J. E. Schneider (1989) Methylene blue plus light mediates 8-hydroxyguanine formation in DNA. Arch. Biochem. Biophys. 273, 106-111.
38. Floyd, R. A., M. S. West, K. L. Eneff and J. E. Schneider (1990) Mediation of 8-hydroxy-guanine formation in DNA by thiazin dyes plus light. Free Radical Biol. & Med. 8, 327-330.
39. Ravanat, J.-L., M. Berger, F. Benard, R. Langlois, R. Ouellet, J. E. van Lier and J. Cadet (1992) Phthalocyanine and naphthalocyanine photosensitized oxidation of 2-deoxyguanosine: distinct type I and type II products. Photochem. Photobiol. 55, 809-814.
40. Floyd, R. A., M. S. West, J. E. Schneider, J. J. Watson and M. L. Maidt (1990) Hematoporphyrin D plus light mediates 8-hydroxyguanine formation in DNA and RNA. Free Radical Biol. & Med. 9, 76.
41. Devasagayam, T. P. A., S. Steenken, M. S W. Obendorf, W. A. Schulz and H. Sies (1991) Formation of 8-hydroxy-(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 30, 6283-6289.